In this episode of Inside the 90, Jami reconnects with longtime friend John Sterling, a sales leader and entrepreneur who helped build Data Stream from a small maintenance software company into a $100 million business before it was acquired.
John shares the origin story, including a pivotal one-day consult from marketing legend Al Ries and the discovery of hiring by "avatar" using the Kolbe A Index. The conversation moves into John's current ventures, acquiring aging industrial software companies, coaching sales teams across industries, and experimenting with AI, including a talking avatar of himself and a growing fleet of AI agents running parts of his businesses. The episode closes with reflections on three major tech waves John has lived through: personal computers, the internet, and now agentic AI.
Key Topics
- The origin story of Data Stream, from a four-person company to a $100 million exit.
- How a one-day consult with marketing strategist Al Ries reshaped the company's growth strategy.
- Hiring by avatar using the Kolbe A Index to find repeatable sales talent.
- Lessons on niching down and staying in a market for the long haul.
- The whopper clause and structuring sales commission plans without caps.
- How sales management and accountability have changed with remote and hybrid work.
- Acquiring aging industrial software companies in the so-called silver tsunami.
- Building an AI talking avatar and a fleet of AI agents across multiple companies.
- Reflections on three major tech shifts, personal computers, the internet, and agentic AI.
Chapters
0:00 - Welcome and reconnecting with John Sterling.
1:00 - Origin story of Data Stream and joining Larry Blackwell's company.
4:00 - Al Ries's one-day consult and the strategy to claim market leadership.
6:00 - Growing from five million to one hundred million and the eventual sale.
7:30 - Discovering hiring by avatar with Bill Lee and the Kolbe A Index.
10:30 - Reconnecting with Jim Wanner and the KeyMark success story.
12:30 - Core lessons, being present, niching down, and the whopper clause.
16:30 - Current ventures, acquiring aging industrial software companies.
19:30 - Sales coaching philosophy and structuring comp plans.
22:00 - How sales management and accountability have evolved over time.
25:00 - Coaching clients across industries, including Myrtle Beach Golf Vacations.
27:30 - Building the AI Sales Professor talking avatar.
30:30 - Deploying AI agents across companies for marketing, finance, and M&A.
33:30 - Reflections on personal computers, the internet, and the agentic AI era.
36:00 - Where to find John Sterling and closing thoughts.
Mentions & Credits
Wonder - https://www.workwithwonder.com
EOS Worldwide - https://www.eosworldwide.com
Data Stream Systems - https://www.infor.com/
Larry Blackwell - https://upstatebusinessjournal.com/tech-innovation/clemson-honors-software-entrepreneur/
Al Ries - https://www.alries.com/
Kolbe - https://www.kolbe.com/
KeyMark - https://www.keymarkinc.com/
Jim Wanner - https://www.keymarkinc.com/profile/jim-wanner/
Sterling Sales - https://sterlingsales.co
Noob School podcast and Sales for Noobs book - https://www.schoolfornoobs.com/
ElevenLabs - https://elevenlabs.io/
Jason Lemkin - https://www.saastr.com/
Nolan Bushnell - https://en.wikipedia.org/wiki/Nolan_Bushnell