Theo Satloff and the shopkeeper inside the machine

Before Theo Satloff set out to put a shopping advisor inside a website, he was helping run a company where the office windows doubled as whiteboards. The team worked without shoes to keep the place clean. It was 2018, the office was upstairs in a once-vacant Waterville building, and the business was called EuroPiste. Artificial intelligence could wait. Ski instructors needed a less cumbersome way to buy their gear.

The problem was wonderfully unglamorous. Professionals qualified for discounts, but had to visit individual brands to collect them. Satloff and his fellow students wanted to gather those purchases into a single marketplace, with a universal checkout. A person whose job involved getting down a mountain should, presumably, be able to get through a shopping basket.

Years later, Satloff is co-founder and CEO of Boston-based Remark. The company combines product experts with AI to guide online purchases. Its territory has widened from outdoor equipment to the decisions people make across a store. The question beneath the business has stayed surprisingly steady: how much easier would buying become if the right person helped?

A shop counter before a keyboard

Satloff's introduction to selling came early. His mother ran a fine jewelry business, and he remembers working behind the counter at six, surrounded by Victorian jewelry and adult buyers. He also spent time around Bergdorf Goodman personal shopper Betty Halbreich. In his telling, those encounters taught him to pay attention to the customer before reaching for a recommendation.

“She put me behind the counter.”

Theo Satloff, recalling his mother's introduction to retail

A jewelry counter is a useful place to begin this story. The object is right there, available for inspection, yet its features alone do not complete the sale. Someone has to understand why the buyer has arrived. Satloff's later work would carry that question into a setting where the counter had become a screen.

His childhood crossed New York and Colorado, giving his eventual career two fitting backdrops: retail and the outdoors. In a 2024 conversation about his entrepreneurial beginnings, he described those early influences and the development of Outdoorly. The route to Remark began with a market he and his collaborators knew from participation, rather than a category chosen from a spreadsheet.

The ski trip that became a business

At Colby College, Satloff studied computer science alongside science, technology, and society. His technical work included building drones using a DJI frame, Navio 2, and Raspberry Pi. Later, his name appeared with Carl-Philip Majgaard and other researchers on a 2020 conference paper about automatic drone replacement during continuing missions. The robotics connection was real, down to the components.

Meanwhile, the business took shape through repeated attempts. In 2018, Satloff described an idea that had been developing since his freshman year. Majgaard recalled a four-day visit to Munich's ISPO winter-sports expo, where the students talked with more than 50 vendors while preparing their pitch. A trade show offered a fairly direct test: would the people selling the equipment take this seriously?

The team won Colby's 2017 business pitch competition and its $10,000 prize. Outdoorly officially launched in September 2019. Satloff's senior year had involved traveling between Waterville and New York, fitting company work around college. Ian Patterson and Majgaard became his long-term Remark co-founders. The partnership grew out of shared outdoor interests and time spent in the robotics lab.

There is a temptation to polish an origin like this until every early choice points neatly toward the eventual company. The succession of names makes that difficult, which is part of its charm. EuroPiste addressed access to discounted equipment. Outdoorly built a marketplace around outdoor professionals. Remark would carry expert guidance into other merchants' stores. The scope changed as the founders learned what people valued.

The people who knew the equipment

Outdoorly's own description framed it as a marketplace connecting brands, professional outdoor experts, and consumers who wanted credible guidance. That arrangement gave expertise an explicit place in the business. A guide's knowledge could help another person decide what to buy, beyond the familiar role of demonstrating a brand by wearing it on the mountain.

By May 2020, Outdoorly had partnerships with more than 80 brands, including Mammut and Klean Kanteen. Its 19-person team included 11 current or former Colby students. Satloff explained the appeal of recruiting people whose computer science training he understood. Interns received substantial assignments, and the team made room for shared Friday lunches and a Yankees game.

Those details give the early company a social texture. Hiring through an existing community made it easier to recognize skills and introduce people to work. Satloff also spoke about helping connections travel back toward Colby. His later involvement on the Halloran Lab for Entrepreneurship's advisory board extended that relationship beyond recruiting.

The business connection eventually traveled in another direction too. In 2022, the founders launched Remark. The audience expanded beyond outdoor shoppers, while knowledgeable people remained central to the proposition. The same practical issue could arise over a saucepan as over a jacket: a description might be accurate and still leave the buyer unsure.

What the software is supposed to notice

Satloff arrived at this work with experience on Amazon's Alexa team, where he focused on reinforcement learning. That background put machine learning beside a much older interest in how a person helps someone buy. Remark's approach uses the knowledge and advisory styles of product experts to shape AI personas, extending guidance beyond the hours when those people can answer directly.

The founders initially expected expensive products to generate much of the demand. Socks complicated that theory. Work with Darn Tough showed them that a modest price could still accompany a purchase people wanted to discuss. The lesson has an appealing lack of grandeur. An online shopper can have a consequential question about an ordinary object. Software designed around price alone may miss it.

A useful advisor needs context. A catalog can describe a product; a conversation can establish which parts of that description matter to this buyer. That distinction helps explain Satloff's interest in guidance before purchase. In the company's design, the question and the recommendation belong within the shopping experience, close enough for the answer to affect the decision.

A funding announcement, with packing tape

Remark announced $10.3 million in seed funding in May 2024. In July 2025, it announced a $16 million Series A led by Inspired Capital, with Stripe, Neo, Spero Ventures, Shine Capital, and Visible Ventures participating. The company put its total funding at $27 million. Its next plans included expanding the expert network and improving training, onboarding, and performance measurement.

Satloff's account of the Series A launch included something more tangible than an investor list. The team packed boxes containing chef's knives, sweatshirts, and notes of appreciation. They made a launch video in-house and rebuilt the website. He invited people to comment “knife” if they wanted to join the Remark cooking club. The announcement had acquired cutlery.

The choice suits a company selling the value of personal attention. A custom gift gives its recipient something specific to remember. It also gives the people sending it a great deal of packing to do. Satloff's post lingered on those hours, giving the funding milestone the scale of an afternoon's shared work.

In an April 2026 podcast appearance, he discussed personalized outbound selling, controlled A/B tests, and keeping the pitch focused. The business case depends on merchants seeing results against their existing experience. A pleasing conversation has to earn its space on a store's website, where every addition competes for attention and budget.

The mirror joins the conversation

The newer product releases show where Satloff's company is taking the idea. On May 20, 2026, Remark introduced Checkout from Chat for Shopify brands. Shoppers could add products, manage their cart, and proceed to checkout within the conversation. Advice and action moved closer together, reducing the need to carry a recommendation through a succession of separate pages.

On August 20, Remark announced real-time Virtual Try-On. The experience opens from a product page, allowing shoppers to see clothing rendered on themselves as they move, without downloading an app. It connects visual exploration with the shopping advisor, so a person can consider colors, accompanying pieces, and questions in the same flow.

The ambition becomes easier to picture through those ordinary actions. Ask about an item. Consider another color. See how a garment looks in motion. Carry on toward checkout. Each is familiar inside a store. Moving them online means deciding what deserves to be recreated and how much effort the shopper should have to spend.

Remark also joined the Massachusetts AI Coalition in April 2026, committing itself to a wider community of companies building in the state. Boston now provides the setting for a business whose earliest desks were in Maine and whose first market research took the founders to Munich. Its geography has followed its changing work.

Satloff has described entrepreneurship as a balance of confidence and humility. The company's history supplies room for both: the confidence to ask vendors for meetings as students, and the willingness to let the business change. His continuing subject is recognizably human. Someone arrives with an intention they may not yet know how to explain. A good shopkeeper begins by finding out what brought them in.