Here’s the Management Mistake We’re All Making, According to 1 Sales Manager

Sponsored by Trimble

Jenna Dobrovolny. Photo Courtesy of Trimble.

Jenna Dobrovolny. Photo Courtesy of Trimble.

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May 18, 2024 at 3:54AM UTC

As a Sales Engineering Manager at Trimble, a positioning technology company, Jenna Dobrovolny manages a team of technical sales engineers that work with customers to make the world go 'round. She sells important positioning systems to customers in a wide variety of industries, all while learning the ins-and-outs of unique businesses.

But Dobrovolny didn’t know she would wind up being a salesperson at one of the most unique companies in the U.S. With a background in marketing, she took a winding path to get where she is today and she has celebrated every minute.

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Recently, she told Fairygodboss about the books that changed her career, how she adapts to such a wide range of clients, and how her role at Trimble has allowed her to celebrate her true self – personally and professionally. Plus, she gave us her best resume advice and clues us in on the manager mistake we’re all making.
How long have you been in your current role, and what were you doing previously?

I’ve been in sales engineering at Trimble for a little over 3 years. Previously, I was in Product Management at Trimble.

What’s the first (and/or last) thing you do at work every day?

I’m a morning person, so I try to get in early. The first thing I do is a mental scan of what my week looks like. I occasionally make to-do lists, but I detest procrastination. If I think of something I need to do, I try to do it right away. I usually have a pretty good handle on my schedule, but I double check my calendar anyway.

What’s the most unique or interesting aspect of your job or company?

I think the most unique thing about my job is the group of customers I get to work with. Our customers are the heartbeat of our economy. Transportation, agriculture and construction all come together to make sure we have clean water, houses to live in, prescription medications to survive, and all the wants that internet shopping has made available to us.

For example, take natural disasters – something that is extremely relevant right now. From the supplies we get when the first disaster strikes to the rebuilding process, we rely on the men and women in our industry – doing a very unglamorous job – to help us put our lives back together. It’s incredibly humbling to step onto a truck yard and realize that when stuff gets real, these individuals are the ones called to action.  

What’s something you think most people (perhaps even current employees) don’t know about your company that you think they should?

I think a common misconception about my company is that you must fit into a certain mold to work here or work in a certain department. While company ‘fit’ is certainly important, my team has individuals from all backgrounds. Some have trucking experience and some that are new to the industry. Some are more advanced in their careers and some are just starting out. I have a bachelors in Communications and Public Relations, and a background in marketing. But about 9 years ago, I got into technology and now I work in sales.

What’s something you’re especially good at at work?

Public speaking. I enjoy it. It’s a rush for me, but that’s probably because I have a bit of an ego.

What about outside of work?

I’m pretty good at handling money. I like organization and money makes sense to me.

What are you trying to improve on?

Trusting people that I work with. It’s not natural to me and has nothing to do with the other person. I’m naturally suspicious and in some cases, that’s just a time-waster.

What’s your favorite mistake?

There was a time a few years ago when I didn’t stand up for myself on something. It was mostly gossip-related. I let my boss at the time dictate how a situation was going to be handled, and I felt powerless. That’s the feeling I am most uncomfortable with.

It taught me not to rely on others to do your bidding. If someone you work with has a belief or understanding about you that is false, say something. I’d rather get a reputation that I won’t take crap than let others define me.   

What’s the one career move you’ve made that you’re most proud of?

Moving into an industry that is mostly male-dominated. It is not uncommon for me to be the youngest and only female in a customer meeting. I’ve always been fairly assertive, but in my business, that’s not seen as a bad thing. I think in other industries a ‘softness’ is required. You try and win over business on a relationship level. My job is to help make our customers more successful and competitive in their own right, and that takes a certain amount of bravado.

What do you love most about your job or your company?

A new employee on my team mentioned that we have a lot of passion for what we do, and I believe that to be so true. We also have an unshakable desire to get better. We’re pretty hard on ourselves. If you value activity over productivity, this isn’t the place for you. We are driven by results.

What are you currently reading/watching/listening to?

I get both the New York Times and FreightWaves (an industry publication) delivered to my inbox daily. I also just finished Anthony Bourdain’s Kitchen Confidential, which I found to be wonderfully relevant to both being a manager and to the food delivery business (many of my customers work in this industry). I think it’s important to read books for business, but it’s also important to read for the human element. I’d rather read a biography about a successful individual than a ‘how to’ book. That said, I’ve read my fair share of good business books as well. Smarter Faster Better by Charles Duhigg was eye-opening. It changed my way of thinking entirely.

What’s your #1 piece of advice for women who are looking for jobs right now?

Your resume must be results and success driven. Don’t say ‘I worked on our RFP process.’ Define how much you improved the process. If you brought in revenue to your company, say how much in dollars. Quantify everything: dollars, percent improved, efficiencies gained. I’ve seen a lot of resumes recently and numbers jump off the page to me. It also shows that an individual knows their value, which becomes extremely important upon salary negotiations.

Who is/was the most influential person in your life and why?

My mother. She is absolutely the hardest working person I know, and her compassion for humanity is unwavering. She’s not afraid to call others out for their lack of understanding, and believes in being fully educated before voicing an opinion. She follows her heart, even when it is contrary to the belief system she was raised with. As her daughter, it’s empowering to see that and it gives me confidence as well.

What’s the most memorable piece of career advice you’ve received?

What other people say and do is not about you. Ever.

What was the best quality of the best boss you’ve ever had?

Allowing for independent action and thought. Delegating and micromanaging can sometimes look like the same thing. When you delegate, you identify a problem that needs solving. When you micromanage, you tell others how to solve it. Micromanaging is a cheap way to manage people. And it’s extremely unsuccessful. Having a boss that delegates and asks for my opinion makes me feel valued.


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