How to Scale Enterprise Sales with A Team of 11 | Scaling Without Breaking | EP 110

Описание: 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.

👍 Like if this challenged how you think about scale
🔔 Subscribe for more honest conversations about growth
💬 Comment with your biggest takeaway
🔗 Share this with someone navigating enterprise complexity

#ScalingWithoutBreaking #StartupLeadership #EnterpriseSaaS #FounderMindset #ProductLedGrowth #Bootstrapped #EonMedia #OperationalExcellence