Startups For the Rest of Us

Episode 791 | TinySeed Tales s5e2: Growing Pains

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In this episode of TinySeed Tales, Rob Walling reconnects with Harris Kenny, founder of OutboundSync, to explore the rapid evolution of his SaaS business just months after transitioning from agency work.

Harris shares how niching down to outbound-focused agencies unlocked sales momentum. He talks about hiring, his Salesforce breakthrough, SOC 2 prep, and why finally spending his TinySeed funding changed everything.

Topics we cover: 
  • (2:27) – Launching a lower-priced version and building expansion revenue
  • (6:40) – How lead-gen shops are outpacing legacy rev ops
  • (12:01) – Hiring full-time: Dev speed, onboarding load, and customer success firepower
  • (18:15) – A surprise Salesforce breakthrough and what it means for product strategy
  • (24:42) – SOC 2 prep, pricing confidence, and finally spending the TinySeed check
    • Links from the Show: 
    • Join the TinySeed Mailing List
    • Apply for TinySeed - Applications reopen September 1, 2025
    • OutboundSync
    • Harris Kenny | LinkedIn
    • Coaching Call Bonus
    • Dynamite Jobs
    • Vanta

      • 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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      Startups For the Rest of UsBy Rob Walling
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