Most founders know they need a go-to-market strategy, but very few understand when founder-led selling should evolve into a real revenue engine, or how personal brand fits into that transition.
In this episode of Life's a Pitch, Jared Gibson sits down with Jess Schultz, founder of Amplify Group, fractional CRO and CMO, former venture capitalist, and active angel investor. Jess works with B2B startups navigating founder-led sales, early revenue growth, and the shift from scrappy execution to scalable systems. The conversation also touches on building a business while navigating new motherhood and why patience becomes a strategic advantage for long-term founders.
Together, they unpack when founders should and should not hire their first salesperson, why most teams make that hire too early, and what founders can do from day one to prepare for a future sales engine. Jess breaks down the importance of call recordings, CRM discipline, and founder-led learning loops that turn real sales conversations into training, content, and leverage.
The episode also explores why founder-led content and personal brand accelerate trust in high-consideration B2B sales, especially for services and early-stage companies. Jess reframes visibility as service, not self-promotion, and explains how content becomes a scalable alternative to one-to-one relationship building. They also discuss the trade-offs between scalability and mission, why some businesses are inherently harder to scale, and how founders can create leverage without defaulting to headcount.
Key Takeaways
✅ When founders should transition from founder-led sales to hiring reps
✅ Why recording sales calls early creates long-term leverage
✅ How personal brand builds trust at scale in B2B services
✅ Why visibility feels uncomfortable but drives pipeline
✅The trade-off between scalability and staying true to your mission
✅ Why no business model is actually "easy"
Connect with Jess Schultz
Guest LinkedIn: https://www.linkedin.com/in/jess-schultz (Amplify Group Founder & CEO)
Instagram & Newsletter Links: https://linktr.ee/jessicatschultz
Amplify Group Website: https://www.amplifyscales.com/
This episode is powered by Outworks.
Outworks helps B2B companies build real, repeatable executive content engines through founder-led strategy, tight systems, and AI-powered content infrastructure designed to scale without losing authenticity.
Learn more at https://www.outworks.io
