Shirley Romig has funded founders from both sides of the table

Most careers pick a lane and stay in it. Shirley Romig picked five. She sold luxury retail at Saks, moved rides across cities at Lyft, ran clubs at Equinox, built a food app of her own, and now writes some of the earliest checks in venture at Techstars. If you drew her resume as a map, it would not be a ladder. It would be a web.

That web is the interesting part. The stops look unrelated until you notice what carries between them: the discipline of making a big, messy operation actually run. Romig is an operator first. Titles changed, industries changed, but the job underneath stayed the same - take something complicated and make it move.

Today she is Chief Operating Officer at Techstars, the global pre-seed accelerator, a role she stepped into after joining in November 2023 as Chief Accelerator Investment Officer. Her portfolio, in effect, is founders - who gets selected, who gets funded, who gets mentored, and how the whole global network holds together. It is a job about early-stage chaos. She got to it by way of some of the least chaotic, most operationally demanding rooms in American business.

01 / The through-lineThe operator who kept changing the game

Romig learned commerce early and formally. She earned a Bachelor of Science in Commerce from the University of Virginia, then an MBA from UVA's Darden School of Business. Two degrees, one campus, and a foundation that pointed her at the retail industry, where she started in corporate strategy.

By 2013 she was Senior Vice President of Corporate Strategy at Hudson's Bay Company, responsible for growth initiatives across Saks Fifth Avenue, Saks OFF 5th, Lord & Taylor and Hudson's Bay in Canada. This was the era when department stores were being asked to become internet companies, and most of them fumbled it. Romig led the omnichannel transformation across Saks.com and helped launch Saksoff5th.com - the kind of work that never trends but decides whether a legacy brand survives the decade.

"Believe in yourself, you can do anything if you put your mind to it."

From retail she moved to the agency side as Head of Retail Strategy at SapientRazorfish, then to fitness as a Group Vice President at Equinox, where she led six lines of business and thousands of field and corporate staff. In 2019 she jumped again, this time into the gig economy, joining Lyft as a Vice President leading Global Operations for the East and Canada and sitting on the senior leadership team.

Read those jumps quickly and they look restless. Read them slowly and a pattern shows up: each move was a bet on range over the ladder. Retail to agency to fitness to rideshare is not a promotion sequence. It is a curriculum.

There is a specific kind of executive who thrives on this. Not the specialist who spends a career going deeper into one function, but the generalist who keeps asking to be dropped into a system she does not yet understand and given a mandate to fix it. At Saks she was learning how a legacy brand converts foot traffic into digital revenue. At Equinox she was learning how a premium service scales across physical locations without diluting the thing that makes it premium. At Lyft she was learning how a marketplace balances supply and demand across cities in real time. Three different businesses, three different unit economics, one operator repeatedly starting over.

That willingness to start over is rarer than it sounds. Most careers reward accumulation - you get promoted for going deeper into what you already know. Romig kept trading depth for a fresh set of problems, and the compounding happened sideways. By the time she reached venture, she was not an expert in any single industry. She was an expert in the shape of the problem that every scaling company eventually hits.

02 / The founder detourWhy she left a VP seat to build a food app

In 2022 Romig did the thing most senior executives only talk about at dinner. She left. Out of Lyft and into a blank page, co-founding and running Mixo, a video platform built to let food creators reach a global audience. The pitch was ambitious in a way that had nothing to do with food and everything to do with connection: use the universal language of a shared meal to make social media feel a little more positive, especially for the next generation.

Mixo did not become a household name. But asking whether it "worked" misses what the detour did for her. For the first time in a long career, Romig was the one sweating the payroll, the one whose idea might break her. That experience is not on the org chart at Techstars, yet it is arguably her most relevant credential there. Founders can smell whether an investor has actually been in the chair.

That phrase - strong convictions, loosely held - is the cleanest summary of how she talks about building. Most founders get it backwards, falling in love with the plan and abandoning the vision the first hard week. Romig's version keeps the ambition fixed and everything else negotiable.

The detour also reframes how she reads a pitch. An operator who has only ever worked inside funded, staffed, running companies tends to evaluate founders on polish - the deck, the market size, the clean answer to the hard question. Someone who has actually tried to summon a company out of nothing evaluates them on something closer to grit. Can this person hold a vision through the stretch where nothing is working and the spreadsheet says stop? Romig has been in that stretch. It changes what she looks for.

03 / The Techstars jobPicking founders, not logos

At Techstars, Romig oversees the selection, funding and mentoring of entrepreneurs globally, along with the accelerator's network partners and ecosystem development. It is a role that sits at the exact intersection of her two lives: the large-scale operator who knows how systems scale, and the founder who knows how lonely week one feels.

The logo on the batch doesn't build your company. The people in it do.

Her advice to founders chasing accelerators is refreshingly unglamorous. Stop optimizing for the brand, she suggests, and start interrogating the fundamentals: How big is the class? Who are the mentors, really? Does the program fit your industry? The prestige of the batch is a vanity metric. The quality of the people who pick up the phone at 11pm is the actual product.

She holds two clocks at once. On one side, she chairs the Nominating & Governance Committee on the public board of Lovesac, the omnichannel home furnishings company, and sits on the board of Mama's Creations - worlds that move in quarters and proxy statements. On the other, she funds pre-seed founders whose entire runway can shift in a week. The skill is not being good at one. It is holding both timescales in your head without losing your mind.

That double vision is quietly useful to the founders she backs. A first-time founder often cannot picture the company they are trying to build - the governance, the operating cadence, the way a business behaves once it has thousands of employees and a fiduciary board. Romig has stood in that future. When she mentors, she is not guessing at what scale looks like; she has run the clubs, the operations and the omnichannel rollout, and she has sat on the board watching a public company answer to its shareholders. She can draw a line from a pre-seed pitch to the far end of the map because she has walked the whole thing.

04 / Off the clockThe games she's happy to lose

Romig lives in New York. Away from the accelerator, she is an aspiring tennis player, a fitness enthusiast, and by her own description a novice at chess. There is a small tell in that list. These are all games she is willing to be bad at.

People who keep playing games they have not yet mastered are the people who keep learning. It is the same instinct that moved her from retail to rideshare to founder to funder without ever pretending she had it all figured out. The beginner's seat is uncomfortable. She seems to like it there.

Her ambitions outside the office run in the same direction as the ones inside it. Part of the reason she built a platform around food and creators was a wish to nudge social media somewhere more positive, particularly for her children's generation - to make the feed feel less like a fight and more like a shared table. It is an unusually earnest goal for a career operator, and it says something about what motivates her underneath the org charts and the board seats. She is trying to build things that leave the room better than she found it.

Range compounds. Titles don't.

Put the pieces together and Romig is easy to describe and hard to box in. She is the operator who learned to fund. The executive who went and got her hands dirty as a founder so she would understand the people she now backs. In an industry that loves a clean narrative arc, her value is precisely that hers isn't clean. It is wide.