Why Founders Get Their First Leadership Hire Wrong

Alan Fecamp, Global Director, GTM and Operations, Zeren offers his insight into building high-performing sales teams, evolving from product-led growth to a commercial engine, and knowing when it’s time to invest in sales leadership.

1. What are some of the most common hiring mistakes founders make when building their leadership teams at Seed to Series B, and what typically drives these missteps?

There are quite a few, actually. One of the biggest is over-indexing on big company experience. Looking for badges can often lead to false assumptions. When you hire an executive from a large, well-established company, they may struggle in a fast-paced, scrappy startup environment. 

Another frequent issue is hiring for the wrong stage of growth: bringing in someone either too senior or too junior for the company’s current needs. Founders often prioritise experience scaling a business to where they want it to be, rather than where it is today. In some cases, they hire too far ahead based on a name; a recognised brand on the CV may look impressive, but it often lacks the tactical fit needed for the current stage of growth. 

Misalignment of culture and values is also common. Hiring a leader based on pedigree, without ensuring alignment with the company’s mission, values, and working style, happens frequently. This is often driven by an overemphasis on technical expertise or domain experience rather than the candidate’s ability to thrive in the specific team culture. 

Rushing to fill leadership roles out of urgency, rather than rigorously assessing fit, is another recurring mistake. Pressure from investors, board members, or an increasing workload can push founders toward a quick hire, but this often backfires. This is one reason why B2B SaaS leadership roles tend to have short tenures at the Seed to Series B stage, with the average around 18 months. 

A lack of hiring structure also contributes. Decisions are often made based on gut feeling rather than a well-defined interview and evaluation process. Many early-stage founders, understandably, do not have a background in recruiting and have not established clear criteria. This leads to subjective and inconsistent decision-making. 

Overvaluing domain expertise compared to leadership ability is especially common in the Seed and Series A stages. Founders often assume that deep industry expertise outweighs leadership or management credentials. That assumption does not always hold. While it is tempting to believe that someone with strong domain knowledge can figure things out, in many cases you need a proven track record to justify the hire. 

The final mistake I would highlight is avoiding tough firing decisions. Keeping underperformers or misaligned leaders for too long often stems from a fear of disruption or concern about sending the wrong signal to the wider team. Founders tend to feel loyal to early hires and worry about how parting ways might be perceived by investors or others in the company. However, holding on too long can have a significant impact on growth.  

2. When a founder approaches you thinking they need a VP or a C-level hire, what are the key questions you ask to determine whether they’re actually hiring for the right role?

Start with what problem they’re trying to solve with the hire. Ambiguity is paramount in these early-stage businesses. 

You might receive an email or enquiry about a particular type of role, but when you strip it back and figure out what problem they’re trying to solve, it turns out to be a completely different person or role title than they need. It’s about identifying whether there’s a specific gap in the leadership team, a problem with execution, strategic decision-making, or if it’s just an operational challenge they’re trying to fix. 

Once you understand what challenges they’re facing, you can begin to flesh out what that role is, from job title to the background of appropriate candidates. The responsibilities and outcomes you’d expect from that person also tie into it. Are you looking for a visionary leader, operator, or functional specialist? What are the outputs they’ll be measured on in the first 6 to 12 months? That often dictates and helps validate the type of person and level of experience you’re hiring for. 

There’s also a cultural element at play, particularly when thinking about US dynamics where titles like VP are used quite frequently in B2B SaaS businesses. Once you strip that back, you might realise what’s really needed is a VP, a director, or a C-level person—and getting that levelling right is important. Quite often, you see these titles thrown around, but when you break it down, what’s needed is an individual contributor rather than a seasoned executive. It’s important to figure that out early on. 

You also need to understand how the role will interact with the rest of the team—who they’ll report to, who they’ll collaborate with, and which existing team members will be key to this person’s success. Once you know where they fit in the ecosystem of collaborators and reporting lines, that really helps define the level and skill set required. 

One thing that comes up because of that ambiguity is whether the business needs to make the hire at all. In some cases, it might make more sense to bring in a fractional leader or advisor as an interim measure to help shape the hiring brief. When they do get to the point of making a permanent hire, that can be a much clearer process. That’s a common scenario and guiding a client through that process to help them arrive at a firmer brief is the way to go. 

Finally, there’s the question of how the hire aligns with the company’s growth stage and budget. If the company is at a point where a C-level hire might not be necessary and a VP would be a better fit, that’s a key consideration. 

3. How can founders determine the right time to bring in senior leadership, and what factors should they consider when balancing immediate execution needs with long-term scalability?

I think it comes down to affordability, and that’s not just about compensation and salary, but also being able to provide the hire with the resources they need to be successful. Salary and cost base is one thing, but when it comes to budgets compared to what they’re used to working with, that’s a separate issue to consider. We always push quite hard on that. 

Depending on the role, bottlenecks and decision-making capability are key indicators. If the founder or early team is stretched too thin and slowing down as a result, a senior leader can help delegate and drive execution. Quite often that’s a COO or a Chief of Staff. If it’s a matter of intellectual or strategic capability, identifying gaps in the senior leadership team becomes important. When you’re scaling beyond the founder’s expertise, whether that founder comes from a sales, product, or operational background, you can often look to backfill that skill set. 

For example, if the founder is a salesperson and wants to move away from founder-led sales, then it becomes clear that a VP of Sales or some form of sales leadership is required. That gives them capacity and helps to accelerate growth. There may also be a need for a strategic thinker, a more structured, long-term vision to sustain and scale the business. 

That ties back to the earlier point about bottlenecks in decision-making. We’d look to determine whether that’s a blocker in the decision-making journey. 

Investor and market expectations also play a role. We’ve worked with founders who are under increasing pressure from the cap table, where each investor has their own view on what should be hired for, based on when they invested. That can heavily influence the type of brief we get and what the board expects. It often ties into fundraising plans. If a company is preparing for Series B, there’s usually an expectation that certain functional leaders will already be in place. If they’re not, it can be harder to raise capital.  

Team growth and complexity also matter. A growing team requires professional management and leadership to maintain alignment and culture. Too many direct reports is a real challenge. You won’t be able to build a repeatable process within a function that enables scale. For example, we had a client recently debating whether to hire a VP of Customer Success or just bring in eight to ten CSMs. Clearly, that’s too many direct reports into a founder-CEO who is already doing everything else. You’ll feel the pain of that when it comes to renewals and other key moments, if you don’t have clear functional expertise and leadership. The scale of functional teams often drives what you need to hire, and when. 

It’s also about balancing immediate execution with long-term stability. We encourage founders to avoid hiring someone who fits only one stage of growth. You need to hire for the now, without getting too far ahead, but also find someone who’s been through multiple close funding stages, like taking a business from Seed to Series A or Series A to Series B. Those key transition points help us assess where the gaps are in the senior leadership team and whether it’s the right time to hire. 

A common pitfall is waiting too long. Sometimes founders raise investment and want to move quickly, but the challenge is to apply the brakes and bring rigour to the process. At the same time, the opposite is also true. Hiring too late, when the company already has a problem, leads to rushed decisions. For example, a bottleneck in the go-to-market motion or a churn issue in customer success. Waiting too long can become a real issue. 

Product-market fit is crucial. I’ve seen many cases where companies think hiring a senior leader will fix things, but they don’t yet have product-market fit. That creates problems and is a major cause of churn. I recently spoke to a Chief Revenue Officer who left his last role for exactly that reason. You need to be close to product-market fit, with a clearly defined role, before making that hire. 

It’s also important to avoid choosing a title over impact. Focus on capabilities and outcomes rather than the prestige of having a certain job title on the team. 

Ultimately, founders should view senior leadership hires as force multipliers. Bringing them in at the right time can significantly enhance execution while preparing the business for sustainable growth. Framing the decision in the right way is a key part of getting it right. 

4. Many founders rely on their network for leadership hires, but this can lead to misaligned expectations or cultural mismatches. How should they balance trust-based hiring with a rigorous, structured approach?

That happens a lot because it feels safe. There’s a built-in trust and sense of familiarity when it’s someone from your network. However, it can lead to blind spots, misaligned expectations, cultural mismatches, and hiring based on relationships rather than competencies. It’s important to balance the trust-based hiring model with a structured approach, and there are a few ways to do that. 

The big one is defining the role clearly before considering any candidates, whether they’re referrals or a search partner. It’s important to outline the key competencies, leadership style, and cultural traits that align with the company’s needs, rather than trying to fit someone from your network into a vague role. 

Use an objective assessment process. Even for known candidates, conduct structured interviews, reference checks, and competency-based evaluations. You can also minimise bias by using external advisors. The right recruiters can add a layer of objectivity to the process. 

Founders should also look beyond their network. Referrals can be a great source, but exploring external candidates helps you benchmark effectively. It doesn’t mean the external candidate will get the job, but it might validate that your direct referral is indeed the right fit. A broader talent search increases your chances of finding the best match. 

It’s also important to clarify mutual expectations. Even when hiring someone familiar, have an open discussion about things like decision-making style and long-term goals. Avoid assumptions that can lead to friction. Familiarity often means you don’t ask the difficult questions you would ask a stranger, and that can cause problems later. 

If possible, pilot the relationship. Work with the candidate in a consulting or advisory capacity before committing to a full-time leadership role. This can be easier to do when the introduction comes through a network, rather than through a formal search. It benefits both sides by allowing them to gauge compatibility in a low risk setting. 

Finally, foster a feedback culture. Structured onboarding and a clear feedback loop ensure that even a trust-based hire is held accountable and feels supported in integrating effectively. 

5. Looking back at the leadership hires you’ve supported that have truly propelled startups forward, what patterns or lessons stand out? What should founders keep in mind to maximise the impact of their leadership team over time?

It’s a great question, and a broad one. I think being prepared to go on a journey with the hiring process is important. 

Sometimes it takes time to land on exactly the right profile, and trying to rush is where problems start. Speed is everything in early, venture-backed B2B SaaS or technology businesses, but those who are prepared to wait an appropriate amount of time and allow for proper due diligence and market coverage usually make the best hires. 

I’ve seen so many examples where the process is rushed, and you can spot it a mile off. Nine times out of ten, it ends badly, the person leaves, or the company must let them go. Allowing the right amount of time, and working with the right partners, is crucial. 

In many early-stage businesses, there’s often a lack of sufficient internal talent capability. You might have a talent team, but they may not be functional experts. I’d strongly encourage founders to bring in the right functional expertise to support them. That external perspective can provide valuable, objective advice. 

Companies that try to handle it directly without that expertise often rely on inbound advertising and lack the knowledge to properly assess candidates. That really affects the outcome. 

Those two points, time and the right support go hand in hand. If you’ve got proper support, everything else tends to fall into place: the right processes, the right advice, and clarity on what types of backgrounds are relevant. That also connects to avoiding badge-oriented hiring. Focus on who’s the best fit for your business, not just someone who looks impressive on paper because they come from a certain company. 

Ultimately, it comes down to getting great advice and mitigating risks. 

Alan Fecamp specialises in placing top GTM leaders in B2B SaaS businesses across Sales, Customer Success, Marketing, and Operations. Contact Alan to discuss your hiring needs and how Zeren can support your growth with the right leadership.