Skeptic to Signed: How an AI Sales Tool Finally Won Over a CMO

How a VP of Post-Sale Navigated 8 Stakeholders to Buy Onboarding Software

Alicia is the VP of everything post-sale at Daxko's boutique division. She inherited a 234-step manual onboarding process and an average of 17 emails per customer deal. After a 90-day internal sprint with her CTO cut the problem by only 30%, a company acquisition finally unlocked the budget to look outside. A teammate surfaced Onramp. The demo went well. Then pricing hit the table -- and it cost more than Daxko's entire Salesforce contract. In this episode, Alicia walks us through: * Why she pumped the brakes on the AE's attempts to reach her boss -- and what it would have taken to actually get there * The moment a pricing comparison to Salesforce stopped the deal in its tracks mid-call * How the AE responded to losing momentum without trying to objection handle -- and why that kept him in the game * What it looks like when a seller earns a seat on the buyer's side of the table If you sell into customer success, post-sale tech, or anything with a complex onboarding story, this one's for you. Guest: Alicia, VP of Post-Sale at Daxko Hosts: Jen Allen-Knuth & Drew Giovannoli -------- Drew Giovannoli | Buried Wins 1:1 buyer interviews that learn from recent wins, lost prospects, and your competitors' customers who never considered you. → buriedwins.com Jen Allen-Knuth | DemandJen Train your sales team to sell the way buyers buy. Workshops and coaching grounded in data. → demandjen.com

The HubSpot Sales Rep Was Great. The Implementation Partner Almost Ruined It.

Rob runs marketing at LockThreat, an early-stage GRC startup he joined with no MarTech stack and one strong conviction: they needed HubSpot. First he had to survive two failed Zoho consultants and months of internal politics just to get approval to switch. The HubSpot sales rep was excellent. The implementation partner was a disaster. And now the guy who fought hardest to bring HubSpot in can't bring himself to recommend it. In this episode, Rob walks us through: * Why two Zoho consultants failed and what finally got him approval to switch * What the HubSpot sales rep did that made the buying process easy * How a cookie-cutter implementation partner broke his data, ghosted him, and then got aggressive * Why a great sales process could not protect his reputation when the partner fell apart If you sell CRM, MarTech, or implementation services, this one's for you. Guest: Rob, Head of Marketing at LockThreat Hosts: Jen Allen-Knuth & Drew Giovannoli More research at buyertruths.com We Surveyed 172 Buyers. Now Let Us Help You Win Yours. Research to understand them. Training to close them. Drew Giovannoli | Buried Wins 1:1 buyer interviews that learn from recent wins, lost prospects, and your competitors' customers who never considered you. buriedwins.com Jen Allen-Knuth | DemandJen Train your sales team to sell the way buyers buy. Workshops and coaching grounded in data. demandjen.com

How a $500M SaaS RVP Bought an AI Writing Tool to Close a Sales Skill Gap

div]:bg-bg-000/50 [&_pre>div]:border-0.5 [&_pre>div]:border-border-400 [&_.ignore-pre-bg>div]:bg-transparent [&_.standard-markdown_:is(p,blockquote,h1,h2,h3,h4,h5,h6)]:pl-2 [&_.standard-markdown_:is(p,blockquote,ul,ol,h1,h2,h3,h4,h5,h6)]:pr-8 [&_.progressive-markdown_:is(p,blockquote,h1,h2,h3,h4,h5,h6)]:pl-2 [&_.progressive-markdown_:is(p,blockquote,ul,ol,h1,h2,h3,h4,h5,h6)]:pr-8"> _*]:min-w-0 gap-3 standard-markdown"> How a $500M SaaS RVP Bought an AI Writing Tool to Close a Sales Skill Gap Keith is an RVP at Bullhorn, a $500M CRM and ATS platform for recruiting and staffing firms. When he noticed a communication skill gap across his 35-person mid-market sales team, he didn't go looking for a vendor. He already knew one. He had been following Nate, the founder of Fluint, on LinkedIn for years and had even bought his sales course before the software existed. No RFP. No competitive evaluation. A paid pilot, a 45-day window, and a budget freed up by cutting licenses from a tool nobody was using. In this episode, Keith walks us through: * How years of following a founder on LinkedIn became the entire buying process * The pilot criteria he used and why qualitative signals mattered more than metrics * How he freed up budget by auditing existing tools before adding a new one * Why the vendor that lost found out they were losing only when Keith told them If you sell AI tools, sales enablement, or anything where adoption is the real risk, this one's for you. Guest: Keith Weightman, RVP at Bullhorn Hosts: Jen Allen-Knuth & Drew Giovannoli More research at buyertruths.com We Surveyed 172 Buyers. Now Let Us Help You Win Yours. Research to understand them. Training to close them. Drew Giovannoli | Buried Wins 1:1 buyer interviews that learn from recent wins, lost prospects, and your competitors' customers who never considered you. → buriedwins.com Jen Allen-Knuth | DemandJen Train your sales team to sell the way buyers buy. Workshops and coaching grounded in data. → demandjen.com

Skeptic to Signed: How an AI Sales Tool Finally Won Over a CMO

Kathleen is a CMO who was first introduced to One Mind through a trusted VC referral, not a cold pitch. What started as a novelty demo featuring digital Deepak Chopra took two years to become a signed contract, as the tech matured, use cases sharpened, and the One Mind team methodically built trust across her entire buying committee. The deal was tens of thousands of dollars, and she signed before her team was even ready to implement. In this episode, Kathleen walks us through: * The exact demo moment that shifted "this is cool" to "this is a real business case" * What One Mind did to multithread around her as a champion and why she had to step back to let it work * How a glitchy live demo at their annual conference delayed the deal by four to five months * Why she signed a contract with a five-month delayed start date and what built enough trust to make that feel safe If you sell early-stage AI tools or anything that requires a long internal buy-in process, this one's for you. Guest: Kathleen, CMO Hosts: Jen Allen-Knuth & Drew Giovannoli More research at buyertruths.com We Surveyed 172 Buyers. Now Let Us Help You Win Yours. Research to understand them. Training to close them. Drew Giovannoli | Buried Wins 1:1 buyer interviews that learn from recent wins, lost prospects, and your competitors' customers who never considered you. → buriedwins.com Jen Allen-Knuth | DemandJen Train your sales team to sell the way buyers buy. Workshops and coaching grounded in data. → demandjen.com

How a CMO Evaluated 3 Headless CMS Platforms (Then Built His Own)

Pete Vomocil 💛 is a CMO overseeing marketing for a 1,800-person company while running new ventures on the side. When his team needed a headless CMS that could serve both heavy-duty engineering and self-serve marketing, his engineering team screened 20 vendors down to 6. Three made it to finalist calls. The vendor with the best sales orchestration won. A year later, Pete ripped it out and rebuilt the entire platform himself in 4 weeks. In this episode, Pete walks us through: * Why he'll instantly disqualify vendors for "woo-woo" * What separated good sales orchestration from great across the 3 finalist calls * The onboarding gaps that killed the deal despite a well-run sales process * Why delayed vendor follow-up led a non-technical CMO to build a full-stack platform himself If you sell CMS, martech platforms, or anything with complex onboarding, this one's for you. Guest: Pete, CMO Hosts: Jen Allen-Knuth & Drew Giovannoli More research at buyertruths.com We Surveyed 172 Buyers. Now Let Us Help You Win Yours. Research to understand them. Training to close them. Drew Giovannoli | Buried Wins 1:1 buyer interviews that learn from recent wins, lost prospects, and your competitors' customers who never considered you. → buriedwins.com Jen Allen-Knuth | DemandJen Train your sales team to sell the way buyers buy. Workshops and coaching grounded in data. → demandjen.com