What happens when you’ve built and sold five SaaS companies, each with its own share of wins, losses, and lessons? If you’re Dave Boyce, you channel that experience into helping other companies scale smarter. Today, as part of Winning By Design, Dave works with growth-stage organizations to anticipate the challenges that come with every revenue milestone—ensuring they’re ready for what’s around the corner, rather than being caught off guard.
In this episode of Go To Market with Dr. Amy Cook, Amy and Dave consider the realities of automation, the risks of inauthentic outreach, and the rise of product-led growth (PLG). Together, they unpack how the SaaS world has shifted from manual Rolodexes to AI-driven self-service, and why empathy—not efficiency alone—is the key to long-term success.
The conversation is candid, practical, and filled with insights that revenue operations leaders, founders, and GTM strategists won’t want to miss.
Here are some interview highlights:
Amy: Tell us a little about yourself and your work at Winning By Design.
Dave: Sure. I’d describe myself as a serial entrepreneur—curious by nature. Over the years, I’ve built and sold five SaaS companies, each with its own battle scars and stories. At Winning By Design, I focus on product—how to package our growth advisory services so they’re easy to consume. We help scale-ups, typically $50M to $2B in revenue, navigate the transformations they’ll face at each growth stage. The key is anticipating change so companies don’t get slowed down by operational debt.
Amy: In our pre-call, we touched on automation. Both of us remember manual Rolodexes, Commodore 64s, and the evolution into CRMs like Salesforce and HubSpot. Now AI is automating entire workflows. What’s your take on the pros, cons, and the future?
Dave: Automation has definitely made life easier, but it also risks going too far. Early on, automation was about efficiency—keeping track of prospects, scaling cadences. But we’ve learned the danger of inauthentic personalization, where messages pretend to be one-to-one but aren’t. Buyers tune it out. The big shift now is from “automation” to “self-service”—giving buyers real control. When it works, it feels authentic, not artificial.
Read more: Empower Sales Managers with Self-Service Territory Management
Amy: I love that framing. Authenticity is key. Mass emails pretending to be personal just don’t land anymore.
Dave: Exactly. Buyers are smarter now. They know what’s automated. The exciting part is how freemium and product-led growth (PLG) models have flipped the script. Instead of selling through coercion, companies like Dropbox, Zoom, and Canva put value directly in customers’ hands. That forced empathy—really understanding the user’s progress and designing around it. Done well, it builds billion-dollar companies.
Amy: So true. Necessity drove PLG. Companies couldn’t afford sales reps everywhere, so they had to make products self-adoptable. Do you think we still need salespeople today?
Dave: Absolutely. But their role is shifting. I love the phrase “automate the predictable so you can humanize the exceptional.” We don’t need humans processing renewals or explaining basic product features—that can be automated. But for high-stakes deals, complex decisions, or building trust? Humans are irreplaceable.
Read more: Broken RevOps Playbook? Here’s How to Fix It
Amy: Well said. What about the workforce impact, though? Entry-level jobs are being automated.
Dave: That’s the tricky part. My son, for example, is a prompt engineer at 18, training digital employees. But not everyone will land in that kind of role right away. History shows we adjust—like when switchboard operators were automated out of jobs—but it takes creativity. Entry-level roles will change. The challenge is giving new workers the reps they need to grow.
Listen to the full podcast episode here.
