Eric Gilpin’s career spans some of the most transformative phases in tech. From scaling Upwork’s enterprise business from zero to $650M to driving G2’s global revenue organization, Eric has been at the forefront of leading revenue teams through significant growth and transformation. His unique perspective combines deep operational experience with a clear focus on creating alignment and driving enterprise value.
In our conversation, Eric unpacked critical strategies for evolving from sales execution to executive revenue leadership, designing frameworks for team alignment, building and implementing leadership values, and navigating the complexities of go-to-market planning.
Listen to Mark's episode on Apple and Spotify.
1. The Value of Thinking Long-Term—Even in a Short-Term World
Mark describes his time at Shopify as a masterclass in long-term thinking. Unlike many public companies driven by quarterly earnings, Shopify’s leadership, led by founder Tobi Lütke, prioritized building for the next century. Shopify was an incredible example of the power of ‘founder mode’.
“Tobi didn’t care about hitting quarterly targets,” Mark shared. “His focus was on creating the best product for merchants and building a sustainable business.”
This long-term mindset permeated the organization. For example, Shopify’s sales leaders weren’t on variable compensation, which was a somewhat controversial decision to avoid incentivizing short-term behaviors at the expense of long-term goals. I know this was difficult to wrap my head around when I first received my offer to join the company.
2. Building Sales in a Product-Led World
Mark’s tenure at Shopify involved launching and scaling Shopify Plus, a sales-driven arm within a traditionally product-led organization. This was no easy feat in a company where engineering and product were driving the culture.
One of the most striking anecdotes Mark shared was about Shopify’s approach to customer acquisition: “The company maintained a list of Fortune 100 brands it had said ‘no’ to—because their requests didn’t align with the core product roadmap. It was a point of pride.”
To integrate sales effectively, Mark and his team had to align deeply with product leadership. This involved understanding the product vision, speaking in terms that resonated with engineers, and framing sales feedback in the context of long-term product value. Engaging effectively with product was one of the most impactful lessons I took from my time at Shopify.
3. Leadership That Builds Followership
Mark has earned a reputation as one of the most respected revenue leaders in SaaS. His approach? Authenticity and vulnerability.
“I used to think being a leader meant having all the answers,” he admitted. “But what I’ve learned is that the real superpower of leadership is vulnerability. It’s okay to say, ‘I don’t know, but let’s figure it out together.’”
This mindset, paired with a deep belief in people’s potential, has helped Mark cultivate teams that are both high-performing and deeply loyal. If and when Mark takes another operating role, he’ll have a lineup out the door of reps and leaders ready to follow him.
4. Cross-Functional Alignment: Lessons in Partnership
A recurring theme in Mark’s story is the importance of breaking down silos, especially between sales, product, and engineering. At Shopify, he regularly sought out product and engineering leaders for informal conversations, often over lunch. These interactions not only built rapport but also helped align priorities and develop mutual respect. He also helped bring the customer to the EPD org.
“One of the most impactful things we did was invite engineering leaders to meet with customers,” Mark said. “Hearing directly from merchants about their challenges made the problems real and motivated the team to act.”
5. Partner Programs: Getting Them Right
During his time at Shopify and in his fractional advisory roles, Mark has seen both the successes and failures of partnership programs. His biggest lesson? Partnerships only work when they genuinely benefit both sides. In my opinion, the benefit is oftentimes superficial. It looks valuable on paper but, in reality, there isn’t something legitimately compelling for the other side.
“If you can’t clearly articulate how your partnership will help the other company grow their business, it’s not going to succeed,” he emphasized. “Logos on a website and revenue share agreements won’t cut it.”
Successful partnerships at Shopify involved deep investment: co-marketing efforts, dedicated partner managers, and clear alignment on mutual goals. Ecosystem and partnerships were a massive super power at Shopify so Mark’s insights here were really valuable.
Final Thought: Why Mission Matters
Mark’s time at Shopify reinforced the power of a strong mission. “Shopify wasn’t just selling software—it was empowering entrepreneurship,” he explained. “That mission created alignment across the entire organization.”
For SaaS leaders, this underscores the importance of articulating a clear “why.” When employees, partners, and customers rally around a shared purpose, execution becomes easier, and growth becomes inevitable. Most of the time, mission is just branding and a false veneer but Berg shows how mission can drive real business outcomes when it’s real.
Mark’s insights are a reminder that great leadership isn’t about quick wins or rigid playbooks. It’s about thinking long-term, fostering collaboration, and building a culture rooted in trust and purpose. Whether you’re scaling a startup or navigating the complexities of a mature organization, these lessons are worth putting into practice.
I’m grateful to have learned a lot of these lessons from Berg. He’s one of the good guys.
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