Leadership

Meet the Team

Co-Founder & CEO

Co-Founder & Chief Innovation Officer

Chief Operating Officer

Chief Revenue Officer

Head of People

Chief Product Officer

How Did Chowly Become The Leader In Digital Ordering Integration?

Sterling Douglass

Co-Founder & CEO

Co-Founder & CEO, Sterling has extensive experience as an entrepreneur, leading start-ups and building solutions for long-standing unsolved problems.

Sterling began his career in data analytics as an actuary in management consulting. His experience in data and client relationships, coupled with his passion for entrepreneurship in the hospitality industry, led him to establish Chowly. Today restaurants use Chowly’s POS integration with practically any digital order platform system to increase revenue, improve operational flow, and save on labor costs.

Sterling currently serves on the President’s Club of FSTEC, Advisory Council of RTN, Venture Partner at Emerging Venture Capital, and is an active angel investor in early-stage restaurant technology startups. He’s also co-hosted and frequently appears on the Hospitality Hangout, Tech Chef, and Kitchen Obsessed podcasts. And was recently named one of QSR Magazine’s “21 Digital Disruptors Shaping Restaurants in 2022.”

In his spare time, you can catch Sterling hiking 14ers in Colorado, snowboarding with his wife Lea, and obsessing over the Chicago Bears.

Fun Fact: I’ve won over a dozen eating competitions/challenges.

Favorite Delivery: Ice Cream

Justin mcNally

Co-Founder & Chief Innovation Officer

Justin is a builder of 3rd wave restaurant technology. Fighting for a connected world where the exchange of information is ubiquitous and effortless, Justin is a strong believer in the seamless exchange of information between systems and without interface. He is driven to create a world where only your profile and preferences are needed to interact with anything, anywhere. 

With a BLA focused on Interactive Arts & Media from Columbia College Chicago, Justin is an experienced founder and entrepreneur with a demonstrated history of working in marketing and advertising. He is skilled in Digital Strategy, PHP, WordPress, Ruby on Rails, and Content Management Systems (CMS). 

When not driving innovation at Chowly, Justin loves traveling with his wife Caitlin and their two awesome girls, Maddison and Max. He also volunteers for Sleep in Heavenly Peace, building, delivering and assembling beds for children in need. 

Fun Fact: I strongly believe in the future of cryptocurrency.

Favorite Delivery: I still can’t decide.

Joseph Lawton

Chief Operating Officer

Joe was Chowly’s first hire in 2016 and as COO leads multiple departments including activations, retention, and support. With a passion for building efficiency, Joe brings a customer-first mindset to everything Chowly does and led the iterative process to create the efficient, scalable model on which Chowly clients rely. 

A foodie himself, he enjoys patronizing local cuisines wherever he’s traveling and is always interested in new and exciting technology in the space. Outside of restaurants or technology he loves DIY projects, golfing, and spending time with his wife and two daughters.

Fun Fact: I’ve aged my own whisky (it was terrible).

Favorite Delivery: Thai

Tom Lawton

Chief Revenue Officer

Tom is a servant leader that quickly adapts to change. He claims that self-education and a “never stop learning” mindset has continuously helped him take the next step in his career — and we’re happy that was Chowly. He has the creative mindset that allows him to share ideas and visions to help take Chowly to the next level.

Tom is passionate about helping others succeed, while helping Chowly grow its revenue through sales and retention. Never settling for less than greatness in all that he does, he naturally develops leaders and provides the utmost empathy, care, and support to all those around him. 

Tom resides in the suburbs of Chicago with his wife and two daughters. You’ll find him spending his spare time with family, grilling on his smoker, golfing, and watching the Packers and Cubs. Tom is also an active member of Pavillion, a community-powered learning platform for executives in technology and SaaS.

Fun Fact: I’m better at golf than Sterling.

Favorite Delivery: Pizza – Lou Malnati’s THIN crust

Jessica Warren

Head of People

Jessica is a People Ops Leader with a Vision for Talent and Culture and brings over a decade of expertise in shaping and optimizing human resources strategies within the dynamic realms of advertising and technology. With a career that kicked off in 2010, she has been at the forefront of transforming organizations by strategically aligning talent acquisition and HR initiatives.

In her spare time, Jessica spends time playing video games, traveling, or just hanging out with friends and family in NYC and “upstate” New York in the Hudson Valley.

Fun Fact: I have the privilege of being able to hang out with, and touch, two very important trophies in the sporting world: The U.S. Open Trophy and the Stanley Cup.

Favorite Delivery: Thai Food

Michael Fineberg

Chief Product Officer

An accomplished executive and transformational leader, Michael has championed technology innovation centered on the customer for world-class companies — like Chowly! He has extensive experience leading strategy and execution across high-performing engineering, product development, and data teams.

Michael’s broad success across core functions bridge the gaps between customers, strategy, technology, support, and security. He is recognized for revolutionizing technology with innovative simplicity that delights customers, transforms businesses, and drives unprecedented profitable growth.

In his spare time, Michael spends time with his wife and two daughters and is both a fanatical reader and an avid sports fan (cheering on the St. Louis Cardinals, Northwestern Wildcats, or Chicago bulls, depending on the season). He also claims to be a budding whiskey aficionado. 

Fun Fact: I share a birthday with Reggie Jackson and Pope John Paul II.

Favorite Delivery: Pizza