A construction worker can start the morning on one project, cross into another jurisdiction after lunch, and finish the day with a paycheck governed by a different rate, trade classification, union agreement, and tax rule. To a horizontal payroll system, this looks like a collection of irritating exceptions. To Anna Berger, it looks like the product.
Berger is the founder and CEO of Trayd, the New York company building payroll, HR, compliance, scheduling, field tracking, and job costing software for specialty contractors. It is an unshowy corner of technology, which is another way of saying that errors have consequences. A missed rate or deduction can travel from the time card to the paycheck, the certified report, and the project margin before anyone spots it.
The idea is personal without being sentimental. Berger grew up in a construction family. She watched her father handle the repetitive choreography of the back office, where paper and spreadsheets absorbed hours that could have gone toward the business itself. More than two decades later, she found the choreography largely intact. The buildings had changed. The software around the people building them had not changed nearly enough.
01 / The useful detourBefore payroll, there were people
Berger did not take the usual route into enterprise software. At the University of Michigan, she studied psychology and completed a minor in writing. She later spent two and a half years in creative advertising before joining Marriott International's global paid-media strategy and planning team. The work sharpened a skill that would matter later: turning a complicated thing into a clear reason to care.
Her first startup began with the familiar misery of a disappointing New York date. Berger and Brenden Simkhai-Strauss wondered whether short-form video could help people understand whom they were about to meet. They began building Curtn while Berger still worked at Marriott, handing nights and weekends to the idea before she moved to it full time. The dating app won backing from Sam Altman and Grindr founder Joel Simkhai.
Then the large dating platforms learned video. Berger moved to Motto, Simkhai's next app, as a founding team member leading growth and marketing. She describes Simkhai as a close confidant who taught her the discipline of details: a large company is built by caring about the small things, particularly at the beginning. Curtn also left a second lesson. When other people say stop, listen closely, then decide whether they are right.
“Believe the no, don't believe the why.”
Anna Berger on hearing investor feedback without surrendering judgment
This is the hinge in Berger's story. Consumer apps taught her speed, positioning, and the discomfort of incumbents entering the room. Construction offered a different kind of problem: old, specific, and stubbornly attached to the industry's daily operation. The opportunity was not waiting in a pitch deck. It had been sitting in the family business all along.
02 / The partnershipA friendship with complementary edges
Berger built Trayd with Cara Kessler, a longtime friend whose career included a decade leading web-platform engineering at LinkedIn. Their abilities meet neatly at the problem. Berger knows growth, brand, sales, and the construction family's view from inside the paperwork. Kessler knows how to turn tangled rules into dependable systems. Berger has written that people should seek collaborators who fill their blind spots. Trayd makes the advice concrete.
They began with a promise that construction workers should be able to reach earned money sooner and subcontractors should be able to run payroll without chaos. That required connecting field attendance to the payroll engine. The company expanded from there because the workflow itself kept going: onboarding determines a worker's classifications; scheduling places that worker on a job; time tracking records the hours; payroll applies the rules; compliance proves what happened; job costing tells the contractor whether the work made money.
One shift, four moving variables
Conceptual map, not a wage calculation. Each variable can change the final check.
A worker can earn four rates in a single day depending on the site, classification, union status, and jurisdiction. Public projects add prevailing-wage obligations. Crews crossing state lines add tax and filing requirements. Collective bargaining agreements add deductions and benefit funds. Most software tries to simplify by shaving off the edges. Trayd's wager is that the edges are the business.
03 / The sale before the saleKeep an ear in the field
From Trayd's first day, Berger led sales. Even as the CEO role accumulated its usual collection of unrelated duties, she wanted the customer conversations for herself. It was not merely a go-to-market decision. Every demonstration was product research. Every objection was a map of the contractor's actual day. She stayed on the front line until the company was ready to hire its first account executive.
This helps explain the language she uses. Berger talks about vacation, not only efficiency. When payroll depends on one administrator's memory and an on-premise system, that person becomes the system. Time saved matters; a back-office employee finally being able to step away matters more. The product promise becomes less abstract when measured in a Friday afternoon returned to someone who used to spend it correcting time cards.
“Get close to your customers. Listen closely and build something they actually need.”
Berger's advice to companies building without fresh capital
That closeness also disciplined the company's market choice. Construction technology has often been sold to general contractors with larger budgets and purchasing departments. Specialty contractors outnumber general contractors by roughly 400 to one, yet the electricians, plumbers, ironworkers, concrete crews, and carpenters deploying labor have received less software attention. Trayd chose them, starting in New York and the Northeast, where union density and regulatory complexity give any payroll engine a vigorous examination.
04 / The stubborn middleOne more pitch
Berger first pitched Trayd in January 2023. The fundraising climate was poor, and rejection accumulated. When Trayd entered Y Combinator's Summer 2023 batch, Berger announced the news with the relief of someone who remembered every closed door. By the end of that year, the company had completed the program, closed a seed round, onboarded its first customers, and started assembling an in-person New York team.
Berger works on global paid-media strategy at Marriott while her first startup takes shape.
Curtn gives way to a role on Motto's founding team and a second look at construction's old paperwork.
Berger and Kessler take Trayd through Y Combinator.
A $4.5 million seed round supports growth across payroll and compliance.
Trayd raises a $10 million Series A and prepares for national expansion.
The Series A came together in three weeks. White Star Capital led the $10 million round; Suffolk Technologies and Y Combinator returned, while New York real-estate and technology investor RXR joined. Trayd reported $15 million in total funding and 600 percent year-over-year revenue growth. The capital is earmarked for national expansion and deeper work across union workflows, compliance, and job costing.
Funding is a milestone, not the story's resolution. Payroll is a weekly referendum. It has to be right again and again, under new agreements, new states, new projects, and new crew configurations. Berger once named consistency as the essential quality in her field. It builds trust, protects compliance, and keeps work moving. In a startup culture fond of the dramatic launch, she has chosen a business judged by its Tuesdays.
05 / The city and the systemBuilding out loud in New York
Berger is emphatic about New York. It is the city where she grew up, the place where she wanted to build, and a market whose energy matches the work. The location is also practical. Construction is visible on nearly every block, while the paperwork remains hidden in offices, trucks, binders, text threads, and the heads of experienced administrators.
She wants Trayd to become the system of record for that hidden operation, the infrastructure layer under payroll, compliance, and workforce management. The ambition is expansive, but the method remains narrow: understand the customer, encode the rule, remove the duplicate entry, and prove the numbers. Before artificial intelligence can interpret construction data, Berger argues, the underlying systems must exist. Someone must first turn the clipboard into a reliable record.
Her route to this point looks less like a pivot than a gathering of materials. Psychology supplied curiosity about people. Writing and advertising supplied clarity. Marriott supplied organizational scale. Curtn supplied scar tissue. Motto supplied precision. Her father supplied the original view of an industry carrying too much administrative weight. Kessler supplied a different set of eyes.
The result is software for a trade in which exceptions are normal and boring is a compliment. Berger is not trying to make payroll thrilling. She is trying to make it disappear into the ordinary confidence of a correct check, a clean report, and an office that can go home on time. Infrastructure rarely asks for applause. It simply has to hold.