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.
What Sales Leaders Can Learn from Scaling with Authenticity: Lessons from Jeff Kirchick
Jeff Kirchick has led sales at four venture-backed startups, including three successful exits. He’s closed seven-figure enterprise deals, built sales teams from scratch, and literally wrote the book on how to keep it real in sales: Authentic Selling.
In this episode of Knocking to 10, Jeff unpacks what makes a startup sales org work (or not), how to scale with soul, and why authenticity is still the most powerful sales tool on the planet.
From Ivy League to First Sales Job: Don’t Fake It
Jeff graduated from Princeton with a creative writing degree and turned down jobs in sports and teaching to take an entry-level sales job at a mobile payments startup. That company, LevelUp, pivoted multiple times, and Jeff learned early on how to thrive in chaos.
He was quickly thrust into leadership—not because he had a playbook, but because no one else was stepping up.
Key Lesson for Sales Leaders: Look for people who take initiative when there’s no map. The best early hires aren’t the ones with perfect resumes—they’re the ones who turn ambiguity into action.
Why Most Startups Get ICP Wrong
After LevelUp, Jeff led sales at NextCaller (acquired by Pindrop), Able AI (acquired by Moody’s), and Allwhere. One pattern he saw across companies: teams spend way too much time talking to the wrong leads.
“You end up kissing a lot of frogs before you realize what makes someone truly qualified.”
Key Takeaway: Don’t just filter by company size and job title. Think about timing, buying behavior, adjacent tools, and even internal politics. And start measuring this early so you can double down on what works.
How to Balance Frameworks with Flexibility
Jeff believes in sales methodologies like MEDDICC—but only when used as a framework for reflection, not a script to follow.
“The moment you start checking boxes instead of listening, you're done.”
Advice for New VPs of Sales:
What AI Can’t Replace
Jeff’s cold email strategy isn’t about fake personalization or ChatGPT-written intros. It’s about signaling shared values and building trust.
“AI can replicate facts. It can’t replicate a shared experience.”
Instead of mentioning someone’s college or job title, Jeff writes emails that show he understands the person on the other end. And it works. His framework has been used across his teams to consistently get replies like: “This is the best cold email I’ve received.”
How to Stay Grounded in High-Stakes Sales
One of Jeff’s core philosophies is detachment from outcome.
“You are not your quota.”
It sounds simple, but it’s a mindset most salespeople and founders struggle to adopt. Jeff credits this attitude with helping him stay centered through rejections, layoffs, and chaotic startup pivots.
Lessons from the Other Side of the Table
Now also an angel investor and advisor, Jeff looks for:
“Experience matters, but clarity of thought and self-awareness matter more.”
Final Advice for Sales Leaders
“Don’t work for a first-time founder without asking the hard questions. And don’t try to lead without listening.”
Listen to the full episode of Knocking to 10 to hear Jeff’s playbook for authentic, effective sales leadership—especially if you’re building from zero.
Follow Jeff on LinkedIn or pick up his book Authentic Selling to learn more.
