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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In this episode, we sit down with Gil Lara, Chief Creative Officer and co-founder at Sprout Social, to discuss his nearly 15-year journey with the leading social media management platform. From his early days in street art and event design to building a creative culture at Sprout, Gil shares the evolution of his career and the pivotal moments that shaped him as a designer and leader. With insights on the changing landscape of design, embracing AI, and navigating the tension between creativity and business, this conversation is packed with valuable takeaways for anyone passionate about design and innovation.

Key Topics Covered:

0:00 - 5:00 – Introducing Gil Lara: Gil’s creative background, his move to Chicago to join Sprout Social’s founding team, and his early experiences with graffiti and event design.

5:00 - 10:00 – Finding Design Inspiration in Unusual Places: Gil shares how everyday objects, like shower controls, can spark creative ideas and the importance of observing the world around you.

10:00 - 15:00 – From Street Art to the Corporate World: How Gil transitioned from graffiti and print design to shaping digital experiences and software at Sprout Social.

15:00 - 20:00 – Building a Creative Culture at Sprout: The early days at Sprout, working on the social inbox, and how design has influenced the company’s evolution.

20:00 - 25:00 – Customer Feedback as a Design Tool: Why listening to customers and integrating their feedback is crucial, and how it can lead to innovative features.

25:00 - 30:00 – Balancing Innovation with Business Needs: Navigating the demands of building a social media management platform while staying true to the creative vision.

30:00 - 35:00 – The Role of AI in Social Media Management: How AI is transforming Sprout Social’s platform and the potential it has to revolutionize customer engagement.

35:00 - 40:00 – The Future of Design Leadership: Gil’s thoughts on passing the torch, embracing change, and preparing for his next chapter after stepping down from his role.

40:00 - 45:00 – Advice for Young Designers: Gil reflects on his career, shares lessons learned, and offers advice on how to advocate for design’s impact within an organization.

45:00 - 50:00 – The Power of Video and Storytelling: The importance of video in conveying a brand’s message and creating memorable experiences for customers and employees alike.

50:00 - 55:00 – Looking Ahead: Gil’s thoughts on the future of Sprout Social, his personal plans, and the exciting opportunities in the ever-evolving world of design and technology.

Key Takeaways:

• The Value of Design Thinking: Gil emphasizes the need for designers to go beyond aesthetics and partner early in the development process to create meaningful user experiences.
• Feedback as Fuel for Innovation: Leveraging customer insights and using them as a tool for continuous improvement.
• Navigating Healthy Tension: The importance of balancing different perspectives and embracing the creative friction that drives better outcomes.
• AI as a Game-Changer: How artificial intelligence is poised to transform the way businesses manage social media and engage with audiences.
• Evolving as a Leader: Gil reflects on his decision to step down, the significance of building a resilient team, and the excitement of pursuing new ventures.

Notable Quotes:

1. "If you're not defining what design is at your organization, someone else will define it for you."
2. "Healthy tension is a part of building something great."
3. "Ther

In this episode, we sit down with Philippe Mesritz, a Fractional Chief Customer Officer and former General Manager at Community Brands, known for transforming SaaS organizations and driving customer retention. Philippe shares his journey from web design and system administration to leading customer experience teams and improving Net Promoter Scores (NPS) by 40 points.

From building customer-centric teams to navigating the evolving role of AI in CX, Philippe’s insights are packed with actionable takeaways. He also shares his philosophy on transparency, vision, and adaptability in leadership, as well as the importance of balancing work and life while maintaining high performance.

What You’ll Learn in This Episode:

🚀 Leadership & Team Building – How Philippe fosters transparency, clarity, and vision to create high-performing teams.
📈 Customer Success & Retention – Lessons from improving NPS and building long-term customer relationships.
🤖 AI in Customer Experience – How AI is transforming CX, and why a human touch still matters.
🔄 Adapting to Change – The role of resilience and continuous learning in career growth.
💡 Future of CX & SaaS – How technology, customer insights, and evolving business models are shaping the future.

Key Topics Covered:

[00:00] Introduction & Philippe’s Background – From early tech roles to leading customer success.
[05:00] Customer Experience in Unexpected Places – Lessons from SaaS to manufacturing.
[10:00] Firing a Customer: The Right Way to Say No – Why sometimes the best CX decision is letting a customer go.
[15:00] Building High-Performing Teams – The power of transparency, clarity, and vision in leadership.
[20:00] Remote Work & Global Teams – Strategies for effective communication and engagement.
[25:00] AI & The Future of Customer Experience – Why AI matters, but human relationships will always be key.
[30:00] Career Growth & Leadership – Philippe’s advice on navigating a dynamic career path.

Whether you're a CX leader, SaaS founder, or someone passionate about customer success, this episode is packed with insights on leadership, AI, and the future of customer experience.

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