I’ve found that most people think about sales incorrectly - with numbers
Numbers get in the way of selling because it isn’t about numbers - it’s about people
Fintech can be distilled into simple concepts - either it’s an infrastructure or application layer product. Within infrastructure, the tech is built to solve problems for and/or grow the application layer product’s “surface area”
Take Middesk - a non-novel product that was built to improve the problems associated with business onboarding for financial products - aka KYB (Know Your Business). Middesk built an API for calling business registration data from their database with only two mandatory inputs - Legal Entity Name and Legal Entity Address
I was able to close 70+ deals in under 12 months (equating to $millions of dollars in bookings) - with less than a year of true software sales experience - by employing a very simple sales method that I created: SWAG
Sell
Without
Acting
Greedy
But with swag(ger)
What that means is simple - when you get on a “call” with a prospect - stop thinking about the sale!
Who is this person in front of you? Where do they live? Do they have a good sense of humor? Do they like to cook/bake? Do they like sports? Do they enjoy their job? What are their main priorities? Who are you to them? Will this product of yours get them promoted if implemented (correctly*)?
Where is the common ground? Find it in the first 5 minutes of the call - shouldn’t be difficult (will dive into that in another post)
Now that you have common ground - what else do they care about besides your product?
Do they need referrals or help elsewhere in their roadmap? Do they need food recommendations for the place they’re traveling to that you’ve been to 5 times? What other challenges do their competitors have that you’ve seen solutions for? What are they missing out on in the industry? What trends would they like to hear about? Which resources or blog posts can you share with them that they can subsequently share internally to look like a market pro?
How can you help them without having to help yourself?
Life is reciprocal; the best way to gain value is to add value to someone/somewhere/something else. Want something? Give something first
Once I started employing this method, the follow up emails started to really flood in. Have you ever been ghosted on a sales call where you set up the time and they don’t show up? I haven’t
I spoke with ~500 different companies, 1-5 decision makers at each - ends up being thousands of people. Not once have I been ghosted for a call / stood up for a meeting / completely ignored with no explanation
Why? I genuinely focused on them first before we focused on Middesk
Once I had established common ground, given them value, answered their questions, and provided referrals to other vendors in the space - the conversation inevitably would return to Middesk
SWAG selling is more than meets the eye - it’s an acronym and a word in of itself. When we did return to Middesk, I looked every prospect right in the eye and laughed at any alternative to using Middesk for the problem that we solved
It’s imperative that any discourse surrounding your product is enshrined in confidence and brute swagger; their competition is or will be benefiting from using your solution, so they should hurry up and get on board
Specific examples are imperative - confidence stems from a foundation of knowledge, experience, and effort. For those 12 months I lived, breathed, and bled fintech and enterprise SaaS. I knew not just the product of the prospect that I was on the phone with (most times better than they did given my FIG investment banking M&A background at Lazard), but also all of their competitors and the founders of their competitors by name
There was nothing more satisfying than getting on a call with product, engineering, and procurement leaders at MX (one of Plaid’s main competitors), chit chatting for a few minutes about themselves, and then immediately letting them know that Plaid not just uses Middesk, but both Will and Zach are investors in Middesk as well. I then immediately started asking questions about their onboarding flow and comparing it to Plaid’s on the spot
The shock and disbelief that I’d mention their main competitor within the first 10 minutes of our first call was not just palpable - it was vocalized. “I can’t believe you just brought up Plaid and said their onboarding flow was 10x better than us just now! We just met! Why would you say that?”
My response? “I’m trying to help you and improve your experience. Happy to keep my observations to myself if your team is happy with your process. Plaid’s volume is Xx higher than yours in new fintech onboarding - but I guess that’s not what we’re here to discuss. I was also going to suggest an API call placement deep dive with our solutions engineers (all ex-Plaid), the adjacent vendors you could potentially use to improve other parts of your process, and how this has impacted their metrics over time. No worries if uninterested”
Outcome? “We didn’t say we weren’t interested, you just took us by surprise! We’d be interested in hearing more about those areas and discussing the onboarding flow with your solutions engineering team. Why don’t we find time later this week to dive into that? We’ll bring the right folks.”
Swag
Middesk had the benefit however of already having 50+ customers (including Plaid, Brex, Divvy, ENGS, and BlueVine), which gave massive credibility and plenty of surface area to “dunk” on folks that we’re already working with their competitors
How would I do it all over again from the start? I’d take a chapter out of one of my favorite books, Good Strategy Bad Strategy, by Richard Rumelt. He discusses how strategy is actually quite simple when you look at it:
Discovery
Pain to solve (all the potential solutions you could create)
Competitors solving it as well (landscape solutions)
Who is experiencing this pain (which personas)
Size of this pain (what hurts the most)
Priorities (how do you ensure your solution is top of their list)
Guiding Principles
How do we want to solve this pain?
What niche / wedge can we own?
What are our competitors focused / winning on?
What are our competitive advantages?
Which lane can we play in to go much faster?
How do we build multiple processes and products that build onto each other?
Action Items (Questions that lead to answers —> actions)
Who should we talk to?
How do we get in front of the decision makers?
How do we find the right fit of culture, technology/product, and strategy that align with what we think we’re solving for? (more on this trident paradigm later)
What questions should we ask them?
What hurts the most for them?
What solutions have they already tried for that pain?
How do they do it today?
What solutions have they already explored?
How would they rank their pain?
What solutions do they need yesterday, today, and tomorrow?
What should we build for them?
Who will pay us yesterday, today, and tomorrow?
Are these solutions we’re building unit economical-scalable?
Is what we’re doing defensible, scalable, and effective for solving the pain? (more on this trident paradigm later)
Then we build a 30/60/90 day plan to execute on the above. More on this, with an example, in another post
Tip of the iceberg style - talk soon
💯