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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In this episode of Inside the Workflow, we sit down with Ashley Smith, GP and Founder of Vermillion Cliffs Ventures. With a track record of driving growth at Twilio, GitLab, and GitHub, Ashley has now turned her focus to investing in early-stage technical founders. We explore her journey from startup operator to venture capitalist, her leadership approach, and what she looks for in founders building the next generation of developer-focused companies.

From her early career answering support calls at Twilio to leading go-to-market strategies for some of the biggest developer tools, Ashley shares invaluable lessons on building strong teams, navigating competition, and the evolving role of AI in software development.

What You’ll Learn in This Episode:

• Building High-Performing Teams – The key traits Ashley looks for in founders and early hires.
• Founder-Led Growth – Why technical founders must embrace go-to-market strategies.
• AI & Developer Tools – The latest trends in AI infrastructure and how startups can leverage automation.
• Scaling Startups – Lessons from Twilio, GitHub, and GitLab on rapid product adoption.
• The Future of Investing – Ashley’s approach to early-stage investing and what excites her in tech.

Key Topics Covered:

[00:00] Introduction & Ashley’s Background – From Twilio support to leading growth at top startups.
[05:00] The Transition to Venture – Why Ashley founded Vermillion Cliffs Ventures.
[10:00] Startup Team Building – What makes a great founding team and early hires.
[15:00] AI’s Impact on Software Development – The shift from hype to real-world applications.
[20:00] Founder-Led Sales – Why early-stage technical founders need to embrace GTM strategies.
[25:00] The Future of Venture – How Ashley sees investing evolving in the next decade.
[30:00] Leadership & Work-LifeBalance – Lessons from navigating startup intensity and VC life.

Whether you're a startup founder, investor, or AI enthusiast, this episode is packed with insights on building, scaling, and investing in the future of software and AI.

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In this episode, we’re excited to welcome Todd Baylis, Chief Customer Officer at Bloomerang, to discuss his journey as an entrepreneur, his leadership philosophy, and the future of nonprofit technology. From founding Qgiv to driving innovation at Bloomerang, Todd shares how he’s transforming donor engagement and helping nonprofits build lasting relationships.

What You’ll Learn in This Episode:

• Todd’s leadership style and how he fosters a culture of innovation and customer-centricity.
• The evolution of nonprofit technology and how Bloomerang is streamlining donor engagement.
• Lessons from entrepreneurship—failing forward, adapting to challenges, and scaling a business.
• The role of automation and AI in freeing up time for nonprofits to focus on relationships.
• Todd’s approach to work-life balance as a leader and family man.

Key Topics Covered:

⏳ 0:00 – Introduction and Todd’s background in nonprofit technology.
💡 5:00 – Leadership lessons: Building a strong culture in remote and hybrid teams.
📈 10:00 – The biggest challenges nonprofits face in donor engagement and retention.
🚀 15:00 – The future of nonprofit tech: AI, automation, and relationship-driven fundraising.
🔍 20:00 – Todd’s entrepreneurial journey: Lessons from growing and selling a company.
🏆 30:00 – The importance of resilience, adaptability, and continuous learning in leadership.

Todd’s insights into leadership, innovation, and customer success make this a must-listen episode. Tune in for valuable lessons on building a business, leading with purpose, and shaping the future of nonprofit technology.

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💬 Comment below with your thoughts on leadership, customer success, and nonprofit tech!

In this episode of Inside the Workflow, we sit down with Dave Blake, Founder & CEO of ClientSuccess, a leading platform that helps SaaS companies drive customer retention and growth. With a background spanning Adobe, Omniture, and decades of experience in customer success, Dave shares his leadership philosophy, industry insights, and the evolving role of AI in customer success.

From his early days in consulting to building a customer success platform from the ground up, Dave’s journey is filled with valuable lessons on leadership, innovation, and staying competitive in an ever-changing market. We also discuss how his competitive nature, personal passions, and family life influence his work.

What You’ll Learn in This Episode:

🎯 Leadership Lessons – How Dave blends competition, collaboration, and a customer-first mindset to build high-performing teams.
📈 Industry Trends – Why customer success is evolving and how businesses must adapt to stay ahead.
🤖 The Role of AI – How AI is transforming customer engagement, helping businesses scale and personalize experiences.
🚀 Building ClientSuccess – The inspiration behind creating a platform designed for CS professionals and how it addresses key industry challenges.
🔮 Future of SaaS & Customer Success – Dave’s vision for the future and how AI, automation, and better insights will drive long-term customer relationships.

Key Topics Covered:

• [00:00] Introduction & Dave’s Background – From consulting to leading ClientSuccess.
• [05:00] The Competitive Edge – How Dave’s upbringing and leadership style shape his approach.
• [10:00] Customer Success Evolution – The early days, key challenges, and why it matters more than ever.
• [15:00] Scaling a SaaS Business – Lessons from Adobe, Omniture, and founding ClientSuccess.
• [20:00] AI & The Future of CS – How technology is reshaping customer retention and engagement.
• [25:00] Leadership & Work-Life Balance – Dave’s thoughts on integrating work, family, and personal passions.
• [30:00] The Road Ahead – What’s next for ClientSuccess and customer success as a whole.

Whether you’re a CS leader, startup founder, or SaaS enthusiast, this episode is packed with insights on customer retention, leadership, and product innovation.

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In this episode, we’re excited to sit down with Melissa Rosenthal, Co-Founder at Outlever, to explore her journey through media, SaaS, and entrepreneurship. From her groundbreaking work at BuzzFeed and Cheddar to scaling ClickUp during its hypergrowth, Melissa shares lessons on leadership, bold decision-making, and building a business focused on customer-centric narratives.

What You’ll Learn in This Episode:

• How Melissa's career at BuzzFeed and Cheddar shaped her entrepreneurial mindset.
• Why ruthless prioritization is essential for scaling a lean team.
• How AI is transforming workflows and driving smarter scalability.
• The shift from outbound sales to relationship-driven marketing.
• Melissa’s thoughts on avoiding burnout and fostering a healthy team culture.

Key Topics Covered:
0:00 – Welcome & Melissa’s Background: From BuzzFeed to Outlever.
5:00 – The path to disruption: Insights from BuzzFeed, Cheddar, and ClickUp.
10:00 – Leadership lessons: Transparency, directness, and building healthy team dynamics.
15:00 – Scaling with focus: The power of staying lean and prioritizing what matters.
20:00 – Embracing AI: How tech enables creativity and scalability for startups.
25:00 – The future of marketing: Why relationship-based selling is the next frontier.
30:00 – Personal growth: Avoiding burnout and balancing priorities as a founder.

Melissa’s journey is filled with practical advice, bold insights, and a fresh perspective on navigating modern entrepreneurship. Tune in for an inspiring conversation that dives into the future of media, marketing, and startup culture!

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💬 Comment below with your thoughts on leadership, marketing, and scaling startups.

In this episode, we’re thrilled to speak with Arturo Suarez Martin, Senior Director of Customer Success and General Manager at PagerDuty Chile. Arturo shares his inspiring journey from developer to director, offering valuable insights into leadership, team-building, and the transformative power of AI.

What You’ll Learn in This Episode:

• Arturo’s leadership style and how curiosity drives innovation.
• Lessons from building reliable systems and leading diverse teams.
• The role of AI in freeing up time for meaningful work.
• Arturo’s personal philosophy on flexibility and growth in career and life.

Key Topics Covered:

• 0:00 – Introduction and Arturo’s background.
• 5:00 – Leadership lessons and inspiration from global experiences.
• 10:00 – Building resilient systems and the importance of reliability.
• 15:00 – The promise and pitfalls of AI in modern work.
• 20:00 – Fostering team diversity and adaptability across cultures.
• 30:00 – Arturo’s career advice: Stay curious and create opportunities for choice.

Arturo’s story is packed with actionable advice and thought-provoking insights. Don’t miss this engaging conversation with one of tech’s most forward-thinking leaders!

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💬 Comment below with your thoughts on AI, leadership, and customer success.