Playing the field: how to evaluate your next sales job with Outreach’s Brian Gerrard

Collin Stewart, CEO

10 May 2018

I read something recently that made me smile.

Ryan Holmes, Hootsuite CEO, wrote a terrific piece in The National Post (one of Canada’s national newspapers) about the current roaring Canadian job market for salespeople, brought on by an ever-growing innovation boom. Even though I’ve been in the industry my entire professional life and spend my days in knee-deep in business development, I’ll admit this idea caught me a bit off guard.

As Holmes discussed in his piece, so often when we discuss the need for tech talent, we focus on recruiting top tier developers and designers. But at every growing firm, there’s a growing sales team. And they too need good people.

But, as any sales professional will attest, not all sales gigs are created equal. Far from it, in fact. And as we navigate the new roles and responsibilities that unfold for salespeople over the next handful of years, understanding how to judge, and ultimately pick, the right roles will be critical.

A lot is coming our way, and we need to be ready.

“My ultimate goal was always to be part of startup that had a great story. I wanted to be a part of those stories you here – the Googles or Facebooks of the world. You join a small team and grow until you’re a billion dollar organization,” says Brian Gerrard, Director of Sales at Outreach, on a recent edition of The Predictable Revenue Podcast.

“But, finding that can be really hard to see when you’re young, and you don’t yet know what to look for.”

What to look for

So, you’re playing the professional field, and your resume has piqued the interest of a few companies. Both look okay on the surface – no red flags, knock on wood – but you can only choose one.

How do you know which is the best opportunity?

Well, naturally, a lot of that depends on where you’re at in your career. For example, are you looking for a senior sales role? Or, is it time to head into management and move on from your quota carrying days?

And, what’s your appetite for risk? Have you caught the early stage startup bug, where you can make your mark on small team? Or, do you prefer an established company with less risk?

For every job hunter, there’s a different answer for those questions, and a litany more. But, according to Gerrard, there are some fundamental features everyone should look for in a new gig:

  • Product;
  • Boss;
  • Culture.    

“In my journey, I always thought evaluating the product was the first place to start, but I realized I was missing all of the other stuff. For example, was I considering the boss as just as a boss, or as someone I really wanted to work with?,” says Gerrard.

“And, what’s the culture like? Is this a job where I will have the freedom to be myself, or are they so stuck on process that they are going to force me into something that I’m not comfortable with?”

Evaluating the product

Good salespeople can do a lot of things… and meet a lot of quotas.

But even the best in the profession struggle when trying to sell a less-than-stellar product. To avoid that pitfall, and a major one at that, it’s critical you learn all you can about a company’s product before joining the team.

Beyond speaking directly to customers – which you could do, of course – gathering information about a product can come from a number of different angles. For example, clients, reviews and competitors. That will help you better understand the particular market, and how people are assessing both the product in question, as well as the others in that space.

Another important product related question: how clear is the value proposition being conveyed? If the company you’re looking at isn’t doing a great job talking about its product, or they have too offerings and their messaging is convoluted, that’s a problem.

In fact, Gerrard faced that very issue years ago and struggled as a result.

“Probably the biggest company I worked for in the past was called Reach Local. It was in their heyday, but for me that wasn’t really a good thing. Territories were basically diminished, and there were so many product lines it was hard to focus, especially when you are working full sales cycle, start to close,” says Gerrard.

“Also, during the time when search engine marketing was on the rise, so it was hard to distinguish what they were doing on the backend versus the thousand other agencies out there.”

Evaluating the boss

Of course, a great, in-demand product will take you a long way. But, what if you work for a tyrant? What if your boss makes your job a nightmare?

Sigh. We’ve all been there. And, it’s tough.

“We’re all different personality types. You have to determine if you vibe with the person, or these people,” says Gerrard.

“Because you’re going to be spending a lot of time together. And, sometimes, it just doesn’t click.”

But, Gerrard says, you have an opportunity during the interview phase to actually interview them and find out what kind of boss you’ll be working for.

To do that, there are some of the tell tale signs to look, adds Gerrard. For example, is this the type of person that talks about how they help the team succeed? Or, is this the type of boss that only talks about numbers and nothing else?

Does this person talk about mentoring team members, and helping them grow and mature as professionals? Or, are they focused on helping themselves?

“I saw a post recently that said to be a good boss you always have to be asking your team what you can do to help. On the flip side, I’ve worked for people that told us once that he was going to get a lower commission cheque because we missed our goals. I’ve seen both sides of the coin,” says Gerrard.

So now, I do a lot of training and team building work, even though I still carry a bag. And I wouldn’t be able to do that if someone hadn’t been that way and taken the time to help me.”

Evaluating the culture

In fairness, the type of boss you work for, and the tone they set, has a lot to do with the culture of the company. If they’re a kind, giving mentor, that will trickle down to the rest of the team.

But the company, aside from the caring nature of its people, will espouse a set of core values. It’s become a somewhat routine trope – few organizations these days don’t do this – but they do give you a glimpse into what is important to them.

For Gerrard, there are three values he always looks for: trustworthiness, support, grit.

Does the company say it what it means? Do its employees help each other out when necessary? And, will the company do what it takes to ensure its people have the resources necessary to get the job done?

Yes? Well, then, you may have a winner on your hands.

“If you can, go spend a day at the company and see how willing people are to help you there. Go put their values to the test,” says Gerrard.

“If they are willing to help you, you’ll know that they truly want a new person that can help get them to the next level.”

For more on Gerrard’s job hunting tips and tricks – including his thoughts on evaluating compensation, growth potential, and the founding team – check out his edition of The Predictable Revenue Podcast.