Running a Remote Friendly Legal Practice

How Dana Denis-Smith harnessed technology to build an unconventional multimillion-dollar firm

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In the spring of 2008, after four years of college and three years training with a city law firm, Dana Denis-Smith achieved her goal and became a qualified lawyer. But during her journey, she discovered something unexpected: she didn’t like the corporate world.

“I was used to being a journalist, where you have the freedom to find your stories, roam the world, and be close to people,” Denis-Smith tells RingCentral. “When I started training to be a lawyer, I had too many ideas of my own for the corporate world.”

So, after qualifying, she typed a quick letter of resignation, cleared her desk, and took the next flight out of town. “I had to recover from the past few years of lawyering,” she says with a laugh. Several months later, sitting atop a majestic Himalayan peak and gazing out over the jagged Indian landscape, Denis-Smith reflected on the past six years. “What was I trying to do with my life?” she asked herself. “Is being a lawyer in a law firm the best way to contribute to the world?”

That moment on the mountain would help define the next phase of Denis-Smith’s professional life. And it led to the creation of Obelisk Support, one of the most unique legal firms in the world. But we’re getting ahead of the story.

The accidental entrepreneur

Denis-Smith was born in Transylvania, Romania, and grew up under Soviet occupation. 

Capitalism was bad, she was taught, and being an entrepreneur was part of that system. “There was no market economy to speak of,” she explains, “so I never really envisioned myself as an entrepreneur or businesswoman.”

When she left school, Denis-Smith pursued journalism––a career path that would take her out of Romania, exposing her to other countries and new economic systems. “I worked for news agencies, traveled around the world, and eventually settled in London,” she says.

Denis-Smith met her future husband, a barrister, in London, and for the first time caught a glimpse of the inner workings of the legal industry.

Over time, the high-powered legal world called to Denis-Smith. She traded her journalist’s notepad for legal textbooks, and after graduating from law school, she landed a training contract at Linklaters, a prestigious city law firm. Suddenly surrounded by suits and constrained by tradition, Denis-Smith felt uneasy. 

The corporate world didn’t sit well with Denis-Smith. Turned out, digging around London for stories as a journalist (which required grit and a certain rebelliousness or disregard for rules) was more entrepreneurial than she’d thought. 

And it didn’t wash with the rule-bound law office. She was too inventive, too experimental, too willing to question the old, traditional ways of doing things. In the spring of 2008, after three years on the job, she handed in her resignation and took off for India.

Sitting on that Himalayan mountain, Denis-Smith wasn’t just questioning her own role in a corporate law firm, but the entire legal sector. During her travels, she heard stories about large corporations sending work to India to save on domestic labor costs. It gave her an idea. 

What if you could outsource legal work? 

Building an Obelisk

The outsourced model fascinated Denis-Smith, but she saw it very differently than others in the legal industry. Usually, people outsourced work to businesses in India because there was a glut of underused—and cheaper—talent. But Denis-Smith realized there was an opportunity to domestically outsource work to a previously hidden UK workforce.

And, she realized, each year, thousands of women left top law firms just as she had done. Some didn’t like the culture, others wanted to have families, and many felt like professional advancement wasn’t an option for them. After they left, few legal businesses offered a way back in.

“Before we came into the market,” Denis-Smith told Fluidly, “the concept of women returning to the legal profession or allowing people to work from home or just redesigning jobs to allow for flexibility were truly pioneering in the legal sector.” 

The country had a huge body of highly skilled but unemployed lawyers. If Denis-Smith could harness those people, she knew she could create a legal firm large and flexible enough to compete with the established players.

But attracting employees would be difficult. Denise-Smith knew these women didn’t want to work for yet another corporate law firm. After all, they left for a reason. So she began planning a radically different kind of business. Instead of a small workforce of in-house professionals, she envisioned a distributed network of contractors with herself in the center, acting as matchmaker. In other words, instead of outsourcing work to another country, she would match the UK’s domestic demand to its hidden workforce.

If her plan was to work, Denis-Smith needed to first find these underutilized workers and then convince them to join her brand new legal firm, something no one had attempted in the industry before.

Denis-Smith’s first port of call was the Law Society, the governing body for lawyers in the UK. She asked whether they ever heard from lawyers who were trying to rejoin the workforce. “Yes,” replied the Law Society clerk. “We actually have quite a few who have been asking what we can do for them.” The clerk put Denis-Smith in touch with four lawyers and wished her luck.

It was a small victory, but proof enough that the employees she had envisioned were indeed out there and ready to get back to work.

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How to land a big fish

Once she had confirmed that her plan could work, Denis-Smith’s next step was making sure it’d work commercially. To test the viability of her business, she commissioned a piece of market research. 

“I had someone call every person who heads up the legal department at a FTSE 100 company and ask whether they would consider sending the work to a [distributed legal firm] like us,” she recalls. While her researchers worked through the phone book, Denis-Smith waited nervously. Then, one afternoon, an email dropped into her inbox with the results.

As she clicked into the message, her heart sank. “The research came back negative,” she says. “Everybody said they would be really worried.” The legal heads expressed concern not just about the efficiency of Denis-Smith’s operation but the security of her distributed workforce, too.

Denis-Smith still wasn’t ready to give up. She knew her outsourced model worked, and she knew some of the companies she contacted were already outsourcing work—some of it highly sensitive and confidential—to overseas companies. “Why were they happy to send all their payroll information to the Philippines, but refused to outsource work to a lawyer who has probably serviced them before?” says Denis-Smith. It didn’t make sense.

Many successful businesses experienced similar resistance in their early days. Dozens of investors passed on Airbnb, for example, believing people would never pay to stay in someone’s spare room. At the time, it was probably a fair assumption. But founders Brian Chesky and Joe Gebbia saw past the hesitation to the golden opportunity on the other side. They persevered and now Airbnb helps tens of millions of customers find accommodations each year. 

“Entrepreneurs often ignore the signals of the market because they think their business is the right solution,” says Denis-Smith. So that’s exactly what she did. She shelved the damning research report and hit the phones.

Denis-Smith wanted to build her business to be one of the big corporates––the Intels, Goldman Sachs, and Vodafones of the world. She pulled out the black book she’d kept from her time as a corporate lawyer and began working her network, hard. While the response was a lot more positive in person than via market researcher, Denis-Smith quickly hit a new problem: scale.

In her very early days, Denis-Smith was introduced to the head of legal at a large bank, who agreed to meet to discuss Obelisk’s service. The executive asked about her capacity. Denis-Smith happily reported that she had 12 outstanding lawyers who could work the equivalent of five full-timers. “What can I do with that?” replied the exec. “It’s just too small for me.”

Faced with a clear objection, Denis-Smith began hiring, building a larger and larger team, until she was ready to land her big fish clients.

When a lawyer outgrows her technology…

With a few tentative bites, including one from the exec at the bank, Denis-Smith knew she was right to ignore the market research. Now, all she had to do was develop her network and grow Obelisk’s capacity in order to interest larger firms.

She grew her firm from 12 to 120 in a couple of months. Then, shortly after, to 500. While growth made her legal firm more attractive to big corporates, it brought new administrative problems.

Denis-Smith had bootstrapped her business for the first few years, doing everything she could herself. “If you remember the film Being John Malkovich, it was like that,” she says. “I had an org chart and my name is on everything.” 

But that scrappy startup mentality was coming back to bite her. She was running Obelisk Support on a rickety, makeshift system. Consider how she managed résumés: “People were manually formatting CVs so we looked professional and that was the worst job ever,” she says. “I could see my team becoming demotivated by things that could have been automated.”

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When Obelisk added its 500th lawyer to its network, its inefficiencies became too large to ignore. Denis-Smith began looking for a technical consultant. “It was a turning point because I realized [Obelisk Support] wasn’t going to work unless we did something quite different,” she says. “I had around eight employees by this point and their jobs were almost breaking them. 

The technology consultant tore down Obelisk’s makeshift systems and began designing a custom management platform for the business.

Now, Denis-Smith managed Obelisk from a custom dashboard. “The system allows us to matchmake much quicker and turn around jobs soon after they land,” she says. And remember that soul-crushing job manually formatting résumés? It’s thankfully a thing of the past. “[Formatting a résumés] is a five-second job,” says Denis-Smith. “Whereas before it probably was the whole afternoon, fighting with a template.”

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Landing Goldman Sachs

With her custom platform in place and her network continuing to grow, it was only a matter of time until Obelisk Support landed its first big client. Then it happened: “We landed Goldman Sachs,” says Denis-Smith. “They gave us a shot, and it was the kind of business you could build on. It was a good case study.”

With its first high-profile client on board, other meaty contracts followed: ING Group, BT, Intel, and Vodafone. For the five years after landing her first big contract, Denis-Smith recorded 1,000% growth in her business and her network consists of more than 2,000 lawyers.

Since the beginning, Denis-Smith has maintained that her goal is to “make work ‘work’ for our clients, our lawyers, and their families.” With 2,000 lawyers able to rejoin the workforce on their own terms, while still working with huge corporations, it’s fair to say she’s achieved that ambition.

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