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From Building Concierge to Co-Founder & Co-CEO with Alina Vandenberghe
Season 2 Episode 2
In this episode of Revenue Career Ladder, Jamie Pagan is joined by Alina Vandenberghe to explore a journey of resilience, conviction, and rapid progression—from calculating utility bills at age eight to leading one of the most innovative SaaS platforms in the revenue space.
Alina shares powerful stories of her early entrepreneurial drive, her rise through the ranks in corporate America, and the lessons she’s learned as a founder navigating bootstrapping, hypergrowth, and team culture at scale. A raw and thoughtful discussion for anyone looking to fast-track their career or lead with purpose.
Expect to learn:
- Why resilience and discomfort early in life can fuel future leadership
- How listening—rather than arguing—is key to influencing senior stakeholders
- The real story behind the Reuters app launch on stage with Steve Jobs
- Why Alina walked away from a high-paid healthtech role to build from scratch
- Key hiring insights from scaling Chili Piper globally
- How to build and maintain company culture in a high-performance environment
- Why numbers, ownership, and empathy are foundational to career growth
Timestamps
00:00 - Introduction and guest welcome
01:14 - Alina’s first job at age 8 and early entrepreneurial mindset
10:42 - First major role at Reuters and the Steve Jobs keynote story
17:00 - Transition to director and lessons in influence and collaboration
23:12 - VP at Pearson and navigating corporate politics
32:36 - Misalignment in healthtech and decision to start Chili Piper
38:48 - Founding Chili Piper and discovering the first product
45:08 - Bootstrapping, VC funding, and evolving founder insights
53:04 - Hiring philosophies and adapting in the age of AI
58:04 - Decision-making culture and onboarding at Chili Piper
01:02:10 - Top 3 career tips and closing reflections
Ready to take the next step in your career journey? Subscribe to the Revenue Career Ladder today and start making your professional aspirations a reality.
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Watch on Stream by Dealfront: https://www.dealfront.com/resources/stream/series/revenue-career-ladder/
Follow Alina Vandenberghe:
LinkedIn: https://www.linkedin.com/in/alinav/
Follow Jamie Pagan:
LinkedIn: https://www.linkedin.com/in/jamiepagan/
Connect with us:
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Facebook: https://www.facebook.com/getdealfront/
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