From waiting tables to attaining the role of SVP of Global Sales at OpenTable, Jenna Swigert's career unfolded as an extraordinary journey of achievement and progression. 

A year ago, Jenna made the bold choice to depart from her 20 year tenure at OpenTable, a workplace where she experienced a career breakthrough and built an enviable resume. 

Today, we caught up with her to gain valuable insights. In this exclusive interview, Jenna imparts wisdom on overcoming sales challenges, emphasizes the significance of authentic connections, and delves into the delicate balance between ambition and patience on the path to realizing one's dreams. Here are some highlights from our uplifting conversation: 

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Can you tell us a little bit about your background and career journey?

So, I’ll start with when I went to business school, which was a great experience. But then, after business school, I worked in the city for a year. But unfortunately, I didn’t like my job, I didn’t know what I wanted to do. So I moved to Aspen, Colorado, for the summer. And, funnily enough, I ended up staying there for four years, just trying to figure out what I wanted to do.

And once I got there, I was so happy to be there. I mean, I was 30 and still did not know what I wanted to do. So, I started waiting tables, and I was taking guided bike trips. Eventually, I got into restaurants and hospitality, and I loved it. I just kept doing it. Ultimately, I didn't want to run restaurants. I moved back to San Francisco, where I managed Fog City Diner for a while. But I didn't love it. All my friends were working nine-to-five jobs. And I was working during these restaurant hours, and they were making way more money than I was.

I just wasn't very happy doing it. But I ended up going back to Aspen for a conference. And while I was there, I sat in and listened to a panel. And one of the people on the panel was this guy, Danny Meyer, who owns Union Square Hospitality in New York. He was on the board of OpenTable at that time, and he was talking to everyone about OpenTable when this light bulb went off. Like, that's what I need to do. That's the perfect combination. I can sell OpenTable and stay within hospitality, but I don't have to be at the restaurant and manage a restaurant anymore. 

So I cold-called them. OpenTable was so small at the time. So, I was able to leave a voicemail on the VP of Sales’ voicemail at the time. I said, I work for Fog City Diner, I love OpenTable because I have used it before. And I'm interested in working for OpenTable now. And he called me back. What's interesting is that I think part of the reason he called me back is that Fog City Diner had just taken OpenTable out of the restaurant. They thought it was too expensive. So it was exciting to him because it was sort of a lead to get OpenTable back into the restaurant. And that's how I got the job!

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How did you get started in your career in sales, and what essentially inspired you?

So, my first job out of college, I was working for a specialty ad agency, which basically sold tchotchkes like hats, bags, and pens with logos on them. And my job initially, I was hired as the office manager to do the bookkeeping and just manage all of the administrative things in the office. And I had a little bit of extra time. So I just took out the phone book at the time, and I started looking at different coffee shops. I decided I was going to try and sell mugs to coffee shops, that was going to be my thing. And I had great success. 

Spinelli was a coffee brand in San Francisco at the time. So I got their account and a couple other accounts. And it was really fun to close those deals. And so then I started calling on the different racetracks, like Bay Meadows and Golden Gate Fields. I landed a couple of those accounts, which were humongous accounts for me at that time. My boss at the time—he was also really entrepreneurial, and he was all about letting me grow and figure out what I was good at and what I liked. [My career in sales] wasn't really intentional. It was just something that I happened upon. 

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What are some common misconceptions about sales, and how would you address them to inspire students who may have doubts about pursuing a sales career?

So to me, like, I think sales kind of gets a bad rep’. You think of sales as sort of pushy, annoying, and selling you something you don't need. That's a lot of the things you hear about sales. For me, sales, what I love about it, is that you can solve a problem for a prospect and help them get what they need or solve whatever problem they have. That's really rewarding. 

And along the way, you are building this rapport and trust with these prospects, which is really fun. And what I really loved about restaurants for all the small businesses I sold to, even with primetime marketing, was building these relationships with all these people who were so interesting, passionate, and funny. So, think of sales as solving problems and just bringing solutions to people to help make their lives easier. I would never want to sell anything if I didn't truly believe that's what I was doing.

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What qualities or skills do you believe are essential for a successful sales professional?

I would say, you know, it's really just being friendly and comfortable. Whether it's in person or on the phone, you need to have a little bit of charisma to get people to engage with you. No matter if you're selling the best thing in the entire world at the best price. If your initial impression is annoying, nervous, or aggressive, you're not going to get their time of the day. You have to be able to build rapport with people. 

So practicing that, but the question many ask is how do you practice? I would say putting yourself out there. If I wanted to get into sales in restaurants, I would probably, get really familiar with restaurants: like how they operate, and maybe even get a job working in a restaurant. This would help when I go to sell to restaurants—I could talk their talk and understand what their problems are. Really, become an expert in what you're trying to sell into. So, you're not a fish out of water.

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What advice would you give to students who are interested in pursuing a career in sales and looking to develop themselves professionally in this field?

The advice that I would give is that there's a lot of opportunity. So you need to seek it out. SDR is generally the person who makes phone calls and tries to book meetings—that's a great place to start. Sometimes it may not be very fun. But if you find a company that's fun, and has a great culture, with a great team, it can be fun.

So look for a job where you're selling anything or booking meetings. I would always want to make sure when I hired AEs (account executives), that they were not afraid to pound the pavement. They didn't feel like they were too senior or that they were above pounding the pavement, knocking on doors, and getting rejected. Because that's part of it; you have to be able to pick up the phone and call and call and call and call or email until someone says yes. So I would say just look for opportunities because they are out there for sure.

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Can you provide some insights on how to balance ambition and patience when it comes to following your dreams? 

I remember my dad was always really supportive, telling me if I was happy, he was. He was always so optimistic. So if I had a job as a restaurant manager, he would see it as an opportunity to be like the VP of Operations of the restaurant group. He always saw potential for me. 

So, it was always nice to have people encouraging me. It gave me the ability to not think of life as this ambitious thing of where I'm trying to go. Instead, I'm able to think of life like, Am I happy? Am I living my best life? Doing what makes me happy, not doing what I think I should do because that's the ambitious thing. It helped me focus on what's important.

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What are some common challenges or obstacles that individuals may face when trying to climb the corporate ladder, and how can they effectively overcome them?

Well, one skill that is super important is being able to work cross-functionally. As a sales leader, I really benefited from the fact that the marketing team could come to me and I could go to them. The product team could come to me, and I could go to them, and so on. So, having all those cross-functional relationships helped the whole business function better. 

[I would say] building these cross-functional relationships is really important. And sometimes it's not easy, particularly [between] product and sales. Because a lot of times, sales wants things faster, and product wants sales to stop selling things that we don't have yet. This is probably true for every technology company. So, that can be a hard relationship. But it's really important to make sure you nurture that relationship because that's going to help you grow in your career. 

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In your experience, what are the most important skills or attributes that help individuals progress from entry-level positions to more senior roles?

I think there's a few things. One is having a positive attitude. If you're going to have a one-on-one with your boss, there's things that you may not be happy about. But [you need to] come up with a solution and talk about the positive things. Don't be a whiner. 

And second, become an expert. I knew Opentable software from the beginning—every release, every contract that was ever signed. I knew everything about it, and I knew what I was talking about. Because of that, different departments and people who came on later could rely on me to answer questions and to help. 

Ultimately, it's loving what you do enough that you give it your all. As for me, I loved restaurants. I loved restaurant people. I loved the software. So it was it. It wasn't like I had my job. And then I had my life. You know, I love the people I worked with. So it was something I really gave my all, all the time. Because it was fun. So I think you have to have fun and love what you're doing.

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What do you wish you knew before starting your career?

I think I would [tell myself] not to worry. I went to business school, where I put all this pressure on myself to know what I want to do. That's a lot of pressure on an 18-year-old kid, to feel like you have to know what you want to do. So if I could do it again, I would say, just do what makes you happy, and do it really well, and become an expert. And everything will fall into place and everything. 

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Discover more about Jenna Swigert and her corporate triumphs by connecting with Jenna on LinkedIn.