SaaSy Talk S01.05: Building a Remote-First Unicorn Company: Challenges and Successes

About The Guest(s): Co-Founder and Co-CEO Alina Vandenberghe created Chili Piper in 2016, the conversion platform for B2B sales, marketing, and implementation teams. With 45,000+ customers like Spotify, Airbnb, Gong, and Shopify, Chili Piper automates scheduling, lead qualification, and routing throughout all stages of the funnel. The born entrepreneur started her first company before high school before she even knew what entrepreneurism was. After building mobile products loved by millions — and that were keynoted by Steve Jobs on stage — Alina decided to take her product management talents to B2B software solutions Summary: Alina Vandenberghe, CEO and co-founder of Chili Piper, shares her journey from Romania to the US and her passion for entrepreneurship. She discusses the challenges of working in corporate America and the freedom she found in building her own company. Alina also talks about the benefits and challenges of working with her husband as a co-founder and the importance of managing conflict in a relationship. She explains why Chili Piper decided to be a remote-first company and how they maintain a vibrant culture despite being geographically dispersed. Alina also provides insights into their hiring process for remote workers and the key characteristics they look for in candidates. She discusses the importance of onboarding and the need for self-accountability in a remote work environment. Alina shares her excitement for the future of Chili Piper and the challenges of scaling the business. She emphasizes the importance of being a problem solver and the joy she finds in building things. Key Takeaways: Alina's drive for independence and freedom led her to pursue entrepreneurship and build her own company. Working with a spouse can be rewarding if there is trust, respect, and effective conflict management in both personal and professional life. Remote work offers flexibility and freedom, but it requires self-discipline and the ability to manage loneliness. Hiring remote workers requires finding individuals who are self-sufficient, have good work habits, and can thrive in a remote work environment. Onboarding is crucial for remote workers to ensure they understand the company's values, products, and remote work expectations. Quotes: "The fact that it's hard and complicated, that's what excites me the most." "I always wanted to be the CEO of a company ever since I was a child." "We recommend that (remote workers) work out of an office, a shared office, a co-working space with other people." "As long as the values that are important to us are instilled and we are supporting their growth... then I think they're going to be okay." "Every stage of the company is really hard because you've not been exposed to it before... it's an ever-evolving skill set." ​Chapters:  (0:00:30) Alina's desire to come to the US for more opportunities (0:02:35) Alina's dissatisfaction with corporate America and desire for independence (0:03:44) Alina and her husband's successful working relationship at Chili Piper. (0:08:19) Characteristics sought in remote workers: self-sufficiency and self-accountability. (0:15:35) Moments of realization that the business was taking off (0:18:44) Transitioning from founder-led sales to external leadership (0:21:19) Work life integration vs work life balance (0:25:52) Balancing CEO responsibilities and collaborating with the board (0:32:39) Excitement about growing Chili Piper and facing new challenges (0:33:57) Quick Fire-Round Subscribe on Spotify:  SaaSy Talk Unfiltered | Podcast on Spotify  Subscribe on YouTube:  SAASY TALK UNFILTERED - YouTube   Subscribe on Linkedin: https://www.linkedin.com/company/saasy-talk-unfiltered Subscribe to our Newsletter: SaaSyTalkUnfiltered | Substack Visit our Website:  SaaSy Talk Unfiltered (transistor.fm)    Follow Ricky Sevta on Linkedin:  Ricky Sevta | LinkedIn   Follow Sean Diljore on Linkedin:  Sean Diljore | LinkedIn