I had the pleasure of speaking on GTM strategy in the era of AI with Chris Sheehan and Sunny Shih from AI Circle (Albert Chun Brian Lee Audrey Wakefield)

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I had the pleasure of speaking on GTM strategy in the era of AI with Chris Sheehan and Sunny Shih from AI Circle (Albert Chun Brian Lee Audrey Wakefield)

Here are some highlights and insights:

Things that separate founders who scale from founders who spin:

1. Define your ICP with ruthless specificity — then hold it loosely. In the AI era, your ICP might only last 6-12 months. Validate with real customer conversations, not assumptions. If you can't describe in one sentence who buys, why they buy, and how they found you, your positioning isn't clear enough.

2. Instrument your funnel from day one. Even a spreadsheet. Source, time-to-close, conversion rates, and deal values. You can't scale what you can't see.

What AI tools can actually do for your GTM right now:

1. Automate the admin that kills your momentum. Prospect research before a call — ChatGPT, Claude, Gemini, with a standardized prompt library. Call recording and transcription so nothing falls through the cracks. CRM data entry that actually happens. Follow-up emails, one-pagers, and decks generated from call data instead of a blank page.

2. On the BDR side: Apollo for cadence tracking, Sales Navigator for prospecting (still one of the best channels), Attio or free HubSpot for CRM. Luster AI for sales coaching, feed it your training material, and it interacts with your reps.

3. For legal: Harvey AI and cheaper tools for understanding contract risks before you loop in outside counsel.

What AI won't replace in GTM:

1. The human discovery conversation. Reading the room when a prospect says "interesting" but means "I'm not buying." Knowing that the founder who spent 25 minutes of a 30-minute call talking about product features just lost the deal because GTM is about solving customer problems, not showcasing capabilities.

2. AI won't teach you to pause when a prospect asks, "Do you have this feature?" and ask why they want it instead of promising it's on the roadmap. It won't help you build the trust that makes an enterprise buyer put their career on the line choosing a startup over an incumbent. It won't do your relationship mapping, three influencers, two champions, one budget holder, and know which one actually forces change inside the org.

3. And it won't replace the first GTM hire you actually need: a curious generalist with 2-5 years at startups, thick skin, high EQ, and comfort talking about money. Not yet. Maybe not ever.D

If you're an AI or SaaS founder figuring out your GTM motion, or an exec wondering why the pipeline isn't converting, I'd genuinely like to hear what's stuck. DM me. That's the kind of conversation I live for.

 

CEO

Go-To-Market executive with 20 years of experience accelerating growth in retail, e-commerce, and marketplaces.

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