Lossdog, the new fintech platform from thinkorswim and tastytrade co-founders Tom Sosnoff and Scott Sheridan, launched in April 2026 with a pointed argument: the best defense against AI job disruption is knowing exactly what you are worth before your employer's AI model, and HR, decides for you.
The Numbers Behind the Anxiety
Something measurable is happening to white-collar compensation. Professionals who have built AI-related skills into their work are now earning 56% more than peers in equivalent positions without those skills, according to the AI Wage Gap Q1 2026 Report. The professionals without those skills are not simply earning less. Their wages are being actively suppressed, their junior hiring pipelines are shrinking, and their employers are using increasingly sophisticated tools to model and manage compensation with a precision that workers cannot match.
The productivity-compensation gap has been widening for decades, but AI is accelerating it. Between 1979 and 2019, productivity grew 59.7% while worker compensation grew just 15.8% — a 44% divergence that compounds across a career into real money. Lossdog's foundational research puts a figure on it: a professional earning $75,000 today will leave roughly $3.9 million in nominal earnings on the table over 30 years, not because of poor performance, but because of structural market forces that have always favored the employer's side of the negotiating table.
AI is adding a new layer to those forces. Employers now use AI-powered HR systems to benchmark compensation against real-time labor market data, model attrition risk, and price individual employees with a precision that Glassdoor salary ranges and LinkedIn guesses cannot touch.
"For decades, productivity gains have not flowed proportionally to the professionals creating that value," Sosnoff said at Lossdog's launch. "Lossdog isn't about what someone deserves; it's about fairness and structural market dynamics that prevent talent from being priced competitively."
The workers who are more exposed are not, counterintuitively, the least educated. Research from the University of Pennsylvania found that educated white-collar workers earning up to $80,000 face the highest automation exposure. A Master's degree now commands a 13% wage premium in the labor market. AI skills command 23%. The credential that took years to earn is already being outpaced by the skill that most employers added to their job descriptions within the last two years.
The Platform Built to Fight Back
Lossdog's response to this moment is a product with deliberate simplicity. Upload a resume. The platform's AI reads it against real government wage records and returns a single precise figure representing what that professional is worth in their specific market, right now. The platform then identifies what is suppressing that number and maps a roadmap to close the gap.
The distinction between a range and a number matters more in a disrupted market than it ever did in a stable one. When AI is actively recalculating compensation benchmarks across industries faster than any individual can track, a static salary range drawn from last year's crowdsourced survey data is an imprecise negotiating tool. Lossdog's use of current government wage records means the figure it returns reflects the market as it actually stands, not as it stood when a peer submitted a salary report eighteen months ago.
"There are two numbers which invariably determine an individual's financial fate, their professional compensation and the performance of their investments", Sosnoff said. "Those are the numbers our platform is focused on."
The platform pairs the salary tool with a portfolio optimization layer that returns four specific outputs: an industry baseline return, a current expected return, a real-time strategic progress grade, and the lifetime dollar value of the gap between what the portfolio is producing and what it should be. The connection between the two tools is deliberate. A professional whose salary trajectory is being reset by AI disruption faces compounding consequences: not just lower earnings, but a retirement savings gap that grows wider the longer the salary problem goes unaddressed. Lossdog treats both as one problem, measured in one place.
Why These Founders, Why Now
Tom Sosnoff has been in this position before — on the wrong side of an information gap so wide it determined financial outcomes. He spent two decades as a CBOE options floor trader, watching retail investors make decisions with instruments they could barely price, against institutional desks operating with analytical tools those investors could not access. His answer in 1999 was thinkorswim, which gave retail traders professional-grade options analytics for the first time. TD Ameritrade paid approximately $750 million for what he and Scott Sheridan built. The two then co-founded tastytrade, bringing the same data-first philosophy to financial education and low-cost brokerage, and sold it to IG Group for $1.1 billion in 2021.
The structural parallel between 1999 and 2026 is not subtle. Then, institutional desks had pricing models and risk analytics that retail traders could not use. Now, employers have AI-powered compensation modeling tools that workers cannot match. The information asymmetry driving financial disadvantage has simply moved from the trading floor to the salary negotiation. Sosnoff's response has not changed: build a platform that closes the gap.
Lossdog currently serves users in the United States with a $100-per-year subscription and is offering free first-year access to the first 50,000 registrants, along with a share of a $1 million cryptocurrency pool. More than 10,000 of those slots have already been claimed. The pace reflects that workers signing up are not simply chasing free crypto. They are responding to a specific anxiety — the growing sense that the market has always known their number, and that they have been the last to find out.
