Podcast Summary: Revenue Builders

Episode: Scaling Sales at a Startup with Chris Risig

Hosts: John McMahon, John Kaplan
Guest: Chris Risig (Five-time CRO at early stage tech companies)
Date: November 2, 2025

Episode Overview

This episode features an in-depth conversation with Chris Risig, a veteran CRO with deep experience in scaling sales organizations at raw startups. The discussion focuses on the delicate journey from finding product-market fit to building a repeatable sales motion, the challenges in leadership transitions as startups evolve, and actionable advice for founders navigating early-scale environments. The tone is candid and instructive, offering concrete takeaways for sales leaders, founders, and anyone involved in startup growth.

Key Discussion Points & Insights

1. The Startup Sales "Jack of All Trades" Phase

[01:10 - 02:53]

• Role Blending: Early-stage sales leaders must wear many hats – not just selling, but acting as unofficial product managers and customer advocates.

• Customer Proximity: Being present “on those first 20 deals” is essential for gathering firsthand insights about objections, customer reactions, and competitive landscape.

• Communicating Insights: Feedback from sales must continually inform product development, requiring clear communication channels between sales and engineering.

  “You’re almost a product manager and a sales professional at the same time...from customer 1 to customer 20, that’s the mode you’re in…”
  – Chris Risig [01:10]

2. Prioritization and Focus: What to Build First

[03:21 - 04:46]

• Resource Constraints: Startups can’t build everything; leaders must filter customer feedback and prioritize features that drive “immediate revenue and differentiate us in the marketplace.”

• Investor Alignment: Early investors look for different proof points than those at growth stage. Open dialogue with investors can help clarify priorities.

  “You really have to focus...what will have the biggest impact in our ability to generate revenue off this product?...What things do we maybe put to the side for a while?”
  – Chris Risig [03:21]

3. Pain-Based Selling and Repeatability

[04:46 - 06:19]

• Hunt for Pain: Acute customer pains signal genuine, monetizable needs – the foundation for early product differentiation.

• Sales Prioritization: The deeper and broader the customer pain, the higher the priority to build solutions addressing it.

• Iterative Learning: Don’t settle for “interesting but not relevant” problems; without significant pain, customers won’t buy.

  “Unless you have something painful enough for a customer to invest money and time in, it’s interesting but not relevant. They’re not going to do anything.”
  – Chris Risig [05:06]

4. Building Repeatability: When to Hire Your First Sales Reps

[06:19 - 07:44]

• Pattern Recognition: When multiple sales campaigns trigger “the same customer reaction at the same point,” repeatability is emerging.

• Scalability Reality: If only founders/early executives can close deals, it’s not scalable. Real momentum comes when new reps can win deals consistently.

• Investor’s Eye: Investors value seeing deals close without heavy founder involvement.

  “Unless you can teach other people beyond the founder and first sales leader to close a deal...you don’t have a scalable business.”
  – Chris Risig [06:41]

5. Founder Dependence vs. Scalable Sales

[08:10 - 13:30]

• Letting Go: Technical founders often struggle to relinquish control of sales, viewing their involvement as a badge of honor or necessity.

• Coaching Founders: Key to scaling is helping founders recognize WHEN to step back, with a general rule: by 6-12 months, effective delegation should occur if product-market fit is validated.

• Vision vs. Focus: Founders’ ambition (“floor wax and a dessert topping”) can overwhelm early teams. The advice: maintain the vision, but deliver value in “bite-sized chunks” that sales teams and customers can understand and buy.

• Burning Capital: Avoid the trap of over-expansion (“spread sales guys all across every city”), which often leads to wasted resources if not grounded in demonstrated ICP fit and repeatability.

  “If that stage goes on more than the first 6 to 12 months, something’s not right. Either the technology’s not solving a problem...or that founder is not willing to give up control.”
  – Chris Risig [09:29]

  “You gotta break that big vision down into bite-sized chunks…especially if you’re building something new in a new category.”
  – Chris Risig [12:03]

Notable Quotes & Memorable Moments

• On Pain-Based Prioritization:
  “The deeper the pain, the more cost involved in not doing something…people spend money to solve that.”
  – Chris Risig [05:06]

• On Early Founder Involvement:
  “There are stages where it’s appropriate for the founder to be in every single sales discussion…but if that stage goes on more than the first 6 to 12 months, something’s not right.”
  – Chris Risig [09:29]

• On Scaling Sales Teams Prematurely:
  “(I've) seen a lot of founders that basically get a bunch of money and spread sales guys all across every city on the continent…and then they try to back up and now they burnt an awful lot of money doing it.”
  – John Kaplan [13:30]

• On Finding Repeatability:
  “When you start to see a recurring pattern… the customer lights up because they have pain…you start to say, okay, now I have some sense of repeatability.”
  – Chris Risig [06:41]

Important Timestamps

• [01:10] – Chris Risig explains the early startup sales/product management duality.
• [03:21] – Discussing prioritization of feature development and investor expectations.
• [05:06] – The necessity of finding real customer pain.
• [06:41] – Deciding when it’s time to hire more salespeople.
• [09:29] – Coaching founders on stepping back from day-to-day sales.
• [13:30] – The pitfalls of premature sales team expansion and the need for disciplined focus.

Summary & Takeaways

• Early sales at startups are intensive, multifaceted, and demand direct customer and product advocacy.
• Real growth begins when customer pain aligns with repeatable solutions and non-founder sales hires can independently win deals.
• Founders must learn to step back at the right moment—clinging too long can stall scale, while letting go too soon, before repeatability, is risky.
• Grand visions should be modularized into digestible, sellable pieces to secure early traction and pave the way for sustainable growth.
• Rapid, unfocused expansion burns capital and rarely results in sustainable sales traction. Stay disciplined and persistent in your focus.

For more insights, listen to the full episode of Revenue Builders with Chris Risig, John Kaplan, and John McMahon.