AI companies win markets when buyers understand them.
I help B2B technology leaders build the GTM clarity to convert buyer interest into revenue: positioning and segmentation through commercial model design.
How I Can Help
Four structured engagements. Each is scoped, priced, and outcome-focused.
Research-backed. Execution-ready.
When you build something worth selling, product centricity comes naturally. The conviction that comes with it is real and worth keeping. The problem is that buyers aren't evaluating your product. They're trying to achieve an outcome: grow revenue, cut costs, reduce risk, or improve the experience of their customers and teams. It's always some constellation of those four things. Vendors who lead with their product make buyers do the translation work. The vendors who win have already done it for them.
"You do not generate demand. You enable buyers."
Recent Thinking
Original frameworks and market commentary, published here and on LinkedIn.
Ready to get GTM-clear?
Most engagements start with a 30-minute conversation. No pitch, no obligation. Just a direct read on where you stand and whether working together makes sense.
Book a Free 30-Minute CallI help AI companies sell to the buyers they already have.
For most of my career, I studied how enterprise organizations buy technology, not how vendors sell it. That distinction matters. The gap between those two perspectives is where most AI GTM strategies fail.
The research background
I spent years as a Research Director at Gartner, where I published original work on AI buyer segmentation, CFO buying behavior, commercial model innovation, and the structural dynamics shaping how enterprise technology gets purchased. That research informed the GTM strategies of major technology vendors and gave me an unusually precise view of where those strategies succeed and where they break.
The operating layer
Alongside that research background, I co-founded ClearlyKept, a software business that gave me direct exposure to what it actually takes to build a product, reach customers, and convert interest into revenue. Research tells you what should work. Operating experience tells you what does.
The practice
Today I work independently with B2B technology companies, primarily seed through Series B, helping them build go-to-market clarity for their AI products. That means sharper buyer segmentation, cleaner positioning, more effective commercial models, and GTM playbooks that teams can actually execute from.
What I believe
- Most AI GTM problems are really positioning problems in disguise.
- The best commercial models are designed around how buyers buy, not how vendors want to sell.
- Strategy without execution mechanics isn't strategy. It's a document.
- Frameworks earn their value when they travel without you.
Based in Charlotte, NC. Working with clients across North America.
Four engagements. All outcome-focused.
Every engagement below is scoped, priced, and structured around a specific outcome. No hourly rates, no open-ended retainers with vague deliverables. If you're not sure which one fits, the GTM Clarity Sprint is almost always the right starting point.
GTM Clarity Sprint
Your AI product has real value, but the GTM isn't landing. Prospects don't self-select correctly. Sales conversations start with education instead of qualification, and the pipeline is inconsistent and hard to explain.
- ICP and buyer persona assessment: who is actually buying, and who should be.
- Positioning and messaging architecture critique: what's working, what isn't, and why.
- AI buyer readiness segmentation: where your buyers sit across the readiness spectrum.
- Commercial model gap analysis: how you're pricing vs. how your buyers actually buy.
- Top 3 prioritized GTM actions with rationale and recommended owner.
Pricing: Seed / Series A: $3,500–5,000 | Series B–D: $6,000–8,500
Book a call to discuss →GTM Build
You know what needs to change. Maybe you've just completed a Clarity Sprint, or you've been sitting on a diagnosis long enough. Either way, you need to actually build the GTM architecture. The team needs something they can execute from, not another deck.
- Full ICP and buyer persona documentation.
- Positioning and messaging hierarchy (website, sales deck, one-pager).
- Buying journey map: Problem Identification → Solution Exploration → Requirements → Vendor Selection.
- Buyer enablement content recommendations.
- Commercial model design, including pricing and packaging recommendation.
- Go-to-market narrative and storytelling framework.
- 90-day GTM execution roadmap with accountability mapping.
Pricing: Seed / Series A: $8,000–12,000 | Series B–D: $15,000–22,000
Book a call to discuss →Strategic Advisory Retainer
You don't need a full-time GTM hire. You need a senior strategic partner who can challenge your thinking, pressure-test your narrative, and help you move faster on the decisions that matter most.
- 2–3 video sessions covering strategy, deck reviews, board prep, and investor narrative.
- Async Slack/email access with a 24-hour response SLA (Mon–Fri).
- Ongoing GTM positioning and messaging review.
- One major deliverable per month: a sales narrative review, investor pitch critique, buyer persona update, or positioning refresh.
Pricing: Seed / Series A: $3,500–5,000/month | Series B–D: $7,000–10,000/month
Currently accepting 2–3 retainer clients. Inquire for availability.
Book a call to discuss →Buyer Readiness Workshop
Your GTM and product leadership team isn't aligned on who your buyers are, how ready they are to buy, or what it means for how you position and price.
- Full-day facilitated session, including pre-session preparation and follow-up synthesis.
- A completed AI Buyer Segmentation Map for your specific product and market.
- Top 3 GTM positioning hypotheses to test in the next 30–60 days.
- Shared language across your leadership team for discussing buyer dynamics.
GTM and product leadership teams at Series A–C companies preparing for a strategic inflection: a new product launch, pricing revision, category repositioning, or Series B fundraise.
Pricing: $9,500–14,000 flat fee
Covers the full day of facilitation, pre-session prep, follow-up synthesis, and travel/on-site expenses for in-person engagements.
Book a call to discuss →Frameworks, observations, and the occasional strong take.
Published work on AI go-to-market strategy, buyer dynamics, and commercial model design. Most of this also lives on LinkedIn. Follow along there for shorter-form commentary.
Kill Your Roadmap. Grow a Rhizome.
The linear roadmap is a bet on a future you can predict. In an agentic world, that bet is increasingly bad. Products that win won't be the ones with the best-planned release schedule. They'll be the ones architected to capture emergent value as it appears. A rhizomatic product strategy replaces prediction with detection: sensing where value is forming in the ecosystem and moving toward it in real time, rather than locking in a feature list six months in advance.
The Autonomous Business Inflection
We're past the point where AI is just a feature or an efficiency play. The companies gaining structural advantage right now are redesigning their operations, products, and business models around autonomous decision-making, not layering AI onto processes built for human speed. That shift has direct consequences for how B2B AI vendors need to position, price, and sell.
Why Your AI Pilot Isn't Converting to Production
The AI pilot trap is real, and it's not a sales problem. It's a commercial model problem. Most AI vendors design their pilots the way they design their demos: optimized for technical validation, not for organizational commitment. The result is a pipeline full of "successful pilots" that never move forward.
Introducing the Buyer Readiness Map
Buyers exist across a spectrum of AI readiness, and where a buyer sits on that spectrum determines almost everything: how they evaluate you, what objections they raise, how long the sales cycle runs, and what commercial model they'll accept. The Buyer Readiness Map is a framework for segmenting your market by AI risk tolerance and strategic expectation, then using that segmentation to design GTM strategy that actually fits the buyer you're targeting.
Let's talk.
The fastest way to figure out whether working together makes sense is a direct conversation. Book a 30-minute call below. No pitch, no pressure. Just an honest read on where you stand and whether there's a fit.
Book a 30-Minute CallPrefer email? Reach out at garrett.astler@clearlykept.com. Expect a response within 1 business day.
Based in Charlotte, NC. Working with clients across North America. Remote-first.