Mark MacLeod's Startup CEO Show brings us an enlightening conversation with Alina Vandenberghe, the dynamic co-founder and co-CEO of Chili Piper. This episode offers a deep dive into the unique challenges and opportunities of co-leading a company with your spouse, as Alina candidly discusses her partnership with her husband and co-CEO. The discussion sheds light on their fluid approach to dividing responsibilities and how they've managed to create a flat organizational structure despite having 150 employees across 38 countries.

Alina shares invaluable insights on hiring for values, detailing how they assess candidates not just for skills but for alignment with company culture. The conversation takes an interesting turn as Alina reflects on her background growing up in communist Romania and how it shaped her entrepreneurial journey, instilling in her a unique perspective on resource management and customer motivations. This episode is packed with practical advice on building a strong company culture, leveraging personal branding for business growth, and adapting to the rapidly changing tech landscape.

Don't miss this opportunity to learn from one of tech's most innovative and authentic leaders.

Timestamps:

01:06 Meet Alina: Chili Piper's Spicy CEO

03:26 Chili Piper: Spicing Up Sales Software

06:11 Raw and Real: Alina's Authentic Approach

10:16 Social Media: The Pipeline Powerhouse

12:20 Speaking Up: Time Well Invested

16:42 Dividing and Conquering CEO Duties

19:42 Remote Work: Born from Wanderlust

29:48 Bootstrapping to Millions: Chili Piper's Journey

35:48 AI: Blessing or Terminator Scenario?

43:00 Corporate Wisdom in Startup Land

48:07 Inspiring Women: Alina's Ripple Effect

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Contact Mark: https://markmacleod.me/

In this episode of the Startup CEO Show, Mark MacLeod sits down with Mark Bordo, co-founder and CEO of Vetster, to explore the world of pet telemedicine and marketplace businesses. Bordo shares the origin story of Vetster, born from a personal need and launched just before the COVID-19 pandemic. He discusses how the company quickly scaled across North America, balancing supply and demand in the veterinary marketplace.

Bordo offers valuable insights into building and growing a successful marketplace business, emphasizing the importance of data-driven decision-making and continuous optimization. He also touches on the challenges of regulatory environments in different states and provinces, and how Vetster navigates these complexities. The conversation delves into Bordo's 25-year journey as an entrepreneur, highlighting lessons learned and strategies for personal growth that have enabled him to stay ahead of his rapidly expanding businesses.

From the intricacies of customer acquisition to the evolution of marketing strategies in the age of AI, this episode is packed with practical advice for aspiring and seasoned entrepreneurs alike. Tune in to gain valuable knowledge on building and scaling a marketplace business in today's dynamic digital landscape.

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Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Contact Mark: https://markmacleod.me/

In this episode of the Startup CEO Show, Mark MacLeod sits down with Christine Song, a multi-time Chief People Officer with extensive experience in both established corporations and high-growth startups. They dive deep into the critical role of people and HR in scaling successful companies. Christine shares her journey from corporate HR to becoming a strategic partner for startup CEOs, offering a wealth of knowledge on building high-performance cultures, giving direct feedback, and balancing employee growth with business objectives.

The conversation explores how HR has evolved from a back-office function to a key strategic role, especially in the wake of COVID-19. Christine emphasizes the importance of HR leaders earning their seat at the executive table by tying initiatives to business outcomes and being willing to have difficult conversations. She also discusses the challenges of scaling company culture, the need for honest communication about work expectations, and the value of investing in high-potential employees. Mark and Christine debate the merits of pushing people out of their comfort zones versus prioritizing employee happiness, offering valuable insights for leaders grappling with these tradeoffs.

Listeners will gain practical advice on improving company communication, implementing effective coaching and talent development programs, and creating a culture of feedback and continuous improvement. The episode concludes with Christine introducing her new venture, Five to Nine Society, an exclusive network for elite operators and founders. Don't miss out on this compelling discussion - tune in now to elevate your leadership and people management skills!

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Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Contact Mark: https://markmacleod.me/