The photograph is pure startup theater: a tall orange billboard turning the corner above Times Square, PARO in enormous letters, $25 million in smaller ones, Nasdaq's congratulations floating over the cabs. Anita Samojednik posted it after the finance marketplace closed its Series C in 2023. Then, with the efficiency of someone who has spent a career clearing queues, she moved directly to the work ahead - enterprise customers, product development, better tools for independent finance professionals.
The billboard made the round visible. The more revealing part was the redirect. Samojednik is an operator, a species of executive less interested in the ribbon than the mechanism behind it. Across more than two decades, her jobs have changed industries and continents, but the assignment has remained oddly stable: take a complicated service, find the brittle handoffs, and build a system that can carry more weight without losing the customer inside it.
At Paro, where she became CEO in January 2021, that customer may be a company hunting for a fractional CFO or an accountant building an independent practice. The system between them now includes machine learning, forecasting tools, and AI agents. Samojednik's argument is not that software has made expert judgment quaint. It is that judgment is scarce, and much of the work surrounding it is needlessly slow.
“Most companies don't have an analysis problem. They have a decision-making problem.”Anita Samojednik, 2026
The education of an operator
Long before the CFO marketplace, there were phones, vendors, and customers who wanted answers. At Vonage in the mid-2000s, Samojednik led outsourcing as the internet-phone company grew rapidly. A vendor who worked with her later remembered a hands-on leader and strong negotiator who personally selected and developed the vendor-management team. It is the sort of recommendation that tells you more than “visionary” ever could: she knew the system closely enough to choose who would run it.
A stint in United Nations procurement followed. Then came Ladders, the online career platform, where she led customer operations as the job market convulsed after the financial crisis. The service team was recast as job-search agents who could do more than process complaints. In 2012, she chaired the customer-service final judging committee for the American Business Awards. Customer support had become an operating discipline, not a room where problems went to wait.
The Samojednik operator loop
Groupon offered the same puzzle at a more theatrical scale. Samojednik moved through international customer service, outsourcing, and global operations before becoming president of Groupon International in 2018. She was running a two-sided marketplace across countries, balancing merchants and customers while technology, local habits, and service teams collided in real time. Her public recipe for contact centers came down to three words: teams, technology, trust.
That trio could double as a blueprint for Paro. A marketplace cannot treat either side as inventory. The experts can leave. The clients can leave. A technically correct match that arrives late, misunderstands the industry, or produces a poor working relationship is still wrong. Trust is the product hiding underneath the platform.
The chief executive who came after chapter one
Samojednik did not found Paro. Michael Burdick and Dan Wywrot started the company in 2015 after deciding that traditional accounting firms were too rigid about which projects professionals could choose and how they could work. Samojednik entered the story first as an adviser, joined as chief operating officer in September 2020, and moved into the CEO job four months later. Burdick became chief strategy officer.
There is an underwritten kind of leadership in that sequence. Founders get the origin myth; the incoming operator gets the inheritance tax. She must preserve what attracted people, discard what cannot scale, and explain the next version without insulting the first. At Paro, the founding promise was professional autonomy. Samojednik's task was to turn that promise into a larger and more predictable marketplace.
Her timing was unusually good and unusually difficult. Remote work had just completed a forced global demonstration. Companies learned that complicated finance projects - ERP implementations, fundraising support, even transaction work - could happen outside an office. Professionals learned they could ask for more control over their time. Samojednik called remote work a “democratization of talent and opportunity,” and argued that geography should stop deciding who gets access to a job or an expert.
The model promised specificity. When describing Paro's matching engine, Samojednik imagined a company needing a Mandarin-speaking CFO with experience expanding e-commerce in Asia-Pacific. Traditional recruiting might call that a brutal search. A focused marketplace sees a set of attributes. The romantic phrase is “needle in a haystack.” The operator's phrase is “structured data.”
Led by Top Tier Capital Partners, with returning investors including Madrona, Revolution, and Sierra Ventures, the 2023 round brought Paro's reported funding to $67 million. Samojednik described it as an up-round with clean terms, a notable detail in a difficult fundraising year. Paro said its revenue had tripled since the 2021 Series B and its average client spend had doubled. The money was earmarked for the platform, enterprise expansion, and research and development.
Software clears the desk
Paro's early technological claim was better matching. By late 2024, Samojednik was describing a wider system: workflow automation for independent professionals, predictive tools for businesses, and software to help allocate talent and shape marketplace supply. The company reported a 95 percent first-match success rate and forecasting accuracy of 97 percent. Those are Paro's own figures, useful as a statement of managerial intent: every fuzzy marketplace problem should eventually acquire a metric.
In December 2025, Paro took the next step and launched two AI agents. One analyzes a business's financial health, benchmarking statements and surfacing vulnerabilities. The other looks for business tax-minimization opportunities, with recommendations reviewed by licensed CPAs. The company presented the combination as an “Intelligent Work Ecosystem,” an ungainly phrase for a sensible arrangement: machines do the first pass; people remain answerable for the consequential pass.
Use software to gather, rank, draft, remind, and flag. Use experienced professionals to add context, challenge the output, and turn it into a decision.
Samojednik's recent writing sharpens the point. She has argued that the largest gains may come not from automating expertise but from reducing the operational drag around it. Paro introduced AI-assisted project management that surfaces follow-ups from client conversations, adapts workflows, and flags risks. Early users, she wrote, reported spending 60 to 70 percent less time on project administration. The claim is more interesting than another chatbot because administration is where highly paid judgment goes to die by a thousand reminders.
This is also where her customer-operations past becomes useful. Every executive can say “human in the loop.” Someone who has run contact centers knows the loop has a queue, a handoff, an escalation rule, and a customer becoming less patient by the minute. The question is not whether a human appears somewhere in a product diagram. It is whether the system brings the right problem to the right human while there is still time to improve the outcome.
AI can accelerate the analysis. Accountability still has a human address.The operating idea behind Paro's latest chapter
Freedom with a back office
The other half of Paro's design faces the experts. Independent finance professionals may want autonomy, but autonomy arrives with sales, scheduling, pricing, client management, and collection. A marketplace that merely finds a gig has solved one moment. Samojednik talks about helping experts grow a book of business and optimize earnings. In that sense, Paro is trying to become the back office for people who are the back office for everyone else.
That ambition contains a productive tension. Businesses want flexibility because variable capacity is efficient. Professionals want flexibility because control over work is valuable. Those motives overlap, but they are not identical. The marketplace earns its keep by making the overlap durable - enough quality for the client, enough agency and repeat business for the expert, enough information for both to choose well.
Samojednik's connection to Columbia Business School offers a quieter parallel. She earned her MBA there in 2008 and has served since 2018 on the advisory board of its W. Edwards Deming Center, devoted to operational excellence. Deming's field is the unglamorous art of designing quality into a system. Samojednik's career has been a tour of systems that cannot afford to regard quality as a final inspection: customer care, e-commerce, talent matching, and now financial decisions assisted by AI.
The Times Square screen has long since changed advertisements. The harder work continues at ordinary scale: a follow-up surfaced before it is forgotten, a specialist found without a month of searching, a model challenged before it becomes a board recommendation. Samojednik's bet is that technology can make expertise more available by wasting less of it. The algorithm gets faster. The accountant gets the question sooner. And the final decision still belongs to someone who has to live with the answer.