In Your Shoes CEO Series: Skilljar Co-Founder & CEO Sandi Lin on Pivoting, Scaling, and Growing

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Skilljar Co-founder and CEO Sandi Lin had a great role at Amazon, running product management teams for programs like Fulfillment by Amazon and Amazon Local. But after four years with the e-commerce giant, she was beginning to feel a little too comfortable. “My dad was an entrepreneur,” she says. “I seem to have a pattern in my life of setting interesting challenges for myself and going for it. I’ve had this feeling all my life of, ‘Can I start a company? Can I do it?’ Some part of myself must enjoy testing myself in this way.” 

Lin couldn’t shake the feeling that she was destined to step out on her own. So, after four years at Amazon, saving up enough money that she could live for one year without taking a salary, she left in 2013 to start her own company. “Amazon is all-consuming, so I didn’t have an idea or a project I was working on the side,” she says. What she didn’t know was that key pieces of Skilljar were already falling into place.

While at Amazon, she had worked (and clicked) with engineer Jason Stewart. After her departure, she asked Stewart if he knew of any great potential technical co-founders looking to leave corporate life for an exciting, to-be-determined startup. “How about me?” he asked. Unbeknownst to Lin, Stewart and his family had also been coming up with a financial plan to make it viable for him to start a company of his own. “It was his dream, too,” she says. “We’re very different people, but we share a lot of the same values and working instincts and patterns. I always wonder how founders start companies by themselves, honestly.” 

Of course, the duo just needed their big idea. So, they started iterating.

Pivoting Toward Success

One of the pieces of advice Lin got early on was to choose a compelling space before you zero in on an idea. “This is during the whole heyday of lean startup,” she says. “I was very aware that the product might change, the business model might change, the idea will change, but preferably you can stay within the same high-level industry that you love.” 

In 2013, online learning was going through “total disruption,” Lin recalls, and it was a space in which she and Stewart were extremely interested. “Now, my stomach almost sank thinking about it again,” she says. “We also wanted to build a big company, and we knew edtech was a tricky category; selling to not-for-profit institutions is hard to build a big company on.” At the time, though, Coursera was really taking off and attracting a lot of attention from institutional investors, as was Udacity. “We thought, maybe there’s something that combines our tenacity and love of learning with a very large business opportunity,” Lin says.

Thus began Stewart and Lin’s season of pivoting. Their first idea was what Lin described as “Yelp for lifelong learning.” They scraped websites like Udacity, Coursera, and Codecademy, putting a search-and-browse structure on top of the content. “That was my first lesson in ‘great product, not-so-great business model,’” Lin says. “Jason and I also felt we wanted to build a business where we could understand product-market fit by having a transaction of value, and not this ad-based, eyeball-based, squint-and-maybe-make money method.” 

Lin and Stewart ended surveying top instructors on the platform. Themes emerged, especially among the core users — solopreneurs like book authors and fitness instructors. These customers kept saying they wanted to launch video training with their book or home-yoga training, for instance. At the time, their only option was to sell content to a third-party distributor or try to build their own platform through WordPress, which “no one was going to do,” Lin says. 

With that opportunity in mind, the startup pivoted to a freemium, small-business version of what Skilljar does today. “That allowed us to get a product into the wild relatively quickly, but in a scrappy way,” Lin says. The general idea was to build a platform where entrepreneurs could upload their content, promote it, and make money. “For that, you don’t need any backend content management or reporting – that’s just an administrative means to an end,” Lin says. “Those early beta customers sent us video files in the mail, or on Box, and I would go and hand-assemble courses in our database in the backend.” Even though the backend was completely manual — “we joked we should charge an implementation fee for the setup,” Lin recalls — Stewart and Lin got their customers’ files up quickly, and people just kept signing up.

Unexpectedly, Lin and Stewart started getting calls about Skilljar from Fortune 100 companies, too. The simplicity of Skilljar’s “video-based training platform with e-commerce” website slogan had an inadvertent effect on these behemoth corporations: It spoke directly to their needs around training their customers and partners — essentially, exactly what Skilljar does. “We are a learning platform, but what makes us different from the HR learning management software (LMS) suites is that we have unique capabilities, expertise, and features for the external learner use-case,” says Lin.

As Fortune 100 companies looked to train their customers and partners, they sought a solution that was modern-looking, technically-scalable, video-friendly, and offered paywall options to monetize content. “One of our earliest customers said this solution had to work on Chrome, have APIs and integrate with Salesforce, without having the training user exist in the HR system,” she says (most traditional LMS vendors focus on the employee compliance use case). “Skilljar just happens to be the only thing out there that fit those needs.” Lin signed Skilljar’s first six-figure deal in mid-2015, and the team immediately found its niche in a more lucrative enterprise market.

Skilljar’s ScaleUp

As part of Skilljar’s pivot to focus on helping larger corporations educate their customers and partners, Lin and Stewart knew they’d need to hire salespeople, and salespeople were expensive — or, at least, more expensive than the capital they had. Lin had a “brutal” time fundraising for Skilljar’s seed round, because the seed startup market was “absolutely flooded” at the time. Despite the challenges, Lin raised a seed round locally in 2015, near the company’s home base of Seattle, to hire Skilljar’s first couple salespeople, a marketing lead, and a few extra engineers. 

The next year, it was a race to $1M in annual recurring revenue (ARR), which the company notched quickly. When Skilljar tripled ARR from $1M to $3M in 2017, Lin knew it was time to fundraise again; it was just a totally different experience this time around. 

Lin collected seven term sheets in 20 days for the startup’s Series A. “We had our traction with customers, but the investor market had also started to understand this problem of customer success more [than when I raised our seed],” she says. 

Skilljar was already a hit when 2020 started with a bang. “Going into last year, we had been able to scale pretty nicely on the revenue front, and then Covid happened,” Lin says. “For us, it really opened up the market and accelerated trends we had already seen in the growth of virtual, distance, and self-paced learning.” As an online learning and customer success platform, Skilljar saw massive spikes in usage throughout the pandemic. “Customer momentum felt really strong, but I knew our organization was still in a startup mindset, not a growth mindset,” Lin says. 

To level up, Skilljar raised a $33MM Series B in October 2020, led by Insight Partners. “What drew me to Insight was that ScaleUp SaaS expertise,” she says. “This expertise is real… and this was the right timing for us. We needed to do a go-to-market overhaul to get us to the next level. I knew Insight’s Onsite program, and their portfolio services, could be game-changing. 

“At the end of the day, with a lot of investors, capital is just capital,” Lin explains. “But this sort of extra potential for value-add, I thought Insight really brought to the table above and beyond.” 

Skilljar aimed to use the capital for key hires, like new sales and marketing leaders that both started in early 2021. They’ve also been working to better operationalize the team’s go-to-market approach.

“There’s a mantra: Repeatable, scalable, predictable,” says Lin.

“Previously, our go-to-market was single-threaded. Our account executives were assigned by geography, but there was not any segmentation by company size. We lacked the rigorous sales processes and comprehensive marketing programs to fit the different customer personas we serve. We have now segmented the markets we’re focusing on, and we can align the rest of the company against those areas. It’s a step function up in complexity, but it will pay off with the improvements in performance and scale we achieve.” 

She’s taking it all in stride. Lin has enjoyed the process of scaling. Every quarter since 2015, she’s looked back at the company and noted to Stewart how unrecognizable it is. Startups and ScaleUps change so much. “I remember when we crossed $1MM ARR, thinking, ‘I can’t even contemplate being a $10MM ARR company,” she says. “Now, we blew past that a long time ago.” 

There are things Lin misses about being a founder-CEO in the earliest days of Skilljar, of course — when the company had a single, 300-square-foot office in Seattle’s Pioneer Square — like the ample time she was able to spend with customers. But the payoff of scaling has been huge. “The underlying financial stability of the company was a big weight lifted from me,” she says. “I love that our impact is so much bigger. We delivered over seven million hours of training last year. We’re impacting millions of learners. We are working with large companies that are doing amazing things, and that’s real value – for them, their customers, and us.

“Last year, it was seven million hours. Can we get to 700 million? I don’t know, maybe,” she says with a smile. “For now, we’ll start with 70 million.” 

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  • Insight Partners, ScaleUp Software Investors

    Insight Partners is a leading global venture capital and private equity firm investing in high-growth technology and software ScaleUp companies that are driving transformative change in their industries. Founded in 1995, Insight Partners has invested in more than 400 companies worldwide and has raised through a series of funds more than $30…