Jeff Kirchick, author of Authentic Selling and veteran VP of Sales, shares how to build trust, close big deals, and scale GTM teams—without losing your voice. From early-stage playbooks to angel investing, this episode is packed with real talk for sales leaders and founders.
In today’s rapidly evolving business landscape, the art of selling is more complex and nuanced than ever before. While many are tempted to adopt a strict adherence to established sales processes, a shift toward authenticity may provide a robust competitive advantage. Jeff Kirchick, a seasoned sales leader, advises multiple seed-stage startups and has successfully navigated multiple high-stakes exits, offers valuable insights into the realm of authentic selling.
Sales careers often begin with a diverse range of responsibilities, which can create a unique path for each individual. Jeff Kirchick’s journey, for example, evolved from diverse beginnings, detailing how he "did English and creative writing as my major" and took a winding path through different interests before achieving success in sales leadership roles.
In the sales industry, authenticity is not just a buzzword; it’s a critical strategy for building trust. Kirchick explains, "People just trust authentic people. If you present an honest version of yourself, it doesn’t matter if you're likable or not, people will believe what you say." The idea that authenticity can cultivate trust is the cornerstone of developing long-term business relationships.
Sales is both a science and an art. While the artistic side might come naturally to some, mastering the scientific aspects requires intentional personal development and strategic frameworks. Kirchick insists, "The framework is a way for you to be accountable and honest about what you have in your deal." This approach helps sales teams use structured methodologies like MEDDIC, while also allowing room for individual authenticity.
Kirchick offers a balanced view of AI in sales, acknowledging its potential without succumbing to the hype. He states, "Generative AI... lacks the context on your shared experience and experience beyond public information." Instead of relying solely on technology for personalization, combining insights to establish shared values with prospects creates a genuine connection that AI struggles to replicate.
Salespeople are often faced with fickle markets and unpredictable outcomes. An essential lesson is to remain detached from isolated results — viewing setbacks as opportunities for learning rather than failures. Kirchick shares, "We place disproportionate emphasis on whatever’s right in front of us," emphasizing the importance of maintaining perspective and resilience.
Kirchick highlights the essential qualities for hiring a successful sales team post-Series A: "Someone who knows how to hire and develop really good talent and build out an A-plus team" is crucial for growth.
The overarching message from Kirchick is the commitment to genuine relationships and taking a long-term view. "Treat people like people and not like dollar signs," he advises. By fostering authentic relationships and being patient, sales leaders can achieve sustainable success and longevity in their careers.
