Grit Rebuilding Front for the AI Era | CEO Dan O’Connell
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Nov 3, 2025 
In this discussion, Dan O'Connell, CEO of Front and former leader at Dialpad, shares insights on navigating AI-driven transformations in established SaaS companies. He emphasizes the importance of balancing legacy systems while fostering innovation, and how courageous decision-making can energize teams. Dan illustrates the necessity of aligning leadership with cultural urgency, and the potential need to sacrifice short-term revenue for long-term gains. He further reflects on personal motivations and the challenge of leading a decade-old company through significant change.
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Legacy SaaS Faces An AI Identity Crisis
- Ten‑ to fifteen‑year SaaS companies face an identity crisis as AI upends markets and requires urgent transformation.
- Leadership must 'burn the boats' on culture and product to seize the AI disruption window.
Make Leadership Alignment The First Move
- Align the executive team and communicate urgency clearly to overcome inertia and adopt AI-driven changes.
- Use leadership commitment to push culture shifts and change management across the company.
Take Bold Bets To Win Categories
- Decide boldly and accept imperfect metrics when pursuing category leadership in a reshuffled market.
- Be willing to trade short‑term revenue to capture long‑term market position if conviction and runway exist.