How to hire your startup’s first senior leader

You don’t wake up one morning and decide it’s time to hire your first startup executive.

You feel it first. Your calendar fills up. You’re making decisions in areas you were never trained for. The team keeps growing, but progress slows because your leadership has become the bottleneck.

This is the moment many startups hit a ceiling. Here, scaling can only come from bringing in experienced operators who can own a function, build teams, and carry responsibility.

Here’s a step-by-step guide to help you do it, drawn from founders, recruiters, and operators who have seen this transition up close.

Step 1: Map the organisation you’re building

Before you write a job ad or start asking around for referrals, pause.

A huge mistake founders make here is hiring reactively. They respond to the loudest, most urgent problem in front of them instead of thinking about the future organisation they are trying to build.

A more useful starting point is to sketch out your future org chart; what your team needs to look like 12–18 months from now, based on realistic growth. This can be done in Figma, on a whiteboard, or even just down in a notebook.

Start by listing the core functions your business will need as it grows, such as:

• Engineering
• Product
• Sales
• Marketing
• Customer Support
• Operations
• Finance
• People & Culture

Once those functions are on the page, describe what actions each one is responsible for. It may look like:

• Sales: revenue targets, building a repeatable motion
• Marketing: brand positioning, messaging, demand generation
• Product: roadmap, customer feedback loops, feature prioritisation

This gives you a clear sense of what success looks like in each part of the business.

Next, write your own name into every role you’re currently covering. This is where patterns start to emerge. Most founders will find their name appears in five or six different areas; that’s normal. What matters is noticing where your name shows up repeatedly, or in functions you can’t realistically lead over the long term.

These are often your pressure points, and they point directly to where a senior hire could make the biggest difference. This exercise helps you:

• prioritise executive hires in the right order
• avoid over-hiring or handing out inflated titles too early
• shift deliberately from “doer” to CEO

This isn’t a one-time activity. Startups change quickly, and the shape of the organisation needs to change with them. Revisiting your org chart regularly, even once a month, helps keep hiring decisions grounded.

When you hire based on where the company is heading, rather than where it hurts today, you build long-term strength instead of just short-term relief.

Step 2: Identify the most critical hire

The next decision is which leadership role to hire first, and this is where uncertainty often creeps in.

It can feel like the business needs help everywhere at once. Sales demands attention, marketing feels messy, the product needs care, and operations are starting to creak. Trying to fix all of this in one go, however, leads to rushed or unclear hiring decisions.

A more effective approach is to focus on the single hire that will unlock the most progress. This isn’t always the area that feels most frustrating day to day. Founders often reach for the role that causes the most stress, rather than the one that creates the most leverage across the business.

To work this out, it helps to return to the org chart you mapped earlier and write down responses to these key questions:

• Where is growth being blocked?
• What work am I doing that pulls me away from my highest-value responsibilities?
• Which function will struggle first without dedicated leadership?
• Which area, if strengthened, would lift the rest of the business?

These questions often reveal a different story to first impressions. Marketing might feel chaotic, but sales may be the real bottleneck if the founder is still closing every deal. The product might be strong, while churn quietly increases because no one truly owns customer success or operations.

It can also help to sense-check your instincts against common industry patterns and timelines. For example:

• Around $1M Annual Recurring Revenue, many startups hire a Head of Sales.
• After building the initial product, companies often bring in a Head of Product to own roadmap and delivery.
• When customer volume increases, a Head of Customer Success or Operations leader can free the founder from firefighting.

Once the most critical hire is clear, the focus should shift to defining the role and hiring well.

Step 3: Define the role

With the role identified, the next step is to define what that role actually involves.

If you want to attract someone who fits your stage, your vision, and your culture, you need to be specific. To help do this, start by writing down:

• the problems this person will solve
• what success looks like in their first twelve months
• where they will need to lead directly, and where they will need to build capability
• who they will manage, and who they will work closely with

This is often called an Ideal Candidate Profile. In practice, it’s a shared working brief that guides how you search, interview, and make decisions. It also gives you a clear way to explain the role to candidates and advisors.

It’s equally important to be honest about the type of leader you need at this stage of the company’s life:

• Team Builder (0 → 1): hands-on, builds foundations themselves
• Company Builder (1 → 10): adds structure, process, and people leadership
• Company Scaler (10 → 50): optimises, systematises, and scales what’s working.

If you bring in a “scaler” too early, they’ll be frustrated by the lack of systems. If you hire a “builder” too late, they might get overwhelmed.

Before moving forward, make sure everyone involved in the decision is aligned. Co-founders and board members should agree on:

• key outcomes for the role
• level of seniority required
• profile you’re targeting
• success measures

When everyone is clear on what you’re hiring and why, it becomes much easier to recognise the right person when you meet them.

From there, you can turn all this thinking into a job description that clearly reflects the work, the outcomes, and the context of the role. This then lets you go out to market for candidates.

Step 4: Run the search

Once you are clear on the role, the next question becomes very practical: how are you going to find this person? You’ve got two real options:

1. run it yourself, or
2. bring in a specialist, such as a recruiter or executive search firm.

Both can work well. The key is choosing one path and running it properly. When founders drift between the two, the search loses focus and strong candidates move on.

Option A: Do it yourself

Founder-led searches work best when you:

• have strong relationships in the function you’re hiring for (warm introductions come easily)
• can assess the role and recognise what “great” looks like at your stage
• can commit real time (expect 10–15 hours a week for sourcing, screening, scheduling, and follow-up)

If you can say yes to all three, you can run it yourself and move quickly. If you can’t, and this hire carries a lot of weight, bringing in help is often the better call.

Many founders assume they can post the role and wait for applicants.

But senior hires rarely happen that way. The strongest candidates are busy, employed, and already being approached by other companies. You need to go out and find them, and you need to do it with intent.

Start with your highest-trust channels: advisors, investors, former colleagues, and founders you respect. Make your ask specific:

• “Any recommendations for a Head of Sales who’s sold a technical or complex product and can coach a small team?”
• “Do you know a product leader who’s built v1 and v2 products from scratch?”
• “Do you know a Head of Operations that’s great at turning founder intuition into repeatable systems?”

The sharper your ask, the better the introductions you’ll get. Once you’ve tapped your own network, you, or your recruitment firm, can expand your reach:

• Use LinkedIn’s advanced filters or Boolean search to find people that match your Ideal Candidate Profile.
• Explore alumni networks, niche communities, and startup leadership groups.
• Ask your investors or advisors to share your role directly with their networks, warm intros beat cold outreach every time.

If you’re doing cold outreach, keep it short and personal. Senior candidates can spot generic outreach a mile away. Make sure you cover:

• Why them: the exact pattern you noticed in their background
• Why you: mission + traction + why this is worth their attention
• Why now: the problem/opportunity they’d own immediately

That gives them enough context to decide quickly whether they want to discuss the role.

Option B: Recruitment firm

A recruitment firm is often worth it when:

• the role sits outside your expertise (for example, you’re technical and hiring your first marketing leader)
• you need a broader or more diverse slate than your network can reach
• it’s a senior or sensitive role where confidentiality matters
• you’ve been self-sourcing for 30–45 days and traction is still light

They’re an investment, and the way to get value is to treat the relationship like a partnership rather than a hand-off. If you decide to go with a firm:

• Give them a strong brief: Share your Ideal Candidate Profile and org chart
• Set clear expectations: Timelines, diversity priorities, number of intros per week
• Support the process: Review shortlists together, give fast, specific feedback.

Choose a firm that knows startups at your stage and understands the difference between early builders and big-company scalers.

Step 5: Screen candidates for fit

A strong resume alone won’t tell you whether someone can operate in the reality of a growing startup. At this stage, you’re often looking for people who can:

• operate without big-company structure or support
• build systems and teams from scratch
• move between strategy and hands-on execution without ego

Before you book an interview, if it’s not clear from what they’ve provided, your first conversations should surface this information quickly.

When you speak with them, ask for short concrete examples:

• When have they built something from zero?
• When have they made progress with limited resources?
• How have they handled ambiguity, pressure, or fast change?

As you listen, pay attention to curiosity, adaptability, and clear thinking. These qualities tend to matter far more at this stage than how many people they’ve managed or which company logos appear on their CV.

As you go, keep your list of candidates focused. Instead of filling it with 20 mediocre options, aim for 3–5 strong contenders in your first wave.

If none feel right, adjust the search and try again. Waiting a little longer is far better than bringing in the wrong leader.

Step 6: Run a tight, credible interview process

This is where many founders lose great candidates. The process stretches out, feedback slows down, and interviewers drift out of alignment. Suddenly, your top pick ghosts you or takes another offer.

The fix is to get your process tight before you go to market. Make sure you have a clear idea of who is:

• Driver: the person who owns the process from start to finish (usually the founder or a recruiter)
• Decider: the person who makes the final call (again, often the founder)
• Contributors: 1–3 team members who test for functional fit or culture add

Do not build a hiring committee. You want input, not decision-by-vote; when everyone’s a decider, no one is.

Next, map out the interview stages. Keep it simple and purposeful, ideally 4–5 touchpoints max. Each one should uncover a specific piece of evidence, and you should know what questions are required to do it.

For example, your process might look like:

• 1. Founder screen – motivation, stage fit, why this company, why now
• 2. Functional deep dive – judgement, domain depth, how they think under pressure
• 3. Working session – real-world thinking on business problems (careful, this is not asking for free consulting)
• 4. Team conversation – how they engage peers or future direct reports
• 5. Final alignment + references – close remaining gaps, confirm pattern of behaviour

It’s also worth testing how they perform in the environment they’ll be working in.

If you’re hybrid or remote, don’t only meet in person, see how they show up over Zoom. Can they hold attention and influence over video? Can they communicate clearly without in-person cues?

Throughout the process, pay close attention to how candidates communicate. Look for signs of clarity, initiative, humility, and follow-through.

• Are they prepared?
• Are they thoughtful in how they ask and answer questions?
• Do they show signs of listening and adapting?

These signals often tell you more than any single interview question.

Step 7: Follow up

Once strong candidates are in play, everything becomes a race against uncertainty.

Set expectations early and run the process in a way that feels swift, decisive and professional. As a baseline, this usually means:

• interviews are booked promptly, without long gaps
• feedback is shared within 24 to 48 hours
• candidates always know where they stand and what the next step is

Transparency goes a long way here. Be clear about your level of interest, the steps in the process, and the timelines you’re working to.

When candidates understand what’s happening, they feel safer committing to the next step and, eventually, to the role. Candidates aren’t only assessing the role itself; they’re observing how you operate. A slow or disorganised process often signals unclear priorities or hesitation at the top.

If a candidate stands out, don’t hesitate just because you planned to meet more people. The ability to recognise quality and act decisively is often what secures the best hire.

Step 8: Make the offer and close the hire

You’ve found your person. The fit feels right, the energy is aligned, and the team agrees. This is the moment that seals the hire, and how you handle it sets the tone for the rest that follows.

Where possible, deliver the offer yourself. This is your chance to speak directly about why you want them in the business:

• why you believe they’re the right person for the role
• what you’re excited to build together
• how this role shapes the next phase of the company

This can be a call, a short video, or a thoughtful email – the format matters less than the sincerity. Senior operators want to feel chosen, not processed. You should walk through the details and share the specifics:

• base salary and bonus
• equity (percentage, vesting, and how to think about upside)
• start date and any additional terms

Don’t assume everyone is fluent in equity. Take the time to explain how it works, using simple scenarios to show what ownership could look like as the company grows. This builds trust and helps candidates make a confident decision.

If you sense hesitation, get curious. Great candidates may have other options or concerns, timing, family, title, or team structure. Invite those conversations openly, so you can discuss how to make it work.

Once they accept, don’t let the energy drop. Make the transition into the company feel just as considered as the interview process:

• confirm the start date and outline the first week
• share internal communication about the hire with care, highlighting what they’ll lead
• if you’re hybrid or remote, schedule in-person time early
• set up a 30–60–90 day alignment session in their first week

As your new leader starts, they’ll need context and trust to find their footing. Your involvement in this phase matters more than you might expect; so expect to answer questions and be active on the ground when needed

And finally, celebrate the moment. A thoughtful welcome, a proud announcement, a sense of occasion – these things set the tone for the relationship to come.

Final thoughts

Hiring your first executives is one of the biggest inflection points in your startup’s life. You’re handing over ownership, and you’re scaling beyond what you can personally carry.

One great executive can unlock the next 12–18 months of progress.

But that doesn’t start with a job ad. It starts with stepping back, making one clear decision at a time, and running the process like it matters. Because it does.