Startups For the Rest of Us Episode 793 | TinySeed Tales s5e3: Building Momentum
Sep 4, 2025
Harris Kenny, founder of OutboundSync, dives into the whirlwind of scaling his SaaS business. He shares the excitement of closing a $20,000 deal that unlocked new opportunities and his journey into enterprise sales. The conversation highlights how SOC 2 compliance has strengthened his product while discussing the impact of new hires on growth. He also addresses the importance of building a Salesforce integration and the strategy of attracting customers away from unicorn competitors, emphasizing the power of market pull.
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Landing A Game-Changing Enterprise Deal
- Harris closed his first enterprise annual contract for $20,000 after navigating procurement and legal review.
- He felt this deal validated the business and boosted his confidence that OutboundSync could scale.
Price To Cover Enterprise Overhead
- If customers require procurement and security, raise your ACV to cover the cost and complexity.
- Charging more offsets legal, security, and sales expenses tied to enterprise deals.
Compliance Forced Product Maturation
- Starting SOC 2 improved product practices like staging, security, and status communication.
- Those compliance-driven changes increased credibility and directly helped win enterprise customers.
