How to Scale Enterprise Sales with A Team of 11 | Eon Media AI | Ashish Agarwal | EP 110

Scaling looks glamorous until enterprise customers start pulling you in ten different directions.

Ashish Agrawal built an AI company serving NBC Sports, Comcast, the PGA Tour, WWE, and U.S. Olympic teams—with just 11 people, no outsourcing, and no external funding. The secret wasn’t working harder. It was refusing to fracture the product.

In this conversation with host Roland Siebelink, Ashish breaks down what it actually takes to scale without breaking: staying product-led while serving enterprise customers, designing workflows that adapt without customization chaos, and building a team that understands customers deeply—not just tickets and specs.

Key Discussion Points

00:00 – Why most teams break as they scale 01:40 – Serving enterprise customers with a team of 11 03:15 – One product, many workflows (without customization hell) 05:23 – Why everyone on the team talks to customers 07:58 – Building an advisory board that actually adds value 11:14 – The hidden value trapped in archival content 13:55 – Pricing based on volume, not complexity 15:05 – Owning the full workflow end-to-end 17:17 – Partnerships, awards, and non-exclusive growth 19:54 – The hardest challenge: helping customers see their own value 22:31 – Why staying bootstrapped was a strategic choice 24:09 – Long-term growth and exit thinking 26:12 – Courage, problem-solving, and founder mindset 32:01 – Creating autonomy without chaos inside small teams

If you’re a founder or operator navigating enterprise complexity, metadata debt, or the pressure to “just make this one exception,” there’s a lot here for you.

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