Welcome to Season 3 of 10/10 GTM: The Podcast for Revenue Leaders!
Our guest for Episode 43 is Diana Kimball Berlin, Partner at Matrix. For over three years, Diana has been collaborating with former founders and company builders to lead Series A investments. With extensive experience as a board member, investor, and former VP of product, she brings a wealth of knowledge to the conversation.
In this episode, Ross and Diana discuss how to partner with product teams, present to executives, and impress VCs as a first-time leader.
Listen to the episode here, and get the key takeaways from our conversation below.
How sales leaders can effectively partner with product teams
Wondering how you can better partner with product folks as a sales leader? Diana has some valuable advice. “When I was at Quip, I watched Bret Taylor in action — he’s a master at bridging the gap between product and sales. Often, these departments are seen as having different mindsets, but Bret excels at integrating their strengths. One of the main lessons I learned from him is the importance of listening to the customer and reflecting back their insights with synthesis, so they feel truly heard and understood.”
This approach is not just about collecting feedback to inform future product development; it’s also about keeping customers engaged and satisfied. When customers see that their feedback is valued and acted upon, they are more likely to remain loyal and enthusiastic about your products. This level of engagement creates a positive feedback loop, driving continuous improvement and innovation within the product team while fostering stronger relationships with your customers.
Diana further explains how this collaborative approach works in practice: “Bret and I would get into a room and chat about what he was learning. This helped us figure out how to extend the insights he collected into a round of user research such as mock-ups, and build it into something that would work for our users,” she says. “This really set the bar for the rest of the team.”
By regularly discussing insights and ideas, sales leaders can partner with product teams to ensure that customer needs and feedback are integrated into the development process. This collaboration leads to the creation of products that are aligned with customer needs and expectations.
Tips for presenting to the board and senior execs as a first-time leader
Many first-time leaders at startups or high-growth companies face the challenge of presenting to the board and senior executives. Diana recommends making the best impression and achieving success by being realistic in forecasting and open about areas for improvement and lessons learned.
“When I’m in a boardroom, I appreciate leaders who are in touch with reality. They know exactly what happened in the last quarter and are actively learning and improving. When questioned, they aren’t defensive; they’re open and honest, willing to discuss what they could have done better and how they’ll apply those learnings in the future,” says Diana.
Diana also keeps an eye on the LinkedIn and social profiles of the leaders and teams Matrix invests in. “I’m on LinkedIn. I see what you’re posting. I follow everyone on the team. And what I love to see is that even when things aren’t going well, you’re putting yourself out there with confidence and perspective every single day. It’s not just about optics. I care about what’s actually happening, but I also want to see that you’re being relentless and proactive about prospecting and raising awareness.”
Strategies for impressing VCs as a first-time leader
Diana appreciates being helpful to her network and doing what she can to get deals across the line for the companies Matrix invests in. But before looping her in, it’s important to do whatever you can on your end to make it easy for her. “I observe how you tee the conversation or deal up for me. This includes the context you give me and how much work you’ve done ahead of time,” she explains.
Leading with your best foot forward for VCs means being proactive, prepared, and considerate of their time and expertise. By providing clear context and demonstrating that you’ve done your homework, you show that you respect their involvement and are committed to making the partnership as smooth and effective as possible.
About Diana
Diana is a partner at Matrix, an early-stage venture capital firm, investing from idea through Series A. She specializes in B2B and AI ventures and serves on the boards of several companies, including Meshcapade and Accord. Before joining Matrix, Diana held leadership roles at Quip and SoundCloud.
