In the inaugural episode of the Revenue Leadership Podcast by Topline, I sit down with SaaS legend, venture capitalist, and author Jason Lemkin to discuss the intricacies of board dynamics and how revenue leaders can effectively navigate these relationships.
This was a special episode for me because Jason and SaaStr were such important resources for me as I figured out the startup game. This was a fun full circle moment.
Jason brings a wealth of experience to the conversation from all sides of the table. As the founder of EchoSign, which was acquired by Adobe in 2011, he has firsthand experience in building and scaling a successful SaaS company. Jason currently serves as the CEO of SaaStr, a social community of SaaS founders and executives, and runs an early-stage venture capital, SaaStr Fund, for which he holds five board seats — including at Owner.com.
His unique blend of perspectives as an operator, investor and board member and provides invaluable insights for revenue leaders at all stages of their careers. It’s a massively important topic that I haven’t heard covered in podcast-land before so I was excited to dive in and learn from someone who has been on both sides of the table.
Here are eight takeaways from our conversation...
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1. Stop worrying you’re going to lose your job
Many revenue leaders operate under the misconception that they’re scapegoats for low performance, but Jason argues this is typically not the case. In reality, boards and executives are often reluctant to let go of leadership, recognizing the disruption and challenges that come with replacing key roles. But be aware that as the company grows and changes, there may be changes to the organizational structure, like a new role being created above your current position. Have open conversations with your CEO about the company’s growth trajectory and how your role might evolve.
2. Run toward bad news
Jason emphasizes the importance of transparency and proactivity in dealing with challenges. When facing difficulties, don’t hide or sugarcoat them. Instead, address issues head-on with your board to build trust and allow for more effective problem-solving. If you’re going to miss your quarter, communicate this early and come prepared with a plan to address it.
3. Appeal to every board member
Recognize that non-founder board members often focus on surface-level metrics like logos and visually appealing pipeline presentations, while operators on boards tend to be more interested in concrete commit numbers and confidence in the sales funnel. Regardless of the board’s composition, they value honesty, optimism, and no surprises. Prepare your presentations with this in mind, balancing metrics with high-level strategic insights.
4. Never play the blame game
As a revenue leader, it’s crucial we take accountability for sales performance. Jason strongly advises against blaming the product for poor results, as this can quickly diminish your credibility with the board. Instead, demonstrate a deep understanding of your product’s position in the market and how to leverage its strengths. Also focus on identifying areas where you can outperform competitors, whether it’s in pricing, onboarding efficiency, or unique features.
5. Yes, the board is going to talk about you…but it’s not what you think
It’s a given that boards will discuss the performance and potential of key executives, including revenue leaders. But Jason reveals that these conversations often centre around confidence in your leadership rather than looking for reasons to replace you. Boards are typically more interested in your strategic thinking, ability to navigate challenges, and vision for growth — so communicate wins, learnings from setbacks, and plans for improvement.
6. Prioritize quality over speed in hiring
Don’t lower your hiring standards to quickly fill positions on your team. Jason says, “There’s no bandaid in leadership.” Bad hires can have long-lasting negative impacts. Get comfortable with headcount gaps, constantly recruit, and build a network of potential hires so you’re prepared when you need to expand your team. Communities like Pavilion can help fill these gaps.
7. Due diligence is crucial
Before joining a new company as a CRO or VP of Sales, thoroughly evaluate both the company and team. Request key data like recent board packs and ask pointed questions about the company’s current state and future plans. It’s your responsibility to determine if you trust and align with the organization and its leadership, and this level of investigation can help you avoid misalignments and set the stage for a successful tenure.
8. Keep good people in your corner
Jason delivers a hard truth about the tech world: “Most people don’t care.” But he also says, “When you find someone that does care about you, try to work with them forever. Promote them, give them the title, and don’t let them go until they have to — then keep them close.” In the tech world, having a network of supportive mentors and colleagues is invaluable. These relationships will offer guidance, support, and opportunities throughout your career.
Get more of Jason’s insights on SaaStr, his LinkedIn page, and his book, “From Impossible to Inevitable.”
Thanks for joining, Jason!
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