The Transaction | The New AI-First Go-To-Market Playbook with David Boskovic, CEO & Founder of Flatfile

The New AI-First Go-To-Market Playbook with David Boskovic, CEO & Founder of Flatfile - Ep 63

August 18, 2025 / 53:02/S2 E63

The old go-to-market playbook is broken, but in this episode we have a B2B SaaS founder who has actually figured out the new GTM playbook to grow in the current market.

This SaaS savant is none other than the one and only David Boskovic, the CEO and Founder of Flatfile, which is the AI-powered data migration solution trusted by enterprise customers like ClickUp, HubSpot, Amazon, ADP, and Toast. David joins co-hosts Matt Amundson and Craig Rosenberg to outline how he and the GTM team at Flatfile developed their new AI-first go-to-market strategy, which is handling ten times the capacity of their previous GTM motions.

David shares which of the 3 ways AI is being deployed works best, why you need to hire for individual contributors based on a candidate’s tastes, and why every Rev Ops team needs to hire an AI Engineer in order to stay ahead of the curve.

Plus, David regales Matt and Craig with potentially the greatest story that’s ever been told on The Transaction, perhaps even better than ‘Maggots on a Plane.’

Also, Craig threatens someone with having to wear a raccoon costume, Matt reveals the secret of what makes Craig great, and Sam the Producer experiments with some AI artwork.

Critical Takeaways

When segmenting your ICP, segment into micro-verticals of 100–500 accounts, so you can then build tailored value propositions, demos, and collateral for each. AI allows this “luxury” level of personalization, which was once reserved for top accounts, to be applied to all targets. This dramatically improves first-call resonance, increases conversion rates, and differentiates your solution in competitive enterprise sales cycles.
AI now allows you to turn things like costly enterprise-grade research into a commodity. Using tools like ChatGPT’s Deep Research or Perplexity you can produce insightful 40+ page market and account reports in hours instead of weeks. Validate quality by testing it with actual prospects. This “luxury” level of diligence, previously reserved for only top-tier accounts, can now be applied to every target at low cost.
Having a CRM isn’t good enough. You should use AI to index every past customer/prospect interaction and extract key insights (budgets, pain points, workflows). Make this context instantly available to reps so every future conversation builds on a rich historical foundation.
Every RevOps team, regardless of size, needs an AI Engineer to rapidly prototype and operationalize AI tools internally. If you want to remain ahead of the curve, you can’t be beholden to the slow development and innovation of tools from other SaaS companies.
Operationalize everything in the company like a product. Treat your revenue org like a software system, debug bottlenecks, design orchestrations, and continuously iterate. The faster your GTM processes can be updated, the faster you can capitalize on new AI capabilities as they emerge.
There are three main ways AI is deployed, Automation/Replacement, Augmentation, and Amplification. Amplification gives you the largest potential outcomes. To use the Amplification approach, deconstruct every GTM role into component tasks, give repetitive or low-value ones to AI, and keep humans focused on peaks of expertise like judgment, taste, and relationships.

Chapters

00:00 - Episode Preview

01:32 - Introducing David Boskovic, The CEO & Founder of Flatfile

02:49 - The Crazy, Raccoon-Filled Story Behind David Starting His First Company

11:35 - Building an AI-First Go-To-Market Engine Internally from Scratch

15:07 - AI Lets You Do The ‘Unscalable’ At Scale with Quality and Affordability

22:02 - Why Segmenting Prospects into Micro-Verticals Increases Your ABM Strategy’s Effectiveness

33:26 - What it Takes to Spin Up an AI-First GTM Strategy & Why RevOps Teams Need an AI Engineer

39:57 - Where is Software Going & Which of The 3 Ways to Implement AI Works Best

47:12 - Why You Should Be Hiring Individual Contributors Based on Their Judgement

51:34 - Sam Debuts Some Interesting AI Artwork of David

Epic Quotes

It is incredibly hard to be optimistic enough about what’s possible” - David Boskovic
“Dream your wildest dreams and see if you can make them happen. And if not, put them on the shelf, not for a year, but for a few weeks.” - David Boskovic
“Part of what makes Craig great is his curiosity. He’s a lifetime learner.” - Matt Amundson

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