Who should your first executive hire be?

It’s a question every business founder wrestles with. The right choice builds momentum; the wrong one can derail your startup before it even takes off.

 

Many founders believe product-market fit determines company  success. But venture capitalists know otherwise. Research shows that 60-65% of startup failures stem from issues within the founding leadership team, not the product or market. 

Our Toronto executive recruitment team works to build and develop C-suite teams for organizations of all sizes and industries, from global companies to high growth start ups. 

Here are our executive recruiters strategies to help growing organizations build a successful leadership team.  

The Right Composition for Your C-Suite

Diversity in your C-suite is critical. Combining product expertise with business acumen creates a more resilient company. The best teams include a blend of technical knowledge and strategic insight. Instead of stacking the team with MBAs, bring in leaders with engineering backgrounds, operations expertise, and experience managing large-scale projects. Think of your executive team like a table—it needs multiple strong legs to stand firm. 

Choosing Your First Executive Hire

Who should your first executive hire be? The answer depends on your company growth trajectory.

Most leaders assume that hiring a Chief Financial Officer (CFO) or Chief Revenue Officer (CRO) should be the first priority. However, while financial expertise is essential, a full-time CFO typically becomes necessary only when revenue nears $50 million. Until then, a strong controller or accounting team can manage financial operations.

Instead, early-stage startups benefit most from hiring a Chief Commercial Officer (CCO) or Vice President of Sales. These roles focus on revenue generation and market expansion, ensuring the company doesn’t get stuck perfecting a product without securing paying customers.

The CCO oversees both marketing and sales, driving market engagement and customer acquisition. A VP of Sales, on the other hand, specializes in building a scalable sales function. The key is hiring a strategic leader who understands how to scale sales operations, build effective teams, and execute go-to-market strategies.

Timing new executive roles

As your company grows, your leadership needs evolve. Early-stage startups should start lean, typically with a CEO, CCO, and COO. At Series A, additional specialized leadership—such as a Chief Technology Officer (CTO) or Chief Marketing Officer (CMO)—often becomes necessary. By Series B and beyond, companies typically bring in a Chief Human Resources Officer (CHRO) to focus on organizational growth.

Successful startups add executive roles at about half the rate of struggling peers. Instead of rapidly expanding leadership, they optimize existing roles and focus on operational efficiency.

Adapting Leadership During Growth Phases

As a company scales, leadership structures must adapt. What works at 50 employees rarely works at 500. Responsibilities often shift, and in some cases, new roles must be created.

A key challenge for founders is recognizing when early executives are no longer the right fit. Founders must be willing to assess team capabilities honestly and make difficult personnel decisions when the company’s evolution demands it.

Startups that adapt their executive structure during growth phases outperform those that rigidly adhere to their initial setup. The ability to reshape leadership roles as the company scales is a critical success factor.

Building a High-Impact Executive Team

Successful startup teams share common traits: they balance business and technical expertise, keep executive teams lean, and focus on sustainable growth rather than rapid expansion.

Building the right executive team isn’t about mimicking other startups—it’s about understanding what drives success and tailoring leadership hires to your specific needs. A founder strong in commercial strategy might prioritize hiring a CFO, while a product-driven founder with weaker people-management skills might benefit from an HR leader. 

The key is to start with the essentials and expand strategically based on actual business needs—not external expectations.

Beyond skills and experience, executive hires must align with the company’s vision. A strong leadership team isn’t just about filling skill gaps—it’s about reinforcing the mission and culture that drive the organization forward.

Every executive hire should solve a specific problem and strengthen the company. Get this right, and you’ll build a foundation for long-term success.

 

Not sure where to start? We can help.

At South End Partners, our Toronto executive recruiters work with large and small organizations across industries to help them find the right leaders for the right opportunities using an objective, data driven approach.

We also provide comprehensive HR consulting services including onboarding support, interview coaching and training, and strategies to develop your superstar teams.

Reach out to find out how we can help you today!