Offsite Our Cake and Eat It Too
Sep 24, 2025
Henry Poydar, CEO of Steady and builder of an AI copilot for teamwork, shares insights on personal and professional transitions as an empty nester after dropping off his twins at college. He discusses the emotional journey of entrepreneurship and how it offers family flexibility. Henry dives into business strategies, advocating for team-based pricing over per-user models, and the importance of customer feedback in shaping products. He also shares innovative trial strategies to improve user engagement and highlights challenges in scaling AI tools for teamwork.
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Price And Market By Outcome Not Minutes
- Lead with outcome and emotional relief, not commodity metrics like minutes.
- Frame Rosie as hiring a reliable employee who prevents missed opportunities and emotional stress.
AI Copilot For Teamwork
- Steady positions its product as an AI co-pilot that removes 'work about work' and preserves human judgment.
- The real value is improving coordination, productivity, quality, and team engagement.
Price Per Team, Not Per User
- Avoid per-user pricing when value scales with team outcomes and network effects.
- Consider per-team pricing to encourage adoption and remove expansion friction within organizations.
