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Startup Hiring and Brand Recognition

This article was originally published by Will Reed and does not necessarily reflect the perspective of Insight Partners. Insight Partners is an investor in Will Reed.

Tackling Startup Hiring Without Brand Recognition

Your founding team, your first hires, and your first rounds of funding. These are just a few of the things that can greatly impact the trajectory of your startup. Something else that influences the direction of your startup? Your branding, and brand recognition (or lack thereof).

Brand recognition is a tricky thing. It can be difficult to build from nothing as a new startup and without it, it’s hard to actually build your company. It’s a bit of a vicious cycle, if you will. Namely, a lack of brand recognition can impact things like startup hiring, because it can be an Achilles’ heel for attracting top talent. This matters, because who you hire as a new startup is crucial to scaling your business, and growing it in the direction you really want.

What exactly is brand recognition, and why can it weigh so heavily on startup hiring? Brand recognition is how well consumers (or potential hires) know your brand and can recognize it. It can be triggered by your logo, colors, and even music. For example, when you see the Starbucks logo, you recognize that it’s one of their coffee shops, or if you hear the first few notes of a jingle, and know the brand instantly.

When a brand has strong recognition, it can lean on that recognition during the hiring process to attract top talent. But here’s the thing: as a new startup, your brand likely won’t have any recognition just yet. So it needs to take a specific approach to hiring new team members, in order to compensate.

What Makes Startup Hiring so unique?

While they might seem like similar processes on the surface, startup hiring is quite different than hiring at a more established company. Firstly, because new startups are still growing and who you hire has greater weight – especially in the earliest stages.

Each new hire can heavily influence the culture of your startup. Specifically, each new hire brings something to the table, and what they bring to the table will impact the direction of your company, what it’s like to actually work there, and what work you’re able to accomplish.

What else makes startup hiring so unique? Candidates might view your startup as somewhat risky, especially when compared to a traditional, more established company. The startup landscape can feel uncertain, and for new hires, choosing a startup over a well-established company can feel like they’re taking a chance.

And it’s not just a feeling: research tells us that about 90% of startups fail, with 10% failing in the first year. In order to attract top talent, startups have to showcase their stability and potential for longevity, so candidates feel secure choosing them.

Budgets for salaries also tend to be different at startups, and compensation can include plenty of interesting options in addition to their pay. Startups typically pay their employees at least a little bit less than a top-dog competitor company would be able to, but they can include different attractive benefits, along with equity and stock options in their compensation package.

Lastly, another element that makes startup hiring unique is the fact that you don’t have a brand to lean on. As we touched on earlier, brand recognition can be crucial to the hiring process. Research reveals that candidates are 40% more likely to apply for jobs at a company where they recognize the brand, when compared to a brand they haven’t heard of. And on the employer side of things, 80% of hiring managers believe that employer branding significantly impacts hiring great talent.

When potential new hires are looking for new employers, a company name that has brand recognition might seem like a more attractive candidate. Startups need to overcome this branding obstacle in order to compete with known brands to top-tier talent.

What Do We Mean By “Employer Brand”?

What exactly does the term “employer brand” refer to, and what does it include? You might have a general idea of what employer brand means, but let’s get super specific. Employer brand refers to the look, feel, and messaging of your company.

It includes stylistic choices (what colors are used in logos, and what fonts on the website), culture choices (what values your company prioritizes and how they’re demonstrated), and messaging choices (slogans and phrases).

Ultimately, your branding should match your startup’s personality, mission, and goals. For example, a more serious company should most likely have a more serious website and direct messaging, not something with bright colors, a cursive font, and playful words.

All in all, employer branding is felt by both your employees and your customers, and it needs to be cohesive and complete, in order for recognition to start building around it. That brand recognition is crucial from a customer’s perspective, but also when it comes to startup hiring.

Why is an Employer Brand More Important Today Than Ever Before?

An employer brand has always been crucial, but it might be more important today than ever before. That’s because of the competitive nature of the startup landscape, combined with the stiff competition from well-established companies for top talent. It’s important to remember that one of the main reasons that startups fail is because they get beat by their competition. But a startup with an incredibly strong employee brand can pull in more top-talent candidates, and can therefore have a stronger team than their competitors.

Employee branding doesn’t only help with startup hiring: it also helps with talent retention. One LinkedIn report revealed that employee turnover can be reduced by 28% by investing in employer branding. Once a startup hires a great candidate, strong branding can help that new hire feel like they made the right choice, and that they’re working at a powerful company that’s on an excellent trajectory.

If employer branding is all over the place, a new hire might feel like the company itself is uncertain, and they might be tempted to leave and head to a competitor that feels more defined and stable.

There’s a third big reason why employer branding is more important today than ever before: and that’s the era we’re in when it comes to digital tools and hiring technologies. When candidates are looking for positions, they’re comparing vacancies online against each other, leaning on a company’s branding and digital footprint to do so.

Who would choose a company with a question mark for a logo, over a company with excellent brand presence? If you’ve looked at different online vacancies yourself, you know just how varied employer brands can be.

Lastly, an employer brand means much more than the colors and logos you choose, and it really comes down to representing the culture at your organization. An employer’s branding needs to match and represent its culture in order to attract talent that’s in alignment. In some ways, an employer brand says more than the words that are used, and really conveys the true messaging and culture of your startup to your audience.

How Do You Put Culture Into Words?

What exactly is culture when we’re talking about a startup? It’s the culmination of formal and informal actions and expectations, and reflects what it’s like to be part of your company, and to work with it. It can include a startup’s values, beliefs, practices, policies, and goals. It also influences how employees execute their jobs and how they work with customers and each other.

Culture is not just created by one aspect of your company, and instead, is the sum of its collective behaviors, actions, and beliefs.

When we’re talking about employees, culture becomes a crucial factor in who a startup hires, and if an employee will be a good fit at a startup. If you have several equally-matched candidates as far as skills go, the deciding factor is cultural alignment.

How Do You Use Those Words to Attract Talent?

The bottom line is that a company’s culture drives how it acts, and who it attracts. And because culture is a culmination of tangible and intangible aspects of an organization, employer branding plays a big role in it. As we mentioned before, a company that has a serious mission will likely use branding to match, so candidates who are in alignment with this brand can apply.

In short: culture, words, phrases, designs, and missions of employer branding will determine which types of candidates apply for vacancies, which is why employer branding is so critical for the startup hiring process.

4 Ways to Build a Proper Employee Brand for Your Startup

With all of that in mind, here are four ways to build a proper employer brand for your startup.

1. Define you goals and values.

In order to create an excellent employer brand, it’s important that there is a clear understanding of your company’s goals and values. It’s not enough to understand what your main product is, or what service you want to provide for your customers. What values does your organization want to complete its work with? What are your long-term visions and goals? How can you define these objectives in ways that can be shared and understood organization-wide?

2. Identify your company culture.

Company culture impacts your employer brand, and your employer brand needs to represent your company culture. In order to define your company culture, you can determine what your company’s attitudes and beliefs are, and create policies around them. You can come up with words, phrases, or ideas that define your company’s culture, and institute policies that embody them.

3. Come up with an EVP.

An EVP, or employer value proposition, are the benefits and perks a company provides to its employees in exchange for their skills and talents. It’s how startups (and other companies) attract highly-skilled candidates, and stand out from their competition.

An employer value proposition is where you get to deliver on the promises and ideals that are shared in your branding and company culture. For example, if your brand is supportive of families, it might offer extended paid maternity and paternity leave, as well as access to reproductive services. The purpose of an EVP is to have a positive influence on candidates, and to answer the candidate’s question of “What’s in it for me?”

4. Establish branding guidelines.

In order for a brand to gain recognition, it needs to be consistent, obvious, and uniform. There can’t be a different version of your logo on Twitter and on your website. Even slight differences should be unacceptable. In order to ensure branding is used properly and consistently, leadership should create brand guidelines, which outline every aspect of your brand. This can include look and feel (colorways and logo usage), along with messaging, phrasing, and even guidance on actions and communications.

Can You Build a Startup Without Brand Recognition?

While it’s absolutely possible to build a startup team without brand recognition, it can be a little bit trickier than if you have a weighty brand to lean on. Here are some tips you can keep in mind when building a startup without brand recognition.

1. Solidify your employer brand.

A strong employer brand is important for attracting top talent, and even though you might not have the brand recognition just yet, you’ll need to create a brand that is designed to be recognized. When potential candidates check out your company, they should understand your company through your branding, and should feel as though it’s professional and in alignment with its purported values. Ideally, one day your brand will have recognition, so you should act like it does from Day 1.

2. Serve your customers (and excel at it).

When it comes to building a startup without brand recognition, guerilla marketing can be your friend. And who is a bigger proponent of your brand than happy customers? Happy customers are likely to brag about your services to a friend or peer in their field, and word-of-mouth recommendations can be a powerful asset for building your brand.

3. Create an online presence.

We all know the saying “Fake it ‘till you make it,” and this can be said for brand recognition. You should have an online presence that oozes your brand, so when prospective candidates Google you, they see your company all over the place. You can create social media accounts that share updates about your company, have a main website that’s user-friendly, and send out a monthly email, for example.

Steps like these can help your startup build the foundation of brand recognition. You might think that having an online presence isn’t all-too-important, but surveys reveal that 79% of candidates use social media in their job search.

4. Have different channels of communication. 

When a brand has recognition, people seek out jobs with that company (even vying for positions) and habitually check their hiring pages for vacancies. Without brand recognition, startups need to maximize their communication channels, in order to reach their target audiences. Your own website and social media channels are great places to start, but you can also branch off into guest posts and different online communities.

5. Be intentional with your hires.

As we mentioned previously, who you bring on board your startup really matters, especially in the earliest stages of your company. These new hires will influence your company trajectory and culture, and will impact how other new hires feel about your organization. Make sure you’re choosing team members who are aligned with your brand and mission, and who ultimately help to further it.

6. Bring on a Head of Talent.

When you’re trying to build out your team, you should eventually aim to have a designated expert on your team, who is focused on recruiting, such as a Head of Talent. Hiring someone to build your team might seem like a big investment, but remember, this is a designated team member who is completely focused on bringing on additional talent through recruitment.

They can build a recruiting network, work with other talent professionals, and identify potential candidates who are an excellent fit for your company and match your startup’s culture.

7. Tap into startup hiring resources

There are plenty of startup hiring resources that can help you source, recruit, and attract top-tier candidates. These include recruiting resources, which might help you set up hiring infrastructure, have deep talent networks to tap into, and know how to focus on company culture. You can also utilize job fairs, hiring platforms, and alumni networks at universities.

How to Use Your Employer Brand in the Hiring Process

Your employer brand can be a powerful tool for many things, such as attracting customers and securing funding. It can also be valuable in your hiring process in many different ways. Firstly, you can lean into your employer brand when writing job descriptions to make sure you’re attracting candidates who are in alignment with your vision and goals. You can also use employer branding to direct what qualifications you’re looking for and what skills you’d like candidates to bring to the table (hard skills and soft skills).

Startups that are hiring should aim to strengthen their employee branding to the point that it helps them compete against larger, more established companies for talent. By communicating your brand’s vision, goals, and methodologies, you can show talent exactly why they should want to work at your organization.

12 Must-Ask Questions When Hiring A CMO

This article was originally published by Will Reed and does not necessarily reflect the perspective of Insight Partners. Insight Partners is an investor in Will Reed.

Most early-stage founders know exactly what it means to be a jack-of-all-trades, because you typically need a wide range of skills not only to conceptualize and create your business, but to run it from day one. But as most founders quickly realize, just because you can do something doesn’t mean you should. Take your company’s marketing, for example.

Just because a founder is skillful in social media marketing doesn’t mean they should be the one to manage the Instagram account. With that in mind, there’s probably going to be a point in a founder’s early-stage startup’s journey that they need to bring on a Chief Marketing Officer (CMO).

Why are CMOs so crucial to an early-stage startup’s success? CMOs take ownership of a business’ marketing plan, but they do far more than just that. CMOs look for ways to drive revenue using powerful marketing and advertising strategies, they oversee all of the marketing employees, and they meet with other executives to ensure the marketing department is delivering on business-wide goals.

Marketing is a vital part of any business, but especially for early-stage startups, which need to make sure they’re not in the 20% of startups that fail within the first year. CMOs take on these crucial responsibilities, and execute them with C-suite precision. If you’re thinking about hiring a CMO, here’s everything you need to know, plus key questions you should ask candidates during the hiring process.

When Is it Time to Hire a CMO?

When you’re assembling your team of leaders at your growing early-stage startup, it can be tricky to decide when exactly to hire for certain positions, especially for leadership and C-suite positions. So, how exactly can you decide on the right time to hire a CMO? Here are a few things you can consider.

Firstly, founders should take into account the current size of their marketing team. If there are only one or two marketing professionals on board (and the plan is to keep it that way for the next year or two) then it might not be time to look for a CMO just yet. But if a marketing department is more substantial, this might mean that having a CMO can benefit a company and its marketing team.

Next, founders can consider why they want to bring on a CMO. Some individual reasons (such as more leads or revenue) might not necessarily warrant a full-fledged CMO. But if a startup has comprehensive, complex needs that require a full-time executive to oversee, then this might be an indicator that a CMO will be beneficial.

Lastly, founders can look at the resources they’re putting into marketing, and that they would like to in the near future. In general, research shows that marketing budgets and spending are on the rise, with spending growing at its highest rate in over a decade. If a startup has a substantial marketing budget, a CMO just might be the right person to manage and direct it.

12 Must-Ask Questions

After deciding that now is indeed the right time to bring on a CMO, early-stage founders then need to execute the hiring process. This involves sourcing candidates, conducting interviews, and ultimately selecting your new hire. Whether a founder chooses to find their own candidates or use executive recruiting services, they still need to ultimately conduct interviews.

From a founder’s standpoint, nailing the interviewing process is critical. Interviews don’t only reveal key details about your candidates. They ultimately reveal if they match your company’s culture, and if they’ll be an excellent fit with your startup in the long run.

Research reveals that almost half of job seekers have turned down jobs because of negative experiences during the hiring process. In order to avoid this and other hiring mistakes during the process of bringing a CMO on board, here are 12 must-ask questions to ensure you bring on the perfect candidate.

How Do You Ensure Strategy Becomes Action?

It’s one thing to have big ideas, but it’s another to be able to actually execute them. Founders should ask this question (or something similar) to see how their candidates plan to actually execute their vision. Components of a good answer might include confirming alignment with business needs, setting goals and timelines, distributing responsibilities, and measuring results with metrics and data.

Pitch Our Company

Sometimes called an “elevator pitch,” this question is tried-and-true for good reasons. This prompt gets candidates to pitch themselves to you on the spot. Not only can you potentially learn a lot about a candidate (such as their skills, background, unique qualities, and why they should hire you) you can also see if they’re able to be persuasive and memorable, which would come in handy if they were to take on the role of CMO.

What’s Always On Your Marketing Dashboard?

CMOs should be data-driven, and should be able to really define what success means for them when it comes to marketing. Asking what’s on their marketing dashboard can reveal what key metrics they value the most, and why. This can help you understand how this potential CMO can use data to drive real results.

How Do You Uniquely Approach Branding?

Branding is a key responsibility of a CMO, and every person is going to bring their own unique flavor and practices to your startup. And while branding matters to your business, it also matters to your customers. For example, it takes visitors to your website just 0.05 seconds to decide if they like it or not.

Asking about your candidate’s approach to branding can help founders gauge their candidate’s perspective on branding, in order to ensure that it’s in alignment with their own perspective, and their company’s goals.

How Do You Approach Market Research?

Unfortunately, some of the top reasons startups fail is due to a lack of research, or because they’re in the wrong market. With that in mind, it’s important to understand how exactly your candidate plans to tackle this key issue, and to make sure they deeply understand it

What’s Your Communication Style?

Every candidate is going to have their own habits and styles, and it’s important for founders to understand if these styles work with their startup. For example, mismatched communication styles between a new hire and the business can lead to confusion and conflict. Questions like this can reveal if a candidate is truly a good fit for a startup.

Pitch Us On an Object in This Room

This classic interview question gives your CMO candidate the chance to show their sales skills, along with their communication and persuasion skills. You can also get a glimpse of how well they can understand customer pain points at a moment’s notice, and if your candidate seems prepared to solve them.

If You Could Restart Your Career, What Would You Alter?

This reflective question can give founders insight into what their candidate’s career actually looked like in the past, and how they’ve grown along their journey. While where your candidate is today is more important than what their past looks like, this question can also reveal habits or traits about your candidate that they may not openly share.

For example, if they say they would have stayed at their earlier positions for more time, you might pick up on the fact that they’ve bounced around a lot. This is then a question you can ask, to ensure they want to stay with your company for the long haul.

What’s Something You’ve Learned in the Last Year?

When someone is running at full steam ahead at an advanced point in their career, they might not always be actively learning lessons. Asking this question can open up the floor for your candidate to share something relatively recent that they’ve learned, which can help founders understand if their candidate is an ongoing learner. You can also gauge what unique insights they can bring to your startup as a leader.

How Do You Lead Inbound vs. Outbound Marketing?

During the interview process, one of the biggest goals is to understand your potential CMO’s specialties, styles, and skills. Asking them specific questions like this about their marketing preferences can help you understand if their style matches your own, and if they’re ultimately in alignment with your company’s culture.

What Would Your Third and Fourth Months Look Like Here?

Joining a new company in a C-suite position is a big undertaking, and the first few months can be a dynamic experience of learning, growing, and transitioning. While the first few months will probably mostly consist of onboarding and becoming acquainted with the role, the 3rd and 4th month might be when your new CMO really gets to come into their own in this position.

What Are the Biggest Marketing Challenges Today, and How Are You Overcoming Them?

The marketing landscape is riddled with ever-changing challenges, and startups need a CMO who doesn’t only understand these challenges, but who can navigate them with ease. Asking this question can help you understand how well your candidate understands the challenges they might face, and how they can overcome them.

What’s Your Executive Hiring Strategy?

This article was originally published by Will Reed and does not necessarily reflect the perspective of Insight Partners. Insight Partners is an investor in Will Reed.

There are plenty of things in life that you can tackle with a fly-by-the-seat-of-your-pants approach. Tonight’s dinner recipe, your next first date, and what you’re going to wear to tomorrow’s event might be on the list. What shouldn’t be on the list of things to “just go for” is executive hiring at your startup.

When you’re a startup focused on growing into your dream business, you need to bring on executives who are going to contribute to your dream, align with your vision, and ultimately help your startup flourish. That’s why when you’re looking to bring on executives, you should deploy an executive hiring strategy.

What is an executive hiring strategy?

In order to understand exactly what an executive hiring strategy is, and what yours should look like, we can start with what a typical hiring strategy might look like. Let’s say you’re looking to hire an entry level employee. Your hiring strategy might start with shoring up your branding, posting your vacancy, combing through responses, and starting the interview process. Once you meet a suitable candidate, you’ll likely hire them.

When it comes to executive hiring, this standard hiring strategy likely isn’t going to cut it (we’ll dive into why in just a moment). So instead, you need a strategic and tactful executive hiring strategy, which involves having answers to critical questions, creating an efficient hiring process, knowing how to reach executive candidates, and holding a successful interview process.

Why can’t you just wing it?

Why does executive hiring require a special strategy, and why can’t you actually just wing it and hope for the best? First of all, reaching incredible candidates with executive potential isn’t as easy as you might think, and they’re unlikely to just end up in your inbox from a job posting. One survey by Statista found that 62% of respondents use executive search firms because it gives them access to “difficult to reach” candidates.

That means if you’re just sitting around waiting for your dream executive to appear, you might be waiting for quite a long time.

Also, it turns out that most executives actually want to be recruited. In one study, 97% of senior candidates in a company said they want to be “found” or “approached.”

And while these candidates might want to be approached, it turns out that there might not be an abundance of excellent executive candidates, making them potentially rare to come across. PwC found that 80% of executives think the top threat to their business is a scarcity of skills on the job market. This means that once you do actually find top talent for your executive vacancy, you want to make sure the hiring process goes off without a hitch.

What to prepare before building your strategy

Before you start building your executive hiring strategy, it’s important to create a rock-solid foundation for it. Here are some questions you can ask yourself, before committing to building an executive hiring strategy:

What do we want this new executive to take ownership of in our startup?

It’s not enough to just have a title and job description when hiring an executive. Your startup should have a very clear idea about exactly what teams, people, results, and goals you want this new executive to take full ownership of.

What skills gaps are we looking to fill?

When you’re a growing startup, it’s very likely that you’re working with limited resources, making executive hires even more important. You don’t want to hire an executive, only to find out that you actually need to hire someone else to perform other tasks or job functions. You should see what areas of your company really need the extra support, and be sure to hire for those gaps.

Is our hiring process streamlined?

There’s no room for error in the executive hiring process. Let’s say you have your dream candidate lined up and ready to go, but they’re asking questions about the job you don’t know the answer to, and your company has been slow to respond to them. This is a very dangerous formula for a candidate walking away.

Your hiring process should have all of the kinks sorted out before you start bringing on executives. While an excellent hiring process is important in general when building a team, it’s even more crucial when it comes to executive hiring.

What is our company culture?

Who you bring on as an executive could have a big impact on many aspects of your company, because that executive will have influence, and will leave their mark on your organization. With that in mind, you should have an excellent understanding of your company culture, so that you’re hiring people who align with it, and who help further it.

Five elements of a successful hiring strategy

With all of that in mind, here are the five key elements of a successful executive hiring strategy:

Identify the basics

Before you start the actual hiring process, there are many key questions that should have answers, and basic details that need to be sorted out. Think of it this way: you want to be able to answer every single (reasonable) question an executive candidate throws your way, especially if it’s something you should already know the answer to.

Basic information might include: where the role is located (or if it’s remote/hybrid), who this person will report to (and who will report to them), what their main functions are, and what their main initial goals are.

Create infrastructure

When it comes to attracting and ultimately hiring executive candidates, your hiring infrastructure really makes a difference. That’s why it’s important to ensure that your team is equipped to conduct this scale of interview process.

If you’ve never hired executives before, this might be daunting, since you might not know what to expect. But essentially, you want to ensure that everyone involved in the hiring process has the tools they need to execute it flawlessly. If you choose to work with an executive recruiting firm, they might help you with this process.

Do a walkthrough

Again, before you even speak to candidates, you should ensure that this executive hiring strategy is completely ironed out, from start to finish. Do a “walkthrough” of the process from the perspective of a new candidate, or have others work through this process with you. You might find that new questions come up, or that you discover a hiccup in the system.

Start sourcing candidates

Once you have a thorough understanding of the executive position, and your hiring process is smooth as butter, it’s time to start sourcing candidates. This is the largest, most comprehensive, and potentially the most challenging part of the executive hiring process. Here are ways that you can start sourcing potential candidates:

  • Post vacancy: While we discussed that this option is unlikely to yield results, some startups do choose to simply post their executive position, in case someone fitting does happen to see it. You might choose to do this in addition to other sourcing techniques.
  • Tap into your network: Your own professional network is likely a great place to start looking for executives. Think about people you know from other companies, and connections from your Linkedin network, for example.
  • Tap into your team’s network: Likewise, your team members probably also have great connections, and potential executive candidates. Put out the call for them to reach out to their network, and encourage team members to send great candidates your way.
  • Partner with an executive recruiting provider: Because of the challenges of finding excellent executive candidates, many startups choose to work with executive recruiters. These seasoned search teams typically have tons of expertise finding executives, have vast networks of connections, and can even help ensure you’re able to conduct a best-in-class interview process. They can also help complete the hiring process in a more timely manner than if you approach it on your own.

Conduct interviews

Once you’ve identified incredible candidates, it’s time to start the actual interview process. Interviewing potential executives is typically quite different from interviewing entry-level employees. There will likely be multiple rounds to this interview process, so it’s best to start with a pre-screening interview, where the basics are all ironed out. This information can then be shared with others in your company if need-be.

During the interview process, you should be sure to share far more than just the job details. Share your company culture, goals, ideals, and what you’re definitely not trying to do. Also, look to get similar information from your candidates, to find out if they truly align with your organization. The interview process should be thorough and help you really get to know your candidate on an individual level.

Seal the deal

Once you finally land on the perfect candidate who is more than happy to join your team, it’s time to make it official. This means having contracts ready and signed, and kicking off your onboarding process. With this in mind, you should have an onboarding plan already in place as well as a transition or integration plan in place, so that your new executive is able to get started seamlessly.

Recruiting Executives for Startups: How To Build the Right Team for Your Stage

This article was originally published by Will Reed and does not necessarily reflect the perspective of Insight Partners. Insight Partners is an investor in Will Reed.


When you’re a flourishing new startup, one of your top priorities is hiring your dream team. While who you hire for entry level and junior positions matters, almost nothing is more critical than recruiting executives for your leadership and C-Suite positions. And you can’t just wait for the perfect candidate to waltz in the door (or reach out via email).

Instead, startup leaders need to be proactive about recruiting executives, and doing so in a way that is very different from more established companies.

While there is much uncertainty around leading an early-stage startup, there’s one thing that’s for sure: who you bring on board as your executives makes a big difference, and needs to be approached in a tactful and particular way.

When to start thinking about recruiting executives

To recruit or not to recruit executives, that is the question.

You might be wondering things like:

  • When is the right time for your early-stage startup to think about recruiting executives?
  • Is now too early?
  • Can my company bring in the type of talent I’m looking for at this stage?

It can be a bit of a balancing act to figure out exactly when to start recruiting executives. You also might feel like your brand isn’t strong enough to attract powerhouse candidates.

But keep in mind that recruiting executives is really an investment in your future success. When you bring influential leaders on board in the earliest stages of your company, they can contribute to your company culture and success in a powerful way.

In short: executives can help propel your company to growth.

And while you might be concerned about your brand “attracting” the right executive candidates, that’s where the process of actually recruiting executives comes into play. Even more established companies often go through a recruiting process for executives.

Why is that? It’s often the case that those executives you really want to hire are already employed. They’re not often combing through Linkedin ads, looking for executive openings (although this is sometimes the case). An executive recruiting process is a proactive approach, where you identify potential hires, even if they’re already employed.

With that in mind, it’s almost never too early to think about recruiting executives. But the keyword there is “almost.” Before you do actually start the recruiting process, and begin actually building out your team, there are definitely some things you should have in place, and some early stage hiring tips to keep in mind.

7 things you need before building the team out

If you’re wondering “Are we ready?” when it comes to building out your team, here are some things you should have in place before you start recruiting executives.

1. Company vision

While your company might still be growing and changing, it’s important to have your solidified company vision in place, before you start recruiting executives. This is crucial for a few reasons. Firstly, it’ll help you identify leaders who can actually contribute to that vision, and who have ideas to bring to the table to help further it. This will also ensure that the executives you hire also wholly believe in your vision, and want to help your company achieve it.

Plus, this will help ensure strong internal leadership collaboration and alignment. You don’t want to have an executive or leader come on board trying to shift your company vision, potentially leading to friction.

2. List of roles to fill

Before you start the executive recruiting process, you should know exactly who you’re looking to hire across the board. This helps you identify potential skills gaps, and where your executives are needed most. Especially for early-stage startups with limited funding, making accurate and pointed hires is important when it comes to resources. If you know exactly what roles you have to fill, you can identify precisely what types of leaders you need.

3. Employer branding

While you might feel like your brand isn’t quite strong enough to pull in top-tier executives on its own, there are some things you can do (even as a new startup) that can help make your brand presence as strong as possible. Having your employer branding solidified and widely used is crucial for unified messaging, forward-facing appearance, and internal solidarity. But it’s also important for being an appealing option for potential executives.

Think of it this way: you don’t want to work with a bank that has logos all over the place, a shoddy website, and graphics that look like they were drawn up on MS Paint. Having concrete employer branding helps your business appear legitimate to everyone, including potential executives.

4. Onboarding process

Your onboarding process needs to be solid for every new hire, so that they start off on the right foot, with all of the information they need to succeed at your company. The last thing you want is to hire your ideal executive and then have them go through a rocky onboarding process themselves. This can jeopardize the hire and the future of their relationship with your company.

5. Finances & accounting

You might be unsure if you have the fiscal resources to hire executives, and it makes sense as a startup. But the best way to understand the state of your finances and accurately gauge your financial situation is to have all of your finances and accounting in place.

For example, you might feel like you have a surplus of cash, but in actuality you have that same amount due in tax liabilities in two months. Or maybe your business isn’t properly keeping track of cash flow in and out of the business. By having an excellent grasp on your finances and accounting, you’ll know exactly where you stand today, and can best prepare for the future.

6. Goals

Where do you want your company to go? Where do you see it in one year, or in five years? Having these goals outlined might seem intimidating, because they might change, or you may think you’re unlikely to reach them. But that’s okay all the same, because setting your goals is the first step to actually putting them in motion.

Potential executive hires will likely ask about your company goals, and you should be able to give them a concrete answer. This also helps identify which executives are the right fit to help you reach them.

7. Logistics

Is your team fully remote, or will you be working on a hybrid system? Are there ways for team members to join calls from anywhere, and do you have a CRM in place? Having a framework for your logistics is important for ensuring smooth sailing across the board, but it’s also important to have in place before recruiting executives. You don’t want to hire an awesome executive only to encounter issues with your daily Zoom meeting. Sort out the biggest technical bugs before you bring on leadership members.

Recruiting executives shouldn’t just be a symptom of growth, it should be a cause.

Some startups wait until they experience growth to hire executives, but this means that they’re playing catch-up. Instead, early-stage startups can take a proactive approach to recruiting executives in order to spur growth.


Note: This article has been updated to reflect the current hiring landscape.

Building People-First Culture

This article was originally published by Will Reed and does not necessarily reflect the perspective of Insight Partners. Insight Partners is an investor in Will Reed.

There’s no other way of saying it: Hiring and retaining top talent can be tough these days.

But there’s a secret weapon that new businesses (especially startups) can leverage to combat hiring challenges, whether they’re looking to fill entry-level positions or recruit world-class executives. It’s called cultivating a people-first culture.

What is a people-first culture, and why does it make a difference in employee hiring and retention? Cultivating a people-first culture in a startup means that the organization is prioritizing the needs and desires of its people and considering those factors when creating policies and systems.

A people-first culture means this prioritization goes above and beyond words and catchphrases but is actively demonstrated and embodied in continued action.

It’s very possible to build a people-first culture, but in order to do so, startups need first to understand what this means to their own leadership and employees, why it’s essential, and how to execute this process. Keep reading to find out how to implement this in your company.

Is People-First Culture Really Attainable?

Creating a people-first culture is attainable, but it requires internal work and plenty of external communication. For example, it’s not simply enough for a startup to declare that it is a people-first organization and update the employee handbook. Rather, the proof is in the policies.

To attain people-first culture, startups need first to get their leadership and decision-makers aligned on what people-first means to the organization. Then, there needs to be processes around collecting employee feedback so leadership can understand what exactly people-first means to their employees.

Afterward, organizations need to craft and deploy people-first policies that resonate with their team members and are actionable. There also needs to be excellent open communication channels about receiving feedback on the new people-first initiatives to ensure they’re performing as intended.

In short: People-first culture is attainable, but leadership needs to “walk the walk” by creating and embodying meaningful people-first policies. This culture applies to everyone, not just a select few.

Why Do Employees Want This?

Employees seek employers with people-first culture, whether they identify it as such or not. Workplace data shows that employees in people-first organizations perform their jobs better and appear happier overall.

For example, research tells us that employees at culture-driven organizations make 26% fewer mistakes, are 22% more productive, and are absent 41% less of the time. They’re also twice as likely to recommend their employer to a friend.

There are many reasons that employees want to work at places that put them first. They want to feel valued and empowered and know their time and expertise are respected.

Employees also want opportunities for advancement, better pay, and to feel respected overall. The answer to these needs and more is prioritizing a culture that reflects these capabilities.

Plus, it’s important to note that employees prioritize the need for people-first culture. It could be the difference between someone selecting your company and working for your competition.

What Exactly Does People-First Look Like?

People-first culture can differ from organization to organization, but there are a few consistent hallmarks that startups can incorporate into their own business. Here’s what a people-first culture might look like at your startup.

Empowered Employees

Empowered employees aren’t only told they’re empowered: Their leadership demonstrates this by trusting them and giving them space to make decisions independently. This approach provides employees with autonomy over their work and supports it with resources.

Empowering employees might look like not hovering over their every move while they work or getting too involved in their small day-to-day tasks. Ultimately, leaders should also trust their employees to make good decisions and demonstrate that trust through actions.

Proper Compensation and Benefits

Inadequate compensation and employee turnover go hand-in-hand, as do proper compensation and a people-first culture. Many employees cite compensation as a reason why they left their job in recent years, and studies show that insufficient benefits are another main reason employees leave.

The point is that employees want competitive compensation and benefits, and it’s no longer enough to make them feel appreciated in other ways (they can’t pay their bills with free lunch, after all). For startup leaders to demonstrate an employee-first culture, compensation and benefits must clearly show how much their employees are valued.

Leaders Who Listen

One main pillar of an excellent people-first culture is leaders who visibly listen to their employees and feedback. Employees want to be heard, share their feedback, and have that feedback taken into consideration. But it’s not enough to just quietly listen; leaders need to show their people that they’re actually listening and considering what is being said.

In order to demonstrate that there’s a culture around listening, leaders can create processes around communication, practice and show empathy, and make themselves available for one-on-one discussions. Leaders can also share feedback collectively, as well as share the ways that feedback is being addressed.

Tight Company Values

Bland and generic company values aren’t going to inspire a team or make them feel unified in a people-first company culture. Instead of using overplayed standard company values, leadership should develop genuine, original, and authentic company values that genuinely mean something to the organization and its people. These tight company values can then be embodied in all other aspects of the organization.

Effective Communication

Effective, clear, and transparent communication is a critical pillar of a people-first company culture. No employee wants to work at a place where they feel like there is one-way communication that is strained, dishonest, or withholding.

Instead, leaders can take steps to demonstrate and encourage effective communication. This includes encouraging employee feedback, holding check-ins and standup meetings, and sharing updates transparently.

Flexibility and Understanding

In the age of remote work, hybrid work, and WFH, employees actively seek increased flexibility and understanding of their work requirements. While not every workplace needs to be hybrid or remote, employees generally demand increased flexibility that improves their work/life balance, physical and emotional well-being, and ability to care for their loved ones. Flexibility and understanding might look like policies around where work can be completed (perhaps remotely if a loved one is sick, for example), when work can be completed, and empowering employees to accomplish tasks in their own ways.

Opportunities for Growth

While startup employees and executive leaders might not be looking to “climb the corporate ladder” in the traditional sense, team members still want to feel like the future of their career matters to their organization. With that in mind, startups should take steps to provide growth opportunities in their employee-first culture. This might include training sessions, specialty seminars, advanced education or leadership training resources, and pipelines to help talented employees attain new roles.

What’s the Business Impact of a People-First Culture?

A people-first culture isn’t only good for the people in an organization, but it’s also excellent for the business itself. As we touched on earlier, employees at culture-driven organizations are better employees: They’re more accurate in their work, more productive, and have better attendance at work.

That’s likely because when people feel valued and cared for by their workplace, they are more motivated to perform their jobs and more satisfied in their roles overall. With that, organizations increase their revenue and retain top talent.

How Do You Start Implementing People-First Techniques?

People-first techniques start with the executive leadership team. Leaders and executives need to clarify what people-first should look like in their organization and create comprehensive strategies around executing it. Then, these executive leaders need to lean on their middle managers to help push these people-first policies and practices.

We Believe People-First Culture Is How the Best Companies Are Built

Top-tier organizations need next-generation practices regarding their culture and people because the corporate culture of years past just isn’t cutting it anymore. When executed correctly, people-first culture doesn’t only contribute to happier and more productive employees but can help boost employee retainment and improve company metrics overall. Now that’s something we can all get behind.


Note: This article has been updated to reflect the current hiring landscape.

Business Critical Hires – Why The Executive Search Can’t Wait

This article was originally published by Will Reed and does not necessarily reflect the perspective of Insight Partners. Insight Partners is an investor in Will Reed.

Plenty of things in life can wait, like ordering that new sweater you were eyeing online or cleaning out the expired condiments from the refrigerator. But when it comes to early-stage startups, one thing that definitely can’t wait is the executive search process, especially for filling critical leadership roles.

The business landscape for early-stage startups today is unlike anything in the past for several reasons, and startups simply can’t afford to have their most crucial positions empty. The truth is that 20% of startups don’t make it past the first year, and that one of the leading reasons why startups fail is because they don’t have the right team in play. Additionally, studies reveal that there could be an $8.5 trillion talent shortage in the near future, fueled by a lack of skilled workers. In short: excellent startup talent can be hard to come by, but at the same time, it’s absolutely essential for early-stage companies.

But there’s a paradox: even when founders and leaders decide that now is indeed the time to fill those critical positions, they can be caught up with massive roadblocks during the actual executive hiring process itself. The average executive search process can take upwards of three months, and while this process happens, vital positions are left empty. With that in mind, there are options for conducting a swifter executive hiring process, so that key leadership positions are filled as quickly as possible.

Here are the reasons why a faster executive search process is better, especially when it comes to critical business hires.

Save On Costs and Resources

There’s a very simple equation when it comes to the executive search process: the longer this process takes, the more money and resources an early-stage startup will spend in the meantime. These costs come from different places. First of all, leaving key positions empty can be costly in itself, especially when they’re executive roles. Studies reveal that empty executive positions can trickle down to costs that equate to thousands of dollars per day (or far more). The quicker a position is filled, the less money is lost in the meantime.

Next, during the executive search process, leaders need to allocate significant resources to the interviewing and hiring process. That’s because the executive hiring process is an in-depth process that takes time away from key executives and other decision-makers who need to vet, interview, and approve candidates. The longer this process takes, the more time is spent. When vacancies are swiftly filled, everyone can return their focus on what matters most: excelling in their roles so the business can succeed.

Meet With Higher Quality Candidates

If it seems like it’s rare to come across dream executive search candidates, that’s because it can be. There are a few reasons for this, and one of them is the fact that higher quality candidates actually don’t sit on the job market for very long. Get this: we’ve found that the best candidates are only on the market for about 10 days, meaning that early-stage leaders need to move very quickly once they identify a key candidate.

Oftentimes, when companies are taking too long with the executive hiring process, incredible candidates can slip through their fingers, because they’re simply too slow to get candidates approved. In these scenarios, once a company and its leadership finally decide to move on a candidate, that candidate might have already been scooped up by another company. With this in mind, a swifter executive search process can allow early-stage startups to have access to top-tier candidates, who are also moving on these quick timelines.

Better Candidate Experiences

Better quality candidates want a better quality executive search experience. Think about it: the best candidates don’t want to sit on hold for weeks and months on end. Instead, they want to move quickly on positions, and they’ll likely respond better to early-stage companies that do move more quickly. Ultimately, when an executive search process is quicker, the candidates involved also have a better experience.

Research tells us that almost half of job seekers have turned down jobs because of negative experiences during the hiring process. When early-stage companies have their dream hire on the line, they should do everything possible to ensure a smooth and positive hiring experience, including executing a faster hiring process.

Better Response Rates

When early-stage companies work quickly to build a grade A team, they’re also likely to experience better response rates from their choice candidates. If a startup is taking 90+ days to conduct the hiring process and to select candidates, it’s likely that incredible candidates will walk out the door in the meantime.

But on the other hand, when a startup is moving on executive search candidates more quickly and keeping the ball rolling, they’re far more likely to receive better response rates from mission-critical hires.

Recruiters and Hiring Managers Love It

Swift executive search processes aren’t only great for candidates: this type of search is also far better for recruiters and hiring managers. When an executive search process takes 90+ days, recruiters and hiring managers have to pour considerable time and resources into filling these vacancies. This means vetting countless candidates, conducting endless interviews, and potentially having candidate after candidate slip through their fingers.

But when the executive search process is speedy and efficient, recruiters and hiring managers can experience excellent flow through the entire process, from finding candidates to getting them up and running in their new positions.

Beat Out the Competition

Let’s face it: startup trends show that the business landscape today is incredibly competitive, with data revealing that nearly 20% of startups fail due to being beat by the competition. With that in mind, early-stage startups need to use every tool in their arsenal to stand out from their competitors, including bringing the best leadership and executive team members on board.

When startups are looking for top-tier executives, they don’t want to miss out on their dream hires because they get scooped up by the competition. If an executive search process is taking the standard 90 days, it’s far more likely that choice candidates will end up going to a competitor. But when an executive search process is happening more quickly, the risk of excellent candidates going to the competition is far less.

Better Team Productivity

While we know just how incredible your team is, they probably could benefit from some more powerhouse executives on your team. When key executives are missing, team members might be lacking hands-on leadership that can drive real results and employee engagement.

But on the other hand, when executive positions are filled, and there are excellent leaders and executives in the driver’s seat, these key players can focus on giving team members specific direction, ensuring goals are met, and keeping employees engaged with hands-on management. This type of leadership can be incredibly valuable across the board, for both employees and their companies, with studies showing that engaged employees are more productive, resulting in a 21% increase in profits. When teams have strong leaders in place, they can simply work better.

Refocus Resources on What Really Matters

When an early-stage startup is spending money, time, and human resources on the executive search process, it can be very consuming. But once those key positions are filled, businesses and leadership can refocus their efforts on what really matters: innovating in their space and excelling as a company.

Executive hiring takes resources. But when that process is speedy and efficient, teams can quickly start putting their new top-tier hire to work, and can start operating as a dream team immediately. This means more resources available for setting and achieving massive goals, instead of having to put off those things for the far-away future.

Why Your Hiring Strategy Should Prioritize Talent Infrastructure

This article was originally published by Will Reed and does not necessarily reflect the perspective of Insight Partners. Insight Partners is an investor in Will Reed.

What’s In Your Hiring Strategy?

When it comes to early-stage startups, founders and leaders sometimes need to “fly by the seat of their pants” when it comes to decision-making. And sure, this approach can work for a lot of things (like where to put the nitro cold brew coffee tap). But there are many critical aspects of early-stage startups that need methodical and proven processes, because of the weight of these decisions. This includes using a hiring strategy for recruiting new talent, especially when it comes to critical leadership roles, like vice presidents.

For early-stage startups, every hire matters, because every new team member has the power to influence the company’s work production, goals, and culture. And because of this, executive hires are even more critical, and there’s even less room for error. In short: bringing on the right leaders is essential, which is where a hiring strategy comes into play.

And of course, one of the most important executive roles to hire for is the position of vice president. A startup’s first vice president will yield incredible power in influencing the trajectory of the company, and startup leaders need to make sure that their first vice president is 100% a perfect fit.

Why Build a Recruiting Strategy?

Why build a recruiting strategy in the first place? Aside from the “set it and forget it” strategy of writing job descriptions and posting them online, is there more work that needs to go into an early-stage startup’s hiring strategy?

Recruiting strategies take the guesswork and chance out of hiring for startups, and instead, gives startups a detailed blueprint to follow that’s goal-oriented and precise. Excellent hiring strategies can help startups attract top-talent, and eventually make their perfectly-timed dream hires. On the other hand, approaching hiring without a recruiting strategy can be haphazard and reactive, and can lead to hiring mistakes.

The truth is that perfect-match candidates can be difficult to come by. Excellent talent can sometimes take some effort to locate. A majority of potential job candidates are passive, but are willing to hear about new opportunities.

What exactly does this all mean? It means that great talent can be hard to come by, especially when it comes to executives. And the best way to reach executives (like your new future vice president) is to develop an excellent hiring strategy.

How Is Hiring Execs Different?

With all of that in mind, it’s important to remember that hiring executives is very different from hiring individual contributors, and they require a tailored hiring strategy. These business-critical hires can be tricky to get right, with data showing that 50% of newly-hired executives are considered to be “failures in their roles,” and many executive positions are seeing growing turnover rates (CEOs are particularly impacted).

Hiring executives is different because these best-of-the-best hires need to not only match the educational and professional qualifications for the executive role, but also the culture and goals of the company as a whole. In order to hire a candidate who is a match across the board and who can help take an early-stage startup to untold heights, a targeted hiring strategy is necessary.

What to Consider Improving in Your VP Hiring Strategy

With that in mind, let’s do a deep-dive into the hiring strategy for bringing on a vice president. Bringing on a VP might be the most specific of the hiring strategies, and it needs a very intentional approach. Here are ways you can consider improving your VP hiring strategy.

Employer Brand

Employer branding is increasingly considered a crucial factor in a hiring strategy, especially when it comes to hiring executives. Lack of brand awareness has historically been cited as a significant barrier to recruitment, and it can be an even more challenging obstacle to overcome when we’re talking about hiring executives.

For early-stage startups, it might be difficult to lean on your brand just yet. Even if your brand lacks the recognition it’s destined to one day have, there are a few things you can do now to make sure your employer brand is as strong as possible.

First, shore up the reputation of your employer brand. Studies show us that most candidates will research companies, and base their decision to apply on employee reviews. In order to do this, you can ask your happiest employees to leave you rave reviews on different job platforms.

Next, focus on your employer value proposition, or EVP. This is the complete set of offerings your startup gives employees beyond just standard compensation. This means that in addition to a competitive executive salary, there needs to be other perks of working at your startup, that make the work “worth it” for a top-tier executive.

Lastly, you can hone in on the employee experience. Employees who have a positive experience aren’t only going to be happier, but they’re going to work better. When your current team is productive, efficient, and happy, your potential new executives will be more than happy to join the ranks.

Creating Compelling Job Posts

Ah, job posts. They’re definitely not what they used to be, and writing that you’re looking for a “highly motivated self-starter” just isn’t going to cut it anymore, especially when it comes to hiring executives. In order for a startup to level-up its hiring strategy, job posts need to be action and goal-oriented. For vice presidents, job posts can include elements such as:

  • Who will be reporting to them, and what teams they’ll have ownership of.
  • What the day-to-day is expected to look like on day 30, day 60, day 90, and day 120.
  • What strategies and goals this executive will be responsible for conceptualizing and taking ownership of.
  • What communication will look like.
  • Professional and educational requirements, along with what cultural requirements the startup is looking to meet.
  • The startup’s core values.

This Requires You to Truly Understand the Role

One of the trickiest parts about writing compelling job posts for executive roles is deeply understanding the role in the first place. It might seem like executive roles are obvious, and that they come with clear responsibilities. But the truth is that executive roles need to be formed with clear guidance and responsibilities.

To understand the role, startup leaders can ask themselves why they want to hire for this role in the first place. What responsibilities, teams, and goals are they looking for someone to take ownership of, and what new talent and skills do they want their vice president to bring to the table?

Honing in on the Interview Process

Revamping a startup’s hiring strategy means also revamping its interview process. That’s because when you have your dream candidate on the line, you don’t want them to walk away due to a misstep in the interview process. Here are ways leaders can hone in on the interview process:

  • Establish your interview strategy: You don’t want candidates to unnecessarily repeat themselves in multiple rounds of interviews for no reason. Ensure that each tier of your interview process is intentional and planned, so that each interview achieves a new goal in the interview process.
  • Tighten up your timeline: The executive interview process can’t be drawn out, because it can cost you excellent candidates. We’ve found that the best candidates only stay on the market for 10 days, while the average search process can take upwards of 90 days (that’s why here at Will Reed, we run searches that take 45 days on average).
  • Be clear with your needs and offer: In order to find their dream vice president, startup leaders need to be clear about what they’re looking for, and what they’re offering. The job description is a great blueprint for sharing and obtaining this information (when written thoroughly, it can be used as a checklist).

Onboarding Employees and Setting Them Up for Success

The hiring process doesn’t end once the ink has dried on a new executive contract. A crucial part of any hiring strategy is the onboarding process, so that that a startup’s new executives are set up for success. Ensure that onboarding happens at a steady, consistent pace, and that for executive roles, it’s the proper balance of technical onboarding and social onboarding. Also be sure to onboard new executives to the startup’s cultural expectations, not only the hard skills required for the job.

How Does This All Tie Into a Formal Talent Infrastructure?

Hiring top-tier talent for executive positions like vice presidents goes far beyond posting a job and waiting. Instead, hiring for these positions requires a detailed and proactive hiring strategy, supported by formal talent infrastructure at an organization. When there’s a formal talent infrastructure in place, a startup’s employer branding, job postings, interview process, and onboarding will all contribute to the recruitment of new executives, and will ensure their success for years to come.


Note: This article has been updated to reflect the current hiring landscape.