AI won't fix your sales team: Coaching and champions still rule

Aug 27, 2026 · The Revenue Builders Podcast
🎧 PodShort 59 min squeezed to 2 AI SprinklerAS Sales Tech New
Episode artwork
Sam Costello
Chief Revenue Officer at Harvest
The Revenue Builders Podcast
59 min squeezed to 2
Full episode from The Revenue Builders Podcast
Quotable Moments

You know, if you want to build something that doesn't fail, you got to build something that you want to build yourself.

Sam CostelloChief Revenue Officer at Harvest
01:55

The ingredients of great companies are actually pretty hard to find.

John CaptainCo-Host, Revenue Builders Podcast
00:02

If you don't build trust, you can't build any skills yet, so you're just randomly going to get the best of the conversation.

Sam CostelloChief Revenue Officer at Harvest
08:56
Key Insights
  • The ingredients of great companies are difficult to find and replicate, including strong founders, large markets, differentiated technology, and inspired sales teams.
  • Distinguishing between a good sales rep and a truly great one often comes down to their ability to identify and articulate the core business problem they are solving and how their solution addresses it.
  • A key to successful sales coaching is focusing on the rep's motivation beyond just money, such as their desire for personal growth and becoming a better version of themselves.
  • The 'Duplo' sales process emphasizes finding a champion first and then building everything else around that relationship.
  • Many companies fail to scale because they don't evolve their champions as the deal size or complexity increases, leading to stalled opportunities.
  • The most critical factor in a successful sales process is having a champion who truly understands the problem, has confidence in the solution, and can influence others within their organization.
  • AI is transforming the sales landscape by automating repetitive tasks, but human interaction and the ability to build relationships remain crucial for closing complex deals.
  • The best way to secure funding for sales initiatives is by demonstrating a clear link between the technology's capabilities and a tangible business outcome for the customer.
Metrics Mentioned
  • Moved from under $1 million in ARR to $100 million in 5 years (Sam Costello's growth trajectory at Harvest.)
  • Spends 40% of time on recruiting (Sam Costello's time allocation as CRO.)
  • Spends 20% of time on customer-facing activities (Sam Costello's time allocation as CRO.)

RevBots.ai View:

  • AI Sprinkler stage: AI bolted on but strategic selling skills still dominate.
  • SaaS Hoarder risk: Coaching tools proliferate without integrated strategy.
  • ARM potential: AI could augment coaching but human judgment remains key.
  • Tab Hopper trap: Founders must systematize champion-building early.
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