In this episode of Inside the Workflow, we sit down with Dan O’Leary, Senior Director of Strategic Partnerships at Box, to discuss the evolution of enterprise SaaS, the power of partnerships, and the role of AI in shaping the future of work. With a career spanning Meta (Workplace), Facebook, and Box, Dan has been at the forefront of scaling partner ecosystems, driving innovation, and improving enterprise collaboration.
From Consumer to Enterprise: A Career in SaaS Innovation
Dan’s journey in enterprise SaaS began with a bold experiment: bringing Facebook’s user-friendly experience into the workplace. At Meta, he helped build Workplace (originally Facebook at Work), a tool designed to help businesses communicate more effectively. However, the shift wasn’t as seamless as expected.
“I remember a CIO telling me, ‘I’ve spent years trying to keep my employees off Facebook at work, and now you want me to bring it in?’” Dan recalled. This challenge highlighted the complexities of enterprise adoption, where security, compliance, and change management play a significant role.
After Meta, Dan returned to Box, where he now leads strategic partnerships. His goal? Helping companies scale their success through technology alliances and deep integrations.
Building Strong Partnerships: A Strategy for Success
Dan believes partnerships aren’t just about sales—they’re about delivering customer success. Whether at Meta or Box, he’s seen how the right partnerships drive value and adoption.
“A partner is just a customer in disguise,” he explained. “They’re the ones inside an organization, helping implement and optimize solutions. When they succeed, the customer succeeds, and so does the business.”
At Box, Dan has been instrumental in developing nearbound go-to-market strategies, focusing on building trust, scaling solutions, and ensuring that customers get the most out of their technology investments.
Leadership & Culture: Communicating with Authenticity
A core aspect of Dan’s leadership philosophy is clear, transparent, and authentic communication. He’s learned that the best teams aren’t just the most skilled—they’re the most aligned.
Reflecting on past experiences, he shared a lesson from his time at Workplace:
“The best leaders weren’t necessarily the loudest or most charismatic. They were the ones who communicated authentically, consistently, and with a clear purpose.”
For Dan, leadership is about empowering teams, fostering strong relationships, and always staying connected to customers and partners.
The Future of AI in SaaS
AI is transforming the way businesses operate, but Dan believes that the real challenge isn’t just building AI-powered tools—it’s making them accessible and useful.
“AI adoption is like changing a diet soda preference—it’s harder than you think,” he joked. “It’s all about meeting users where they are, making the experience seamless, and delivering real, tangible value.”
At Box, AI is being used to enhance workflows, extract key insights from content, and simplify complex processes. The key, Dan says, is ensuring that AI augments human work rather than replaces it.
Work-Life Balance & What’s Next
Outside of work, Dan prioritizes family, fitness, and fun. He’s an avid runner—often seen jogging with a stroller, logging hundreds of miles with his kids.
“My son even has a Box employee badge,” he laughed. “I try to integrate work and family as much as possible. If you can do that, it doesn’t feel like a trade-off.”
Looking ahead, Dan is focused on helping companies and people reach their full potential. And maybe one day, he joked, he’ll trade SaaS for a power-washing business or a wood-chipping venture.
For now, though, he’s focused on building partnerships, scaling innovation, and shaping the future of enterprise technology.
Want to hear more? Check out the full episode for deeper insights into Dan’s journey, leadership philosophy, and predictions for the future of work.
