Like many high schoolers, Sarah Weigand’s first job was in retail, working as a cashier at a sporting goods store in the Florida Keys. She quickly realized she had a knack for sales and decided to pursue a career in it. Today, she’s come a long way since minding the register and is a VP of sales at KnowBe4, the world’s largest integrated security awareness training and simulated phishing platform.
“What I love about sales is the game of it,” she says. “Not one sale is the same. You’re meeting new people, matching them up with the right product, caring enough about their success to work with them through any boundaries to purchasing they might have, and getting them to the finish line.”
At KnowBe4, Weigand has worked her way up from sales rep to her current role as VP of Regional Enterprise Sales in the span of six years. And as a relatively new mom, Weigand has discovered the secret to managing the demands of her fast-paced job while prioritizing her daughter.
Here, Weigand talks about the challenges of working in a new-to-her industry, how she achieves work-life balance, and her advice to anyone interested in pursuing a career in sales.
What led you to your job at KnowBe4?
I knew a few people who worked here—some of the very first employees. I had always heard that Stu Sjouwerman, our founder and CEO, was an incredible leader. When I was looking to leave the marketing company I was working for, I knew that it was important for me to find a job that had a great product to sell, a great person to work for, and room to grow. I spoke to the employees who worked here and I was convinced it was the perfect next step.
What attracted you to work at KnowBe4?
I had never sold software, let alone SaaS (software as a service), so I was really intrigued by the idea of getting to apply my current sales skills to a new product and learning about a totally new industry. On top of that, I knew it was a really strong product and that the leadership had very clear goals for the future. I was excited about being able to be a part of a company that was destined for huge growth.
What are you responsible for in your role?
My number one responsibility is hitting and exceeding my teams’ overall sales goals. I track and monitor the teams’ stats to ensure they are moving in the right direction to enable success. I look at the deals and work with my reps on an individual basis to help strategize the current sales opportunities they have. We discuss next moves and even how to break into accounts we are lacking traction in.
What has been your experience as a woman working in sales?
I’ve found that being a woman in sales has probably assisted me more than anything. I’ve found women oftentimes are more empathetic and emotionally intuitive, which is very beneficial in a sales cycle. I am able to look at a deal, read the person’s emails or listen to a sales call, and I can fairly easily think about that specific buyer’s needs and correctly recommend next steps or strategies. Of course, there have been times, especially when I was newer in the IT cybersecurity space, where I could tell the prospect didn’t think I had a clue, but I never let that bother me. I always thought, “They can think what they want, I don't need them to think I am a genius, I need them to want to buy from me, I need them to think my product is genius.” I was confident in my ability to get them there despite any preconceived ideas they might have had, and part of that confidence came from never agreeing my gender was a barrier in the first place.
What have been the keys to your success in balancing a fast-paced job in sales with parenthood?
Setting priorities and planning my days is a huge part of making each day run smoothly. I am also not shy about where my family ranks in my list of responsibilities. I have a 2-year-old and she is my number one. I was lucky to find excellent care for her once I came back from maternity leave, which enabled me to be fully focused while working. The fact that I stay very busy is also great because the time flies.
The other major key is a super strong support system, people you trust, and a boss/leadership team who understands how important that balance is. It was important to have friends and other coworkers with similar values and mindsets: career-oriented parents who love their babies and their work! I am very close with other successful women who also have young children, and we are constantly sharing what’s working and helping one another navigate each new experience.
What advice do you have for working parents who may be struggling to find this balance between work and family?
One of the biggest things is planning ahead, taking into consideration your family and work schedule. By doing this, it’s easier to make sure you don’t over-commit. Commit to only what you know you can do well. And ask for help! As an executive, sometimes you want to just do it all, but it’s hard. You have to be OK with handing over certain responsibilities to people you can trust, like your team leads and managers—and at home your partner and even family members. Make a list of the items only you can handle, then delegate the rest of the work and responsibilities to the appropriate people.
How does KnowBe4 encourage its employees to have work-life balance?
We have unlimited PTO, which I think in and of itself speaks to the viewpoint on work-life balance from the top down. It gives people the choice of what to do with their time, and it’s a freedom that innately creates happy employees who feel like they don’t have to squish all the out-of-office adventures they want to have into a certain predetermined amount of time.
What advice do you have for anyone interested in a sales career, especially those who hope to attain a leadership role?
I would say to succeed in sales you need to be a master of discovery. Read and ask questions: Instead of “always be closing,” always be asking. When you get an answer, train yourself to wonder more rather than simply accept it or draw a conclusion from it. Instead, dive deeper into each response. For example, if you ask a prospect what their favorite color is, and they say, “blue,” your first thought should be, “I wonder what shade?”
Once you are really solid in your sales skills and have the stats to support it, moving into a leadership role comes far before you actually take the position. You have to act like a leader before you even apply—meaning you already take the responsibility, care for team members, and exhibit the practical skills that are necessary. You have to exemplify leadership before getting the promotion.