Startup Sales Hiring: Is Big Corporate Experience a Blessing or a Curse?

August 13, 2013

Building your company’s first sales team is a challenging, risky endeavor, and it can be tempting to tap someone with senior experience at an established corporation to bring a sense of stability and order to things. But before you go after the big gun, find out why many experts caution against it.

Startup Sales Hiring: Is Big Corporate Experience a Blessing or a Curse?

Given the choice between hiring a sales rep whose resume features tenure at mostly smaller, lesser-known organizations, or a rep with experience selling enterprise software for larger, well-known corporations — whom would you target to get your startup’s or expansion-stage company’s sales function off the ground?
You’d hire the “BigCo” rep, right?
After all, that person has likely proven their ability to sell, and their experience working for big companies (something your startup undoubtedly aspires to be) can only help as your business scales. That’s not to even mention the BigCo rep’s network. From that perspective alone, the decision might seem like a no-brainer.
Except that isn’t, writes serial entrepreneur Jason Lemkin.
In a post on his blog, Lemkin argues that bringing BigCo sellers into a startup environment presents certain risks. Namely, all-star salespeople who have only worked for behemoths like IBM,, and Oracle are almost always a terrible fit for true startups.
In fact, one of the biggest mistakes Lemkin says he made as the CEO and founder of electronic signature software company EchoSign, was hiring a renowned sales leader away from a much larger corporation. In doing that, the business, “spent a ton of money, hired the wrong people, and, worst of all, lost its way.”

The Argument for Hiring for Fit, Not Resume Pedigree

That being said, Lemkin acknowledges that hiring based on BigCo experience can be beneficial. Ultimately, the sales leader he hired at EchoSign did directly contribute to more than $6 million in revenue, a number that more than justified that person’s six-figure salary.
But that alone doesn’t mean it was a good long-term decision, Lemkin admits.
The reality, says entrepreneur and investor Mark Suster, is that most startups are better off hiring what he calls “evangelical” salespeople first — the types of sellers who aren’t overly robotic and reliant on more conventional sales wisdom.
In other words, Suster writes in a post on his blog, startups need salespeople who can think creatively and work with customers to help them understand vaguely defined problems. And above all else, startups and expansion-stage companies need people who are comfortable with a lack of structure, process, and product.
Mark Suster


“I always tell people to hire somebody who wants to punch above their weight class.”  — Mark Suster


All too often, BigCo reps who have grown accustomed to a certain degree of predictability, consistency, and the benefits of having an established market presence are not the right fit for that type of environment. For one thing, they may be used to relying on a steady stream of quality inbound leads and find it too difficult to build a solid pipeline without them. But even those with plenty of success hunting for their own deals may find it’s a different story when they don’t have the instant authority and credibility of a big company logo on their side.
Companies that are building out their first sales roles need someone who is comfortable representing a brand no one has seen before and building relationships and trust from scratch.

What Startups and Expansion-Stage Companies Should Really be Looking for in Sales Reps

In a perfect world, Lemkin says startups would hire people who display a balanced combination of sales experience and cultural fit with your organization.
Unfortunately, those types of candidates aren’t exactly easy to find (let alone recruit and hire). So, which skills, qualities, and characteristics should startups put on their “must have” lists as they build their first sales teams?

Passion and competitive spirit

As you interview sales candidates, KISSmetrics and CrazyEgg founder Neil Patel says that you’ll likely hear a lot of hyperbole about how great they are and what they bring to the table. What really matters, however, is how easily those candidates are able to convey their passion for selling and their desire to compete on a higher level.


While ZipRecruiter VP of Sales Kevin Gaither is hesitant to suggest that the “perfect sales candidate” exists, he does think that the best startup salespeople share some common qualities. One of them is optimism, which Gaither says is critical in a startup sales environment that’s likely to involve a lot of rejection.


Let’s face it — the startup world is an uncertain one, and selling software for a business that is still discovering who and what it wants to be can certainly feel like a very turbulent roller coaster ride. That’s why sales consultant and author Doug Dvorak suggests that startups target salespeople who are highly flexible and adaptable. Because, ultimately, salespeople will not only have to frequently alter the sales messaging, strategy, and processes they employ, they’ll also need to be able to quickly fit into your organization’s unique culture.

What Do You Look for When You Hire?

At the end of the day, the reality is that the skills that work for salespeople at the enterprise level do not always translate to those that are required of startup selling.
So, while you may think that hiring a BigCo sales rock star is the obvious choice, the consensus among startup experts and seasoned entrepreneurs seems to suggest otherwise.
Are you building your company’s first sales team? Or do you have experience building those types of teams in the past? If so, which skillsets or characteristics do you look for? And would you rather hire someone with a sparkling resume, or someone who is less qualified but more willing to learn?

We’d love to hear from you in the comments section below!