Chris Combs and the Trouble with a Signed Contract

A signed contract is supposed to settle things. At Backupify, the software company where Chris Combs and Vishal Sunak worked, thousands of signed contracts produced a fresh question: could customers’ data be moved from Amazon Web Services to another storage system? The answer depended on what each customer had negotiated. Knowing the price and payment schedule would not do. Someone had to find the promises.

Datto’s acquisition of Backupify in late 2014 exposed the difficulty. The agreements existed, but the information needed to act on them had not been organized for this question. Individual concessions, notice requirements and obligations were scattered through the paperwork. A business could have its customer records in order and still struggle to explain what it had agreed to.

Combs later recalled the available solution: read the agreements individually. “It was every bit as painful as it sounds.” There is a peculiar comedy in software people confronting a task whose working method amounts to opening the next file. For Combs and Sunak, it became the starting point for LinkSquares, which they co-founded in Boston in 2015.

The product would change over the following decade. Combs’s early writing offers another way to follow the story: through his interest in the people who buy software, the things they politely decline to say, and the patient work required to earn their business.

Twenty investors, and more than twenty introductions

LinkSquares was not Combs’s first attempt to turn document work into a company. In 2009, he co-founded Ucloser, which provided transaction management systems for real estate firms. As its chief operating officer, he worked on business and corporate development while also taking an interest in product and interface design. Documents, relationships and the experience of using software were already sharing his attention.

Ucloser closed a seed round in 2012 with 20 investors, mostly angels. That is quite a cast for an early company. Combs’s account of the round, however, dwelled on what the investors brought besides money. Early backers introduced later ones. Conversations led to prospective customers and industry partners. Advice ranged from supporting the product to arranging the business itself.

Even people who declined to invest could make useful introductions. He was learning to see fundraising as a collection of relationships with consequences beyond a bank balance. It is a useful detail in a career that would later include responsibility for strategic partnerships and corporate relationships at LinkSquares.

His education included Centre College in Danville, Kentucky, and study at the University of London. His subsequent work at Backupify placed him inside the acquisition that supplied the next company’s problem. The professional thread was already there: helping businesses manage documents and working out how to sell the tools.

The dangerous charm of “sounds interesting”

The two founders began with an experience they understood. Discovering who else would pay to solve it required conversations. Their early work led them toward in-house legal teams and general counsels, the people responsible for knowing what a company’s agreements contained. Combs concentrated on customer discovery and sales; Sunak concentrated on engineering and product development.

In September 2015, Combs compared finding early customers to dating. The analogy had some practical teeth. Both parties were deciding whether to spend more time together. A customer agreeing to use an unfinished product also accepted bugs, changes and the possibility of uneven support. That customer might then be asked to provide references and influence product decisions.

For the employee championing the purchase, a budget and a professional reputation were involved. Combs’s advice gave that risk its due: communicate promptly, consider flexible early pricing and recognize when a prospective customer does not fit. A first sale could shape the product. Choosing the customer deserved care.

By December, he was writing about another complication: the conversation that feels like a sale but never was one. People like being encouraging. Peers may want to preserve a networking relationship. A friendly executive may offer a meeting without becoming a serious advocate for the product. Every pleasant exchange can look promising if the founder needs it to.

Combs called these encounters false positives. His response was to question the opportunity more closely and examine why a deal might fail. The observation is funny because it is recognizable: courtesy has excellent manners and no purchasing authority.

An afternoon full of calls

By September 2016, Combs had given his account of startup life a deliberately unexciting title: The Boring Life of a Focused, Disciplined Startup. Friends asked how things were going. The fuller answer involved repeated work on marketing, discovery conversations, demonstrations and the steps a buyer needed to take before purchasing.

He described afternoons filled with calls. A nearby prospect might get an offer of an in-person visit, giving the founders a chance to observe reactions to the product. The work also meant noticing where buyers disappeared from the process and adjusting the next attempt. Failure supplied information, provided someone returned to the telephone.

His emphasis was specific: establish that the person has the problem and might pay before investing in a demonstration. Feedback from someone outside the likely market could send a young company in an unhelpful direction. A full calendar was no guarantee of progress.

Combs also described enjoying time with other founders, including mentoring over coffee or lunch. Yet he was clear about how much of the working week belonged to less sociable repetition. His early company needed a process that could produce customers reliably. That ambition puts the apparently dull afternoon in a different light.

The artist gets a spreadsheet

A separate 2015 essay supplies a clue to how Combs thought about this work. Asked what someone in early technology actually does, he placed it “somewhere between an artist and a scientist.” He then worked through departments that refused to stay neatly on either side.

Sales required presentation and delivery, but also attention to conversion rates. Marketing involved both a brand and measurable results. Interface design could use research to influence creative decisions. Even financial projections involved presenting a future that did not yet exist.

The question he posed for founders was whether their combined abilities covered both kinds of work. Read beside his sales essays, it makes a coherent picture: imagination gets an idea into the conversation; evidence helps decide what to do with it. His interests in product design and business development belonged in the same job.

“somewhere between an artist and a scientist”

Chris Combs, on working in early technology, 2015

When the paperwork financed the company

LinkSquares initially addressed the agreements a business had already signed. By June 2020, its Finalize product extended the offering into creating and approving contracts before signature. The original problem had opened a door into a wider set of tasks for legal teams.

Financing marked the changing scale. A $4.8 million seed extension was announced in March 2019, followed by a $14.5 million Series A in February 2020. A $40 million Series B came in 2021. In April 2022, LinkSquares announced a $100 million Series C led by G Squared.

There is a pleasing return to the opening problem here. Combs later described using Ansarada’s secure data room for LinkSquares fundraising. The company born from difficulty organizing information during an acquisition now had investors of its own asking for documents. Access, security and orderly delivery mattered on this side of the table, too.

The numbers tell part of the story, though Combs’s account remained practical: getting investors the information they needed in a secure environment. The financing process had its own document problem. Familiarity with that inconvenience had become useful experience.

A different chair, a familiar concern

On February 24, 2025, Combs moved from chief business officer to interim chief executive. Sunak stepped away from daily responsibilities while remaining a founding board member and adviser. A decade after the founding, the colleague associated with commercial relationships was taking responsibility for the business as a whole.

During 2025, LinkSquares developed its LinkAI offering and introduced capabilities for asking questions of contracts and monitoring agreements. Its year-end account reported more than 1,300 teams using the platform and 13 million contracts entrusted to it. Those are company-reported figures for that year, with all the distance from the early sales calls that they imply.

In June 2025, Combs discussed the development of predictive and generative contract tools with Zach Posner on Legal(tech) Briefs. The discussion returned to early customers as well as technology. At a 2024 LegalTechTalk appearance, his advice had similarly stressed particular customer problems, appropriate hiring and employee ownership. He described stock ownership for all LinkSquares employees as a way of sharing the company’s purpose.

The leadership changed again on March 10, 2026, when LinkSquares appointed Bill Hewitt interim CEO. Combs’s tenure belongs to a defined chapter in the company’s history. The co-founder’s earlier work, from finding buyers to building partnerships, runs through the longer story.

The promises that remain after the signature

Away from work, Combs has listed boating, snowboarding, soccer and attending sporting events around the world among his interests. The list offers a little fresh air after so many documents. His public writing, meanwhile, keeps returning to the human difficulty of business: whether someone means what they say, whether a relationship fits and whether a process can survive repetition.

Those concerns give the LinkSquares origin its staying power. An acquisition raised a question the paperwork could answer only with considerable effort. Combs and Sunak made a business out of reducing that effort. Along the way, Combs kept attending to the conversations that would determine whether anyone bought it.

The signature had looked like the end of the work. For Chris Combs, it turned out to be a place to begin.