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Two Days of Learning, Fun and Team Building at Insight’s Scaling 2020 Summit

Travis Kassay, Barrie Markowitz | September 30, 2019| 1 min. read

Two days, 75 CROs and CMOs, hundreds of conversations, and more than a dozen content rich sessions.

Our hosts, Gary Survis and Pablo Dominguez, Insight Operating Partners that manage the Insight Onsite Marketing and Sales Centers of Excellence, respectively, set the theme for Scaling the Summit: alignment. The conference agenda was designed as a single track for all attendees - not different tracks for Sales and Marketing. Why? Because alignment and coordinated planning between Sales and Marketing is crucial for the success of scale-up growth companies.

More than 65% of the participants noted that they had already started planning for 2020, which made the energy electric as these executives considered how they could put their newfound knowledge and peer’s best practices into action.

Below we highlight a few insights gleaned from the keynotes and panels:

Behind the Scenes: Marketing & Selling to Key Decision Makers

How do C-level leaders purchase software and learn about new products? The panel of Amy Heidersbach (CMO of Alteryx), Todd  Abbott (EVP Global Sales and Services of Mitel) and John Elbasan (CIO of Wilkie, Farr and Gallagher) shared their thoughts on ways that software teams can market and sell to people like them: their trusted sources for learning, how they secure the best value from business partnerships and what marketing tactics are effective. The session was insightful and provoked an engaging post-panel discussion since participants sell to enterprise decision makers.

See our specific blog post on this topic that provides detailed do’s and don’ts.

Building Your Model Together: Diligent’s CMO-CRO Alignment

Building on the theme of alignment, Amanda Carty and Jeffrey Hilk, CMO and CRO of Diligent, led a panel on Building Your Model Together. This “behind the scenes view” into how Amanda and Jeff collaborate demonstrated the strong results that a true CMO & CRO partnership can deliver.

The Diligent team focuses on leadership level alignment – they have identified that by proactively and visibly prioritizing collaboration and joint accountability they’re able to create a culture that fosters teamwork and maximizes output. In practice, this means both taking the hits, and victory laps, together. 

The Diligent-led session on how sales and marketing collaboration pointed out that it’s the leader’s responsibility to find and encourage their teams to partner, and equally, the leader’s role to act quickly when they don’t. For teams who have historically not needed to collaborate, or rely on the other to get their job done, the first few joint projects are critical to educate one another about what their counterpart brings to the table, and build mutual respect. Jeff and Amanda discussed a situation where regional Marketing and Sales were constantly arguing and blaming each other for the region’s underperformance – a scenario that is may be all too familiar for some businesses. Rather than have that disagreement escalate, the leaders, whose close partnership was clearly visible, acted quickly as a team and replaced both leaders in that region. 

This swift action sent a strong message to their global organization about the importance of partnership and collaboration. They further reinforced this value set by aligning the marketing bonus structure to sales performance. A strong signal that the two teams are in it together. The approach might seem radical, but they’ve been able to eliminate infighting, optimize output and significantly grow the company’s revenue.

If you’re at the early stages of Marketing-Sales alignment, seek out the quick wins to visibly demonstrate that alignment works, and make sure to share the positive results across your organization. By getting everyone to ‘buy in’ to the fact that a strong partnership will amplify success, the model can be replicated enterprise-wide. Bottom line, aligning Marketing and Sales teams into a joint Go-to-Market team is difficult and certainly doesn’t happen overnight, but pays off via a more collaborative culture and improved results. The tenor starts at the top.

Motivational Speaker: Kikkan Randall (Olympic Gold Medalist)

If the standing ovation was anything to go by, a clear highlight of the summit, was Kikkan Randall’s life story which exemplifies planning, grit and determination.  Kikkan is an Olympic gold medalist in cross country skiing, mother, breast cancer fighter, and now, motivational speaker. Kikkan spoke of her initial ten-year plan to become an Olympian; her quest has parallels that are relevant for all leaders, teams, and planning in a business setting.

Kikkan is a strong all-round athlete and, early in her career, she engaged in multiple sports. An initial physical set-back left her unable to continue her regular training regimen, forcing her to be creative and recalibrate her choices and goals. She refocused her aspirations to cross-country skiing – becoming, initially, the only woman in a field of 20 men.  

With this foundation, Kikkan set out to build a squad of women competitors who could be her teammates. As the group of women cross-country skiers grew, the goal of Kikkan’s Olympic coach was for the women to be the best teammates – both on, and off, the snow. The coach encouraged the athletes to bond through non-ski activities, and as they got to know each other and grow closer, they started to have more fun. This enabled them to all work harder, ski faster, and it boosted overall team performance. Her advice to business executives:  take the time to do fun things with your team – it will pay back many times over in improved results.

Kikkan encountered multiple setbacks during her career but her tenacity, creativity and grit enabled her to persevere in the face of these obstacles and several disappointments. She continued to re-calibrate her plan and the actions she would have to take to achieve it.  After 16 years of competing internationally, including time off to have a baby, Kikkan won a gold at the 2018 Pyeongchang Olympics. The American team was not a favorite to win, and achieved the gold against all odds.

With this victory marking the pinnacle of her career, Kikkan was aghast, a short while later, to discover that she had breast cancer. Unlike her athletic pursuits, this time the outcome was not in her control. She had to rely on her medical team, and the multiple disciplines working together.  She created the same team environment of fun and communication to get through the ordeal. She also focused her energy on making a positive impact by creating and selling "it's going to be okay" socks. Sales from this swag go towards AKTIV Against Cancer, a nonprofit whose mission is to ensure that physical activity is an integral part of a patient’s cancer treatment. Kikkan’s is now cancer free now and has turned her setbacks into a new path towards success, just as she did during her skiing career,

While difficult to summarize such a stellar career, Kikkan’s roadmap to success has applicability to B2B SaaS leaders: 

  1. Set a goal, and map out a plan and timeline to get there
  2. Prepare for adjustments since progress is not always linear
  3. Build the best possible team to accomplish the goal
  4. Learn and have fun together since this will engender better performance and efficiency
  5. Put in the work since nothing can be achieved without training
  6. #1-5 above significantly increase the likelihood of beating the odds
  7. The traits for a winning career can be applied in other areas of life

Leadership Insights: Selling Your 2020 Plan to the Board of Directors

The Summit concluded with members of the Board of Directors from both Insight Partners and Conga, sharing their candid advice on the best way for CMOs and CROs to engage with their Boards. The Q&A from moderator Pablo, drew laughs and sighs from the  panelists as they discussed what Boards care about most. 

Here’s a selection of advice from Insight MDs Hilary Gosher, Nikitas Koutoupes, Adam Berger and Conga CEO Matt Schiltz, learned through hours at the boardroom table: 

  1. Be truthful. If you aren’t delivering on your numbers, it’s OK to ask for help. The Board is there to help you improve the company, so if you share your challenges and the plans to address them, the Board can provide you invaluable advice. By contrast, obfuscating reality is likely to be discovered, at some point, and doesn’t reflect well on the company’s executive team.
  2. Communicate before (and after) the board meeting. The actual board meeting is the least important meeting, rather, it’s the culmination of a series of internal meetings, and one-on-one conversations with Board members before the board meeting. A board meeting shouldn’t be a mad scramble to pull materials together, it’s an opportunity to review the strategies already in place to assess their effectiveness and get the Board’s perspective and the benefit of their experience. The executive team should do a run-through prior to the board meeting, and a retrospective afterwards to review the insights, and the process (what went well and what could have gone better).    
  3. Participate with a Purpose. Ensure that Board Members know who is in the room, and why they are there. Your Board is ‘employed’ to look at your company with a critical eye —if an executive in the room doesn’t contribute or add value, the Board will likely question their capability and value.  If a junior team member attends the meeting to learn and absorb, this is fine as long as the CEO sets this context and manages expectations with the Board members.  
  4. Use the Board’s Expertise. Smart executives and CEOs leverage the expertise of their Board Members. Your company has bench of business leaders supporting your success, and this is an exceptional asset. Ensure you understand the capabilities and skills of your board members, and maximize your valuable interactions with them to help you achieve the company’s goals.

During the two days at the Summit, we were reminded that when you put 75 sales and marketing executives together in a room, the velocity of sharing is invaluable. Each participant contributes to the debate, best practice sharing, and to the ambience. It’s fun to see the energy generated by high powered leaders at the top of their game. Our key take away? Sales and Marketing are naturally aligned in their desire to ensure that scale-up companies accelerate revenue growth. We can lose sight of this given the pace of business. 

The benefit of Insight’s Scaling2020 Summit is that it provided an opportunity for the teams to (re)recognize the need to consider both sides during decision-making. Alignment, collaboration and cooperation are the key ingredients for a strong go-to-market motion that drives scaling. In 2020, and beyond.