Fintech’s — Don’t waste your most precious asset. How to motivate and keep your sales team.

So you’ve managed to hire some excellent sales talent, now you’ve got to convince them to stay and more importantly enable them to generate significant revenue.

This article isn’t just aimed at companies with poor work culture either — the Fintech space is exploding in growth and competitors will appeal to your staff more easily than you think.

According to New Sales Simplified by Mike Weinberg, 62% of sales hires fail. You need to be proactive in your retention strategy and invest in your team. Financial incentives are easy, but providing progression and growth is not. Salespeople that feel valued and developed stay with the company and deliver results, those that are not don’t…

Some key problems that come with high employee turnover:

  • Hiring and onboarding is more costly than training existing staff
  • Hitting aggressive sales targets requires a solid knowledge base of your product and market
  • There’s no value-add in hiring fresh talent if sales leaders don’t stick around to upskill

Managing via email and/or sales CRM is not an option.

Training, supporting and enabling existing teams scale sales much quicker than employing fresh talent externally.

Working in an industry with long sales cycles means that losing staff can equate to big opportunity costs.

What the Numbers Tell You

Before we get into the ways you can retain and motivate, let’s consider the cost of a single sales hire failure:

  • Typical Salary Package — $200,000
  • Recruiters Fee — $40,000
  • Average Deal Size — $150,000 ARR
  • Expected Y1 Revenue — $300,000 (2x deals)

A senior sales professional at this level will typically require 3–6 months to get up to speed, taking into account the necessary product knowledge, technical knowledge and pipeline development required. If they’re not the right fit, you could be looking at another 3–6 months to re-recruit for the position and ultimately let them go. All in all that’s 12 months lost.

By hiring poorly or not investing adequately in sales enablement, those first-year costs are significant. That’s $540,000 spent through hire costs and opportunities lost, not factoring in training and upskilling time for the next new hire. Just for 1 sales hire… Imagine if you did this for 3–5!

Now the intangible costs. Within the first year these grow significantly. Uncapitalised partnerships, lost revenue, plus disruption to team culture and internal collaborative rhythm. Investing $10,000 to 20,000 per team member on sales training and enablement will not only protect and motivate new hires but also lead to greater long-term ROI.

Here’s what you can do to ensure you retain top sales staff. (Hint: a little love goes a long way.)

  1. Hire for the Right Position

Hire the right person for the right business, but also at the right time. Spending a little time upfront to understand what you really need from a candidate will increase your chances of retaining them.

Startup culture is fluid, as is the evolving fintech market. Experience means nothing if your prospective sales hire can’t adjust from a corporate to a fast-moving scale-up setting. Will they meet your needs for the role for the next 2–3 years?

Sales teams are familiar with buyer personas, but it’s rare that companies build personas for recruitment purposes. Get this right first, and you’ll be ahead with your retention strategy before you’ve spent anything on investment.

2. Clear and Simple Commission Structures

Fintech is a competitive space, and I’d argue that the market is very much candidate-led. Generous packages with stock options and other financial perks are standard to get decent people through the door. But sales hires need to see clear incentives to hit the ground running from Day 1. Sales cycles are long and complex, and for a new hire, unclear. An open and achievable commission structure combined with clearly defined KPIs will motivate sales staff to get the job done.

Commission structures may also need to be flexible. Teams pushed to close bigger deals with longer terms, or perhaps focused on a niche customer base, may need a different incentive than others. It’s worth considering what works at team-level rather than company-wide.

Startups are risky by nature and there’s no guarantee of job security. Achievable financial incentives give staff a reason to stay.

3. Collaboration over Competition

Competitiveness is almost instinctive in sales, but no deal is done by someone operating on their own. Your sales staff might manage their own pipelines but they’ll do best when they’re comfortable to lean on each other and especially the sales leader for knowledge sharing and advice.

You’ve also got all the other stakeholders involved in the buyer journey. Marketing Officers, Solutions Engineers, Product Managers. Account Executives, Customer Success Managers, even Legal departments. Removing friction means more time in front of customers, ultimately improving job satisfaction.

This isn’t about relationships, though. All of these departments often have competing objectives. The top-level goal should always be revenue growth and customer acquisition whether a team is client-facing or not. Aligned objectives will make life easier for your sales team and make work more rewarding.

4. Long-Term Career Development and Mentoring

Sales is a multi-disciplinary career. You need to invest in your team’s development beyond upselling and cross-selling. Mentoring from senior leaders on a 1:1 basis is a proven method of motivating sales staff. Wider coaching sessions from C-level executives will build on this even further.

But your staff also need to be experts in other areas. They need to know Product and understand the tech stack. They need to know why your solution does what it does and what else is on your roadmap. Technical understanding allows effective handling of sales objections.

This cross-functional development is not something every company can provide. If you can then you’ll develop more well-rounded salespeople and empower them to do the job well.

5. Constructive Sales Meetings and Retrospectives

Reflecting on team performance at the end of the month by holding a Retrospective is an open and honest way to discuss, learn and grow. Using the Scrum framework to run a sales sprint is another great way to maximise team potential. Agile works because it allows for constructive feedback and building trust between team members, and it’s an excellent way to give sales hires an opportunity to learn and develop.

A lot can be learned through such working practices. Your sales teams will inevitably work closely with Product and Marketing, so get them reading from the same page. Adopting agile methodologies throughout your business will not only make your staff more effective but synchronise collaboration too.

However you do it, remember that the purpose of any sales meeting is to help the team sell more, not to report sales data to senior management. That is a byproduct of these sessions and not the aim.

Personal development is a huge driver in employee retention. This employee-orientated way of working is not about punishing underperformance, but failing fast and learning from it.

6. Create a Winning Culture

Individual incentives are only one side of the coin when it comes to motivating sales staff. They need to enjoy what they do, and that relies heavily on carving an amazing work culture. Make people want to make you money, and the benefits will reap themselves. Sales leaders and CEOs need to inspire and engage, and to lead by example.

There will be periods when targets are missed. Record achievements suddenly mean nothing when the first of the quarter comes and the stats reset to zero. Sales is tough, so a winning culture provides a boost when staff don’t feel like they are winning at all. A tennis match is won one-point at a time. Get your staff excited about all the small successes that happen before a deal is won. And when you do win a deal… celebrate!

7. Be an Enabler

Company, Customers, and Competitors. Do you know these inside-out? Probably. Do your sales team? Probably not.

Documenting your sales processes, culture and strategy is really key. If you don’t define how you do things, sales hires can’t be expected to just come in and fit the mould. Having a solid sales playbook and embedding effective on-the-job learning is how you enable staff. Tangible resources are as useful to personal development as practical training. And that means career progression.

Motivation comes in many forms, but job satisfaction and personal development are really the key drivers. Provide the external motivators (culture, reward, training) and salespeople’s internal desire to achieve will start to grow.

To end this piece a last word for CEOs and sales hires.

Sales follows strategy. If strategy is unfocused or chaotic, sales will suffer severely….. a crystal clear picture of the mission is required for the sales team to execute the strategy.

And if you’re a salesperson still trying to integrate into a new role, my advice is this: allocate your time to learning as much as humanly possible. Show huge amounts of activity in developing an understanding of product, tech and marketing, and build strong relationships with those teams. How you spend your first 6–9 months on the job is how you prove you’re the right fit. While it seems counterintuitive to not focus all of your efforts on selling, you’ll be laying the foundations of a successful sales career in the months to come.



CEO of Humble Technology — Commercial Advisory for Fintech. CEO of Humble Grape — wine bar, wine merchant, and events company.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
James Dawson

CEO of Humble Technology — Commercial Advisory for Fintech. CEO of Humble Grape — wine bar, wine merchant, and events company.