Jim Freeman, ex-Amazon Prime Video VP, joins Ticketmaster as CTO to lead 'AI-first' push. October 20, 2026 Ticketmaster has appointed former Amazon executive Jim Freeman as its Chief Technology Officer. The Live Nation-owned company has also hired Rachel Smith from Block as its first SVP of Data Science and Machine Learning, and ex-Disney executive Chuck Mortimore as SVP of Product. Ticketmaster announced the appointments on Monday (October 19), alongside the addition of the team behind AI startup Ragie. "Reliable, secure and personalized experiences depend on how effectively we use technology and data," said Saumil Mehta, Global President of Ticketmaster. "Jim, Rachel, Chuck and the Ragie.ai team will help us move faster, build better tools and deliver better outcomes for fans, artists, venues and clients." As CTO, Freeman will be responsible for the technology behind Ticketmaster's products for fans and clients, including what the company calls "a new generation of agentic, AI-powered tools." "Jim, Rachel, Chuck and the Ragie.ai team will help us move faster, build better tools and deliver better outcomes for fans, artists, venues and clients." Saumil Mehta, Ticketmaster Freeman will also oversee Ticketmaster's global engineering organization and platform modernization, continue work on its defenses against bots and "bad actors," and lead a push to make "every function AI-first" across the company. Ticketmaster says Freeman has spent more than 30 years running engineering teams at consumer technology businesses. As a VP at Amazon, he helped build and launch Prime Video, then scaled the service to more than 30 million monthly active users worldwide. He also launched Prime Video Direct and Amazon Channels, and expanded the service's device partnerships and distribution. Freeman later served as CTO of European fashion marketplace Zalando, which now connects more than 62 million active customers with 7,000 brands across 29 markets. Most recently, he was a Senior Advisor at Permira. Freeman fills a position that had been vacant since February, according to Variety. Ticketmaster's previous CTO, London-based Carlos Alvarez-Coch, left shortly before the US antitrust trial against Live Nation began on March 2. Smith joins Ticketmaster from Block, where she helped scale the data science teams behind Square, Cash App, and TIDAL. She was responsible for more than 120 data scientists across those businesses. At Ticketmaster, Smith will build what the company calls a "center of excellence for data science," extending its existing analytics work and making data more central to product development and business decisions. Ticketmaster says the move will create its first dedicated data science and machine learning organization, with a focus on fraud detection, bot mitigation, and the fan experience. Mortimore, meanwhile, will lead Ticketmaster's product strategy for identity, access, and trust. His remit covers how fans access and manage their accounts and tickets, as well as protections against "bad actors and unauthorized access," according to Ticketmaster. Mortimore has held product leadership roles at Disney, Stripe, Visa, and Salesforce over more than 20 years, following earlier engineering roles at Netscape and Sun Microsystems. At Disney, his most recent employer, he consolidated identity across the company's global businesses, including its theme parks, Disney+, and Hulu. Ticketmaster said the Ragie team, whose work focuses on AI infrastructure and retrieval technology, will help staff across the business build AI tools and put them to use. Ragie announced on July 27 that it was joining Ticketmaster, a deal Variety reported as an acquisition. Ragie's website still describes the company as a "fully managed RAG-as-a-Service platform," and now carries a banner announcing that "Ragie joins Ticketmaster." RAG, or retrieval-augmented generation, is a technique that lets AI models draw on a company's own documents and data when generating answers. The appointments come almost a year after Mehta joined Ticketmaster as Global President, with a stated aim to "accelerate an AI transformation" at the company. Mehta previously spent more than nine years at Square, where he was most recently Chief Product Officer and Head of Business Org. In May, Ticketmaster cut around 350 jobs, or 8% of its global workforce, primarily in engineering, product, and design, according to Pollstar. "The purpose of [these cuts] is stronger prioritization, especially in engineering product and design," Mehta told Pollstar at the time. "That comes with flattening layers, consolidating ownership, changing how teams are structured and ensuring that we put more energy behind specific initiatives." Ticketmaster's controls on bots and ticket brokers are also the subject of a lawsuit brought against Live Nation and Ticketmaster by the US Federal Trade Commission (FTC) and seven states in September 2025. The complaint alleges that Ticketmaster knowingly allowed brokers to use hundreds or thousands of accounts to exceed artists' ticket limits, and that those tickets were then resold on Ticketmaster's own resale marketplace. In a court filing on October 13, Live Nation and Ticketmaster denied the FTC's claims, calling the lawsuit "misguided." "In 2025, Ticketmaster detected and blocked nearly 260 million attempts daily by bots to access its services, and currently blocks tens of thousands of suspected inauthentic account-creation attempts each day," the filing states. Separately, a federal jury in Manhattan found in April that Live Nation and Ticketmaster had illegally monopolized primary ticketing at major US concert venues, along with the market for large amphitheaters. Live Nation and Ticketmaster have asked the court to throw out the verdict or order a new trial. The coalition of 33 states and the District of Columbia that pressed the case to a verdict, after the DOJ settled its claims a week into the trial, is seeking the divestiture of Ticketmaster. Ticketmaster's revenues rose 15% year-over-year to USD $852 million in Q2 2026, with adjusted operating income up 14% to USD $331 million. The company says it processes more than 600 million tickets annually across more than 35 countries.Music Business Worldwide

Block (XYZ) grew lending-led gross profit 43%, but are its costs catching up? Published October 19, 2026 at 3:40 pm EDT Court filings made public on October 8 revealed that the Federal Trade Commission is investigating whether Block (NYSE:XYZ) left customers with frozen Square and Cash App accounts without enough help. That is an awkward headline for a company whose results have rarely looked better. The surprise in the second quarter was where the growth came from: lending to Cash App customers, not payments or bitcoin. So the question is whether the costs of that lending, and of running after a large staff cut, are starting to catch up with the profit. Square sells card readers, payment processing, and software to restaurants and shops. Cash App lets tens of millions of people send money, spend through a debit card, and borrow small amounts. Growth is strong, and the price looks modest beside it, yet the adjusted profit behind that price leaves out costs that are rising fast. Gross profit rose 25% in the second quarter, with Cash App up 31%. Much of that came from Cash App Borrow, the short-term loan product, which helped lift consumer lending originations 59% to $18.9 billion. Block's Financial Solutions unit, where that lending shows up, grew gross profit 43%, up from 20% a year earlier. Bitcoin moved the other way. Gross profit from the bitcoin business fell 31% because the company cut a trading fee and activity slowed. That business sells a lot of bitcoin but keeps little as profit, so lending now matters far more to the results. Investors who want more stocks like this one can find Block in our recent list of 9 Best Bitcoin Stocks to Buy Now. Square's payments business is speeding up. Square is picking up speed too. Its gross profit grew 13%, helped by a one-time tariff reimbursement, and US payment volume growth reached 10%, the strongest pace since the second quarter of 2023. That ends a slower stretch at the end of 2025. If you're interested in digital payments, we recently compiled a report on 7 Best Fintech Stocks to Buy as Digital Payment Volume Surges. Costs are rising behind the adjusted profit. Bloomberg noted that the FTC's filings point to Block's large workforce cut and its push to use artificial intelligence. They also say customers got little help even after finishing identity checks, so the probe is about how a leaner operation treats the people it serves. Costs already show up in the results. Transaction, loan, and consumer receivable losses rose 99% on a GAAP basis, mostly because Block is making more loans, and legal accruals pushed up administrative expenses. That is why adjusted earnings per share of $1.02 sit far above the GAAP figure of $0.15, and why net margin over the past 12 months was only 1.43%. Management expects growth in loan losses to cool through the rest of 2026, and it says loss rates on its Borrow cohorts remain healthy. If that holds, lending keeps growing without eating the profit. A shareholder is betting on exactly that, while hoping the probe adds little to the legal bill. Investors are pricing in an earnings rebound. Block trades at about 19 times estimated 2026 earnings. This forward P/E divides the share price by the profit per share analysts expect, so a lower number means investors pay less for each dollar of expected earnings. That sits well above the sector median of 10.88 but far below Block's own five-year average of 41.10. It also rests on adjusted earnings, which leave out the legal and restructuring charges above. Growth explains most of the premium to peers. Analysts expect adjusted earnings per share to rise about 71% in 2026, so the multiple is far less demanding against that growth. For investors looking for cheaper growth names, our list of 10 Undervalued Growth Stocks to Buy Now covers more names. Big investors have been adding. Hedge funds holding Block rose to 76 in the second quarter from 63 in the first, so more active funds now back the story. Short sellers, who borrow shares to profit from a drop, hold 3.08% of shares outstanding. That is a small bet against the stock, and it pays off if loan losses or legal costs weigh on the price. So are the costs catching up? In the GAAP results, they are, while adjusted results still show profit pulling ahead. Block's next report, due early next month, will show whether loan losses are cooling as promised and whether legal charges are still climbing.