In this episode of Sales Is King, Dan sits down in the new Midtown Manhattan studio with Craig Bowman, SVP of Public Sector at Trellix and author of the new book Craft: CIA Elite Selling. Craig brings a wild career arc to the mic—from clandestine work with the CIA and the intelligence community to building high‑performing sales teams at Adobe and now leading public sector growth at scale.
Craig unpacks how CIA tradecraft, “mission first” thinking, and AI can radically upgrade how you prospect, qualify, and win in complex B2B deals.
Key topics covered
- The CIA recruitment story: from a mysterious hotel lobby interview, underground parking garages, and VCR‑filled rooms to landing his first role under commercial cover.
- Moving from intelligence to entrepreneurship: starting, scaling, and selling his own government contracting company, then returning post‑9/11 for a new mission.
- Jumping into sales at Adobe: how he was recruited, doubled his salary, and built a new intelligence division by deeply understanding the mission—not just the tech.
- “In the mud with the customer”: why Craig literally went to the southern border with CBP to understand the mission and coined his mantra about getting in the trenches.
- Influence maps vs org charts: why the real power sits with the “knuckle‑draggers” in the back of the room, not just the CIO, and how to find and engage true influencers.
- Frameworks without rigidity: his take on MEDDIC, Challenger, and why you coach the bottom half differently while using top performers as mentors to “shift the middle.”
- The AI inflection point: how he rewrote his book mid‑stream to integrate AI, and why he now spends 70% of his time using AI agents as a personal chief of staff.
- Craig’s live AI workflow: daily scripts that summarize email, corporate updates, and account intel; auto‑generated dossiers, personas, and value hypotheses.
- The 90‑Second Takeover: how to send a pre‑meeting hypothesis of value, then open meetings with clarity, validation, and a working session instead of random discovery.
- Humility as a superpower: the intern experiment that proved “humility emails” beat cold calls, and why genuine curiosity and asking for help unlock meetings.
- AI from the buyer’s side: why your customers are already using AI to shortlist vendors and how you should be using AI the same way to qualify where you can truly win.
- Metrics that actually matter: the question Craig asks every customer about how they’ll measure value 7 months after buying—then how he uses that in MEDDIC the right way.
- The seven criteria of a successful seller: why he evaluates inputs (character, curiosity, rigor) rather than just outputs (pipeline, quota).
- Mentors and pivotal leaders: from his grandfather and tough college professor to powerful women leaders in the intelligence community and sales leaders like Ken Karsten.
Who this episode is for
- Enterprise and public sector sellers trying to win complex, multi‑stakeholder deals.
- Sales leaders looking to blend frameworks like MEDDIC with modern AI and real coaching.
- Rev leaders who want their teams “in the mud with the customer” instead of stuck on Zoom.
Listen for these takeaways
- Why you must deeply understand your customer’s mission—and often physically go to the “border” or “boat”—before pitching technology.
- How to build influence maps, not just chase titles on an org chart.
- A tested AI + email play that interns used to book meetings your team “could never get.”
- A simple question that turns MEDDIC metrics from guesswork into a mutual accountability pact.
Connect with Craig
- Book: Craft: CIA Elite Selling on Amazon (hardcover, ebook, and audiobook).
- Bonus material & AI scripts: unlock the members section using the book, or message Craig on LinkedIn if you bought the audio version.
If you’re tired of canned discovery, bad qualification, and random acts of prospecting, this conversation will change how you think about mission, AI, and what “elite selling” really looks like.
