"Creativity is the most obvious clue of a great sales culture, which is also an engaged culture."  - Brogan Taylor

Brogan heads Enterprise Sales for North America at Freshworks. He is a SaaS revenue growth and GTM expert. Brogan is experienced at building winning sales teams in multiple categories with venture-backed start-ups through F100 companies. He is adept at building high-velocity sales machines, yet differentiated by scaling the innovation, customer focus, and internal teamwork required to win the trust of the world's largest enterprise companies.


What makes a great sales culture?

Number one is the team. It's always all about the team. You can have a tremendous product, great market fit, but if you don't have the right team, nothing else works.


What about the Freshworks sales culture attracted you in particular?

There is a certain soulfulness to this company. I felt it was going to do something great. I think it's fun to be disruptive, to challenge the status quo. Software as a Service has been around for 20 years or more. It's time for a fresh approach — something built from the ground up that really resonates with the market and customers. That sounded like an awful lot of fun to me. 


What are some hallmarks of a happy sales culture?

Creativity is the most obvious clue of a happy sales culture, which is also an engaged culture. When I see salespeople being incredibly creative, it tells me the organization feels both free and secure. They are enthused by what they're doing. People shouldn’t be waking up at night worried about where they stand in the rankings. They should be waking up energized by some great idea they have, a new campaign they want to build, or a new way they have thought of to meet customers’ needs. Our CEO uses the word craftspersonship. It's one of our core values.


What are some characteristics of high-performing sales teams?

We always talk about great salespeople being great listeners. But empathy matters too, and that starts with team leadership. When you have empathy, you can look clearly at all your strengths and weaknesses. You can collaborate to make things collectively better. Sales teams can be great catalysts. They are on the frontline interacting with customers. They receive product feedback and have an ear to the ground in the marketplace. Sales is an incredibly cross-functional team with great energy and good skills for communicating. 


What do you think of sales leaderboards?

If you focus exclusively on the leaderboard, you’re focusing on top performers at a given point in time. Occasionally, you might have a Big Deal closer or perennial Top Gun on the team, but when you focus on just the top performers, it’s easy to miss other sources — and other kinds — of strength on your team. For example, you might have someone on your team who is an incredible copywriter, who can write great campaigns. You might have someone who is incredibly analytical, adept at account analysis and go-to-market strategy. There will be other folks who really enjoy transactional deals. Then, of course, you have the enterprise-type skill sets, which are totally different. How much healthier and stronger do we become, when we can consistently identify and tap into our team members’ greatest strengths?


How do you solicit feedback and other inputs from your sales teams?


Many companies including Freshworks have moved to pulse surveys, in which our employees tell us about their strengths, how we can improve, and places where we might need to adapt. They give us great information about how we can pivot in the market. You do have to be wary of something I call “context collapse.” That is when you look at the summarized results and think you understand what is happening. While using pulse surveys, it’s imperative to dive into the comments, to look at which organizations people represent, what are their interdependencies, and what might be influencing the opinions and feedback. Never just look at the headlines! Meanwhile, in weekly one-to-ones in our Slack channel, we try to encourage a spirit of candor on the team. It’s a challenging, fun mindset. Instead of talking about what happened in the past, we try to focus on possibilities — so, the old design theory that starts by considering where you are today and where you can go from there.   


Are there risks to team happiness in trying to scale a sales organization quickly?

People often think headcount is the key to growth. I believe you need to build a culture of success first. You need to ensure the right product-market fit. You need a core of people working at or above certain levels of productivity before attempting to expand the sales force. You can’t expect sales reps to be marketing people, to drive demand in raw, new markets. You need to build a nucleus of success, prove your ideas, and then you can look to expand the sales workforce. Another common mistake I often see in startups is trying to establish channel or partner relationships before they have proven product-market fit or their positioning for selling within a specific market. You start by building a culture of success with your core team. Only then should you attempt to scale up.

(The interview was conducted during the second half of 2020. It has been edited for brevity and clarity.)