In this episode, I sit down with Mark Roberge, a legend and true polymath in the world of revenue leadership and entrepreneurship. Mark was the first salesperson at Hubspot, where he eventually became CRO and is now a faculty member at Harvard Business School and a co-founder of Stage 2 Capital.
What makes Mark’s perspective particularly valuable is his ability to view sales leadership challenges through multiple lenses, as a former operator, an educator, and now an investor. This multifaceted experience allows him to offer insights that are both deeply practical and forward-thinking, especially when it comes to sales technology and AI.
Mark and I dove into one of the biggest topics in the world of GTM today: AI.
Where is it going? What should we be building towards? Should I build or buy? Who the hell is going to win? Am I going to be replaced by an Optimus sales bot??
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Approach the AI revolution with balance
Recognize the transformative potential of AI in GTM, but don’t get caught up in the hype cycle. Mark advises leaders to be proactive yet cautious, likening the AI transition to the cloud revolution. “We have to appreciate the potential of the movement toward an AI tech landscape and infrastructure,” he says. Look for opportunities to experiment with AI tools, especially in areas where they’re outperforming traditional methods. The real game-changing companies often emerge during what Mark calls the “winter” season when skepticism is high.
Design pilots for success
When engaging with new vendors, especially for AI tools, clearly define success criteria for pilots up front. Mark stresses the importance of getting all stakeholders to agree on business goals and involving necessary departments (IT, legal, security) early in the process. Document the “gives and gets” and be crystal clear about what success looks like. This approach ensures that pilots are meaningful and lead to informed decisions.
Mark shares some very pragmatic insight on how to structure pilots. One of my favourite takeaways was the idea that “You have to have a design big and start small.” He’s seen success with companies seeing innovation bottoms up, encouraging exploration with 1-2 reps then scaling what works. This is very different than the tops down approach that many companies are taking.
Buy or Build?
One of the biggest challenges revenue leaders face is deciding whether to buy off-the-shelf software or build custom solutions in-house. Mark emphasized that, in most cases, buying is the better option because building custom software often leads to higher costs, delays, and complexity that distract from core business objectives. Building tools in-house can be tempting, but more often than not, those custom solutions are eventually replaced by widely available products. Instead of focusing on custom builds, leaders should invest in buying and configuring the best existing tools to meet their needs.
“If you see a problem and have a cool idea, it’s likely that others are seeing it too. Most of the time, it’s better to buy than to build because horizontal apps will eventually replace what you create in-house.”
Mark pointed out that focusing on innovation in your core product is where time and resources should go. For everything else, leveraging external solutions that have a broader market base will likely serve you better in the long run.
Diagnose before prescribing solutions
Before implementing new tools, thoroughly understand the root problem you’re trying to solve. Mark recommends following a “symptoms → opportunity → solution approach”. This helps ensure you’re addressing real issues, not just chasing shiny objects. By getting to the core of the problem, you can determine whether a new tool is truly the best solution or if additional headcount, coaching, or another strategy might be more effective.
Delegate tech evaluation
Evaluating new technology doesn’t have to be your primary focus as a revenue leader. There’s no “right” amount of time to dedicate to it. Mark suggests delegating to a colleague in RevOps if technology evaluation doesn’t excite or energize you. However, stay involved in final decision-making and use these evaluations as an opportunity to understand broader market trends.
Cultivate authentic leadership
I loved our quick fire round at the end of the pod. Mark shared some gems from his leadership career and his personal journey.
Good leadership sometimes requires going against your natural tendencies. Mark shares his personal challenge of overcoming conflict avoidance to become a more effective leader. Identify areas where you need to grow and actively work on them. At the same time, recognize and nurture the diverse strengths within your team and coach them to be the best versions of themselves. As Mark says, “There are a lot of ways to be successful in sales — even within the same team and company.”
You can get more from Mark on LinkedIn and learn about Stage 2 Capital here.
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