In this episode of Inside the Workflow, Scott welcomes Nick Francis, Co-founder and CEO of Help Scout, for a deep, thoughtful conversation on entrepreneurship, customer support, product vision, and doing hard things—both in business and life.

Nick shares the 14-year journey of Help Scout, from its early days as a simple shared inbox tool to its transformation into a mission-driven customer support platform with a new pricing model designed for the AI era. He opens up about founding the company with close friends, the influence of hospitality on product design, building remote-first culture with intention, and why he’s obsessed with solving the customer support problem.

In This Episode, We Discuss:
• The founding story of Help Scout & TechStars beginnings in Boston
• Why great customer experiences are at the core of their product
• Lessons from hospitality and brand building
• Adopting a remote-first culture and maintaining team connection
• How AI is transforming customer support—and how Help Scout is adapting

Whether you’re a founder, product builder, or support leader, this episode is packed with wisdom on building a durable business while staying true to your values.

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In this episode, we sit down with Nicholas Thompson, CEO of The Atlantic and former Editor-in-Chief of Wired, to explore his path from student newspaper founder to leading one of the most influential media organizations in the world. With a deep understanding of journalism, tech innovation, and business leadership, Nicholas shares his thoughts on editorial independence, AI’s role in publishing, and building resilient teams in a fast-changing media landscape.

From running newsrooms to navigating the future of AI-driven journalism, this conversation is full of thought-provoking takeaways. Nicholas also opens up about what keeps him grounded, the importance of trust in leadership, and why great content always comes first—no matter the business model.

What You’ll Learn in This Episode:

• The Evolution of Modern Journalism – How Nicholas’s early experiences shaped his leadership at The Atlantic.
• Business vs. Editorial – Why a clear line between content and revenue is key to maintaining trust.
• AI & the Newsroom – The promise and perils of artificial intelligence in journalism.
• Leadership Style – How Nicholas fosters a culture of open debate, autonomy, and values-driven decision-making.
• Career Advice – Why mentorship, ambition, and meaningful work matter in shaping a successful path.

Key Topics Covered:
[00:00] Introduction & Nicholas’s Background – From student journalism to the CEO seat
[05:00] Lessons from The Thinker – Early insights into editorial debate and business strategy
[10:00] Building Strong Cultures – How to manage rival teams and competing business goals
[15:00] Trust in Journalism – Why editorial independence is non-negotiable at The Atlantic
[20:00] Embracing AI – How Nicholas uses AI in his daily life and what it means for journalism
[25:00] The Future of Media – Competing with TikTok, evolving revenue models, and building resilience
[30:00] Career Reflections – Advice for aspiring journalists and early-career professionals

Whether you're in media, leadership, or just fascinated by the intersection of journalism and technology, this episode offers powerful insights from one of the most thoughtful voices in the industry.

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In this episode, we sit down with Dan O’Leary, Sr. Director of Strategic Partnerships at Box, to explore his journey from building SaaS partnerships at Meta to leading strategic growth initiatives at Box. With deep expertise in partner ecosystems, AI-driven collaboration, and enterprise SaaS, Dan shares valuable insights on leadership, scaling businesses, and the evolving role of AI in workflow automation.

From navigating competitive SaaS markets to fostering strong partnerships that drive customer success, this conversation is packed with actionable takeaways. Dan also shares his perspective on balancing work and life, the importance of communication in leadership, and why partnerships are more than just a growth strategy—they’re a way to deliver real customer value.

What You’ll Learn in This Episode:

🚀 Leadership & Team Building – How Dan fosters strong teams through clear communication and transparency.
📈 Scaling Partnerships – Why strategic partnerships are key to SaaS growth and how to make them successful.
🤖 AI in Enterprise Collaboration – How AI is reshaping workflows and driving productivity.
🔄 Adapting to Change – Lessons from returning to Box and evolving with the industry.
💡 Future of SaaS & Content AI – What’s next for AI-driven collaboration and partner ecosystems.

Key Topics Covered:

[00:00] Introduction & Dan’s Background – From Meta to Box and the evolution of SaaS partnerships.
[05:00] Building Enterprise Software at a Consumer Tech Company – Lessons from launching Workplace at Meta.
[10:00] The Role of Partnerships in SaaS – Why partnerships are more than just a sales channel.
[15:00] AI & The Future of Work – How AI is improving collaboration and decision-making.
[20:00] Leadership & Communication – Why great leaders focus on authenticity and clarity.
[25:00] Balancing Work & Life – Dan’s perspective on prioritization and making time for what matters.
[30:00] What’s Next in SaaS & Partnerships – Predictions for the future of collaboration tools and AI.

Whether you're a SaaS founder, enterprise leader, or curious about the future of AI-driven workflows, this episode is full of insights on leadership, partnerships, and innovation.

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✅ Enjoyed this episode? Like & share!
💬 Comment below with your thoughts on AI, partnerships, and leadership.