How to win: early fintech sales hires (Part 1)
One of the hardest things to get right - your first 1-3 sales hires
Fintech is different. Fintech is hard. Buyers are pretentious by nature “finance bros x 1000” and hate the concept of being “sold to” more than most
Some folks may think that any old salesperson will do the trick. That the product, if good enough, with a pain point that’s real, will generally sell itself
Hear me clearly: This is FALSE 9.9/10 times
This piece will focus on three sections for how to hire based on attributes:
Mandatory
Ideal
Red Flags
I’d argue that the only true likelihood of winning in early fintech sales is to find someone who has the qualities featured in the mandatory piece below
If you find someone who has many of the Mandatory & Ideal attributes
Pay them a lot of money and never let them go
There’s room for some folks without these qualities to pleasantly surprise you - do you really need to risk it though?
Especially after you’ve just closed your first 10-15 “founder sales” and raised your seed round?
Why risk it? I don’t see the risk / reward tradeoff panning out for this biscuit
If you find folks with more than one of the Red Flags - RUN
The most dangerous folks in the startup world are “executives / C suite”, especially within sales
Their literal job is to be the most convincing person, aka best liar, you’ll ever meet
Don’t. Be. Fooled.
MANDATORY
Domain knowledge/expertise (Immense curiosity)
Immense charm/finesse/likeability (Innate storyteller)
Natural leader (Immense hunger)
These are all necessary for true early (fintech) sales success. Folks may be able to drum up a bunch of “work” and seem busy - but they will never truly succeed without these
Why? Let’s break each down
Domain knowledge/expertise (Immense curiosity)
Notice how we didn’t start out with immense raw intellect
Intellect can make up for a lack of expertise, to begin with, but it’s quite difficult to measure in an interview cycle unless you’ve already known the person for a long time
It’s all about respect
Why is domain knowledge/expertise necessary?
Because most of your fintech buyers will be pretentious/arrogant / and stuck-up on their own areas of expertise and will not respect anyone they don’t immediately feel is capable of potentially doing their job for them
Let’s take an example from Middesk
Ian Harriman was the first sales hire at Middesk and flourished - closing 50+ deals during the height of Covid in his first two years, with some of the biggest names (i.e. Revolut, BlueVine, Radius) in fintech and finance
He also came from a successful company with relevant domain expertise - Checkr
He brought 4 years of reg-tech & API experience, and countless experiences selling into financial institutions
The mental expansion he had already gone through re: APIs, regulatory policies, relevant persona-based selling (compliance / BSA / operations / product/engineering, etc.), was immensely relevant to what he’d do at Middesk
He’s also an immensely curious person!
Even though when I joined I rolled up to him, he never once balked at asking me questions on financial products where he knew I had more relevant experience from my FIG investment banking days (i.e. variety of lending products)
That persistent humility in a high-performing individual is extraordinarily rare
Immense charm/finesse/likeability (Innate storyteller)
THIS IS SO IMPORTANT FOR EARLY SALES
Why?
We all know that in early sales, you have to sell the thesis before you sell the product; especially an API, platform, point solution, or anything with an implementation that takes longer than a few weeks
Early sales folks have to sell a product that is 6 months out in the future - today
The ducking and diving, live on a call is not easy, especially if you’re not the founder
Founders who are past the initial 10-15 “founder sales” often underestimate the tacit credibility that is given to them during those calls which is essentially this: they get away with “shit”
What does “getting away with shit” really mean?
Objections come less often and are much easier to finesse away
Folks give founders grace because they are subconsciously in awe of them fighting the good fight - aka starting a company
The tacit assumption that the product is better than it is, better than described, because it’s coming out of the founder’s mouth
Early sales hires need immense finesse to be able to swat away the obvious objections that come, but also to paint a picture of a brighter future. Charm, likeability, and innate storytelling is the only way that most early sales get done. It helps with:
The demo not being even close to what the product will be in ~3-6 months
Conducting that early discovery live on a sales call that gets added to the roadmap
Finessing the early pricing challenges that startups face; pressure testing buyers
They need to SPIKE on this. Don’t. Be. Fooled
Natural leader (Immense hunger)
This one is obvious and yet often misunderstood. Sales is all about leadership:
Getting buyers to come along with you for the “sales journey”
The steps in a sales cycle are essentially assigning your buyer “work to do”
If you are not a natural leader, they won’t listen to or respect you
You’ll often find them punting on the work because they don’t care
Galvanizing folks internally to help you get the sale done
Another overlooked aspect is that sales are not done alone by the sales lead
You need so many other people to be bought in to help, often for little to no credit and basically never for extra money
Why should ops, solutions/sales eng, eng - basically anyone but the founders - help the sales lead to close the deal?
And yet it’s imperative that they do so!
People need to see the future that the sales lead is painting and be bought in
The future that is: lower cost, improved performance, higher profitability
The promotion that they’ll get by helping to get the deal done
The relationship that they’ll build with you that will pay dividends for years
The only way that sales leads can muster the extreme effort to be a leader 24/7, while not being compensated as a leader (commissions are great, but sales folks typically get underserved on base & equity) - is to be extremely hungry
Hungry for success (not money - there’s a nuance here) & glory
Hungry for promotion and increased responsibility (“the best ICs don’t want to manage - but have to because no one else will do it better” - Steve Jobs)
Hungry for your job (this is an Ideal trait - that they themselves want to be CEO)
True hunger for success fuels people to do this immense work day in and day out
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This may all sound like a lot - it’s not. Wait till you see Part 2 for the list of Ideal traits
This is great. Can’t understate the importance of selling vision - a different reality wherein the product in question tangibly improves quality of life in ways big or small. Subbed!