Jess Levin Conroy and the business behind the beautiful wedding

Jess Levin Conroy sometimes arrives at a hotel and pretends she has no wallet. She wants to see how the staff will handle payment. Her husband, she has said, has stopped standing beside her at check-in. One can sympathize. A holiday ought to begin with a room key, rather than an examination of the hotel’s administrative arrangements.

The exercise fits a career spent looking behind attractive surfaces. Conroy founded Carats & Cake, where wedding photographs connect couples with the businesses that made the celebration. Today she leads ROH, a financial infrastructure company for hotels. Follow her from one business to the other and a question keeps appearing: what does it take to make the lovely thing actually work?

An advice meeting with consequences

Before there were wedding vendors or hotel finance teams, there was retail. After the University of Pennsylvania, Conroy entered Lord & Taylor’s training program. She liked fashion and wanted to understand its commercial machinery. The large-store environment proved a poor fit, so she sought advice about where else she might belong.

A conversation with Chris Burch became a job interview. At Burch Creative Capital, she progressed from analyst to associate. The attraction was proximity: she could watch entrepreneurs turn their ideas into businesses. Burch also encouraged her to consider building something herself. In her telling, the suggestion initially felt like criticism. Eventually she heard encouragement in it.

There is a pleasing awkwardness to this part of her story. The future founder did not immediately recognize herself in someone else’s assessment. She needed time to work out what it meant. An invitation to become independent can sound remarkably like being told to leave.

Conroy’s next move was toward a classroom. At NYU Stern she concentrated on finance and accounting. She wanted to participate intelligently in decisions about money, rather than sit through them without understanding the terms. “I am a big believer in building a strong foundation,” she said. Entrepreneurship would require enough fluency to know which questions to ask.

The sequence suggests an appetite for understanding the business beneath the product. Fashion brought her into retail and investment work. A desire to understand investment work brought her to school. Weddings would soon give her somewhere to apply that education. Each move added another piece to the same practical curiosity.

Who made the wedding?

The wedding idea began during a business-school discussion of De Beers. Diamonds led her attention toward engagement rings and then the industry around getting married. It is an unusually appropriate origin for a wedding company: a student thinking about a diamond business discovers an opportunity several purchases further down the aisle.

Conroy investigated the market and the difficulties couples encountered. Her earlier work with luxury brands had given her a way to think about an aspirational customer. But the opportunity she described centered on the local businesses producing the celebration: photographers, florists, caterers and planners.

Consider the difference between admiring a picture and commissioning what it shows. A photograph gives you an effect. Planning requires names, locations, availability and people who can produce that effect under the conditions of your own event. The connection between those two activities was the useful territory for Carats & Cake.

By October 2013, Conroy described the site as featuring roughly 30 weddings a week across more than 35 cities. The early business already had a geographical dimension. Wedding inspiration travels easily; the people doing the work still have to be found.

That makes the photograph more than decoration. It becomes a way into someone’s portfolio and reputation. A couple can begin with a scene they like and move toward the professionals responsible for it. For the vendor, the same scene can introduce the work to a prospective customer.

Conroy could also enjoy the scene on its own terms. She liked transformable wedding dresses and defended the place of dessert at the end of an evening. A cheese tower might have its charms, but it ought to leave room for something sweet. There is room in a business plan for cake.

A notebook, and a willingness to listen

A friend and mentor gave Conroy a notebook labeled “Big Ideas” around the time she entered business school. She reserved it for substantial goals, including fundraising and user milestones. As those goals came to pass, the book acquired the status of a good-luck charm. A spreadsheet may do the arithmetic, but it seldom inspires affection.

The notebook offers a small counterweight to the scale of running a company. A goal can be written down, considered and returned to. It has a place to live before it has a place in the world. Conroy’s account makes ambition seem like an ongoing practice, with pages available for whatever comes next.

She also describes learning through conversation. As the wedding platform grew, customer behavior became a guide to what the team should build. “Their needs inform what we build next,” she said. The statement gives the people using the product a continuing role in its direction.

In 2019, she described becoming a more attentive listener, trying to understand the meaning behind people’s words. Rejection was part of that education. The useful task was to find information inside the resistance. Saying no to a proposal and explaining a recurring difficulty can happen in the same conversation.

When she felt lost with the business, she reached out to mentors and owners she admired. Asking for advice had survived the transition from employee to founder. Her reading included Phil Knight’s Shoe Dog. She had little interest in erasing every early mistake: “We wouldn’t be where we are without the mistakes we made.”

“We wouldn’t be where we are without the mistakes we made.”Jess Levin Conroy, 2019

The invoice after the party

Over time, the work took her further into the operations of hospitality businesses. The distinction matters. Finding a customer creates an opportunity; processing the resulting business requires another set of tasks. Someone has to keep agreements, invoices and payments connected as the booking develops.

In a later account of ROH’s origins, Conroy described seeing innovation concentrated on bringing revenue into hotels. More signed contracts could also mean more staff time spent supporting them. Growth carried additional administrative work. That was where she saw an opening.

It is easy to understand why that problem might attract someone with her background. Carats & Cake had put her in contact with the businesses delivering events. Her business-school education had made the numbers less mysterious. The next questions concerned what happened once the customer was ready to buy.

On February 1, 2023, she announced ROH. The name, pronounced “row,” draws on the hospitality term “Run of House.” Carats & Cake became a sub-brand, continuing as a wedding community and marketing channel. The original business remained part of the story while the parent name made room for a broader hotel audience.

The relationship explains the change more clearly than a simple label such as wedding founder or fintech founder. Her work had moved through discovery into sales and finance. ROH gave that expanding scope a name. The people at the hotel, as much as the couple planning the event, now occupied the center of the product discussion.

A larger room to work in

In April 2025, ROH announced $9.2 million in new financing led by Highgate Technology Ventures and Acrew Capital. The investment accompanied an expansion of its commercial relationship with Highgate. Properties in the hotel group had piloted the platform before the wider commitment.

The company said it had managed nearly a quarter of a billion dollars in invoices during 2024. That figure describes invoices managed, rather than company revenue. Keeping the distinction clear matters in a business built around other people’s money. The scale of activity and the economics of the provider answer different questions.

Her attention had moved into hotels with varied stakeholders and varied revenue streams. In August 2025, she identified integrations as a focus: information needed to move between ROH and the systems hotels already used. Existing tools and existing habits were part of the environment she had to serve.

Partnerships widened the potential audience. Small Luxury Hotels of the World named ROH its preferred payments management platform in 2025. Preferred Hotels & Resorts added it to its Alliance Partner Program in March 2026. These relationships placed the product in a wider international hospitality conversation.

Then, in September 2026, ROH announced a strategic advisory board. Its first members were Alex Cabañas, Sloan Dean and Pavan Kapur, bringing experience in hotel ownership, management and commercial strategy. Conroy described wanting their perspectives to sharpen product decisions and the company’s approach to the market.

That decision has an echo in the advice meeting near the start of her career. Experience is something she continues to seek in other people. The circle has changed in size and composition; the willingness to ask remains recognizable. A founder can retain responsibility while inviting someone else to complicate her thinking.

What the guest should notice

The interesting measure of such a business may be how little of it a guest has to think about. A hotel stay comes with enough decisions already. People generally prefer to spend their attention on the trip, the company and the room, rather than the progress of an invoice through several departments.

Conroy’s stated ambition is financial visibility for every dollar entering and leaving a hotel. For the people behind the desk, that is a considerable undertaking. For the person approaching it with a suitcase, a good outcome could look pleasantly ordinary: a payment understood, a confirmation received, an employee available to help.

Her two business chapters share that human scale. A wedding photograph points toward the florist who made the arrangement. A hotel payment points toward the people who must account for it. The polished result depends on work that can disappear from view when it is done well.

The founder, meanwhile, continues to make a habit of looking. At a wedding, behind the picture. At a hotel, behind the transaction. Her husband may have found a sensible place to wait while she checks in. Conroy has found another question worth staying at the desk to ask.