Behind the Investment – AtomicJar

Insight Partners has a rich history of investing in developer testing tools. We’re proud to have supported companies like SmartBear, Tricentis/QASymphony, Browserstack, Waldo, and others which help their  customers accelerate release cycles and deliver better, more stable end products.

An emergent technique within testing we have closely monitored is integration testing – the testing of interdependent code and resources to ensure components operate as expected. As developers shift toward microservices, testing the interconnection of application components is becoming ubiquitous and an integral part of the development process.

Testcontainers has widely become the leading open-source software for integration tests, with ~7 million monthly Docker downloads and a vibrant and passionate developer community. The community’s growth is accelerating. Using Testcontainers, developers can spin up testing environments for common integration and UI tests using Docker containers, which act as “throwaway” instances for production-like replicas of external resources (e.g., databases, web browsers, other microservices). This enables faster creation and execution of integration tests and mitigates many painful issues for developers that come from spinning up and taking down tests manually.

There are lots of obstacles to using integration testing, particularly for more complex software. Keeping local testing environments up-to-date with new code releases is cumbersome. Running integration tests is taxing on local developer machines. Replicating tests from one machine to another is not as simple as it seems. Many developers we’ve spoken to have had some form of the “works only on my machine” problem where a test is successful on their laptop but not a teammate’s!

The Testcontainers’ founders set out to build a cloud-hosted, commercial version – driven by the simple belief that running Testcontainers in the cloud would provide clear improvements to development velocity and better enterprise deployments.

For this they are now launching Testcontainers Cloud (TCC). Through this new product, developers can seamlessly route integration tests to cloud servers and fine-tune their test environments to production-grade specifications, resolving the “works on my machine” problem. By sending tests to the cloud, developers also free up local compute resources and enable tests to run up to 3x faster. Developers do not even need Docker installed on their machine and can now take advantage of Cloud IDEs and other live collaboration tools.

With the launch of Testcontainers Cloud to public beta, AtomicJar offers a full suite of integration testing products. AtomicJar streamlines integration testing for software projects, regardless of scope or complexity.

Before making our investment, we conducted extensive diligence that included surveying hundreds of developers, talking to many of AtomicJar’s beta customers, and deeply understanding the product and its roadmap and were amazed by the size of the opportunity that will continue to grow as microservices continue to get adopted by companies of all sizes. We are thrilled about AtomicJar’s potential to improve the productivity of the almost 90M software developers across a wide range of industries, geographies, and software development methodologies. We’re excited to partner with them as they help lead the “shift left” of best-in-class software testing and delivery.

How to Select an Investor in 2023

Preparing to raise capital in 2023 might feel daunting given the market, but it doesn’t need to be. For great businesses, there are investors (like Insight) who are ready to invest.

Before thinking about raising money, we’re going to assume founders have checked off some of the basics listed below:

  1. Know your specific business needs for the investment. This should be deeper than the amount of money you need to raise. Founders/CEOs seeking funding should have a well-defined business plan that outlines company growth goals, target market, financial projections, and competitive advantage. This helps articulate the value of your business to potential investors and demonstrates an understanding of the industry and market.
  2. Prepare your leadership team. Fundraising takes time away from running the business, which means your leadership team must have the skills, experience, and dedication to execute the business plan and drive the company’s growth. Assemble a team that has a diverse range of skills and expertise needed to achieve the company’s goals.
  3. Have a clear plan for using the funding. Investors want to see a clear plan for how the new funding will be used to drive the company’s growth and generate a return on investment. Be prepared to present a realistic, detailed plan for how the investment will be used to achieve specific milestones and grow the business.
  4. Finally, map the market of potential investors. Asking other entrepreneurs for advice and introductions is a great way to start the fundraising process.

Once these steps are done, you’re ready to begin seriously contemplating your next fundraising partner. Deciding to bring someone new onto your cap table can significantly strengthen your business for the years ahead and inject the capital needed to move from a startup to a scaleup.

Some tips for founders:

Prenup discussions on the second date.

Being prepared with your goals and expectations for raising capital is great, but in today’s market, it’s important to have an open mind and willingness to have a conversation. In the negotiation of final documents, there is always a clear set of rights regarding rules of engagement if things go right — and if things go wrong. While this can feel as off-putting as discussing a prenuptial agreement early in a relationship, it is important all sides understand rights and agreements for all scenarios. Consider your position if things go wrong. What happens when things go wrong is as important as the conditions when things go right.

Consider dilution in addition to valuation.

You’re obviously seeking out capital, but don’t simply fixate on your company’s valuation number or the specific amount of money you want to raise. The more important consideration in the long run will be understanding the percentage of the cap table you are hoping to raise. While value is always important, if you are only raising primary capital you should consider dilution more than the post-money value. For example, if you are hoping to raise $25M at a $125M post (20% dilution), you can offset a 25% price disappointment by lowering the amount of capital raised. You can raise at $80M while limiting the raise to $20M. This is also 20% dilution. The only difference between the two deal structures is $5M on your balance sheet. The point? Valuation matters, obviously. But it’s only one of the variables. You can control the impact of valuation by adjusting the investment amount.

You want a partner that has enough capital to ideally support you through your next few rounds, and ultimately, deliver enough value to scale your business in meaningful ways beyond a sky-high valuation or fundraising amount.

Have conviction in what a new investor can do to add value.

This means two things. Firstly, what does the investor’s investment horizon look like? Do they have the capital and patience to be able to support you long-term? Secondly, how will the investor work with you and your team? It’s critical to know the skillset of your lead investor and ensure that they understand your industry, business, and goals for the years to come.

Besides the financial support of your investor, different firms will have different levels of deeper support available. At Insight, for example, there is a large team set up to support each individual portfolio company, streamlined through a portfolio management function. This ensures impactful, personalized support is delivered when and where it is needed most for each portfolio company.

Most CEOs and founders who choose to work with Insight are particularly excited by having access to Insight Onsite, a team of more than 130 of the software industry’s best operators, dedicated to supporting portfolio companies as they scale up. Understanding what resources different investors have available to you will help you strategically map out your board and partners to best support you at your stage of growth.

Select an investor with a network you can leverage through your journey.

Investors can be incredibly valuable partners and bring a unique perspective to the boardroom. However, being a CEO (or another C-Suite role) at a growing business in today’s climate can be an intimidating and lonely job. Insight’s portfolio of 600+ companies provides CEOs with an unparalleled peer network to lean on and learn from. Having a pool of people who are in your shoes and navigating the same challenges can be one of the most transformational assets for CEOs when building their business.

Insight’s portfolio experience programming is one of the most robust in the industry, made possible because of the global breadth of the portfolio. In 2022 alone, executives accessed nearly 80 intimate digital roundtables and webinars, and over 30 in-person events. Many of Insight’s CEOs choose to participate in the MINDSET CEO Summits, where, alongside their peers, they’re able to dive deep into the leadership and operational challenges they’re facing today and walk away with trusted advice on what to do next. Insight’s portfolio events are all designed to forge strategic connections and actionable tactics.

Raising money can be a challenging process, especially in 2023. But prepared with the proper guidance and expectations, finding the right partner can be transformational to the future of your business.

4 Reasons Founders Should Bookmark the New Insight Website

With more than 25 years of experience, Insight has established a top-tier position in software investing through times of market turbulence, a global pandemic, political unrest, and multiple tech hype cycles. Coming off a record-breaking 2022, we’re excited to tell our story with a completely new website. The new site is a testament to the expertise of Insight’s team and our dedication to being the best partner to software companies at every stage of growth.

Here are the four useful things founders should bookmark on the new site:

  1. Sectors: Powerful insight into the market
  2. Onsite: Insight’s secret engine for scale
  3. Stories: The journey from startup to ScaleUp
  4. Ideas hub: More than a blog

Sectors: Powerful insight into the market

Sector pages offer an unprecedented look into the pulse of the market as Insight sees it. These new sector pages showcase how we’re tracking a space, how much we’ve invested in the sector, and our most recent investments. This data is live and updated regularly, so be sure to bookmark sectors of interest and check back frequently.

In this section, you can find:

  • How much Insight has invested in a particular sector
  • How many companies we have invested in within the space
  • Thoughts from our investors on the space and what we’re looking for
  • How many companies Insight is tracking in the space
  • Our recent investments

For example, you can see from our AI/ML sector page that (at the time of writing) Insight has invested $4.7B across 104 companies in this space, tracking over 13,612 companies since 2016.

With our expansive network of buyers, builders, and talent, founders should bookmark their sector’s page to stay up to date on Insight’s investment activity in the space.

Onsite: Insight’s secret engine for scale

As an investor, Insight’s responsibility is to help our portfolio companies grow and scale. What sets Insight apart from other investors is our team of 130+ operators in sales/customer success, marketing, product/tech, and talent. The Onsite team provides operational expertise to accelerate our founders’ vision. See examples of the specific engagements our Onsite team has made in our sectors pages, or click into the team page to browse Onsite leadership and get a sense of the expertise they offer.

Insight Onsite engagement

Stories: The journey from startup to ScaleUp

There’s a reason our portfolio stories are featured at the very top of our homepage. Insight is a dedicated partner at every stage of ScaleUp growth, and our team knows software better than anyone. Our new homepage is focused on telling these success stories to celebrate our portfolio and inspire the next generation of founders.

Monday.com IPO

For example, from Insight’s homepage, you can read the story of our portfolio company monday.com. Beginning with Insight’s investment in series B, advising with a company rebranding and creation of a successful channel partners program through Onsite expertise, and participating in their series C fundraising round. In mid-2021, the partnership and hard work paid off as Insight supported monday.com through a successful IPO.

There’s a reason top founders partner with Insight — we’re committed to doing the hard work required to scale a company, and we’re equally committed to celebrating success.

Ideas hub: More than a blog

Just by reading this, you have discovered our new ideas hub. In this section, you’ll find curated content on the growth strategies, benchmarking data, industry insights, and stories that founders and leaders need. Bookmark this page as our team publishes exclusive ScaleUp reports and industry data on the topics data ScaleUps need to be successful throughout the year. Prefer to get this content in your inbox? Sign up for our newsletter, Field Notes, at the bottom of this page.

With more than two decades of investing experience, Insight’s team has learned the patterns that identify winners. With our new website, any founder can take advantage of this expertise and knowledge.

5 Strategies Marketing Leaders Need to Succeed in 2023

The famous Roman Stoic Seneca once said, “Luck is what happens when preparation meets opportunity.” Ultimately, you need both to succeed. The same might be said to marketing leaders in 2023: prepare, prepare, prepare!

There is no way to predict how the macroeconomic climate is going to shift or how it will impact B2B SaaS marketing teams. But one thing is clear — marketing leaders have their work cut out for them to thrive in what is likely a challenging environment. Many best practices that previously worked will be challenged, and agility remains critical.

Based on Insight’s close partnership and expertise in helping companies scale, we’re tracking the emerging questions we believe will shape marketing strategies in the coming year:

  1. How should you change your digital marketing strategy?
  2. What role will customer marketing play?
  3. Events: In-person? Virtual? Hybrid?
  4. How can personalization and generative AI help?
  5. What can be done to keep the marketing function whole in the face of organizational restructuring?

Read on for the marketing strategies we think will make a meaningful impact this year.

Organic efforts can yield higher ROI

One of the most significant challenges B2B SaaS organizations will face is the increasing cost of demand generation. With buyers pushing decisions out, there is a need for more touches to drive leads through the buyer’s journey, and marketers will have to be creative in order to keep their costs low.

Additionally, social media is becoming increasingly difficult to use for targeting given the recent changes across the major platforms and increased scrutiny around privacy. Facebook, LinkedIn, and TikTok have all seen CPM (cost per thousand) increase significantly in 2022. Facebook, and parent company Meta, is particularly difficult since they’ve been at the center of numerous data-related scandals, while Twitter’s shifting focus and paid options have been difficult for marketers to navigate. Twitter’s Ad Manager volume and roster of advertisers both fell sharply in October and November 2022. LinkedIn remains a great platform for targeting, though limited inventory and expensive ad spaces are becoming more common.


Key Insight: Your ROI on investing in stronger organic will likely be higher than paid digital. Reallocate budget to content and SEO.


Invest in customer marketing

As businesses started to experience a slowdown in new business ARR in 2022, customer retention and expansion became critical. Across the Insight portfolio, we saw our companies experience a 4% increase in expansion ARR between Q3 FY21 and Q2 FY 22, while new ARR was flat over the same period. Furthermore, our high-performing companies tend to see greater marketing spend efficiency due to a focus on retention and expansion.

marketing spend vs new and expansion ARR

It’s clear that customer retention will continue to be a major focus for B2B SaaS marketers. As the world continues to grapple with an unfolding economic crisis, businesses across all industries need to fight harder than ever to keep their customers from jumping ship and going to competitors that offer a cheaper price. Investing time into creating an effective customer marketing function is essential.


Key Insight: Expansion revenue will be cheaper and easier to drive than new logo this year. Consider reallocating both budget and people resources to these initiatives.


For more on the importance of customer retention and the role of marketing, read How to Grow by Marketing to Customers.

Shift the events mix

Overall, 41% of Insight portfolio companies indicated event budgets in 2023 will remain the same compared to 2022, while 25% are increasing budgets, and 34% are experiencing a decrease in budget.

events budgets in 2023

With inflation hitting everything from travel expenses to on-site cappuccino machines, events may become a more difficult and expensive prospect in 2023. Data from Insight portfolio company, Bizzabo, suggests that in-person events remain important and are here to stay: 72% of event organizers indicated that in-person events remain a crucial part of their overall event strategy, 98% plan to host at least one in-person event next year, and 85% plan to host at least three.

However, for companies experiencing significant budget constraints, virtual event platforms could provide the solution. Think webinars, tailored content facilitated by virtual assistants and AI bots, as well as interactive 3D experiences. These solutions can help marketers reach new customers and keep current ones engaged in a more cost-effective manner, allowing them to maximize their budget. According to Bizzabo, 68% of event organizers plan to have a virtual component at their next in-person event, and 53% are “focused” or “very focused” on a virtual events strategy for 2023.


Key Insight: Maximize your event budget by getting the right mix of virtual, live, and hybrid events. Make sure to include multiple tactics to drive multiple objectives for events such as brand building, pipeline acceleration, and partner marketing.


For a full playbook on how to think about Hybrid Events, read Virtual, In-Person & Hybrid Events? Oh, My!

Enlist help from AI

Personalization will be key in 2023. As the target market continues to become more demanding, B2B SaaS markets must lead the way in providing a bespoke journey for each customer. From tailored content and products to automated emails and personalized ads, marketers need to find ways to make their customers feel like they are the only ones that matter — and it needs to be done at scale.

Many companies are also starting to experiment with generative AI in creative ways. From creating short-form bespoke content and LinkedIn posts, to brainstorming webinar ideas and product names, the use cases for generative AI are expansive. Be careful to validate content produced by generative AI to ensure the facts are correct.


Key Insight: Personalization demands more content than most marketing teams are capable of creating. Begin experimenting with tools like Jasper and Writer to leverage the power of generative AI and bridge the gap.


For more on generative AI, read What Marketers Need to Know About AI-Generated Content.

Keep marketing’s seat at the table

Marketers will need to fight hard to keep the marketing function whole in the face of organizational restructuring. Marketers need to be aware of the dangers of “siloing” their team. It’s becoming increasingly common to split off demand generation and put it under the CRO’s domain, product marketing connected to the product organization, and marketing operations placed under revenue operations. As B2B SaaS organizations continue to become more complex, it’s important for marketers to have a seat at the table and ensure that their efforts are aligned with business goals. Tools like BlueOcean can help marketers quantify their collective business impact by providing insight into how ads, content, brand messaging, and more compare to competitors. By directly tying brand value and other marketing activities back to business impact, marketing leaders can maintain a seat at the table.


Key Insight: While some marketing activities may seem to fit better under another functional area, the loss of integrated messaging and tactics will cost the organization far more.


2023 is likely to be an interesting year, but with the right strategies in place, B2B SaaS marketers can emerge as winners. So, start preparing now and maybe your organization might get lucky with a strong year of performance.

Editor’s note: Jasper, Writer, BlueOcean, and Bizzabo are Insight portfolio companies.

How to Grow by Marketing to Customers

With many ScaleUps prioritizing customer retention and growth in 2023, marketers must deepen the impact of their customer marketing program.

Engaging customers is good for business, as they can be a company’s most efficient source of growth. GTM teams can generate additional revenue from customers for as little as 1/10th the cost of new business. It takes less time, effort, budget, and companies typically win customer opportunities at a higher rate.

When new business demand wanes or customer churn increases, ScaleUps must respond by changing how they market throughout the revenue cycle. But, in our mid-2022 survey, only 11.1% of Chief Marketing Officers (CMOs) reported feeling “very well prepared” amidst increasing macroeconomic uncertainty. Meanwhile, 87.3% were experiencing softening demand.

CMOs’ uneasiness might, in part, stem from their comparative lack of engagement with customers after the deal is won. Throughout recent boom years, most CMOs have focused on generating new business. As a result, they’re ill-positioned to retain and expand business from existing customers.

From Insight’s Budgeting & Planning survey of ScaleUp companies, we know that customer marketing has received the least investment out of the seven key marketing functions. By comparison, the typical ScaleUp adds a CSM for every 19 enterprise and 34 mid-market customers. Additionally, just 1 in 5 account-based marketers say customer expansion is in their remit.


Read more: CMO Playbook for Economic Headwinds: Make Your Move Before It’s Too Late


To mitigate softening demand and diversify a business’s revenue mix, marketers must help expand customers. Doing so will supplement near-term deficits in growth and improve marketing’s efficiency over the long term.

“It’s a team effort. Marketing must play a role in driving growth throughout the revenue cycle. They connect sales with new buyers and help close deals. After the sale, marketing partners with customer success to deepen our relationships with our existing customers, driving product adoption and expanding across divisions or territories within a single account.”

-Tal Kain, CEO of Velocity

How? By collaborating with their peers in sales and customer success to do the following:

  1. Forecast addressable customer revenue
  2. Set objectives, goals, and KPIs
  3. Develop a post-sale strategy
  4. Resource and integrate post-sale teams
  5. Execute a joint tactical playbook
  6. Operationalize a unified “go-to-customer” process

Forecast addressable customer revenue

Why it matters: Know the size and types of opportunities within your customer base to decide where to focus and how much to invest. Consider how investments in customer retention and expansion impact your firm’s “Rule of 40” performance (e.g., X% growth rate + Y% profit margin = 40%).

Analyze your current opportunity mix:

  1. How quickly and efficiently do you generate profit?
  2. What changes could you impart on your opportunity mix by investing in post-sale marketing
  3. How might your changes to your opportunity mix impact how efficiently you generate profit?

Based on your forecast, scope your post-sale marketing initiative:

  • Pilot. If the size of the opportunity seems modest or uncertain, plan a narrowly scoped, but representative, pilot. You might focus on improving one or two post-sale outcomes by deploying a small tactical play in a limited customer segment.
  • Sprints. If the opportunity is significant and certain, introduce customer marketing elements in waves, evaluating their impact along the way.

You’ll likely need to make tradeoffs, prioritizing which investments you make within your opportunity mix.

“As a startup company, your rapid-growth strategy for Year 3 should have a lot more customer opportunities than Years 1 and 2.”

-Kerry Cunningham, Senior Principal of Product Marketing, 6sense, and co-author of The Demand Unit Waterfall™

Set objectives, goals, and KPIs

Why it matters: GTM teams must align on goals and how they measure their progress toward said goals.

Once you’ve forecasted the ideal opportunity mix, define your objectives to focus your post-sale program plan. You could:

  • Accelerate time-to-value.
  • Improve product adoption and/or drive more utilization.
  • Upsell to more and/or higher price tiers.
  • Cross-sell the same buyers to additional products.
  • Cross-sell new buyers within a customer account.
  • Secure renewals, reduce churn, and/or prevent downgrades.

Once you’ve homed in the changes you seek to impart on the customer lifecycle, determine which KPIs best measure those changes and set goals for each KPI.

You can use benchmarks to help you set goals. But the benchmarks aren’t your goal, they’re a conversation starter. Consider variables, such as growth stage, expansion motion, and customer characteristics.

Develop a strategy

Why it matters: Businesses must focus on just a few key ways they can provide value to customers–beyond the product itself–and a few key ways in which they can enable staff to deliver on said customer value.

Here’s how:

  1. Brainstorm all the levers you could employ to create value.
  2. Prioritize those levers which create the most value. Pick no more than a few.

Once your go-to-customer strategy is set, refine your customer marketing strategy. Develop customer ICPs, personas, and buyer journey models. Then use those models as a basis for your post-sale messaging strategy.

Customers can be different than buyers in several ways:

  1. Marketers should clarify the differences between pre- and post-sale customer profiles.
  2. They must get to know which personas emerge once the buyer has purchased a product.
  3. They must understand their customer’s journey.

With these insights in hand, marketers can develop messages that motivate a customer to move through the post-sale cycle.

Resource and integrate post-sale teams

Why it matters: Resource your post-sale team well enough to deliver value to the customer, without burdening post-sale efficiency. Hire the right people and place them into the right structure.

Start first by identifying who in your company already owns each part of the customer journey (e.g., Customer Success Manager, Account Manager). Then, consider which marketers might be best suited to partner with them:

  • What capabilities do I need?
  • Given my targets, how will I resource the team? Which hires must I prioritize?
  • How will I balance in-house and outsourced talent?
  • How will I structure my staff?

Your opportunity mix offers clues, as does the functional scope of other GTM teams. Though the marketing team could outsource some of the work, it’s best done by in-house staff who have the skills and business acumen to engage precious customer points of contact.

Execute a joint tactical playbook

Why it matters: GTM teams can employ a nearly endless array of tactics. So, they must draw on their go-to-customer strategy to determine which tactics to execute. The delivery must be well-orchestrated if the message is to have its intended effect. The right tactics, at the right time, with the right people.

Like a sports team might coordinate its offensive players against the defense, a GTM team executes a post-sale play oriented to a target customer’s traits and the business’s objectives.

  1. Based on your objectives and strategy, which plays will you run?
  2. How do those plays suit your customer ICP, personas, and journey?

Based on your answers, create a playbook in partnership with cross-functional GTM teams.

Operationalize a unified “go-to-customer” process

Why it matters: Ensure customer-facing stakeholders know what, when, where, and how to support the customer.

“Our marketing team is partnering with customer success to offer additional value to our customers. We host product release webinars for customers, where they learn how early adopters are putting to work new software capabilities. We’ve found our customers respond better to learning from their peers — and are more likely to ask for a demo — versus a marketing email alone.”

– Jamie Walker, EVP Marketing at Keyfactor

Build boosters and remove blockers to ultimately create value for employees, suppliers, and customers.

  • Incentives. Evaluate your performance-based pay to ensure incentives align to customer outcomes and KPIs.
  • Recognition. Revise your internal communication and meeting cadences to celebrate customer wins.
  • Technology. Evaluate your tech stack to determine if you have the right tools, configured to meet the requirements of customer engagement. If you don’t, procure new tools and/or change the configuration of your existing ones.
  • Vendors. Evaluate the capabilities you have on-staff, the capabilities you need, and the gap between. Outsourcing might be the most efficient way to fill these gaps.
  • Enablement. Seek out ineffective elements of your cross-functional customer operations. Then, develop a “learning agenda” that addresses those elements via an enablement program.
  • Documentation and monitoring. Evaluate your operational performance. Then, define essential processes and monitor their performance.
  • Report. Brainstorm the key questions post-sale staff must answer for themselves. Then, consider which metrics they’ll need to answer those questions and how best to present the metrics in a self-service dashboard or report. Finally, decide which systems to use for reporting.
  • Automate and outsource. Audit your processes and procedures for opportunities to outsource and automate.
  • Fun and relationships. Foster an engaging culture for your post-sale staff and create avenues by which they can build relationships with your customers.

For many businesses, customers represent a compelling source of efficient growth. This growth results from strategically creating value for customers, as well as for employees, suppliers, and partners.
GTM teams can carefully craft tactical plays, executed by way of tightly coordinated go-to-market operations, to deliver an excellent customer experience. In doing so, they’ll earn their customer’s loyalty and advocacy, generating better margins for the business.

 


Examples in practice

To illustrate the strategies outlined above, let’s use an imaginary drone data analytics company to show how these principles work in practice.

Forecasting addressable customer revenue

A drone data analytics company offers software modules that each process three different types of aerial images: photographs, infrared, and thermal.

  • Most customers start by purchasing the photography module.
  • The software provider licenses the modules on an annual subscription and charges a small fee for each image processed.
  • Infrared costs more than photographs; thermal is the most expensive.

Here’s how they might evaluate their opportunity mix:

  1. Increase Utilization: Photography. The marketing team forecasts that it would cost $0.05 per image to drive more photograph processing (i.e., increase utilization). But they earn just $0.01 in revenue for each image processed.
  2. Cross-sell Infrared to the same buyers. They expect that marketing the cross-sale of the infrared module would cost $2,500 per sale, but earn the business $10,000 ARR.
  3. Cross-sell Thermal to different buyers within existing customer accounts. Supporting cross-sales of the thermal module would likely cost $5,000 per sale, but earn the business $20,000 ARR.

So, the marketing team will prioritize support for the thermal module, since it has the best dollar-cost return ratio, followed by infrared (if they have budget leftover). They won’t help drive more photographic image processing, since they forecast a net negative outcome.

Set objectives, goals, and KPIs

KPIs (Output Metrics)

1. Cross-sell thermal modules to 50 new buyers within customer accounts.
2. Cross-sell infrared module to 100 existing buyers within customer accounts.

Key Results (Input Metrics)

1a. Generate 100 cross-sale opportunities
1b. Improve win rates for thermal cross-sales from 35% to 50%

2a. Generate 135 cross-sale opportunities

Develop a strategy

Customer Value
• Community. Create an “advanced imagery” community, where pro users of infrared and thermal imagery can share best practices with novices.
• Training. Develop an “advanced imagery training program” to help photo users learn how to use infrared and thermal imagery.
• Discounts. Offer “existing customer” discounts for infrared and thermal modules.

Staff, Vendors, and Suppliers Value
• Incentives. Offer a spiff/bonus to relevant GTM staff for attaining net new cross-sale goals.
• Training. Direct all GTM staff to take the same “advanced imagery training program” we offer to customers.
• Data-based targeting. Develop a predictive data model to identify prime cross-sale targets.

Resource and integrate post-sale teams

The drone company will hire:
• Community Marketing Manager
• Learning & Development Content Marketing Manager
• Product Marketing Manager, Infrared and Thermal Sensors

They’ll outsource:
• Customer community event production
• Technical copywriting
• Training content design

Execute a joint tactical playbook

Here is an example of how a customer marketing playbook could look for our drone company.

customer marketing playbook example

Designing Your First President’s Club

Many senior revenue leaders have asked Insight Partners to help structure their President’s Club contests for the year. Based on these conversations, we’ve laid out some guidelines to make your President’s Club truly memorable, and more importantly, something that really motivates your sales team.

What is President’s Club?

Let’s start with the basics – President’s Club (as known as Achiever’s Club, Winner’s Circle, etc.) is an annual contest that is awarded to an elite group of sales reps, sales leaders, and sales technical resources for achieving specific goals — typically attainment of quota. This concept started way back in 1907 with NCR as a way to motivate and reward top-performing reps, and the reward mechanism has now spread throughout the corporate world. For sellers, the financial incentives for overperformance are significant and motivate many. A President’s Club award that comes with peer recognition and a unique prize is highly motivational for many people. When the contest stakes are meaningful, they can drive high-performing behavior and encourage reps to go above and beyond their normal performance expectations. When deployed well, the incentive can have a material impact on the overall performance of the company.

At what stage of my company’s growth should we introduce a President’s Club?

One question we get often is, am I too small to have a President’s Club? The short answer is that it depends on the culture of your company and the focus you want to place on driving and rewarding the sales team. If your sales team is smaller than 25, you can probably leverage other reward mechanisms (e.g., provide upgraded suites at Sales Kickoff for your top reps) versus having a Club event. Once you begin to scale above 25, the Head of Sales should determine, with the support of your CEO, Finance, HR, and Marketing whether a Club event makes sense for the team, and then jointly align on how to structure the program.

What are the criteria to attend President’s Club? Most organizations seem to pick 100% of quota attainment.

Although achieving 100% of quota is a significant accomplishment and should be recognized with an award and announcement, if you’ve designed your compensation plan and quotas well, 50-65% of your reps should be close to achieving or exceeding 100% of plan. That’s a significant percentage of your organization, and it reduces the exclusivity of President’s Club. Many companies send anywhere from 5% -20% of their top performers, and the percentage depends on how exclusive you want to make the event.  The number you send could increase in a year where the company significantly outperforms expectations and decrease when the company underperforms.

So, I should just make it a moving target where 20% win? Then at least I know how much I’ll spend.

There are pros and cons to the two main ways of setting criteria — fixed percentage of team members, and fixed target criteria.

Fixed Percentage of Team

This approach is the most predictable in terms of financial impact. The company determines a set percentage of the sales team that can attend and they use a stack ranking by role to determine the winners. Many companies require that winners achieve a minimum performance threshold (100% of plan) to avoid the risk of sending reps that have underperformed. This is simple to model and simple to explain to the organization.

The challenge with this approach is that it can demotivate some reps. If you’ve outperformed all year and are going to finish at 135% of plan, but would fall outside of the top 20% of reps, should you be left out of the fun? What happens if someone beats you out on the last day of the year for that final spot?  Not only would that impact you as a rep, but the story may flow through the organization and could demotivate others.

Fixed Target 

This approach sets performance criteria for the reps to win President’s Club. This is typically a percentage of plan and may include a minimum sales dollar/euro amount. For example, if you model out your expected performance for the year and expect 23% of people to achieve 135% or higher, then you should set your award criteria at 135%. Anyone who hits that target and meets any other criteria you stipulate should be able to win the award. The benefit of this approach is that you can recognize everyone that achieves those targets, motivating a broader portion of the organization.

One challenge to this approach is the financial modeling needed to budget appropriately and the risk that more than the expected percentage achieve the target. This could drive up costs but hopefully also comes with a commensurate performance improvement. The other risk is that high performers could relax a bit once they hit the criteria and save some deals for the following year.

What other criteria should be considered?

The most common criteria outside of quota achievement considered is tenure. It’s typical to exclude sales reps who have been on quota for less than 9 months of the year. The reason for this is that it’s difficult to set accurate ramp quotas for new reps, especially if they inherit active territories.

Other criteria can include things like a minimum revenue amount, a minimum amount for a specific product (if you’re trying to ensure balance across products), or a certain amount by region (if you have sales team distributed globally). Just don’t make the contest so complicated that your reps can’t understand it.

Who else besides quota-carrying sales reps should be eligible?

  • CRO/Head of Sales always attends. They’re the host of the event so even if the organization doesn’t achieve overall company goals, the Head of Sales needs to be there. If you have leaders that oversee an entire region (EMEA), it is also common to see them attend if members of their team are also attending.
  • Sales Leaders are typically included based on their team achieving 100% of plan. For player-coaches, it’s possible to include a personal performance requirement in addition to the team performance.
  • BDRs/SDRs/Sales Engineers, Sales Ops. Some companies exclude these support functions in an effort to keep the award exclusively to quota-carrying reps. Personally, I’ve always liked the idea of rewarding a small percentage of sales support functions. This type of recognition can have a material impact on the motivation of team members who typically don’t have a high variable component to their pay. However, given the roles these individuals have, they shouldn’t be eligible to have 20% of the organization win the award. Typically, this group is limited based on overall sales performance with a varying percentage of individuals being eligible based on how the organization performed; for example, if the organization hit 100% of its sales target, 5% of support personnel could be eligible with that number scaling to a higher percentage as the performance of the sales org increases. The selection is done by the head of sales with input from the team leaders and alignment from finance on budgeting.
  • Non-Sales Functions. In most companies, the President’s Club is a sales award only, and other groups are not eligible to participate. However, some companies may elect to allow a small number of non-sales people (customer success, product development, services, and marketing) to win the award as a motivational tool; in these cases, the number of non-sales people should be significantly smaller than the sales attendees. Remember, this contest is designed to motivate front-line sales reps and reward them for outperforming. Usually “wild card” non-sales slots are not used until your sales organization scales to a much larger size (e.g. +75).
  • Executives. This depends on the size of the sales organization and the number of individuals attending the President’s Club. The CEO should attend since this sends the signal that sales is important to the company — plus, it gives the sales team access to the CEO. For larger companies where there are 20-30 people attending, it may make sense for other direct reports of the CEO to attend. This further shows the company’s support for the sales organization and having the company’s top executives in attendance sends that message. This is also an opportunity for the executives to hear about what’s on the sales reps’ minds and understand the challenges they’re facing in the market.

So, we’ve figured out who should win and what the criteria is, but what exactly are the awards?

The most typical award is to participate in a group trip — an event where all the winners go together to celebrate their success with their peers and the executive team.  The trips are usually to beach resorts or to interesting tourist destinations in North America (Napa Valley, NYC or Cancun, Mexico) or Europe (London, Paris, Rome). The location of the trip depends on the size of your team, the budget you have and the location of your organization. If you’re just starting out with your first PClub, then we recommend that you keep it local to your region and expand the locations to international over time (as additional motivation as your company grows).

What’s included in the trip?

Most award trips are all-expenses paid for both the winner and their significant other. This includes coach airfare, standard hotel rooms, dinners and activities. If an individual wants to upgrade their airplane seats or hotel room, they can do this at their own expense.

Are the trips taxable?

Yes, award trips are taxable (even if you have a few hours of training included) and are not considered business trips. In the U.S., the attendees are responsible for the taxes on the trip amount. This is fairly common, although some companies may choose to gross up the paycheck of award winners to cover these taxes.

We’ve never had incentives like this before, what’s the best way to start?

It’s tempting to go straight to the amazing destinations and hope for the best. However, if you haven’t established a culture of contests, the impact that you get from the trip will be muted. We recommend a multi-year path to build up the hype and drive a culture of competition in your organization. If you’re not sure where to start or if it’s later in the year and you are just kicking this off, we recommend going with an award of some type rather than a trip. There are a few standard award categories that companies use.

  • Travel vouchers: These are simple and easy, but they don’t establish a way to show off to the winners’ peer group that they’re one of a select group of winners. If you go down this route, we’d suggest that you create an internal page for winners to share some photos from their award trip.
  • Cars: Some companies award one-year leases for high-end cars. The challenge with this is the insurance requirement — does the company cover or does the employee? Additionally, what do you do if the employee leaves the company before the lease is up? Our experience with these types of awards is that they’re difficult to administer and therefore we don’t recommend them.
  • Watches: Rolex or similar high-end watches are good contest prizes.  Not only are they motivating, but they can be worn as a badge of success for years to come. Personalize the watch by having the company logo engraved on the back.

Once you’ve started to build the culture of competition, then you can up the game by doing a moderate trip, and then bump it up again the following year with a trip to a more unique destination.

One thing to keep in mind is that your awards, destinations, and events should all take into consideration the diverse nature of your sales team members and the culture of your business.

At what stage should we do President’s Club?

As mentioned above, President’s Club awards can be given at any stage of a company’s development.  However, trips should probably not be considered until you have 30 or more sales reps. The reason for this is that if you only have 10 sales reps and only 20% can win the trip, you’ll have the executive team hanging out with only 2 reps.  We’d recommend that until you scale to 30 reps, you stick to vouchers, cash awards, or watches.

When and how do we announce this incentive?

To get the maximum value from the contest, we suggest a staged approach to the announcement.

At the sales kickoff, announce that this year, the contest prize will be a President’s Club trip with the location to be announced in Q2. Get the hype going at kickoff but keep the location a secret. In Q2, send out an email or print announcement to each sales rep’s home announcing the contest location. This gives maximum impact on the announcement and ups the excitement level. In Q3 you should be ready to email a video of the venue to further motivate the organization. Q3 is also when you should start a regular cadence of tracking and announcing the standings of those people who are eligible for incentive. In Q4, send out monthly notices counting down to the end of the year. And, shortly after year-end, send out the announcement of who won the award.

What kind of budget should I have for this type of event?

Watches, car leases, and travel vouchers offer the opportunity to spend $8-10,000 per winner. Trips will vary based on destination and the types of activities included, but a good rule of thumb is $15,000 per couple.

This is a significant expense. Sales operations should manage the structure, the program, and report on the results. We recommend you hire an event planner to manage the booking of the trip, flights, hotels, and activities, including a final dinner. Depending on the size of your team, you could manage this internally with Ops and the support of marketing, and an administrative assistant.

 

Done effectively, President’s Club trips and similar incentives can energize an organization and drive significant outperformance. They can also help retain and motivate top talent. So, while you’re thinking about your plans for the new year, give some thought to where you’d like to celebrate your success and start planning for President’s Club.

Six Best Practices for Your First 90 Days as a Data Leader

For newly hired data leaders, the first 90 days are crucial. For existing data leaders, it’s prudent to take a step back at least once a year, think about the business with fresh eyes and ask: What would a new data leader try to address in the next 90 days?

Regardless of title, CxOs of young and established organizations realize their ability to make excellent data-driven decisions is a must to achieve the company’s business goals. In the current resource-stretched climate, the CTO, CIO, or CxO often wears the data leader’s hat. This is especially the case at early-stage companies too small to have this position. But while the role of the data leader is still often shared, a data leader’s acumen and approach for data-driven decisions can be adopted by many leaders to have a significant impact on revenue and growth.


Key Insights

Every enterprise and business case is unique, but today’s data leaders have established a set of best practices to chart the digital pathway to profitability:

  1. Unify data and AI strategies
  2. Cultivate an open data culture
  3. Solve customer problems
  4. Capitalize on early opportunities
  5. Align stakeholders on priorities
  6. Inspire the team

Unify Data and AI Strategies

Young organizations often struggle to create meaningful data strategies. The key is to recognize where emerging trends and company needs intersect, and then create a roadmap to fulfill short- and long-term needs with technology that provides a competitive advantage. The data leader is aware of the importance of aligning data and AI strategies to better serve the organization’s overall mission.

A 2022 survey revealed that over half of the data executives surveyed expect AI to become “critical” to multiple facets of their business by 2025. While most companies expect to adopt AI technologies, many data leaders are looking even further ahead to more advanced forms of artificial intelligence. Techniques such as generative AI — capable of creating rather than simply predicting — has a fast-growing number of use cases.

 

Read more: 8 Tech Investors Share Predictions for 2023

 

A sophisticated AI model requires a modern data stack. Companies that can invest in their data infrastructure will be able to more successfully capitalize on emerging AI techniques. A full-stack approach to ETL (extracting, transforming and loading) data, creating data lakes and lakehouses and de-siloing data architectures can give companies a real competitive edge.

Similarly, powerful AI needs DevOps and MLOps tooling to support it. As the role of AI grows within an organization, data leaders will need a more robust foundational toolset if they want to identify which features of their data provide signal (a process known as feature engineering). This also holds true if they want to improve model training, deployment, and monitoring. Additionally, not all MLOps stacks are created equal — AI working with unstructured data requires different pipelines than those working with structured data. The same distinctions exist for generative versus predictive AI.

Today’s data leaders are seeing these AI trends play out in real-time and are adapting their enterprises to take advantage of what AI can offer for data-driven decisions and strategies. This is important not only to promote growth and accelerate innovation but to build resilience during periods of austerity. With the global economy in a period of stagflation (stagnation and inflation), the ability of business leaders to extract value from data could be a deciding factor in how well a company weathers the storm.

Cultivate an Open Data Culture

How a strategy is defined is up to leadership, but how well it is executed is often a function of company culture. Executives are reshaping their organizations to become more data-oriented, but the vast majority still point to culture as the greatest challenge in becoming a data-driven organization.

Successful data leaders hit the ground to build a data-driven culture by identifying stakeholder needs and responding to them with data-driven decisions. Bear in mind that the ultimate stakeholder is the customer. Organizations invest heavily in research to identify who their customers are, what their needs are, and how they differ by region and culture. Expanding these data sources and creating channels where data can be translated into actionable insights is a fundamental part of a data-driven culture.

The organization itself has hurdles to overcome: diversification of customer base, changing business priorities, and infrastructure and scalability concerns. External regulators demand certifications and scrutiny to ensure compliance with standards.

To succeed amid this tangled web of expectations, data leaders have established a practice of identifying objectives that are mission-critical to meet — those actions or failures that could cause a loss of stakeholder confidence.

Solve Customer Problems

Without data, there is no visibility in customer buying patterns, adoption, and behavior. For SaaS companies in particular, identifying a common enterprise data model is foundational to learning about their customers and fulfilling core business responsibilities. This is especially critical in the wake of multiple mergers and acquisitions, when customers may have to deal with multiple quotes, orders, contracts, and invoice formats that don’t match.

At the heart of all data is customer identity data, and your process for customer identity conflict resolution will be key. Unified data models allow businesses to integrate multiple data streams into enterprise resource planning pipelines. How to create and interpret information gleaned from data models might be beyond the technical capabilities of the data leader. However, data gleaned from the data model can provide an easily accessible wealth of information about how well the organization as a whole is able to fulfill customer needs.

Read more: 7 Habits of Effective Data Leaders

Merging these data streams provides much better visibility into customer buying behavior. This includes better insights on lead generation, sales conversions, annual recurring revenue (ARR), customer acquisition cost (CAC), net revenue retention (NRR), and more. More insights allow for better decision-making in every department of the organization. As with software quality and usability for an engineering department, this is a case of operational details determining strategic success. For companies growing through mergers and acquisitions, this is especially important.

Capitalize on Early Opportunities

Understanding where the business’s data organization performs against key performance indicators (KPIs) is an important part of a data leader’s job. Data leaders use a series of self-assessments to understand the strengths and weaknesses of their organization’s data strategy and capabilities. To really deliver value, however, executives often chart a series of phases for their data strategy — the so-called “Crawl, Walk, Run” progression.

As with any “baby steps first” approach, the essential “crawling” phase sees the development of the initial capability by building out the data stack and analysis pipeline. Once a process is in place, leaders can advance to the “walking phase” — fixing the parts of the process that are present but broken. The good news is the switch from walking to running is the easiest, as process fixes eventually become process optimizations.

It’s also important that this process is iterative. At some point, a process can no longer be optimized. In strong data-driven organizations, there is a point at which the team will look for more advanced technology to build, introducing more capabilities than previous optimizations could accomplish. This is also where the data leader’s leadership in building a data-centric culture, their attention to instituting policies for governance and security, and their investment in technologies such as generative AI and MLOps pay off.

This step is important for new data leaders. The average tenure of a data leader is 30 months, significantly shorter than for other executives. Data leader turnover, driven by a gap between expectations and results, often happens because leaders do not seize these early opportunities. This applies equally to data leaders hired to build data departments, and to those hired to make structural architectural changes (especially after a big data breach). Data leaders that fail to deliver demonstrable improvements — both in the department’s operations and overall business impact — struggle to make it past the two-and-a-half-year mark.

Align Stakeholders on Priorities

Balancing a host of competing priorities — investing in emerging tech, building culture, and process optimization — is difficult. Today’s data leaders have adapted by creating a prioritization framework along two axes:

  1. Importance to the business
  2. Difficulty of implementation

Understandably, data leaders often pursue the low-hanging fruit first, consisting of high-priority and low-difficulty items. Although those characteristics seem mutually exclusive, there are changes data leaders can make to secure easy wins. Achieving success for these items can be as simple as instituting transparency policies to keep the board updated on data-driven processes, such as the company’s data privacy and security efforts.

In 2021, less than half of surveyed corporate boards received reports about cybersecurity risks. Another survey revealed progress continued to be slow — only 37% of surveyed board members felt confident that their company was secure. Providing transparency and clear reporting can be on the lower end of the required-effort scale, while it boosts the board’s confidence in the company’s data initiatives and security posture.

Data leaders can use clear reporting to secure buy-in from board members and other stakeholders, demonstrating that their leadership and priorities are leading the company to a better place. Creating this continuous feedback loop helps keep board members, other executives, vice presidents, directors, and even customers, on the same page. It also smooths the way for future initiatives.

Inspire the Team

Finally, every data leader is a team leader. Inspiring the data team to reach new heights provides a force multiplier for growth. Storytelling using data and visuals can serve as a way to lead by example to inspire the team, ultimately changing the company’s trajectory from being a follower to becoming a leader — even a disruptor — in an industry segment.

Investing in technologies like generative AI not only unlocks new capabilities for the company but also provides opportunities for employee growth. It creates better data scientists and engineers.

It also ensures that, as the company grows from early-stage to ScaleUp, the data department remains competitive from a talent standpoint. Data leaders today are capitalizing on the investment in new trends to attract diverse and capable data professionals.

Taking charge of an existing data department — or taking on the role of building one — is a daunting challenge. But data leaders are tackling that challenge with careful prioritization, an eye on the technological horizon, and attention to the intersection of customer problems and business opportunities. They identify low-hanging fruit and communicate their early successes. Make that your plan for your first 90 days, and you’ll be off to what everyone can see is a great start.

How to Plan a Virtual SKO that Educates, Motivates, and Entertains

November and December are always frantic times for sales leaders, as they are focused on closing out the current year while simultaneously preparing for the upcoming year. There are a hundred things to consider, from redesigning compensation plans to setting quotas, and capacity planning. And then there is the daunting challenge of hosting the sales kickoff (SKO). Each year, sales leaders develop multi-day, in-person events to train and update their sales teams on new techniques, processes, and tools, celebrate the successes of the past year, and energize the team for the year to come. With increasingly distributed teams, lingering concerns about the pandemic, and constrained budgets, more teams may be considering hosting sales kickoffs virtually.


Key Insights

  • With increasingly distributed teams, lingering pandemic concerns, and tighter budgets, teams are considering hosting virtual team events, including sales kickoffs (SKOs).
  • Planning a virtual SKO requires different planning and presentation than simply hosting your normal SKO over video conferencing.
  • Virtual SKOs can offer unexpected benefits from physical events, including opening the SKO to the entire company and offering guest speakers who may have previously been out of budget.

Making a sales kickoff virtual isn’t just doing last year’s event over video; it’s fundamentally different in both planning and presentation. And if you plan ahead and follow these tips, it can be even better than those in-person events. One of the biggest opportunities is the ability to extend the SKO into a full company kick-off. For a minimal additional cost and effort, everyone in the firm can hear the vision of the CEO and sales leaders, get insight into the sales strategy, and most importantly, understand precisely their role in helping sales achieve its goals. Another key benefit of the virtual event is the flexibility it offers when booking guest speakers: By avoiding the logistics of flying guest speakers to events, you can engage someone from anywhere in the world, or even engage someone previously outside of your budget range.

Virtual SKOs require a different approach than in-person events

To help you plan a successful virtual sales kickoff, here are 5 key considerations and a few useful tips from our portfolio and from Jacco van der Kooij, Managing Director of Winning by Design.

Drive impactful engagement

It’s easy to multitask during a virtual event, so you have to create something that is compelling and holds the audience’s attention.

  • Hype it up by leveraging short-burst videos to create breaks in the presentations and mix in music to change the mood.
  • Keep the sessions short and succinct — approximately 45 minutes.
  • Spread the sessions over a few days with no more than a 4-hour session block, rather than holding an 8-hour-long marathon event.
  • Leverage music, video, and interactive presentation tools to shake things up.

Plan and practice

We’ve all had those moments where the video platform doesn’t work right, or a presenter forgets that they’re on mute. In a normal meeting, it’s mildly annoying; in an SKO with 100+ people on the call, it’s disastrous.

  • Double the amount of time needed to create the event.
  • Test your technology with each speaker, and always have a backup plan.
  • Practice the transitions to create smooth and natural handoffs.
  • Record sessions in advance, and stick to the timing.
  • Have one dedicated moderator and one dedicated tech support person.

Teach them something new

This is true even in physical events, and in a virtual one, you can’t keep your audience captive.

  • Use breakout rooms to engage smaller groups.
  • Assign pre-work for attendees.
  • Train the trainers in advance. Make certain that they can drive impactful sessions.
  • Ask your reps in advance for feedback on what they want to hear or learn about. Also, at the end of a segment, ask one member of the audience to summarize their key takeaways. Then have them select the next person to do the same.

Let them catch up with their peers

One of the best parts of SKOs is being able to share best practices and war stories with peers. Make your virtual event memorable by giving them this capability when they weren’t expecting it.

  • Plan specific times for catch-up sessions.
  • Create coffee chats or happy hours with random assignments of attendees to breakout rooms.
  • Create “wedding table” assignments for breakout rooms to ensure teams socialize.

Keep it going after the event

Because a virtual event costs a fraction of a physical event, you can hold follow-on events throughout the year.

  • Create a reinforcement program to drive home key learnings from the SKO.
  • Host a mid-year event. Things change rapidly; a mid-year meeting allows you to course-correct.
  • Use Slack channels or Teams chats to collect ideas live during the sessions and to communicate with the attendees throughout the year.

The shift from physical events to virtual may seem daunting, but if you keep the above considerations in mind, you will create a game-changing event. Take advantage of technology and the reduced cost to expand the reach of your event and energize the whole organization, not just sales. But most importantly, remember that during your event, you should always aim to educate, motivate, and entertain.

10 Steps to Crush Your Sales Kickoff (SKO) Event

If you are a sales leader, you likely spent the last few weeks scrambling to close deals before the year end. As a result, you’re probably starting January by finalizing your compensation plans and quotas and planning two of your most important events of the year: the Sales Kickoff (SKO) and President’s Club.


Key Insights

  • Sales Kickoffs (SKOs) and President’s Clubs are two of the most important events of the year for revenue teams.
  • SKOs should energize the organization, inform and excite everyone about the company’s strategy for the year, and get the whole sales team heading in the same direction.
  • The most successful SKOs are well-prepared, align around key themes and messaging, celebrate the previous year’s success, and are delivered in an engaging, interactive format.

Designed well, these two events should excite the sales team for the year ahead. They help you set and sell a strategy that inspires everyone to roll up their sleeves (again), and also celebrate the team’s accomplishments from the previous year. If you put in the effort and attention to detail, you’ll put yourself in the driver’s seat as you scale up your business.

How to design a successful sales kickoff

SKOs may have a bad reputation amongst sales reps. This is largely due to a history of poorly planned events, filled with boring presentations, delivered to hundreds of people simultaneously with minimal interaction. Nobody wants to sit through that. To top it all off, these events are costly, and reps are out of the field for 2-3 days, meaning that there isn’t any revenue being generated.

Executed well, SKOs should energize the organization, inform and excite everyone about the company’s strategy for the year, and get the whole sales team heading in the same direction. If you adhere to the following criteria, you’ll deliver a sales kickoff that will align your team and make them productive this year and beyond.

  1. Have a well-defined strategy for the year. This is your chance to explain the strategy to the entire sales organization and rally them around a common aspiration. Make sure that the message is clear and that all the presentations delivered during SKO align with that strategy. Ensure your reps know their role in executing the strategy by giving them clear marching orders, as well as collateral that supports their key talking points with prospects and customers.
  2. Make the content interactive. Back-to-back presentations are boring for anyone, so refrain from a parade of presenters and instead create a series of workshops or rotational sessions. The best kickoffs combine amazing presenters (who present for 60 minutes in the main room) with round-robin sessions and workshops for 30-45 minutes. The best workshops impact how the sales team engages their prospects and clients and/or leverage and explain the tools and techniques that help them to do their jobs. The movement and change in pace will keep the sales reps’ attention, and the interactivity helps ensure that all reps are participating. If there are new products or features being launched, this is the opportunity to ensure that everyone is aligned on the messaging and sales pitch. Marketing, product, and tech leaders, along with the CEO, should describe their strategies and how their activities will support the sales team.
  3. Celebrate successes from the past year. SKOs provide the opportunity to have a formal look back on the previous year (what worked, what didn’t) and applaud your superstars. Take some time to talk through what happened — both good and bad — and then highlight anyone who achieved plan or showed exceptional effort to help another rep or the overall team. Small award plaques are a great way to present top performers with something that acknowledges the value they have contributed to the company. Bring them up on stage while their peers applaud them, have someone read a sentence of why they’re being recognized (e.g. Sally Jones achieved 145% of plan and $750k in sales), and take a picture with the CRO and CEO. By proactively building a culture of success and recognition in your business you will make your team excited and proud to be recognized in front of their peers.
  4. Leverage themes and imagery. We’ve all sat through dozens of kickoffs where we are going to “Race for 202X” or “Ignite Sales 202X” or something similar. Those themes sound corny and can fall flat if they’re not woven throughout the entire meeting. Likewise, these types of themes can have a major impact if they’re integrated into all communications, internal branding, and contests for the remainder of the year. That theme should show up in your contests (i.e., Q1 – Start your Engines, Q4 – the Final Lap). Pick a theme, stick with it, and make sure it’s different from themes used in the last two years.  Work with marketing to be creative. Sales themes can become tired and overused.
  5. Be prepared for the meeting. If possible, you should communicate sales territories, compensation plans, and quotas in advance of the SKO. Clarity in segmentation, compensation, and territories will help to ensure your sales teams apply the material presented to their specific situation. Plans don’t have to be 100% complete, but the closer to final you can be, the better the outcome of your kickoff. If the sales reps go into the sales meeting blind, the best they’ll be able to do is apply it to last year’s activities. More likely, they’ll just listen without being able to truly connect the material with the activities expected of them. This is one reason that SKOs are often in late January or early February. The timing enables management to finalize strategy and plans before presenting to the team.
  6. Get new hires off to a great start. If you’re going to hire new sales reps, try make sure that they’re onboarded in time to join the kickoff sessions. There is no better way to indoctrinate them into your team’s culture than by surrounding them with their teammates and sharing stories. One of the best parts about an SKO is the networking that your teams can do, especially if you have a global team. Having your new hires meet the top reps from each region will help accelerate their onboarding process. For those that join after the kickoff, you can repurpose some of the material for your onboarding training.
  7. Keep logistics simple. Pick a location that is near (the majority of) your team or easy to get to. You don’t want to have people waste an entire day getting to the location or getting home. Also, plan dinners at the hotel or nearby restaurants. This ensures that you can continue to build a solid networking experience for your sales teams and that they don’t waste too much time going to a new location after sitting in sessions all day. Finally, don’t forget to provide enough time for breaks. Your teams will still need to engage with customers, so give them sufficient time to catch up on emails and calls in between sessions.
  8. Stick to a reasonable budget. Because you’re celebrating success and kicking off the new year, you want a venue and event that reflects the company. We’re not suggesting that you host your kickoff at the Ritz Carlton, but make sure that the venue is designed for corporate events, and then invest in the key items that will make the event memorable. Make certain that you have audiovisual (AV) support, lapel microphones, large projector screens, and the ability to play music over the AV (which is essential to fill the time as presenters walk to the stage). Invest in a few small gifts for attendees (notebooks with the company logo, clothes with the company logo, or similar), a little something for them to take the experience away with them. These should preferably reflect the theme for the year (e.g., “Racing to Win”). Expect to spend around $2,000 per attendee for a professional event. This spending guidance varies based on the location, duration of the event, distance traveled, etc.
  9. Require attendance. 100% of your reps should be there to hear the company’s strategy and to network with their peers. If you’ve announced a save-the-date well in advance, you should require 100% attendance; sales reps should be expected to modify customer meetings or other plans if you’ve given enough notice. The best SKOs also have 100% attendance from the executive team — that’s right, even your CIO and General Counsel should be there — this is the chance to show the sales organization that the entire company is behind them and supports their efforts. Given the investment in the SKO, you should maximize the ROI through full attendance.
  10. Assign an owner and rehearse. Successful SKOs are successful because someone has been orchestrating the event and sales leaders are engaged early in planning the agenda and cadence of the content. Someone in your company should be managing the SKO, whether this is sales ops, sales enablement, marketing, or if you have a larger organization, an event manager. This person or team will ensure that presenters practice their speeches, stay on time, and ensure smooth handoff between presenters. Even if you are doing an SKO for the first time and you don’t have a dedicated team working on your SKO, you can still make this work with some basic project planning.

The SKO is your chance to start the year strong and get your team motivated and excited about the new year. Remember, align the team on a single strategy with a few big bets. Celebrate the previous year’s successes, but focus attention on what needs to be done this year. Make your kickoff the jumpstart that your organization needs to ensure this year is your most successful year yet.

2022: Year in Review at Insight

2022 is (nearly) a wrap! Insight Partners concludes 2022 with more than 750 investments over the firm’s history, over $50 billion in all-time commitments, and over 400 M&A transactions to date for the portfolio.

Insight Partners by the numbers 2022

Notable 2022 Milestones

Additionally, in 2022 the firm announced its largest fundraise to date, with $20 billion raised in Fund XII (inclusive of the Fund XII buyout fund). This year’s fund represents one of the largest global fundraises to date dedicated to investing in high-growth technology and software companies driving transformative change in their industries.

2022 also introduced the first ScaleUp event from the firm, drawing over 1,700 registrants and featuring presenting partners Citi and Nasdaq. 2022’s event focused on the future of AI technology. Stay tuned for the announcement of 2023’s ScaleUp event.

Portfolio Company Engagement in 2022

Other 2022 highlights include a focus on portfolio company engagement with some of Insight’s key sectors, including IT infrastructure, cybersecurity, fintech, e-commerce, and DevOps. Especially notable is the engagement with early- and growth-stage companies focusing on scaling up.

number of portfolio companies Insight engaged with in 2022

 

2022 Awards and Recognition

Insight received multiple firm awards* showcasing individual investor and firm achievements, including:

Insight’s Secret to Scaling

Finally, 2022 highlighted the impact of Insight’s Onsite team, a group of 130+ experts in sales, marketing, product, and talent dedicated to helping the Insight portfolio scale up. The Onsite and portfolio experience teams logged countless hours supporting over 450 companies, contributing nearly 800 guides, benchmarks, and handbooks to the exclusive Insight portfolio GO community platform, and hosting 200 digital and in-person events in 2022.

insight onsite impact numbers 2022

 


Read more: Here’s what makes Insight’s portfolio experience different.


 

 

*The awards referenced herein are the opinions of the parties conferring the awards and not of Insight Partners. These parties, which are not affiliated with Insight, issued the awards. For the awards given to individuals, Insight submitted nominations on behalf of certain of its personnel. The parties’ recognitions are not indicative of Insight’s future performance and were not based on evaluations of clients or investors of Insight. There can be no assurance that other parties would reach the same conclusion as the foregoing. Insight paid a fee in connection with its applications for Inc. award consideration, as well as to secure award receipt from GrowthCap after being notified of the selection of certain of its personnel for awards. In general, the receipt of compensation influences, and is likely to present a potential material conflict of interest, relating to any granted award.