Episode 793 | TinySeed Tales s5e3: Building Momentum
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this compelling episode, Harris Kenny of Outbound Sync shares his breakthrough moment after three months of flat revenue, landing his first enterprise deal worth $20,000 annually (01:44). Rob Walling guides listeners through Harris's strategic journey from a simple connector app to a sophisticated B2B SaaS platform that's now pulling customers away from industry giants like Outreach. The conversation reveals how investing in SOC 2 compliance (06:19) and professional infrastructure transformed not just his sales process, but his entire approach to building a scalable software company. Harris demonstrates the power of moving fast and staying ahead of market demand, becoming the first Smart Lead integration in HubSpot's marketplace (20:23) and positioning his company as the bridge between cold outreach tools and CRM systems.
Speakers
Harris Kenny
Founder of Outbound Sync, a B2B SaaS company that integrates cold email tools with CRM systems. After running a profitable agency for five years, Harris pivoted to building software and was accepted into TinySeed's startup accelerator, recently closing his largest enterprise contract worth $20,000 annually.
Rob Walling (Host)
Serial entrepreneur and co-founder of TinySeed, the startup accelerator for ambitious SaaS bootstrappers. Author and creator of Tiny Seed Tales podcast, Rob brings decades of experience building and scaling software companies to guide early-stage founders through the challenges of startup growth.
Key Takeaways
Strike While the Market Momentum Builds
Position yourself ahead of the market curve by identifying early adopters and serving them exceptionally well. Harris recognized that his current customers represent "the very beginning of a big chunk of a bell curve of the market that's going to be changing its process." (04:04) When you're taking customers away from established players like Outreach—a unicorn that created the sales engagement category—you're not just competing, you're reshaping how an entire market thinks about their problems.
Transform Compliance Into Competitive Advantage
Don't just endure SOC 2—weaponize it. Harris discovered that implementing SOC 2 requirements forced beneficial changes: staging servers, web application firewalls, and incident response protocols that actually caught and prevented security issues. (07:09) The investment improved product quality, enhanced customer support, and directly increased sales through credibility. When customers received detailed incident reports and saw the professional status page, it demonstrated enterprise-grade reliability.
Build Integration Velocity as Distribution Strategy
Speed to market beats perfection in platform integrations. Harris built a Salesforce integration using a "connected app" approach—essentially a private unlisted app—to move faster than going through official app exchanges. (18:34) This allowed him to go from $0 to projected $2K MRR in Salesforce revenue within a month, becoming the first Smart Lead integration in HubSpot's marketplace—even before Smart Lead's own integration. The pattern: ship fast, get paying customers, then pursue official marketplace approval.
Engineer Financial Constraint as Growth Catalyst
Structure your personal finances to create productive pressure without destructive stress. Harris moved from an LLC with flexible distributions to a C-corp with fixed salary constraints, forcing more disciplined financial planning. (12:26) He implemented detailed budgeting (YNAB) to understand personal spending patterns and identify opportunities to reduce his salary drag on the business. The goal: extend runway while maintaining family stability, creating sustainable pressure to reach the critical $30K MRR threshold for default alive status.
Harvest Market Pull Signals Into Product Roadmap
Transform customer requests into strategic intelligence. When prospects started asking "Do you support Lemlist? Do you support this? Do you support that?" Harris recognized this as market pull—a waitlist forming for additional integrations. (22:00) This data became strategic input: three requests for one tool versus two for another provides concrete direction for development priorities. The evolution from simple connector to comprehensive platform happens when you systematically capture and act on these demand signals.
Statistics & Facts
- Harris closed Outbound Sync's largest contract ever—an annual $20,000 deal—marking a significant milestone as his first major enterprise contract. (01:44)
- 35% of Harris's household income currently goes to childcare, creating financial pressure that he expects will ease as his children reach school age. (16:53)
- Outbound Sync is projected to grow from $0 to approximately $2,000 MRR in Salesforce revenue within just one month, representing about 15% of total company revenue. (19:25)
