SaaSy Talk Unfiltered: Building a Remote-First Unicorn Company

Insights from Alina Vandenberghe, CEO of Chili Piper

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In this article, we delve into the fascinating journey of Alina Vandenberghe, Co-Founder and Co-CEO of Chili Piper, as she shares her experiences and insights on building a successful remote-first company. From her childhood dreams of being a CEO to the challenges of managing a board and the joys of parenting, Alina provides valuable lessons and perspectives on entrepreneurship, remote work, and the future of the tech industry.

Introduction: The Thrill of Complexity and the Pursuit of Freedom

Alina Vandenberghe, CEO of Chili Piper, is a woman driven by the thrill of complexity and the pursuit of freedom. From her early dreams of being a CEO to her journey from Romania to the United States, Alina has always been drawn to the world of entrepreneurship. She thrives on the challenge of building something from scratch and the joy of seeing her ideas come to life.

In this thought-provoking interview, Alina shares her experiences and insights on various topics, including the decision to build a remote-first company, the dynamics of working with her husband as a co-founder, and the importance of managing conflict and differences of opinion. She also discusses the challenges and rewards of being a parent while running a high-growth startup, and the critical role of a supportive board in the success of a company.

Building a Remote-First Company: The Power of Nimbleness and Independence

Alina's journey into the world of entrepreneurship led her to the realization that she was not made for the confines of corporate America. She craved the freedom to make her own decisions and have a positive impact on the world. This desire, coupled with her love for building things and the nimbleness of startups, led her to co-found Chili Piper as a remote-first company.

Alina explains that the decision to build a remote-first company was born out of necessity at first, as they were bootstrapped and couldn't afford to hire people in New York. However, as the company grew, they realized that the diversity of culture and the freedom to choose their own working hours and schedules were invaluable. They made sure to hire people who were well-suited for remote work and created a culture that embraced collaboration and self-sufficiency.

Alina acknowledges that remote work has its challenges, such as the potential for loneliness and the difficulty of brainstorming and collaborating without being in the same physical space. However, she emphasizes the importance of creating a supportive environment and providing opportunities for remote employees to connect and network with others. Chili Piper offers perks such as paid Airbnb stays and food expenses for team members to meet in person and foster relationships.

The Power of Collaboration: Working with Your Spouse

One of the unique aspects of Alina's journey is that she co-founded Chili Piper with her husband. While many people find it challenging to work with their spouses, Alina and her husband have managed to build a successful partnership. She attributes their success to their ability to manage conflict and differences of opinion, both in their personal and professional lives.

Alina explains that the key to working well with your spouse is to have a strong foundation of trust and respect. She emphasizes the importance of solving conflicts in the personal realm, as unresolved issues can spill over into the professional realm. Alina also highlights the significance of small things in a relationship, such as household chores and daily routines, and how they can impact the dynamics of working together.

Navigating the Boardroom: Building a Supportive Relationship

As Chili Piper grew, Alina faced the challenge of managing a board and navigating the dynamics of the boardroom. She considers herself fortunate to have a supportive board that shares her values and looks beyond economic measures. Alina believes that a positive board relationship is crucial for the success of a company, as it provides guidance, support, and accountability.

She acknowledges that not all entrepreneurs are as fortunate and that managing a board can be challenging. Alina highlights two key factors that can make or break the relationship between an entrepreneur and the board. The first is the fear of criticism, especially when entrepreneurs are already self-critical. Alina advises entrepreneurs to address their own insecurities and be open to feedback as a way to grow and improve.

The second factor is the need for support. Running a company is demanding, and entrepreneurs often face numerous challenges and setbacks. Alina emphasizes the importance of feeling supported by the board and encourages entrepreneurs to communicate their needs and ask for help when necessary. She believes that creating an environment of trust and support is a skill that both entrepreneurs and board members can develop.

The Journey of Growth: From Startup to Scale-Up

Alina's journey with Chili Piper has been filled with moments of excitement and challenges. She recalls several "this is it" moments, where she felt a sense of validation and confidence in the company's potential. These moments came when ideal customers expressed their willingness to invest in advance and when her co-founder consistently closed significant deals.

However, Alina acknowledges that every stage of the company's growth presents new and unique challenges. As Chili Piper prepares for a $200 million ARR and a potential IPO, Alina is excited about the opportunity to scale the company and tackle the complexities that come with it. She recognizes that each stage requires a different set of skills and experiences, and she is eager to continue learning and evolving as a leader.

Conclusion: The Ever-Evolving Journey of Entrepreneurship

Alina Vandenberghe's journey as the CEO of Chili Piper is a testament to the excitement and challenges of entrepreneurship. From her childhood dreams of being a CEO to building a remote-first company and managing a supportive board, Alina has navigated the complexities of entrepreneurship with grace and determination.

Her insights on remote work, collaboration, and managing conflict provide valuable lessons for entrepreneurs and leaders in any industry. Alina's emphasis on the importance of self-reflection, communication, and support highlights the key ingredients for building successful relationships and fostering a positive work culture.

As Chili Piper continues to grow and evolve, Alina remains committed to the pursuit of freedom, the joy of building, and the positive impact she can make in the world. Her journey serves as an inspiration for aspiring entrepreneurs and a reminder that the path to success is not always easy, but it is always worth it.

The future looks bright for Alina Vandenberghe and Chili Piper, and we can't wait to see what they will achieve next in the ever-evolving world of tech entrepreneurship.

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Ricky Sevta

Ricky is a seasoned leader with over two decades of experience in the B2B SaaS and construction technology industry. He has held senior leadership positions at Simpro, Schneider Electric, and other leading companies, consistently delivering exceptional results and guiding businesses to new heights of success.

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