In this latest episode of our series, CEO Confidences: The Challenging Art of Building Great Teams, Jean de Rauglaudre, CEO and co-founder of Collective, offers a candid look into leading a startup through both its initial stages and a profound strategic pivot. Originally launched as a marketplace for freelance teams, Collective recently evolved into a social network dedicated to freelancers. Jean shares invaluable insights into recruiting a co-founder, scaling a sales team, and redefining an entire business model after three years.
Here are the key takeaways:
1. The Startup Spark: Turning Passion into Purpose
Jean’s journey with Collective began three years ago with a mission: create a platform to empower freelance teams to operate seamlessly. His freelance experience during business school gave him firsthand insights into the freelance market’s challenges and untapped potential. Although his background in consulting at McKinsey provided rigorous training, it did not include recruiting—a skill he had to learn through hands-on experience.
For Jean, passion is a critical ingredient in venture building, fueling resilience over the long haul. He explains, “The topic should be exciting enough to handle all the problems that come with it.”
2. Finding the Idea: A Strategic, Methodical Approach
Jean and his co-founders saw that the freelance industry was ready for transformation. They engaged deeply with venture capitalists and industry experts to analyze gaps and explore ideas in the market. “We spoke with VCs, investors, and business angels to understand what was lacking in the market”. They then aligned on what truly motivated us, building a product that would have a true impact on the future of work.
3. Building the Foundation: Leveraging Recruitment Support
Jean credits much of Collective’s initial team-building success to his collaboration with Hexa (formerly known as eFounders), a startup studio renowned for supporting early-stage tech companies. Hexa provided invaluable recruitment resources and mentorship, helping to source candidates, refine interview processes, and shape the company’s hiring strategy. With Hexa’s guidance, Jean not only built a strong team but also gained a foundational understanding of effective recruitment practices.
“Hexa’s motto is to build great teams,” Jean explains, emphasizing how working alongside experienced recruiters helped him develop essential skills.
4. Learning from Missteps: The Challenge of Finding the Right Fit
In the early stages, Jean faced significant challenges in hiring for key roles, especially in leadership. His first CTO hire, for instance, did not work out—a realization that came after recognizing a misalignment in entrepreneurial appetite and the will to take risks. “We didn’t realize it right away, but soon, frustrations emerged, signaling that the partnership wouldn’t work out,” he shares. "It's a bit like romantic relationships. The entrepreneurial journey is so demanding that you need to be 120% sure of your choice to commit fully. For me, if there’s doubt, there’s no doubt.”
Jean’s next CTO hire, however, was someone deeply aligned with Collective’s vision and was adamant about being a co-founder, not just an employee.
This lesson recalibrated Jean’s approach, showing him the importance of finding candidates with a true entrepreneurial spirit and a high tolerance for risk.
5. The Pivot: Redefining Collective’s Vision
Pivoting Collective from a platform for freelance teams to a social network was not an easy decision. Initially, the business model encompassed both software tools for freelancers and a marketplace service to connect teams with companies. However, this dual approach became financially unsustainable. Jean and his co-founders faced a difficult choice: retain the service side or transition to a product-focused model aligned with their tech aspirations. "I think that was the hardest moment of my professional life. You have two big choices.”
“We had two choices: keep the service side, which was generating revenue, or pivot to a product-focused model,” Jean explains. The decision to pivot wasn’t just about financial sustainability; it was about reconnecting with their initial ambition of creating a scalable, tech-driven platform that could become the “LinkedIn for freelancers.”
6. Evolving Team Culture: Managing Internal Transformation
The pivot required Collective to let go of half its team, an emotionally challenging process. "One key thing is to hold yourself accountable. And in this case, I had no shame in admitting that I made a mistake.” Jean’s team demonstrated remarkable resilience, understanding that change is an inherent part of startup life. To navigate this transition, Jean talked with other cofounders having undergone a pivot, maintained open communication, explaining the pivot’s rationale and how it would shape Collective’s future.
“Startups are environments where risks and pivots are part of the journey,” he reflects. His transparency fostered trust within the core team and underscored the importance of owning up to hard decisions.
7. Adopting a “Hire Slow, Fire Fast” Strategy
In Collective’s post-pivot phase, Jean adopted a “small team, big community” strategy. This meant focusing on hiring only key individuals who would act as “mini-entrepreneurs” while delegating specific roles to freelancers from the Collective network. This approach has kept the team agile while tapping into specialized expertise on an as-needed basis.
Jean believes balancing strategic hires with freelance support creates a more sustainable model, aligning with Collective’s mission to empower freelancers and maintain low operational overhead.
8. The Resilience Factor: Rediscovering Motivation Post-Pivot
Jean’s pivot also challenged him to redefine his own motivation. While the startup’s pre-pivot phase was filled with high-energy demands, especially around sales, this new phase required a different approach. “It’s hard to recreate a new source of energy from scratch, but I knew it was the right choice for Collective,” he reflects.
This period, initially draining, helped Jean reconnect with Collective’s core mission, which in turn recharged his drive that is so necessary to embark the team.
Conclusion
Jean’s experience offers a candid view of building a startup team—from the exhilaration of creating something from scratch to the challenges of aligning with co-founders, navigating a business pivot, and staying true to one’s vision. His journey demonstrates the resilience, adaptability, and strategic foresight essential to leading a team through the ups and downs of building a business.