What happens when momentum hits and your biggest challenge becomes keeping up?
In this episode of TinySeed Tales, Rob Walling catches up with Harris Kenny, founder of OutboundSync. Revenue is growing, the team is moving fast, and enterprise leads are coming in. But with success comes complexity: support load, pricing strategy, and product demands are all increasing. Harris is hiring again, learning to say no, and figuring out how to keep the momentum without losing focus.
Topics we cover:
- (1:40) – Closing his biggest deal ever and what it unlocked
- (4:26) – Learning how to do enterprise sales
- (6:20) – How SOC 2 made the product stronger
- (12:18) – New hires are paying off
- (18:23) – Building the Salesforce integration
- (22:13) – Getting pull from the market, not pushing
- (24:10) – Taking customers from unicorns
Links from the Show:
- TinySeed SaaS Accelerator - Applications close on September 9th
- Coaching Call Bonus
- Invest in TinySeed
- YNAB (You Need A Budget)
- Dynamite Jobs
- OutboundSync
- Harris Kenny | LinkedIn
If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!
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