Want to Join a Scaling Sales Team? Look for This Green Flag

Rapid change is hard to pull off. Here’s how a sales leader at Highspot handles it.
Written by Eva Roethler
January 13, 2022Updated: January 13, 2022

Scaling a company is an exercise in change management. And according to research firm Gartner, half of change initiatives fail, and only 34 percent constitute “a clear success.” This could lead people to see rapid change as a red flag.

Instead of making that blanket judgment, what if we examine the main reason changes fail? 

Gartner found the vast majority of organizations manage change from the top down, but change management works more effectively when organizations embrace an “open-source” approach to change where leaders engage the workforce to co-create strategic decisions, employees are responsible for planning how to implement the change and communication encourages open conversation about the change. Open-source principles can increase change success from 34 to 58 percent, along with a wealth of other benefits. 

In short, a grassroots approach to change management may be a green flag for jobseekers joining growing companies. What does that look like in action?

Highspot is a sales enablement platform experiencing a period of high growth, with more than 100 open roles. That’s part of the reason why Sales Director Brie Tobin encourages her team to remove friction by questioning the way things are done. 

“I want my account executives to challenge the status quo and make me defend why we do something or validate if a process that served us a year ago is still serving us — that’s how we continue to grow as a team and as a business,” said Tobin.

Built In Seattle connected with Tobin for insights into these strategies, and more, as the company continues to grow. 

The office at Highspot.
Brie Tobin
Director, SMB and Commercial Sales


How do you scale effectively during periods of high growth?

I’m constantly thinking about scaling and how we build a sustainable business. In a high-growth environment, an abundance of free time and an empty to-do list don’t really exist. Without scalable processes in place, time is wasted and the business suffers.

A great place to start is by reflecting on the question, “Is this the best way to accomplish the intended outcome, or just how we’ve always done it?” Apply that question to different areas of the business such as sales processes, internal meetings or onboarding. To scale, you have to remove friction. 

One of the most effective ways to understand what’s not working and where I can take action is to check in with my front-line managers and individual contributors often. Asking, “What’s one thing you’d change about how we do things today?” can lead to really impactful insights and quickly highlight potential friction points in the current process. Keeping a pulse on my team’s day-to-day and seeking feedback informs how I prioritize my efforts to support them and grow our business.


What’s the most important characteristic you look for in a salesperson, and why?

Genuine curiosity. When someone is curious this impacts how they learn, how they show up on customer calls and how they solve problems. I want my account executives to ask, “Why?” To support our customers and demonstrate our value we have to understand their current situation, challenges and goals deeply. You can’t do this unless you’re genuinely interested in learning about them. 

I want my account executives to ask, ‘Why?’”

What’s your blueprint for building a successful sales team? 

Hire the right talent, build trust with your team, provide role clarity, and over-communicate expectations and how you’ll hold someone accountable — then hold them accountable. Lead by example. Don’t ask your team to do something you wouldn’t do yourself. Be human, relatable and approachable. Provide as much transparency as you can around how and why decisions are made, how it impacts the individual, what behavior are we asking them to do now and what’s in it for them. If people buy into the direction we’re taking them, they’re more likely to execute on what’s being asked and succeed.


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