Founders, meet your first sales hire
They’re one-of-a-kind and not who you might expect them to be
In my previous Medium post, I discussed “5 mistakes founders make when hiring their first sales rep.”
As a follow-up, I’m writing about the characteristics that founders should look for when recruiting their first sales rep in order to give this hire (and your company) the best chances to succeed.
They’re egoless
Founders, forget that you ever watched Glengarry Glen Ross. Your first sales hire isn’t someone who lives by ABC (“Always Be Closing”) or is motivated by the prize of a Cadillac Eldorado.
This person should be low/no-ego and is motivated by intellectual curiosity and their passion for the startup’s mission over everything.
I’ll shy away from an in-depth discussion about behavioral characteristics in favor of pointing you towards the words of more experienced business leaders. Take, for example, this quote from ex-Disney CEO, Robert (Bob) Iger:
When hiring, try to surround yourself with people who are good in addition to being good at what they do. Genuine decency — an instinct for fairness and openness and mutual respect — is a rarer commodity in business than it should be, and you should look for it in the people you hire and nurture it in the people who work for you.
Bob Iger’s memoir, The Ride of a Lifetime: Lessons Learned from 15 Years as CEO of the Walt Disney Company, is a must-read for startup founders in my opinion.
I’m also a big fan of Danny Meyer’s hiring philosophy.
They’re not a transactional seller
Good sellers move quickly when they see the right buying signals. A mentor of mine (and the best sales leader I know) likes to say that “time kills all deals.” A sales rep who drags their feet loses deals.
That being said, an early-stage startup’s first sales hire has to be able to expertly balance execution and patience.
Your first sales hire should be a relationship-builder, not a “do-anything-to-get-it-over-the-line” closer. Transactional sellers, reps who prioritize deal speed and volume over identifying pain points and solutions, do not make for good first hires.
As frustrating as it is to admit, I believe early-stage startups need to do a better job of recognizing the long-term, mutual benefits of selling at the right time, not in the now. An organization’s first sales rep sells when the product aligns with their prospect’s expectations, needs, and budget.
In practice, that means occasionally admitting that your product and/or team is not ready to accommodate all of a prospect’s needs. It’s better to wait 6–12 months to win a deal than frustrate and churn early adopters of your product/service. Your first sales hire should be able to make these decisions and not sell deals that will impact your company’s reputation or product in the long-term.
Founders, to separate transactional sellers from relationship-builders and consultative sellers, ask them “What would your prospects say about you?” and “What’s your relationship with your clients after they’ve been passed to Customer Success/Account Management?” You’re looking for the folks who care more about people than their own metrics.
They can make their own decks
There’s a running joke that if you ask a sales rep to make a deck, you’ll get a hodgepodge of poorly-formatted, stylistically inconsistent, and cringe-worthy stock photo-filled slides. These jokes are not all totally unwarranted, unfortunately.
An early-stage startup’s first sales hire needs to be able to make their own sales deck. No if’s or but’s about this one. I’m not arguing that this person needs to know Sketch or Figma as well as Salesforce or Outreach, but they should be able to produce their own sales and marketing collateral in Google Sheets at the very least.
Founders need to make compelling, investor-facing decks during the fundraising process. A startup’s first sales hire should be held accountable to do the same for all sales and business development processes.
A sales rep’s ability to make a good slide deck is an important litmus test of whether or not they’re a true self-starter. If this person can’t make their own deck, don’t expect them to be able to do basic sales ops administration and other slightly-out-of-scope tasks.
An early-stage startup’s first sales hire makes their own sales materials; they actively avoid putting work on other people’s plates and has an “if not me, then who?” attitude. There’s no task too big or too small for them and that starts with the sales deck.
They’re meticulously organized
Founders and engineering teams talk about technical debt… a lot. But early-stage startups rarely ever talk about what I’ll call “sales debt.”
Examples of sales debt include an unorganized CRM with outdated opportunities and thousands of burned-through leads, poorly-named folders and documents, and the inability to draw basic insights from sales process-related data.
A first sales rep has to create scalable processes that reduce sales debt and help future reps ramp efficiently. This type of process-building requires someone who is more analytical and data-driven than your everyday sales rep.
An early-stage startup’s first sales hire should have strong attention to detail from day one. They organize their collateral in Google Drive with easily-recognizable folders and document names, not on the desktop of their laptop.
Similarly, they should practice second-to-none sales hygiene and documentation in your CRM. Expect them to lead by example and keep all opportunities up-to-date.
Founders, you shouldn’t need to “track down” sales materials and deal info from your first sales rep.
The best early-stage sales leaders I know don’t leave the office at the end of the day without making sure their pipeline is up-to-date in the CRM. They always know the company's ARR and how close they are to hitting individual and team quota that month/quarter. They can tell you why they lost any of their deals from the previous quarter. They understand sales through data points and trends, not emotions and anecdotes. This should be the norm, not an exception.
They care more about equity than cash
In my previous Medium post, I wrote that “Founders should also guide their first sales hires to think in terms of long-term value, not short-term gain. If someone is looking to make a lot of money in a short period of time, an early-stage startup is almost certainly not the right place for them.”
Let me emphasize this last point again. Early-stage startups are not the right place to make a lot of money in a short period of time.
Sales reps are typically among the highest-paid employees in every company, but that’s not why one would join an early-stage startup. Founders, your first sales hire should be someone who wants to stake their career at your company and is hungry for a life-defining win. Avoid folks whose eyes light up from the prospect of open territories and uncapped commissions.
Consider it a good sign if they ask for more equity. As a founder, you want your first sales hire to grow alongside your organization and reap long-term benefits, rather than focus on the short-term gains of sales commissions (which you should still pay them of course).
For anyone who watched The Last Dance or witnessed the Chicago Bulls dynasty of the ’90s, remember Scottie Pippen. Despite being one of the best players in the NBA at the time, Pippen was the 122nd highest-paid player in the league in his final season with the Bulls.
Years later, when asked about this discrepancy, Pippen said “I’m one of the best players to ever play the game, I understand what my value.” It’s also worth noting that Pippen would eventually outearn his Bulls teammate and all-time-great, Michael Jordan. This likely wouldn’t have been the case had Pippen focused on his salary, rather than his career and personal stock.
Founders, look for the Scottie Pippen’s of SaaS sales, individuals who know their value and prioritize winning in the long-term over commission checks and President’s Clubs.
Sales at an early-stage startup is really hard, even if you have a world-class product (“that sells itself.”)
So, founders, hire someone who is egoless and believes in the long-term success of your startup, but also understands that sacrifices are made along that journey. Don’t underestimate the importance of organization, attention to detail, and a self-starter’s mentality. Good luck!
