Maura Reilly always knew she wanted two things out of a career: to work with various types of people and to be able to flex her creative muscles. That led her to study marketing in college, but, she says, “I didn’t see myself in a typical advertising role like many of my classmates.”
With that realization in mind, Reilly decided to work in real estate as a sales and marketing associate after graduating—and her interest in sales was sparked. When an opportunity arose to join a sales and account management program at a logistics company, she jumped at the chance. After a few months of juggling both roles, Reilly decided account management was the best path forward.
“It provided the best of both worlds: I was continuously meeting new people as my book of business expanded while simultaneously growing relationships with current partners,” she says. “Account management even gave me the opportunity to be creative in how to consistently raise the bar and problem solve for these partners.”
Today, Reilly is a senior account manager at the retail technology company Upside, where she helps restaurant partners solve pertinent and challenging problems.
Here, she shares how she’s achieved professional growth, why she values Upside’s work culture, and the one lesson she teaches new hires.
What attracted you to Upside, and how did you know the company would be a good fit?
I was introduced to Upside by my husband, whose friend worked there. When looking into the company, I learned that the founders built an app that benefits and profits everyone involved, from the merchant to the user to Upside itself.
Before I was offered the job, I knew the company would be a good fit. During the interview process, I met with four people from various teams and had great conversations with each of them. I could tell that Upside had growth potential, and it was full of collaborative, hardworking people. I knew instantly that I wanted to be a part of it.
What are you responsible for in your role?
As a strategic account manager, I’m responsible for ensuring the success of some of Upside’s largest restaurant partners. I succeed when I can understand our partners’ business objectives and optimize our product to help them achieve their goals. For example, depending on a restaurant’s goals, we can pull levers behind the scenes to increase Upside transaction volume, focus on the return on investment, or shift our user behavior to different days of the week and times of the day.
Why does working within Upside’s restaurant business excite you?
It excites me because of the opportunity ahead of us—we’re just getting started. While Upside’s fuel business has been around for eight years, we’ve been working with restaurants for a fraction of that time, and growing our number of partners exponentially year over year. I can see a day when Upside is the first app that people check before deciding to dine out, and I look forward to it.
What are a few of your biggest accomplishments at Upside, and what have been the keys to your success?
My biggest accomplishments are linked to partner health and growth. I’m proudest of the work I’ve done to grow our partnership with a national pizza brand from 80 locations in March 2022 to more than 700 locations two years later. This growth, mostly through word of mouth and referrals, eventually garnered the attention of the brand’s corporate office, which is now interested in partnering with Upside as well. This win was a joint effort across sales, leadership, marketing, analytics, and more.
From an account management standpoint, the most important skills that helped me were being organized, thoughtful, and strategic about each account. It was—and still is—important to me that every franchisee feels heard, whether they have two restaurants or 200 restaurants.
How have you grown as an account manager since joining Upside, and how have you helped the company grow as well?
The biggest shift I’ve noticed in myself since joining Upside in 2021 is my confidence. Through the repetition of daily tasks—such as external account reviews or outreach, and engaging with internal stakeholders—I’ve learned a lot about our product and the restaurant industry as a whole.
This confidence has led to success for the company. I’ve grown comfortable sharing feedback and suggestions with the team, some of which have resulted in new processes, talk tracks, or product offerings. On a wider scale, my self-assurance has allowed our partners to view me as a trusted adviser. With this trust, I’ve guided partners toward expanding their business with us or better optimizing what Upside has to offer. This has also resulted in countless referrals, which helps Upside grow while rewarding the referrer and referees.
What are some unique challenges of your job, and how have you overcome them?
One unique challenge is that no two Upside restaurant partners are the same. My book of business spans different cuisines across many regions of the U.S. Additionally, the decision makers owning Upside at each restaurant include different roles, from finance to marketing to operations. As a result, the headwinds that each restaurant is fighting as well as their goals and criteria for Upside vary greatly. It’s my job to curate an Upside product and experience that suits the needs of each partner.
Another challenge is that people don’t always say what they’re thinking. To combat this, I’ve learned to read between the lines and think ahead to what questions, concerns, or feedback might be on the horizon from these partners.
What do you like best about Upside’s company culture?
My favorite part of Upside’s culture is the transparency. Every Friday, Upside holds an “ask me anything” forum, where people can submit questions for our CEO. I genuinely appreciate this time because it allows all of us to keep a finger on the pulse of what’s happening within the company.
This transparency also extends to our mission: to advance the economic power of people and businesses. We don’t shy away from proving that we do exactly what we say we do—driving attributable transactions and profit to our partner businesses.
We understand you’re a mentor for new hires on the account team. What are the most important lessons you teach them?
I’ve been shaped by numerous mentors in my two years here, so it’s nice to be able to pay it forward. The most important thing I’ve taught newer account managers is to listen. Continuous selling and presenting information is a large part of our job, but a bigger, and often overlooked, part is asking good questions and listening to the responses you hear. The more we know about our accounts, the better we can serve them, and thus retain them.
How would you “sell” working at Upside to a candidate?
The aspect of working here that I love the most is the collaboration. In any given week, I work with teammates in sales, marketing, analytics, accounting, and project management. I genuinely enjoy the camaraderie that’s been built through this work over the years.
One of my favorite Peloton instructors always says, “Take the work seriously, but never yourself,” and I feel that phrase perfectly describes Upside’s employees. Upsiders are some of the smartest people I know while also being humble and helpful. I’ve learned and achieved so much during my time here while enjoying the ride—thanks to this amazing team.
As someone who works with a lot of restaurant partners, what is the most memorable meal you’ve ever had at a restaurant?
The most memorable meal I’ve had was at Roister in Chicago. It’s been a few years, but I still find myself thinking about the “Roister chicken” every so often. The restaurant is owned by chef Grant Achatz, whose restaurant Alinea has three Michelin stars, and the food was delightful.
However, what really made the evening memorable was the overall experience. I sat around the hearth and watched as the chefs prepared everything from start to finish. Being able to witness the skill and effort that went into what we ate made it all the more special.