ChallengeHer Series: An Interview with Preeya Voss

For too long, the sales industry has excluded, diminished, or downright ignored the voices and perspectives of women sellers. To combat this inequality and to balance our industry in favor of inclusiveness and diversity, we’ve launched an initiative we call #ChallengeHer. With this, we’re featuring women in sales at Challenger, bringing to light their unique stories about work, leadership, and the day-to-day challenges and triumphs.

“If you are your most authentic when you think no one’s looking, your personal brand starts to evolve in a positive way around you.”

PREEYA VOSS, VICE PRESIDENT OF SALES AT BETTERUP

What is your name and role?

My name is Preeya Voss and I am Vice President of Sales, North America, at BetterUp.

How long have you been in sales?

I have been in sales for 17 years. I started as a sales development representative at the Corporate Executive Board (CEB, now Gartner), calling into sales executives.   

What are the characteristics you look for if you’re hiring a new salesperson on your team?   

Every organization is different in what they prioritize; for example, BetterUp is a mission and values driven company so there are strong themes of this in our interview process.

There are a couple of core things that are important to me in any sales organization. The biggest is self-awareness. It’s something that you have to be very intentional to assess and measure during the interview process. I think it’s very important, especially in this new hybrid world that we’re living in.  

Additionally, I look for individuals who are curious and eager to learn with a beginner’s mindset. In today’s environment, change is the only constant, and if you’re able to approach your work with an open mind and fresh perspective, that’s where the magic happens—both for customers and your growth goals.

When you made the shift from independent contributor to manager, what did you do to prepare yourself? Did you read books? Did you talk to folks internally? Did you get external coaching or guidance? What did you do to feel prepared for that role?   

The first time I stepped into leadership, I was woefully unprepared, as I believe every first time manager is. The first development feedback I received was to read more books on sales, so I’ve definitely leaned into that (including the Challenger Sale!).

I’m a huge advocate for coaching and mentorship at any stage of your career; there are insights/strategies that I worked on with my first coach that I still tap into today. The lessons are just as relevant today as they were when I was in my first manager role.

What is it about leaders that you admire?   

I’ve been fortunate to work for some incredible leaders who have modeled the right behaviors. I admire how they communicate with the team, how they foster community, how they’re authentic, how they create a safe space and drive accountability to do great work. What’s most impressive are the leaders that operate with grace under the most challenging circumstances.

This is the challenge I give to every individual who is interested in exploring leadership. Think about yourself on your worst day. Go to that headspace where you’re not motivated, you’re frustrated, you’re on the edge and thinking, “I don’t want to do this anymore.” Go to that place now and imagine you have a team of people looking up to you for direction. How are you going to operate in that moment?

We can all talk about ourselves at our best: when you’re winning deals, when you’re at 140% of quota, when the company’s doing well. We all can do that. It’s those moments of adversity that really expose who is an inspirational leader.

What advice would you give to women who want to get into sales leadership?   

Negative self-talk is detrimental, especially if you’re the only woman on a leadership team. We are all self-conscious. We all have our doubts. But, you can’t let that negative self-talk dominate how you show up. You’re in the job for a reason. You’ve earned this and it’s okay to make mistakes. That’s all part of learning.

This self-judgment or lack of self-confidence made me doubt myself a lot. I’d leave meetings and think, “Did I sound like a total idiot?” or “Why did I just say that?” or “What are they going to think of me?” These days, that’s an internal narrative I work hard to keep at a minimum.

Of course, I can’t turn it off completely. But when you beat yourself up, it doesn’t allow you to focus on the things that are impactful. You just kind of spin in those moments.  

You’re better off shifting to think: “I’m in this role, what impact can I make?” instead of, “I’m in this role and what do others think of me?” If you can lean into that confidence, there’s power in those positive affirmations.  

One thing in your control is your mindset. If you can say, “It’s going to be scary, but I’ve got this,” there’s a lot of power in that.   

---