Sam Lessin and Andrew Kortina on their voice assistant’s workplace pivot

The founders of Fin are betting on the consumerization of the enterprise

Sam Lessin, a former product management executive at Facebook and old friend to Mark Zuckerberg, incorporated his latest startup under the name “Fin Exploration Company.”

Why? Well, because he wanted to explore. The company — co-founded alongside Andrew Kortina, best known for launching the successful payments app Venmo — was conceived as a consumer voice assistant in 2015 after the two entrepreneurs realized the impact 24/7 access to a virtual assistant would have on their digital to-do lists.

The thing is, developing an AI assistant capable of booking flights, arranging trips, teaching users how to play poker, identifying places to purchase specific items for a birthday party and answering wide-ranging zany questions like “can you look up a place where I can milk a goat?” requires a whole lot more human power than one might think. Capital-intensive and hard-to-scale, an app for “instantly offloading” chores wasn’t the best business. Neither Lessin nor Kortina will admit to failure, but Fin‘s excursion into B2B enterprise software eight months ago suggests the assistant technology wasn’t a billion-dollar idea.

Staying true to its name, the Fin Exploration Company is exploring again.

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The Fin Assistant

Dopamine hits

Two years after Lessin and Kortina spoke to TechCrunch about their new voice assistant technology, we chatted with them again about Fin’s pivot to workplace analytics software. What’s clear is that they have a lot to overcome. Success in a new space requires them to learn the ins and outs of enterprise software after more than a decade focused on consumer products and an ability to prove the value of a B2B tool that until recently, didn’t exist, all while kissing their beloved consumer technology world goodbye.

“When you’re younger, [consumer is] more exciting; when you’re older, you’ve done that a lot,” Lessin tells TechCrunch. “The dopamine hits, it’s not that they aren’t cool, they are just less cool than they once were. [Enterprise software] has a longer gestation period and you have to be a little more self-motivated. You can’t focus on what other people are doing and you have to have more conviction that you are building the right stuff.”

Lessin joined Facebook in 2010 after the social media behemoth acquired his file-sharing startup Drop.io. Lessin, who was classmates with Zuckerberg, is well-known in Silicon Valley circles not only because of his four-year stint as a Facebook vice president or his marriage to The Information founder Jessica Lessin, but also because of his fruitful career as a venture capitalist. The Fin co-founder doubles as a partner at Slow Ventures, an early-stage fund with investments in Casper, PillPack, Slack, Allbirds, Postmates, Airtable and others.

“It’s not like CEOs wake up in the morning and say I really need an operational analytics platform.” – Sam Lessin

Kortina’s resume includes co-founding Venmo, where he remained chief financial officer until 2014. As the story has it, the two co-CEOs, also old friends, were “doing nothing” and thought they should do something together. Thus, Fin was born.

Unsurprisingly, it didn’t take much effort for Fin to raise venture capital funding. In 2016, the company closed a $30.75 million Series A from Kleiner Perkins, CRV and Accel, according to PitchBook. At the time, they had little to show for themselves beyond a rough idea. When you’ve successfully sold a company to Facebook and created one of the most popular payment apps in the market, attracting capital can be as simple as a few phone calls and an informal pitch deck.

Surprisingly, Fin hasn’t raised another dime since its 2016 Series A, Lessin confirms to TechCrunch. Perhaps once Fin finds its footing in the enterprise space, Lessin and Kortina will seek additional funding. For now, they explain, “capital is not a constraint.”

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Fin co-founders Sam Lessin (left) and Andrew Kortina.

As they get comfortable with the slow-moving and complex world of enterprise software, the Fin team must familiarize themselves with new tools, mechanisms and processes critical to building a successful B2B tool: “To be candid, this is the first time Kortina and I have used Salesforce,” Lessin admits.

“If we were doing a consumer app, [we] could move a lot faster,” Kortina added. “At Venmo, it was similar in a sense that we had to spend a lot of time on compliance and security, some of which was incredibly important because it made things more secure and some of which was less important.”

More dopamine hits may have accompanied the Fin Assistant company-building process but the business opportunity for Fin Analytics, a measurement platform that uses data to help companies improve operations and optimize performance, is bigger and better. VCs have invested nearly $15 billion in U.S. business and productivity software startups so far in 2019, per PitchBook, and eye-popping initial public offerings from Zoom, PagerDuty and others highlight Wall Street’s growing appetite for B2B upstarts.

Closing the process operations gap

Lessin and Kortina are in a unique position to leverage their consumer expertise as the consumerization of the enterprise — the idea that companies should take a consumer-first approach to product design — takes off. Somewhat by accident, they’ve created a solution for businesses more cost-effective and productive than a consulting firm, which have historically been brought in to help big enterprises better understand what they can improve, as well as where and who they can cut.

Fin Analytics was created roughly two years ago as a byproduct of the Fin Assistant. The team needed a measurement platform to track and analyze operations work, Lessin explained, and there were no tools on the market: “It was a critical piece of infrastructure that just didn’t exist anywhere,” Lessin said. “Fin Analytics was the most important thing we built because it’s something no one else had but everyone needed.”

“Now we have to evangelize the space,” Lessin concluded. “It’s not like CEOs wake up in the morning and say I really need an operational analytics platform.”

The founders declined to disclose the number of companies using Fin Analytics, but said it was “dozens” and “more than a handful.” Since launching the platform around the end of 2018, they’ve experimented with the business model. Currently, they are granting entire companies access to the tool for a monthly fee ranging from $1,000 to $10,000-plus depending on the size of the operation.

The challenge for Lessin and Kortina will be pitching their product to the enterprise world and convincing executives a tool that closes the “process operations gap” is something they can’t live without. If they can do that, they have a shot at building the successful company investors at Kleiner Perkins, Accel and elsewhere undoubtedly expected when they put cash in Fin three years ago.

Although Lessin and Kortina were hesitant to use the term “pivot” to describe Fin’s foray into data analytics, successfully transitioning into an entirely new sector would put them in a class of high-flying businesses whose first business idea didn’t work too well (Slack, YouTube, etc.) but whose second idea was a bona fide rocket ship.