This Former Apple Executive Brought His Company Through 2 Tough Pivots and Now Has McDonald's, Comcast and Whole Foods as Clients Inkling creates software that aims to make the lives of so-called 'deskless workers' easier.

Matt MacInnis says that he's wanted to be an entrepreneur since he was a teenager living in a small Canadian town. And he points to one moment during his freshman year at Harvard in 1998 that set him on a path to running a company whose clients include McDonald's, Whole Foods and Comcast.

An Apple representative had visited his computer science class and during a presentation showed off Mac OS X. Afterwards, he spoke to her and she mentioned the company was recruiting a campus rep. MacInnis, a self-admitted Apple nerd, signed up.

"If I hadn't just walked down and had that conversation with her, I never would have gotten that job and I never would have been connected to Apple," he says. "Some other life would have happened, but this trajectory I'm on, it all sort of can be rooted to that one 10-minute conversation."

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That trajectory saw him working at the tech giant, where he did education marketing and business development. While content at his job, he was still looking for an opportunity to pursue his entrepreneurial ambitions. That moment came in 2009, when MacInnis saw the device that his boss Steve Jobs would eventually show off a year later: the iPad.

"I saw the iPad in development and knew that it was going to be an exciting technology," he says. "So, we started a company to kind of tackle the question of textbooks on iPads."

The company MacInnis co-founded, Inkling, started by selling digital textbooks directly to consumers. But despite what seemed like a good idea (Apple sold 3 million iPads in the first 80 days after its release), it wasn't long until that business model fell apart. Inkling would have to undergo two hard pivots before getting to where it is today: a company with tens of millions of dollars in revenue and growing at more than 50 percent year over year. Now, it's the maker of an app for the web and iOS and Android devices that acts like a digital content system to help employees get their jobs done. Think: digital training manuals, tips, references and company announcements. Also, with its messaging service, task organizer and analytics tool, it is a full-stop service for so-called "deskless workers" -- most of the people in retail and food.

Now with $95 million in funding and 100 employees, MacInnis explains how he went from book dealer to workforce problem-solver.

The first pivot: Jumping from B2C to B2B

"The original hypothesis around digital textbooks was a good one. We got Sequoia as the main investor and a lot of shit went right," MacInnis says. "The only part of the business that didn't go right is that 18 year olds don't give a shit about textbooks. So publishers cared and investors cared and we cared, just not the people who had to spend money."

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Upon this realization, Inkling decided to make the drastic switch from a business-to-consumer model to a business-to-business model. It started after Starbucks came calling with a good idea. The coffee giant said that rather than ship binders used to train employees every quarter, it would use Inkling to make those materials available to employees on iPads. Inkling started to license its tools to companies such as Comcast and KPMG, allowing them to convert their materials into digital content to be read on mobile devices.

Because of this shift, Inkling went from making very little off consumer textbooks to building tens of millions of dollars in recurring revenue, according to MacInnis.

But this model wasn't enough to sustain the business. About two years ago, MacInnis admits that the company scaled way too quickly, with 25 percent of its 160 employees working on the sales team. There just wasn't enough business for its digital content project to keep going.

"We knew that the content thing itself was interesting, but it felt like a one-legged stool," he says.

Inkling needed a new solution. It went to its customers to find out what they were missing. The answer was in retail.

The second pivot: Taking on the world of retail

Managing a large store such as a Walmart, Target or Kohl's is a complicated affair. These retailers can employ up to 200 people, who all have moving shifts. When you zoom out to the regional manager level, that headcount could quadruple.

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Inkling's current offering simplifies these managers' jobs, as well as everyone under and above them. With its tools, Inkling not only provides digital versions of training guides and employee manuals, but there are also interactive quizzes and demonstrations, so an employee on the floor of a furniture store only needs to look at their device to create a matching display. Once they're done, they can snap a photo that is sent to their manager. Managers can keep running tallies on tasks they've assigned. Meanwhile, co-workers can message each other without the need for phone numbers.

"In 2013 to 15, we were like the Bentley of the employee handbook," MacInnis says. "Today, the core experience is really messaging."

Inkling's business model now is 80 percent subscription revenue and 20 percent services revenue, MacInnis estimates. It has dedicated teams who create branded versions of Inkling for each big client, most of whom work in retail and the food industry.

Top to bottom

Inkling has been in business for seven years, and underwent two pivots. MacInnis says that the company's culture and a strong belief in its product is what helped it thrive.

"When I go in and pitch customers on the platform, I'm pitching them on reduced labor expenses, improved labor efficiency and ultimately better customer experiences" MacInnis says. "But I honestly don't care about that part of our business. The emotional part for me is when we put this exact sort of interface in front of [store employees] and they just started giggling. They're so excited to use it because it would simplify all this crap that they do today over text message and email and stuff."