In this episode, Joe and Raza speak with Firas Raouf, co-founder and general partner at Companyon Ventures, a Boston-based VC firm specializing in early-stage B2B software and AI startups.

Firas shares insights from 25 years as a founder, operator, and venture investor—helping companies transition from founder-led sales to scalable, operationally disciplined organizations. The conversation focuses on how early-stage founders should think about creating their first board, the mistakes to avoid, and why great board dynamics depend heavily on execution.

Key takeaways

• Career beginnings

• 25 years ago, Firas co-founded three startups — two were during the dot-com era and one that became VC-funded, giving him firsthand experience sitting on the receiving end of board advice and investor expectations.

• Then, Firas was invited to join OpenView while working at Insight Venture Partners and was able to spend 10 years seeing OpenView and its portfolio companies grow.

• Later he co-founded Companyon Ventures

• How Companyon Ventures supports the expansion stage investing

• After early product-market fit, companies hit the "now we need to scale" moment.

• Companyon Ventures specializes in this transition, helping founders build their first leadership team ,operational discipline, KPIs and dashboards scalable go-to-market engines a plan for capital needs

• Early-stage boards are about support

• Firas emphasizes that early boards are not oversight bodies like public-company boards. Their purpose is to surround the founder with people who can help them think strategically, navigate challenges, and build a scalable company.

• A board can include a seat for common shareholders, lead investors and an independent board member, who is someone with whom the CEO is comfortable.

• Since lead investors can become a long-term board member, Founders must evaluate who they are letting in, not only the valuation. Once someone is on the board, they're not easy to remove.

• Boards must evolve as the company evolves

• As companies grow, the expertise they need changes. Firas suggests cycling out board members after two years.

• After 18–24 months, it's common for a board member's value to plateau, making board refreshes, new independent directors, or role rotations both healthy and necessary.

Quotes

• "A happy board tends to reflect great execution. An unhappy board tends to reflect poor execution."
• "I do think that you should keep things fresh, so to speak, and so any board member really that has been there more than two years, it's rare that you haven't picked their brain dry."
• "It's not just about valuation, it's also about who you're going to let into your company, into your house, because once you let them in, you can't get rid of them."
• "The board of directors for an early-stage startup is the opportunity to have a number of people around the table that can help you navigate and scale your company."

Links

Companyon Ventures- Boardroom Confidential

Guest Bio

Firas Raouf is the co-founder and general partner of Companyon Ventures, a Boston-based VC firm that invests in early-stage B2B software and AI startups. Before launching Companyon, Firas was part of the founding team at OpenView Venture Partners, where he helped pioneer the "expansion stage" investment model and partnered with dozens of software founders to scale their go-to-market operations. Today, he focuses on helping founders transition from founder-led sales to scalable growth by building leadership teams, operational discipline, and repeatable GTM engines. Firas is known for his hands-on, operator-turned-investor approach and his passion for guiding first-time founders through the challenges of building high-growth software companies.