Why Walking in the Shoes of Sales Reps can Help Sales Ops Pros

June 8, 2016 Mark Emmons


Like many people in the tech industry, Dhiraj Singh got his start as a front-line Sales Development Rep. Then he quickly worked his way to Account Executive. These days, as a manager, he’ll still occasionally spend time shadowing a salesperson.

You need, he said, to walk in those shoes.

That’s especially the case when you’re in sale operations, Singh believes. In fact he said it can be a huge advantage for a sales ops practitioner to have felt first-hand that stomach-clenching, white-knuckle experience of trying to persuade people to buy a product.

“It just gives you a lot of empathy,” said Singh, the inside sales and operations manager at real-time memory database company MemSQL. “When you’ve been an SDR and an AE, you can look at it from a perspective of, ‘What can I do to make their lives easier?’ You can think back to your days of being in their position and seeing issues from their perspective. It’s really, really helpful.”

Sales ops has become the lynchpin to the modern sales team. These are the people in charge of building an efficient sales process, managing technology tools and finding insights through data analysis, that will allow the team to, well, sell more stuff.

But they also perform a delicate balancing act. Their primary role is helping the business. And that means they also play the part of hall monitor — telling salespeople what they can and cannot do.



It can be a good cop/bad cop kind of job. Jin Daikoku has been both. In addition to his role as director of inside sales at cloud app security company Netskope, Daikoku handles the sales operation duties.

“I have this awkward position where sometimes I’m trying to be the buddy and friend of salespeople, and make sure they’re enabled for success,” he said. “But I have to be the cop sometimes who says — ‘Hey, this isn’t your account.’ Inevitably, I’m the one making the judgement calls. I imagine that every sales ops person finds themselves in that situation from time to time.”

That’s why, Daikoku added, it helps to have been a salesperson himself.

“Nobody wants to be told what to do or that they’re doing something wrong by someone who hasn’t been in that position and lacks empathy,” he said. “It’s different when you have that shared identity.”

Earning the respect and trust of the sales team sometimes can be a challenge for sales ops specialists. Yes, they’re there to help in any way they can to close more deals. But they’re also bringing a new, data-driven philosophy to a profession that can be stubbornly old-school. And guiding salespeople — particularly those who have had success doing it “their way” — can be like herding cats.

“When you’re dealing with sales, these aren’t fall-in-line, tell-me-what-to-do kind of guys,” said Craig Rosenberg, co-founder and chief analyst of the research firm TOPO. “They all think they’re entrepreneurs. So rounding up the troops isn’t easy.”


The sales seat

It’s also not easy to maintain the “swim lanes.” That’s sales ops-speak for setting up equitable territories that gives every rep a fair chance of meeting their quota.

But the reality is that the power structure is shifting, said Peter Kazanjy, the founder of the sales ops community Modern Sales Pros. Historically, salespeople had an information advantage because of their relationship with customers and prospects. But now those relationships live in CRM — the domain of sales ops.

“It’s a dog-and-the-tail type of thing,’” Kazanjy said. “Before, a salesperson could say, ‘Well, I’m hitting my number. I know what I’m doing. Now you can say, ‘You might be hitting your number, but it’s because you’re in a really rich territory and maybe we need to split it up because that’s not good for the business.’ The sales operations person’s role is to be looking at the big picture and trying to align that with the goals of the salespeople.”

It’s easier to have difficult conversations when you have that sales background, he added. Kazanjy explains what he means by using the analogy that sales ops is like being a product manager. The sales team is the customer.

“The most important thing as a product manager is knowing your user,” he said. “So having that sales experience is really important to understanding their pain points. You have to understand the goal and the actions that go into achieving that goal. That way you’re building ‘features’ into the sales process. When you’re empathetic to the needs of the salespeople, you can propose real solutions.”

And having that real-world selling experience can also help sales ops earn the trust of the manager that any proposed changes will boost productivity, Singh added.

“If I were going to build out my own team, I’d want someone in a sales ops role who has been in sales.”

Tweet this

“You do not want to be the person preaching everything without support,” he said. “It’s true that once people understand that your whole job is to help provide value, then you can work more effectively. But your biggest asset is still going to be your VP of sales and your sales manager. They’re going to have far more power to make things happen on the team.”

Jonathon J. Leon Guerrero learned early that everything you do in life involves selling. As a teenager he worked in retail before moving into SaaS sales after college. So in his sales ops role at LeanData, Leon Guerrero is always focused on automating the kinds of tasks that would have made his life easier as a sales rep.

“If I were going to build out my own team, I’d want someone in a sales ops role who has been in sales,” Leon Guerrero said. “They’ve dealt with having a quota. They’ve done cold-calling. They have a basic appreciation for the role. For instance, I know how to look at leads and opportunities because I’ve been in that chair. I know the kinds of things that should be part of reports because those are the kinds of things that I wanted to see in reports.”

Just like Singh and Daikoku, he has walked in those shoes.


About the Author

Mark Emmons

Mark Emmons is the staff writer at LeanData. He previously was a reporter at the San Jose Mercury News, Orange County Register and Detroit Free Press. He can be reached at mark@leandatainc.com.

Follow on Twitter Follow on Linkedin Visit Website
Previous Article
Without the Right Structure for your Sales Team, Bad Things Happen
Without the Right Structure for your Sales Team, Bad Things Happen

Just think if a four-way intersection was missing the traffic light. What would happen? Nothing good, said ...

Next Article
Welcome to the Sales Operations Era
Welcome to the Sales Operations Era

For the longest time, Jonathon J. Leon Guerrero had trouble figuring out just the right analogy to help exp...