My Go-To Sales Plays for Winning in Fintech & B2B

Over the years, I’ve honed a set of sales plays that have consistently helped me build relationships, establish trust, and close deals in the competitive fintech landscape. These strategies have been my secret sauce for engaging prospects, delivering value, and driving measurable outcomes. Here’s a rundown of my favorite plays and why they work so well for me.

1. Curating Initial Content to Nurture Prospects
One of my top plays is reaching out to new prospects with curated, high-value content—like a white paper or industry report—and asking for their feedback. I love this approach because it’s a low-pressure way to start a conversation. It’s not about selling right away; it’s about providing something useful and building a connection. For example, I’ll share a report on credit risk trends with a Chief Risk Officer and ask for their thoughts. This often creates a sense of “social debt,” where they feel inclined to engage further, setting the stage for deeper conversations down the line.

2. Treating Prospects Like They’re Already Clients
I’ve found that treating prospects with the same care and attention as paying clients can be a game-changer. This means acting as if they’re already on board—offering guarantees, being intellectually honest (even if it means recommending a competitor), and reducing their risk with things like endorsements or a 30-day cancellation policy. I once worked with a fintech in LatAm where I offered a familiarization trip to our offices and a quality guarantee. It built so much trust that they moved forward faster than expected. This play works because it shows prospects you’re a true partner, not just a vendor.

3. Establishing Thought Leadership with Content
Positioning yourself as a thought leader is crucial in fintech, where expertise drives credibility. I love creating and sharing content like blogs, books, or industry commentary to educate prospects. For instance, I’ll share insights on customer experience trends, referencing reports like JD Power’s take on digital gaps, and then host a workshop to dive deeper. This play helps me stand out as a trusted advisor, not just a salesperson, and it often leads to long-term relationships with prospects who value the knowledge I bring to the table.

4. Breaking Bread to Build Relationships
There’s something powerful about sitting down for a casual meal or coffee with a prospect—especially when the stakes are high. I call this “breaking bread,” and it’s one of my favorite ways to connect with key decision-makers. I’ll invite a prospect to grab a coffee while I’m in town, keeping the conversation light but meaningful. This play has helped me build rapport with C-level execs at major fintechs, making them feel more comfortable and turning transactional interactions into genuine relationships. It’s a simple but effective way to humanize the sales process.

5. Hosting Workshops for Actionable Engagement
I’m a big fan of hosting workshops to engage prospects across the sales cycle. After a successful initial meeting or referral, I’ll offer to run a workshop tailored to their objectives—say, helping a fintech map out a credit product launch. This play works because it’s hands-on and collaborative, giving prospects tangible actions they can implement while showcasing my team’s expertise. I’ve seen workshops uncover new needs and accelerate buy-in, often turning a prospect into a client faster than traditional pitches.

6. Running a Proof of Concept to Prove Value
When a prospect needs to see results before committing, I turn to a proof-of-concept (POC). I’ll offer a short, focused POC—like a 7-day trial where our AI scores their credit applications, cutting false positives by 25%. This play is a favorite because it provides hard evidence of value, addressing skepticism head-on. I’ve used this with fintechs looking to reduce risk, and the measurable outcomes (like a 25% improvement) often seal the deal. It’s a powerful way to move from “maybe” to “yes.”

7. Combining Curated Content with Workshops for Outreach
One of my go-to hybrid plays is combining curated content with a workshop. I’ll start by sending a prospect a relevant piece of content to spark their interest, then follow up with an offer to host a workshop to dive deeper into their challenges. This one-two punch is great for outreach because it starts with value (the content) and moves to action (the workshop). I’ve used this with prospects in the US and Canada, where the initial content piques their curiosity, and the workshop cements our partnership by delivering actionable insights.

Why These Plays Work for Me
These plays have become my favorites because they balance relationship-building with tangible value. In fintech, trust and expertise are everything, and these strategies let me show prospects I’m a partner they can rely on. Whether I’m nurturing a new lead with content, building rapport over coffee, or proving our value with a POC, each play helps me move the needle—turning prospects into clients and clients into advocates. If you’re in sales, I’d love to hear your go-to plays—what’s worked for you in building those critical connections?