Albert Katz went to the interview wearing his only dress shirt and a pair of glasses. He was 23, back in Miami after living in Boston, and having trouble finding a job. A recruiter had suggested a finance position. Katz went along. The other candidates, as he remembers them, came with rather more imposing credentials. Somehow, he got the job.
It is a pleasingly unceremonious beginning for a chief executive. There is no childhood declaration of destiny, no business plan rescued from a school notebook. He had wanted to program computers, then considered finance. The interview supplied a new direction. His account leaves room for chance, which is more than many polished career stories allow.
Today, Katz is the New York-based co-founder and CEO of Flagler Health. In August 2026, the company announced a $50 million Series B. Between the borrowed confidence of that interview and the financing announcement lies a career spent finding out what happens when a good idea meets somebody else’s working day.
A spreadsheet with people attached
During his years as a CFO and COO, Katz’s responsibilities reached well beyond financial reporting. He negotiated lending lines with banks, worked on acquisitions, improved accounting processes and introduced an employee benefits package. He also hired and trained administrative staff. Finance and operations shared a desk, at least in the scope of his job.
That combination matters. A financial model lets an executive arrange the business into orderly columns. Hiring asks the executive to persuade an actual person to join it. Training asks whether the organization can explain itself. A benefits package turns an expense into a decision about what working there should offer. The figures acquire names.
His earlier consulting work at CrowninShield involved statistical and financial models for securities litigation. There, analysis supported arguments about markets and losses. In an operating role, the analysis had another destination: decisions that colleagues would have to carry out. Katz had experience with both the model and the organization expected to live inside it.
An editorial reading of Katz’s move from financial analysis to operating roles and founding Flagler.
Before the title, the coffee
His first encounter with startup life came earlier. An uncle, Zoi, arranged an unpaid summer internship while Katz was still in high school. There was coffee duty, along with presentation slides and conversations about getting a product to market. He later recalled being happy there, while allowing that his contribution probably seemed larger to him than to anyone else.
The modesty makes the memory useful. A teenager can discover an appetite for a kind of work before having much ability to do it. The internship offered proximity: a chance to see people making decisions in a business that was still being formed. Katz remembered that feeling years later, when asked about his entrepreneurial beginnings.
His education eventually took him through the University of Miami, a finance master’s at Babson and an MBA at Wharton. The sequence brought business and computing into the same career. It also gave him repeated opportunities to change the question he was asking about what he wanted to build.
The classroom had a company in it
Wharton was more than a line added after his operating years. The school’s summer 2022 records place Katz at Flagler in Miami. Its 2023 placement list places him at Flagler in New York. The venture was already part of his student life, then became the work on the other side of graduation.
There is something revealing about that continuity. Business school can provide a pause between careers. In Katz’s case, the company appears on both sides of the transition. The questions of a student and the obligations of a founder overlapped. An assignment could finish; the business would still need an answer the following week.
By spring 2024, Flagler had appeared in Wharton Magazine and in the Poets&Quants selection of MBA startups. It had also been a finalist in Penn’s 2023 Venture Lab Startup Challenge. Such milestones give a young venture occasions to explain itself to people beyond its immediate circle. Explanation becomes part of the work.
The signature was only the beginning
One early lesson concerned whose approval counted. Katz has described an approach that concentrated on executive buyers and their business priorities. The daily users wanted attention too. Feedback from the people doing the work changed how the team approached the product. The purchase decision and the experience of using it were separate conversations.
For someone with his operating background, the distinction has a particular bite. Executives can make a persuasive case for a new system while employees encounter it as another thing to learn. The organization may agree on the desired result and still disagree, quietly and repeatedly, about the way to reach it.
That is where a founder’s confidence faces a useful inconvenience. The customer can be enthusiastic about the ambition and dissatisfied with the experience. Listening requires enough patience to hear both. A signed agreement may reward the sales pitch; sustained use asks the product to keep the promise after the meeting ends.
“The biggest challenge has been focus.”
Albert Katz
A longer list needs a shorter answer
By August 2025, Katz was describing focus as his biggest challenge. He acknowledged the temptation to pursue too many opportunities, with each new problem appearing urgent. His account emphasized the discipline of choosing what to decline. The ambition remained broad, but the work needed boundaries.
There is a familiar indignity in that problem. An entrepreneur spends time persuading people that a company can do something, then has to explain why it will not do every adjacent thing. The second conversation may require more conviction. A growing list of possibilities can make a small team less effective, however flattering the list looks.
Katz’s emphasis on focus gives his career a useful tension. He has worked across several functions and wants to build a broader platform. Breadth is part of the attraction. Making it workable requires decisions about sequence, attention and what can wait. The calendar has a vote, even in an ambitious company.
Who answers when he calls?
Company building also changes the relationships around the founder. SignalFire backed Flagler’s Series A and participated again in the Series B. Bessemer led the later round. The accompanying photograph of Katz beside SignalFire partner Sooah Cho puts faces to a relationship usually reduced to a line in a financing announcement.
Katz’s own description of another investor relationship is more domestic. In a testimonial for 186 Ventures, he praises the team’s willingness to answer the telephone, offer direct advice and make him feel supported. He measures their contribution through what happens when he needs them, rather than through the size of the firm.
“They pick up the phone whenever I call, shoot it to me straight, and treat me like family,” he says. The attraction is easy to understand. A founder already has plenty of conversations in which someone is selling something. An available person willing to speak plainly offers a different service.
The $50 million round brought Flagler’s announced funding to $63 million. Those figures describe capital raised by the business. The more personal part of the story sits in the working relationships: who helps make a difficult decision, who knows the context and who is still reachable after the announcement has passed.
Series B led by Bessemer Venture Partners
$63m announced total fundingThe pleasure of being outperformed
One of Katz’s more candid public moments concerns sales. Welcoming Chris Keller as Head of Revenue, he admitted that carrying sales alongside his other responsibilities had been intense. He credited Keller with bringing better results than he had managed himself. The welcome contained the unmistakable note of someone glad to put down a heavy bag.
That is a small but consequential change in a founder’s job. Early ownership can mean doing whatever the company requires. Later, ownership includes finding someone who can take a responsibility further. The founder’s competence must leave enough room for another person’s. Otherwise, every successful hire encounters the same ceiling: the chief executive’s available hours.
Katz’s account makes room for relief alongside pride. There is no need to pretend the transition is effortless to recognize its value. A company gains another leader; the founder gains time and a colleague with a different set of strengths. The work continues, with fewer tasks depending on the same pair of hands.
A flag at the end of the memo
There is another Katz to meet at the bottom of his January 2024 newsletter. After the business discussion comes a little flag trivia: South Africa’s national flag has six colors. A company update briefly becomes the sort of fact somebody might offer across a dinner table.
The detail is slight, and that is its charm. A founder’s public voice need not consist entirely of progress reports and requests. Katz leaves a little space for a reader to enjoy something with no quarterly target attached. Even the most purposeful memo can survive a momentary excursion.
His career has involved more substantial changes of direction: computing, finance, operating responsibilities, business school and founding a company. The present challenge is to let other people carry more of what he once carried. He got through the early interview with one dress shirt. Building the company now calls for a larger cast.