SaaStr 642: Founder-Led Enterprise Sales: Failure Points on the Path to $100m ARR with TigerEye and PlanGrid Co-Founder and CEO Tracy Young - The Official SaaStr Podcast: SaaS | Founders | Investors Recap
Podcast: The Official SaaStr Podcast: SaaS | Founders | Investors
Published: 2023-03-15
Duration: 1083
Guests: Tracy Young
What Happened
Tracy Young, CEO and Co-Founder of TigerEye and PlanGrid, reflects on her journey taking PlanGrid from inception to $100 million in ARR before its acquisition by Autodesk. She highlights the importance of organizational structure, noting that early experiments with non-traditional structures at PlanGrid, like avoiding titles, led to communication chaos as the company grew. The lack of a clear hierarchy and communication strategy made it difficult to maintain direction as the team expanded.
Young stresses the significance of core values in a startup, drawing from her experience at PlanGrid where not adhering to their own values led to internal conflicts. At her current venture, TigerEye, she ensures core values are clearly defined and actively used in decision-making processes. This approach helps avoid the damaging effects of finger-pointing and misalignment within teams.
Hiring executives is another area where Young learned valuable lessons. She points out red flags such as executives using 'I' instead of crediting their teams, dreading one-on-ones, and blaming peers for issues. She advises trusting gut instincts when it comes to personnel decisions, emphasizing that ignoring these instincts can lead to larger problems down the line.
Young discusses the challenge of maintaining product market fit, recounting how PlanGrid initially succeeded by digitizing construction records but struggled when scaling to enterprise clients. The delay in adapting their product to enterprise requirements contributed to their decision to sell the company, as competitors who focused on enterprise features outpaced them.
Life events also play a critical role in startup dynamics. Young shares personal experiences, including the loss of her co-founder to cancer, underscoring the inevitability of life's challenges. She emphasizes choosing a mission worth dedicating time to and staying present despite the ups and downs inherent in building a company.
Finally, Young reflects on the broader lessons from her entrepreneurial journey, emphasizing the need to balance creativity between customer-focused solutions and organizational structure. She advises founders to channel creativity into solving customer problems rather than experimenting with internal structures, which can lead to unnecessary complications.
Key Insights
- Tracy Young learned that non-traditional organizational structures can lead to chaos as a company grows. At PlanGrid, the lack of clear titles and hierarchy initially worked for a small team but became a bottleneck as the team expanded to over 150 people.
- Core values must be actively integrated into company culture and decision-making. At TigerEye, Tracy Young ensures these values guide hiring, firing, and strategic decisions, preventing the internal conflicts she experienced at PlanGrid.
- Hiring at the executive level requires careful attention to red flags. Tracy Young notes that reliance on 'I' statements and a tendency to blame others are indicators that an executive may not be a good fit.
- Maintaining product market fit requires anticipating market shifts and adapting products accordingly. PlanGrid's delay in catering to enterprise clients led to stagnation at $50 million ARR, demonstrating the need for timely strategic pivots.