How to hire your first salesperson: a founder’s guide

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Ebsta and Pavilion’s 2024 B2B Sales Benchmark found that only 24% of sales reps hit their quota. Three-quarters failed. If you’re a founder about to make your first sales hire, those odds should terrify you. You’ve been closing every deal yourself. You know the product, the customer, the objections. Now you need to hand that to someone else and trust them not to burn through your pipeline and your cash.

I’ve made this hire dozens of times, for my own companies and now coaching founder-CEOs through it. The same mistakes come up every time. This guide exists to stop you making them.

When should a founder stop doing sales themselves?

When you’ve closed 10-20 customers yourself and you can describe exactly why they bought. Not before. Steve Blank, founder of the Lean Startup movement, was clear about this when I interviewed him on my podcast: founders must validate the sales process personally before handing it off. If you can’t articulate your sales process step by step, no hire will fix that.

The trigger isn’t revenue. It’s time. You’ve proved the product sells. You know who buys it and why. But you’re spending 60-70% of your week on sales calls when you should be running the business. Founder-led sales has become the bottleneck, and every week you stay in that seat is a week the company doesn’t grow.

If you don’t enjoy selling, the problem compounds faster. You can force yourself for a quarter, maybe two. But if you don’t get genuine energy from the process, you’ll quietly stop doing it. Leads rot. Pipeline dries up. You blame the market when the real problem is that selling isn’t your thing. That’s fine. That’s exactly why this hire matters.

What type of salesperson does a scale-up need first?

A closer. Not an account manager. Not a sales manager. Not a lead generator. Someone who can take a prospect with some interest in your product and persuade them to buy. Full stop.

This is where the average scale-up founder goes wrong. In the tech world I’ve always inhabited, people think: “What type of salesperson do I hate? I’m not going to hire one of them.” So they end up recruiting someone pleasant who can’t close. You’re not hiring for likability. You’re hiring for results.

Look for people who’ve closed new business for: a) a company that looks like yours, b) a product that looks like yours, and c) a customer with similar problems. All three? Worth interviewing. Two? Maybe. One? Move on.

Hire for slope, not intercept. A candidate who’s been promoted two or three times in three years at a high-growth company proves they can navigate ambiguity and scale fast. That trajectory matters more than their current job title or the logo on their CV (resume).

First sales hire: screening cheat sheet

Green flags	Red flags
Closed new business at a company similar to yours	“Sales Manager” or “Head of” in current title
Promoted 2-3 times in 3 years (slope over intercept)	18-month stints followed by moves
Previous product was harder to sell than yours	Only worked with established playbooks and warm leads
Self-sourced pipeline in previous roles (PG mastery)	CV (resume) vague on targets, attainment, and wins
Can walk you through their sales process unprompted	Can’t pitch your product after being given prep time
Start-up or scale-up experience with direct impact	Wants 70/30 base-to-commission split
Rates themselves 8+ on a luckiness scale	Needs proposals, decks, and collateral before they can sell

Justin Roff-Marsh makes this point well in The Machine (I interviewed him about this on the podcast). Your first salesperson should spend 80% of their time in selling conversations. If you’re setting up a sales function from scratch, you don’t need a sales manager. Anyone with “manager” on their CV goes straight in the bin.

Should you hire one salesperson or two?

Two, if you can afford it. Think of it as A/B testing humans.

If this is your first sales hire, you’ve got no process for understanding what good looks like. I’d estimate you have a 25% chance of getting it right first time. Recognise that you could waste 12 months: three months to hire, six months to work out they’re not performing, and three more to find a replacement. Hiring two doesn’t double your risk. It halves it. If one fails and the other succeeds, you know the problem is the person, not the product.

With two people, your odds improve immediately. One will almost certainly be better than the other, giving you a benchmark. They learn from each other, they compete with each other, and neither is the only person doing the job. Having someone to compare notes with creates consistency in your process faster than any training programme. There’s also a retention argument: isolated “lone ranger” reps have significantly higher attrition than those who work alongside a peer. Loneliness kills motivation.

Both hires must be comfortable with ambiguity. You haven’t nailed everything down. There’s no playbook, no established territory, no CRM full of warm leads. Someone who’s only worked in companies with established sales processes will struggle. You need people who can make it up as they go along and enjoy doing it.

What is the single most important trait to screen for?

Resourcefulness. The team at Topgrading have tracked dozens of competencies that predict sales success, and this is the one that matters. Resourceful people don’t constantly come to you asking for help. They work out how to make things happen. They find the contact, write the email, book the meeting, chase the deal. Your job isn’t to motivate them. There’s plenty of innate drive already.

Closely related: your first hire must have pipeline generation (PG) mastery. If they’ve never survived the dark, lonely room of making 19 cold calls with no answer and still picked up the phone for the 20th, they lack the resilience your business needs right now. Later, you can hire people who close warm inbound leads. Right now, you need someone with proven PG chops who creates conversations from nothing.

When I recruit, I look for people who describe themselves as lucky. People who rate themselves 8, 9 or 10 on a scale of luckiness are usually A-Players. They own their outcomes rather than blaming the leads, the territory, or the economy. That mindset matters. For the full treatment of this question and how to score it, see the five-stage interview process.

Harvard Business Review research on sales compensation found that financial incentives alone are a poor predictor of top sales performance. The best salespeople are motivated by influence, status, and impact. They like working in scale-ups where they can see their fingerprints on the business. Less bureaucracy. More room to shape things. You’re offering exactly this environment.

How should you interview a salesperson for a scale-up?

Start with a written screen before you meet anyone. Send candidates a Google Doc with a dozen biographical and behavioural questions. This filters out roughly half your applicants immediately, and it tests written communication. If someone can’t write a coherent paragraph about why they want this job, they won’t write compelling outbound emails either.

For the candidates who make it through, don’t ask them to “sell me this pen.” Ask them to sell you your product. There are enough explainer videos, case studies, and marketing pages online that there’s no excuse for a candidate not to understand your value proposition before they walk in. If they haven’t done the research, they’re lazy. To stress-test them, cut their allotted presentation time in half without warning. Watch how they adapt.

Then ask them to walk you through their sales process, step by step. If they look at you blankly, they’re not an A-Player. A strong candidate will have a clear, repeatable method and will be able to explain how and why each step works.

Context matters more than past success. At Rackspace, I hired people who’d been spectacularly successful at Dell. They failed with us. At Dell, there was a well-established playbook: do these things in this order, use this script, and 9 times out of 10 you close. That doesn’t transfer to a scale-up where there’s no process, no brand awareness, and no inbound pipeline.

Test their understanding of solution selling. In most scale-ups, customers have already done 80% of their research before talking to a salesperson. You’re not looking for order takers. You need someone who’ll proactively ring people and persuade them to buy, even if those people had no intention of buying when they woke up that morning.

Probe the difference between their environment and yours. If they’ve only sold established products with strong brand recognition, ask them directly: “How would you approach a market where nobody has heard of us?” Their answer tells you whether they can operate in your world.

What red flags should you watch for on a salesperson’s CV?

Screen out anyone who’s been in a sales role for less than three years. An 18-month stint followed by a move almost always means they didn’t hit target. Look for performance metrics on their CV: target, attainment, and notable wins for every role. A strong salesperson is visibly proud of their numbers. If the CV is vague on outcomes, that tells you everything.

Look for previous experience in start-ups or scale-ups where they had a direct, measurable impact. The right people know they thrive in chaos. They get bored when businesses become structured. That restlessness is a feature, not a bug.

Check they’re not a maverick who won’t fit with your team. The right person knows they’re doing something in your company that no one else can do and earns status, respect, and influence as a result. Not through politics. Through results.

Above all, ask yourself one question: would I buy my own product from this person? Your early leads are precious. If you wouldn’t trust this candidate with your best prospect, don’t hire them. No matter how impressive their CV looks.

What should you pay your first salesperson?

Bluebird Recruitment’s 2025 UK SaaS Salary Benchmarks put a mid-market Account Executive at £40,000-£60,000 base with OTE of £70,000-£100,000. For a first sales hire at an earlier-stage scale-up, the SMB band is the starting point: £30,000-£40,000 base, £50,000-£70,000 OTE with a 50/50 base-to-commission split.

But here’s the thing: for your first hire, be prepared to pay 10-25% above benchmark. You’re only hiring one person. You need the right one. Don’t be cheap. Whatever you save on salary is dwarfed by the cost of a failed hire. Twelve months of wasted time and a dead pipeline costs you far more than an extra £5,000-£10,000 on a base salary.

If someone’s pushing for a 70/30 base-to-commission split, they’re telling you they want to manage accounts, not win new ones. Wrong profile.

Don’t lead with money as the primary incentive. The salespeople who are most motivated by commission cheques are rarely your best long-term performers. Offer competitive pay, but sell the opportunity. The autonomy, the impact, the chance to build something. That’s what attracts the right profile for a first sales hire.

Equity can work, but be specific about vesting and what it’s actually worth. Vague promises of “a piece of the company” attract dreamers, not doers. If you offer equity, make it clear, time-bound, and tied to performance milestones.

What does success look like in the first 90 days?

Don’t set an annual target for a new hire in their first quarter. Set 90-day milestones that measure activity and learning, not closed revenue.

Timeframe	What good looks like	Red flag
Days 1-30	Understands product, customer, and competitive landscape. Shadowed you on 5+ calls. Can demo and handle top 3 objections solo.	Can’t demo after 30 days. Not asking sharp questions. No curiosity.
Days 31-60	Running own discovery calls. Building pipeline independently. Consistent outreach cadence visible.	No conversations generated by week six. Still relying on you for introductions.
Days 61-90	First proposals out. At least one deal moving toward close. Has a point of view on what’s working and what isn’t.	Waiting for you to tell them what to do. No pipeline. No opinions.

If by day 90 they can’t clearly describe your ideal customer and the buying triggers, act. Don’t hope it improves. It won’t.

Where should you look for your first salesperson?

LinkedIn is the obvious starting point, but don’t just post a job advert. Headhunt. Look for salespeople at companies two stages ahead of yours who might want to go back to an earlier-stage environment where they can have more impact. People who’ve done the 0-to-1 journey before and want to do it again.

Your network is underrated. Ask your existing customers who the best salesperson they’ve ever dealt with is. Ask your investors. Ask other founders. The best sales hires come through referrals because the kind of person you want is rarely actively job-hunting. Fast horses run with fast horses. Get your best people to refer their best contacts.

Specialist sales recruitment agencies can help if you’re specific about the brief. The key phrase is “new business closer for an early-stage scale-up, not an account manager.” Most agencies will default to sending you account managers unless you’re blunt about what you need.

Once you’ve made your first hire and want to build out the team, here’s the full five-stage interview process for scaling your sales function.

Frequently asked questions

When is a founder ready to hire their first salesperson?

When you’ve personally closed 10-20 customers, can describe your sales process step by step, and selling is consuming more than half your working week. The trigger isn’t revenue size. It’s the point where founder-led sales becomes the constraint on growth. If you haven’t validated the sales process yourself, no hire will compensate for that.

Should I hire a sales development rep (SDR) or an account executive (AE) first?

An account executive who can close. Full stop. Your first hire takes prospects from first conversation through to signed contract. An SDR generates leads but can’t close. You need someone who does both. Layer in an SDR later, once you have a repeatable process and consistent pipeline. Not before.

What if my first sales hire does not work out?

You’ll know within 30 days. If they’re not asking sharp questions, show zero curiosity, or haven’t generated a single pipeline conversation in their first month, they’re wrong. Don’t wait. The cost of hoping is 12 months: three to recruit, six to confirm what you already knew, three more to replace. Set 90-day milestones from day one and review ruthlessly.

How long before a new salesperson starts delivering results?

In a B2B scale-up, expect 3-6 months for a new salesperson to become fully productive. The first 30 days are learning. Days 31-60 should produce pipeline. Days 61-90 should show deals progressing. If your sales cycle is six months, adjust expectations accordingly, but activity metrics (calls, meetings, proposals) should be visible within the first 60 days.

Should I hire a VP of Sales instead of individual reps?

No. Hiring a VP of Sales before two reps are consistently hitting quota is burning money. Hire a player-coach who’ll carry a bag and build the playbook. Find a hungry Director, not a seasoned VP who wants to manage managers. Full guide on hiring your first head of sales here when you’re ready.

Can I hire a salesperson on commission only?

You can try. The calibre will be terrible. Commission-only roles attract people who are either desperate or juggling five side gigs. Neither will give your product the attention it needs. If cash is tight, offer a modest base with aggressive commission rather than zero base. Paying nothing says you’re not serious. Good people read that signal instantly.

Four ways I can help (ranked by impact, and by how much effort it requires from you)

1. Book a call — the deep end. We’ll tear into what’s really blocking your growth, rebuild it properly, and leave you with a plan you can actually execute. Bring coffee.
2. Grab the book F**k Plan B — the playbook for founders who’ve decided to go all in. Covers hiring, culture, and building something that actually works. No theory.
3. Grab the A-Player Hiring Toolkit — four free AI-powered GPTs: Job Scorecard, CV Analyser, Interview Questions, and Job Advert creator. Built on the hiring system Dominic used at Rackspace and Peer 1.
4. Subscribe to the newsletter — easiest lift. Free tool every week: short, sharp frameworks for hiring, scaling, and not losing your mind.

Your move. Write the job scorecard this week. Talk to three people in your network. Stop waiting for the perfect candidate. They don’t exist. Start the process and refine as you go.