Rainmakers Swiping Left on Your Fintech?

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Recruiting the BEST #fintech Salespeople

It’s rare that a day goes by when a #fintech #CEO asks me why they can’t land any top-tier sales talent...and most of their sales candidates are quite lackluster. 

For those I know, it’s a quick call - I ask how they’re handling recruitment, offer a few targeted tips, and move on.

However, I’ve realize I’m constantly giving the similar advice over and over. So I thought I'd share with you my recommended sales recruitment cheatsheet for recruiting epic, quota-killing, zero-drama rainmakers! 

ᏚᏢᎾᏆᏞᎬᎡ ᎪᏞᎬᎡᎢ: Lead with your GTM, not your product.

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Let’s get real: the amazing salesperson you’re dreaming of hiring isn’t combing job boards. They’re being courted—personally. They’re getting emails and LinkedIN requests directly from CEOs along with discreet pings and calls that show the CEO is really interested in them.

And if your initial outreach comes from HR or someone junior in your organization, the immediate response is swipe left as it smells of indifference.

You're Selling Yourself more than the company or role

As stated above, the first outreach should be from the CEO (CRO is ok but CEO is better) – but it’s very important it is not from HR, your head of ops, a tech person and especially not anyone who introduces themselves as, “I’m someone who manages recruiting.”

Why the CEO? At a startup, the best sales hires are interviewing you – as a person. They’re evaluating whether you have what it takes to lead a startup – today and tomorrow. Do you have the insight, leadership skills and grit to realize exponential growth? For them to swipe right, and move forward with a formal interview process, you need to convey commitment, conviction, credibility, and confidence in that very first interaction.

 Are you worth the reputational risk that they spent years earning?

Start the Conversation with Strategic Clarity, Not Just Vision

Convince them you did your homework, and your product is ready for prime time. They’ll be listening for your GTM plan. If you speak in lofty, vague vision terms and get bogged down in product features before volunteering your market strategies, they’ll assume you don’t get the importance of revenue - swipe left.

After your 1 or 2 sentences on vision and product, go immediately into the following:

• Target Markets and why you selected these markets.

• Decision Makers and how you help them – include current/future proof points.

• Key Industry Trends that makes buyers (not markets) care about your solution right now.

• Competitive Landscape where you win, fall short, and how you’re closing the gap.

• 12 Month Growth Plans that’s not just ARR but #clients, #accounts, AUM transactions...

If you’re not answering with clarity and conviction, you’re probably not yet ready for a true pro. That’s ok, YOU should swipe left because nothing’s more expensive than hiring a misfit.

Transition Next to Culture

Top salespeople also want insight on what it's like to work in your fintech - does it align with their vision of success and fulfillment, or does it signal burnout and dysfunction? Here's a few agenda items you'll want to cover in this part of the call:

• What are your Cultural Values? Don’t give them a list, tell them stories.

• How Departments Work Together – in good times and when they’re struggling.

• Besides salespeople, who else is part of the sales process and in what capacity?

• Showcase how you’re an innovative, learning organization and open to feedback.

• Tell them about your KPIs – what you track is proof of what’s most important to you.

• Inject some stories to prove your team is great - aligned, collaborative and energized.

Life’s too short to settle. Great people want to be part of something bigger than just a job – a culture that’s proud, alive and buzzing. This is a biggie for swiping right.

Now You Can Finally Talk About the Role - Don’t Wing It

 Before the call with that top-tier candidate, get crystal clear on the role. This isn't about having the “right” answer—it’s about job clarity. High-performing salespeople thrive on clear success paths. If you can't articulate what winning looks like, they can't determine if they belong.

• Is this a hunter role with a full enablement stack (decks, demo system, CRM workflows)?

• Are they expected to build the sales process and foundational artifacts?

• Which conferences you attend and speak at? What’s the conference and T&E budgets?

• Do you expect them to spend most of their time prospecting or working/closing deals?

• Will they carry a direct quota, a team override? Is it a player, a leader, or a player-coach?

• Are they also doing marketing: conference planning, social media, campaigns, etc.?

• If your solution is highly customizable, do they have access to a sales engineer?

• What's their involvement in client onboarding and long-term client management?

• How do they contribute to product strategy and priority setting?

• What’s the compensation model – base/OTE split? Is there unlimited upside?

Rainmakers take calculated bets – but they need clarity to know they’ll win. If it’s more internal than selling, expect to pay more in base; if it’s all about the sales and if you’re ready for prime time, they’ll go for a commission-heavy plan.

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Final Words: Don't Freestyle - Follow the Flow

Recruiting elite sales talent is basically your business development outreach playbook in disguise. You need to first create interest, excitement and rapport before you start with the qualification questions. Skip the steps or go out of order, and just like that dream candidate is working at your competitor.

 Be the fintech rainmakers can’t resist. The one they swipe right on – and fight to close.