How to win: early fintech sales hires (Part 2)
This one will seem a bit idealistic to some - but hear me out
In the first part, I highlighted a few Mandatory Attributes for how to win with early fintech sales hires. Let’s clarify a few things:
I’ve seen a few different models for sales hires #1 - 3
An AE, who ramps quickly, but still needs support getting to the next level
A sales lead that becomes a great manager within the Sales org
A hybrid AE/PM that is fine to IC and then wants to run revenue entirely
Obviously, there are exceptions to every rule - so let’s focus on the non-obvious
There are many examples of the benefits to the culture and performance of a company of ‘promoting from within’ if you look for it
Sam Buck from Ramp - from SDR #2 to CoS in 3 years
Anneika Patterson from Ocrolus - from BD to CoS in 3 years
Charley Ma while at Plaid - from Growth #1 to NYC GM in 3 years
The cultural continuity and continuous promotion of these team members is not just good for the culture - it’s great for business
It shows that hard work and perseverance truly pay off
This inspires the rest of the team to work at peak performance
Maintains and compounds the tribal knowledge the best have garnered
As a rule - I don’t believe in layering and have seen it backfire in every example
The “professional managers” are the absolute worst people to hire in sales, especially at any stage before series D
They typically can’t sell the product themselves, are used to a low work / minimal-effort environment, and have lost their edge (or never had it)
The consequences are clear:
They don’t earn the respect of the team (especially top performers)
They are typically bad at ramping the new AEs/SDRs they hire under them because they are slow to ramp themselves and are typically too egotistical to ask for support from folks they layered
They don’t know how to become force multipliers and slow down the momentum of the legacy team that they took over
Steve Jobs put it best - “The best managers are the great ICs (Individual Contributors) who never wanted to manage, but knew they had to because no one could train or lead the team better”
If you must layer - please listen to Machiavelli’s advice from The Prince, chapter 7, on taking over a principality leveraging another’s arms & fortune
He outlines how your new sales lead should do it quite clearly actually
Thus - we focus on hiring (aka most likely poaching) the ideal - the early fintech sales hires that you can’t wait to promote over and over again
Now we get into the IDEAL ATTRIBUTES…
But before we do that - a side note from a lesson learned from Izhar Armony, a CRV GP for the last 26 years - that has bugged me enough to mention this: Humility
Izhar astutely mentions that Humility is one of the key traits to not just great leaders, but more specifically a great sales leader, in this amazing podcast - here
While I believe Humility is part and parcel of each of the other Mandatory Attributes I mentioned for winning early fintech sales hires:
Domain Knowledge (Immense Curiosity)
You need to be humble to be aware of your own limitations and ruthlessly seek to fill any gaps in your knowledge
Immense Charm (Innate Storyteller)
You need to be humble to be open to feedback on what makes people feel good, what resonates with them emotionally, and what makes them tick
Natural Leader (Immense Hunger) (link)
You need to be humble to understand how to inspire, how to successfully motivate, and how to encourage others to lead you
I still think it’s worth calling it out regardless because of how incredibly important it is that you find someone who has a great dose of Humility
For folks who know me - this may be a break in reality for my personality
However, while I purportedly have a Steve-Jobs-like self-confidence, I’ve also taken so many L’s in life that Humility has been steeped in my bones
IDEAL ATTRIBUTES
I’ll slice this up into 2 parts to find folks that can help you win early fintech sales -
The tangible things they can do during the process to show you what they got
The intangible attributes you can look for to show you what’s likely underneath
Tangible:
Proactive Pipeline (Natural network)
Poaching Plans (Friendly firepower)
GTM Genius (Product-strategy prowess)
Intangible:
Unnaturally Urgent (proclivity for action - link)
Prefers Painful Pleasure (leans into the hard thing)
Brutal Boxer (can take a punch)
Honorable mentions:
Former athlete/army brat (runs / hits the gym often)
Rigorous routines (makes their bed every morning)
Cool, calm, and collected (even in the face of pressure)
Let’s get into it - shall we?
TANGIBLE
Proactive Pipeline (Natural network)
This one is my favorite; however, I’m biased because it’s what I’ve done and it’s what anyone I’d ever recommend would do as well to earn the top spot
Proactive pipeline is simple - before anyone worth their salt wants to join your seed-stage startup (regardless of who led the round) they’ll chat about the company with their friends, who should ideally be a natural network for you to tap into once they join
In chatting about the company, they’ll of course ask folks who would be your ICP what they think: if the pain point you’re solving for is a problem for them, if they’re looking for a solution, and how much it’s a pain for them (prioritization)
As we talked about before, especially in this economic uncertainty, the “need to haves” are much more valuable products than the “nice to haves”. The latter gets kicked all the way down in terms of project prioritization, especially now (Dec 2022)
SO - before the hire even thinks about chatting about the comp for the role (***RED FLAG if they ask too early) they’ll prove their value by introducing you to 3-5 ICPs and start building pipeline early. Most likely they’ll even join the first few calls as well
This shows they can properly explain the product, the value, and how you’ll win
This shows they understand the problem & pain that you’re solving for well
This shows that they can properly identify your ICP, even ideally better than you
If you think this is too much to ask - I’m sorry to hear it & pls up your standards : )
Poaching Plans (Friendly firepower)
This one feels quite natural to me and hopefully to all of the founders that are reading this (and the one-day founders who are current [aspiring] sales leaders)
Any [future] sales lead who’s had time and experience in the field has at this point (or else quite frankly you may not want them) made some friends, even across specialties
Coming into the new role, they should have an idea of the first few hires they want to make that could flesh out and complement their weaknesses. These include:
Solutions Engineering lead
Product Marketing lead
Sales hire #2 and 3
This is wildly important because of one simple reason: most people suck at their job. Given this widely held belief, the only way to increase the statistical likelihood that any hire will perform their job well is to poach them from an adjacent firm:
Where they’ve attained domain knowledge
Shown their ability to charm their peers & colleagues
Established some level of leadership qualities or signs of impending ability
Poaching is obviously the best and highest likelihood of success in hiring motions.
You get folks who understand most of your value chain (for another article) and can quickly fill in the gaps with intense training and reading
You get folks who are at the right stage of company (for another article) and are culturally aligned with what you need them to do & when you need it (grit)
You get folks who have learned many mistakes already at someone else’s expense and are ready for the next challenge, and ideally want to step it up a notch as well
Here’s where most people go wrong:
They poach portions of teams from the “wrong firm”
Irrelevant topics of domain knowledge
They poach portions of teams from their partner firms
This upsets people and is a lazy way to do it
They don’t focus on this as the #1 method because they think it’s “too hard”
This is lazy and wrong - don’t be these people
GTM Genius (Product-strategy Prowess)
This isn’t as natural to many people but it drew from my natural inclination to learn from others on what works - GTM-wise - and how it all ties into product strategy
The Product function can be defined into a bifurcation - strategy and execution:
Strategy - what are we going to build and in what sequence?
Execution - when will it be built and shipped for feedback?
How this plays into GTM is simple:
Where will our customers experience us? (directly from a salesperson, finding us by themselves [self-serve], or via a partner?)
How will our customers experience us? (in our own dashboard, via an API, or via a partner’s experience?)
What will our customers experience from us? (what will be our wedge product, what should come next, and how do we seek to find those answers?)
The tangible vetting you can put an early sales hire through is then simple as well:
Have them detail to you where & how they expect your product to be experienced
Do they see this as a PLG, SLG, Product-led sales, or partnerships-led motion?
In what sequence do they believe you can best grow?
What do they think you should build first? Next? And then? Why?
How do they envision validating these theses?
What do their discovery questions and motions feel like?
The point isn’t for them to be right 100% of the time. The point is to see their reaction
INTANGIBLE
These are the intangibles that they can’t always prove to you are habitual vs. sporadic
Unnaturally Urgent (proclivity for action)
When they say they are going to do something - how long does it take them to do it?
How quickly do they respond to your emails? Your texts? Your intros?
How quickly do they introduce you to the prospect that they mentioned?
How quickly do they follow up with the case study that you proposed?
Do they message you during their downtime with suggestions?
Are they thinking about you and your company even between interviews?
How excited are they about the potential role that’s in front of them?
Are they suggesting GTM ideas? Prospect ideas? Improvement ideas?
Do you feel their urgency? Can they show you a track record of urgency?
Many if not all of the greatest folks I’ve ever encountered have a proclivity for action that’s unmatched, even amongst their peers
When they want something, especially in a revenue-generating role, they chase after it like their life (and self-worth) depended on it
They want to prove to you, and ultimately to themselves, that they’re capable
The best separate themselves from the pack with ease. Experience it for yourself
Prefers Painful Pleasure (leans into the hard thing)
Doing the hard thing is a mentality - until it becomes reality. Here’s a perfect example:
Jarad Gilmore (amazing manager whom I respect dearly for a plethora of reasons) always leaned into the hard thing and never shied away from basically anything
During his time at Middesk, he’s led and worked on everything but the code:
Partnerships / Sales
Revenue Operations / Finance
Solutions Engineering
Account Management / Customer Success
Business Operations
Product Strategy & Management
He never says “no” to any task and has countless times told me he prefers the Stripe model of team composition and building:
Move people with the right skill into any role that requires it AT WILL
He showed me explicitly and simply this: the right revenue people prefer pain
They know that they can figure it out and prefer to get it done than to pass the task off to someone else who may not do it as well - regardless
Does your potential sales hire feel the same? Have they displayed this in the past?
Do they have examples of them going out of their way to work cross-functionally?
Do they balk at your suggestion that they’ll need to pick up multiple functions?
Do they shy away from sourcing pipeline, closing deals, AND building the team?
They need to be excited about pain & want to do it because they know they’re the best
Brutal Boxer (can take a punch)
Hit them. Hit them hard, repeatedly, and with a smile. How do they react?
Can they take a punch? How do they react to:
Negative feedback from you
Losses in life across the board (family, spousal, friends, etc.)
Disappointment in sales and in their career
How will they react when you lose deals because the product you built isn’t there?
When the original growth they saw before they joined slows down?
When the pitch isn’t landing with customers and you need to reorient it?
When investor after investor passes on you because “you don’t have the numbers”?
Do you want them in your corner? Do they run away? How do they react to negativity?
Dig into this. It’s important that you have someone in your corner who’s solid as a rock
//
Honorable mentions:
Former athlete/army brat (hits the gym very often)
Shows that they could commit to something difficult for a long period of time
Shows they’re interested in working on hard things that improve themselves
Shows that they are open and receptive to taking feedback & implementing
Rigorous routines (makes their bed every morning)
Clear room - clear mind. Don’t underestimate how helpful it is to be clean
Routines are extremely helpful in sales, as it’s more about just showing up
Early wins in the morning help set the rest of the day up for success
Cool, calm, and collected (even in the face of pressure)
Nothing like getting shit on, live with a prospect, especially if recorded
You want someone who can handle anything that gets thrown at them
How do they react when there are 2 days left in the qtr and $115k open ACV?
//
I reflect on these myself - regardless of position - as all of the above are attributes that don’t just make great salespeople, but also great founders and partners. Take a moment to reflect on these - are they representative of you as well?
//
If you find anyone (most likely via poaching) w/ the mandatory and some of the ideal - HIRE & PROMOTE THEM; & most important of all, show them the love they deserve
I know this was long - but so will your nights be if you hire wrong
: )