I speak to lots of salespeople every month who are looking to leave their jobs. Having been on both sides of the fence, as an individual contributor, revenue leader, and now recruiter, I’ve got a pretty clear view of why great sales talent walks out the door and what you can do to keep them. 

The insights I’m sharing here aren’t theoretical, they’re based on my own experience, and  conversations with top performers in Seed and Series A businesses when they’re thinking of jumping ship.

Lack of recognition

Recognition isn’t just about hitting quotas and getting a pat on the back. It’s about making your salespeople feel genuinely valued as human beings, not just revenue generators.

I still remember, ten years later, when my CEO took me to dinner in Paris and got to know me as a person, rolled out the red carpet. I can’t remember the specific deal I’d closed or even the commission amount, but I remember that moment clearly. 

That’s the power of recognition. Your salespeople love getting appreciation, especially from the founder. It doesn’t have to be Paris, it can be:

• Taking them out for a proper dinner when they hit a milestone
• Public recognition in team meetings or company-wide communications
• Small but meaningful gestures that show you see them as individuals
• Face time with leadership that goes beyond pipeline reviews

The key is making it personal and memorable. Your salespeople are driven by achievement, but they’re also human beings who want to feel appreciated for their contributions.

Lack of progression

This one hits close to home because I’ve made this mistake myself. I once hired an SDR and told them they could become an account executive in six months. Six months later, during their review, they asked about the AE role. I had to tell them they weren’t ready yet.

That person immediately started thinking there was no progression path because I’d set a specific timeframe in their head. People don’t forget these promises. If you tell an AE they’ll be head of sales in nine months, they’ll remember that exact timeline.

Here’s how to handle progression properly:

Set Realistic Expectations

• Be conservative with timelines during the interview process
• Focus on skills and achievements rather than arbitrary timeframes
• Clearly outline what progression looks like in concrete terms

Create Meaningful Growth Opportunities

• You don’t need to jump straight from AE to head of sales
• Give them additional responsibilities like weekly pipeline reviews
• Let them present to VCs or join board meetings to share data
• Create sales manager roles with team leadership components

Provide Exposure and Development

• Monthly meetings with your VC for relationship building
• Involvement in strategic planning sessions
• Mentorship opportunities with other leaders

Motivated salespeople are naturally ambitious. They want to build their careers, potentially run teams, maybe even start their own businesses eventually. If you can’t provide a clear path forward, they’ll find someone who can.

Confusing compensation plans

I’ve seen commission structures so complicated that salespeople need a bloody calculator to figure out their earnings. There are thresholds, accelerators, team components, and conditions that would make an accountant’s head spin.

I used to work out my commission in my head before meetings even started. If I knew I was walking into a £50k proposal with a 10% commission rate, I’d already calculated that £5k in my head. I knew exactly how that money would contribute to my house deposit or holiday fund.

The best salespeople are money motivated, and your compensation plan should be:

• Simple to understand – they should calculate it mentally in seconds
• Attractive for overachievement – reward them well for exceeding targets
• Transparent and consistent – no surprise changes or complex conditions

When salespeople can’t easily understand how they’ll be paid, they start questioning whether they’re being treated fairly. That uncertainty breeds distrust and ultimately drives them away.

The equity advantage

Just recently, we had a head of sales reject an offer that included more money, a bigger team, and everything seemingly more attractive than his current role. Why? Equity. He’d been at his company for four years, his equity was about to be recognised, and it was worth serious money to him.

That company managed to retain a top performer not through salary increases, but through long-term value creation. Equity in SaaS companies can be incredibly tax-efficient and creates golden handcuffs that keep your best people engaged long-term.

Consider equity as part of your retention strategy, especially for senior sales roles. It aligns their success with the company’s growth and gives them a compelling reason to stay through inevitable challenges.

Flexibility

Here’s something that might surprise you, we’ve placed people who took £20,000 less in basic salary just to get a fully remote role. They valued the flexibility, the time with family, and the money saved on commuting more than a higher base salary.

About 80% of the salespeople we speak with now want something more remote-first or flexible. If you’re demanding four days in the office while competitors offer remote work, you’re handing them a recruitment tool.

Flexibility doesn’t mean lower productivity. It means:

• Trust in your people to deliver results regardless of location
• Competitive advantage in attracting and retaining talent
• Cost savings for both you and your employees
• Better work-life balance leading to longer tenure

The make-or-break first 30 days

Your onboarding process sets the tone for everything that follows. Salespeople will recognise good or bad onboarding immediately, and they’ll interpret it as a signal of how much you value their success.

If you hire someone and give them a one-hour session before saying “let’s see how many opportunities you can create,” you’re setting them up for failure. They’ll know it, and they’ll leave.

Proper onboarding includes:

• Comprehensive product and market training – not just feature lists
• Clear route to on-target earnings – show them the path to success
• Realistic timeline expectations – 60-90 days to get properly ramped
• Regular check-ins and coaching – invest the time upfront
• Introduction to key stakeholders – including VCs and leadership team

Build that backwards sales plan together. Walk them through the commission structure in detail. Get them excited about the opportunity and the growth potential. Roll out the red carpet in those first 30 days, because six months later, you’ll see the dividends in performance and loyalty.

Product market fit

You can have great culture, excellent compensation, and perfect onboarding, but if your product isn’t landing in the market, your best salespeople will leave. They know when they’re onto something and when they’re not.

I’ve seen companies in the UK going from zero to £100 million ARR in record time. Salespeople at companies like those aren’t leaving because they know they’re on a rocket ship. When your product is flying off the shelves before you hire salespeople, adding sales talent is just fuel to the fire.

When you’re struggling with product-market fit, top talent gets headhunted by companies with strong traction. They’re attracted by the promise of easier sales, higher earnings, and the CV benefit of joining a high-growth success story.

If a salesperson gets reached out to by a company doing £50 million ARR in less than 12 months, they’re thinking about earning multiples of their current target while getting equity in a company that could make them rich. That’s also a CV showstopper: “Joined at £2 million ARR, grew to £100 million in two years.”

Pay market rate

Early-stage companies move at incredible velocity. The company your salesperson joined 12 months ago isn’t the same company today. I learned this lesson the hard way.

I joined a company as the first boots on the ground, literally carrying photocopiers across London in Ubers and setting up desks ourselves. I started at £55k basic salary. Twelve months later, we had a £15k-per-month London office and strong traction.

The market started reaching out offering £70-80k roles. When I told my CEO, he basically said “stay loyal.” So I got a job offer and resigned. Suddenly, he wanted to add £25k to my basic salary.

You have to constantly review market rates for your existing team. The cost of replacing someone including recruitment fees, onboarding time, and the risk of failure, far exceeds the cost of keeping them properly compensated. That compensation can be cash, equity, or a combination of both.

That job I took at £55k when we had no customers became an £85k role when we had traction and revenue. The salesperson proved their worth, and the market recognised their value. If you don’t, someone else will.

Retain top talent

Retaining great salespeople isn’t rocket science, but it requires intentional strategy and consistent execution. 

• Recognition
• Clear progression paths
• Simple compensation
• Equity participation
• Flexibility
• Proper onboarding
• Market-rate compensation

I’ve been on both sides of this equation. As a salesperson, I knew when I was valued and when I was just a number. As a recruiter, I see the patterns of what makes people stay and what drives them away.

The choice is simple. Invest in retention strategies that cost relatively little, or keep paying the massive hidden costs of constant turnover. Your best salespeople are already being courted by your competitors. The question is whether you’re giving them compelling reasons to stay.

The companies that get this right keep their top performers for years, building institutional knowledge, deeper client relationships, and sustainable growth. The ones that don’t? They’re always hiring, always training, and always wondering why their revenue growth isn’t more predictable.

Which company do you want to be?

Author: Matthew Codd

I’m Matthew, I have 15 years of commercial leadership experience, helping VC-backed B2B technology companies scale revenue and transition from founder-led sales.  

I use my experience to help early-stage start-ups with GTM expertise, sales best practice, and hiring insights.  

I co-founded Cosmic Partners in 2022. We are SaaS sales recruitment specialists for VC backed B2B tech companies.