Ep. 31: Avoiding POC Hell to win a $4 million enterprise deal in 10 months with Jake Dunlap

Jake Dunlap, CEO and Founder of Skaled Consulting, has worked on thousands of deals, and now he shares his expertise with organizations looking to accelerate their growth. In this episode he recounts a three part deal that grew to $4M in ten months and the sales strategies and philosophies to get there.


  • Jake Dunlap is CEO Skaled Consulting.
  • Has worked on thousands of deals and shares one from earlier in his career that shaped future strategies

Key Challenges:

  • Adapting to client budget cycles.
  • Overcoming traditional contract limitations.
  • Navigating enterprise decision-making timelines.

Key Learnings:

  • Importance of aligning with client budgets.
  • Using "proof of concept" and "proof of scale" for deal expansion.
  • Flexibility in contracts secures larger partnerships.


  • (1:28) Discussion on Strategic Sales Contracts and Aligning with Client Budget Cycles
  • (6:05) Challenges in Adapting Sales Strategy to Enterprise Decision-making
  • (10:06) Insights on Utilizing "Proof of Concept" to "Proof of Scale" for Deal Expansion
  • (15:04) Jake's Learnings on Flexibility and Customer-Centric Contracts
  • (19:30) Conclusion and Key Takeaways

Order Jake's new book at: https://www.jakedunlap.com/the-innovative-seller

Find Jake on LinkedIn:  https://www.linkedin.com/in/jakedunlap/

Join the Innovative Seller Community Summit: https://www.jakedunlap.com/the-innovative-seller-community-summit

Custom GPTs for Sales: https://skaled.com/insights/custom-gpts-for-sales/

Workshop + Prompt Pro: https://bit.ly/accelerator-and-prompt-pro

Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast

Questions, comments, ideas - reach out to: https://www.linkedin.com/in/andrewkappel/

Ep. 31: Avoiding POC Hell to win a $4 million enterprise deal in 10 months with Jake Dunlap
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