Shuffle co-founders Chris Watts (left) and Mathew Lee. (David Rzegocki Photo)

Two years ago, while Matthew Lee was on a sabbatical between jobs, he reflected on his career highlights.

“There are certain jobs that I had that I really loved, and some were just a job,” Lee said. “The key component was the people.”

That got him thinking about the ways he could use technology to improve work experiences for others by helping people engage with their colleagues. He perused his professional and personal network and realized that his childhood friend Chris Watts had made a tool that randomly matched people to connect for lunches. The two had first met in 2001 when Lee immigrated to Seattle in seventh grade, and stayed on touch over the years.

Lee invited Watts to Malaysia, one of his sabbatical travel destinations and his birth country. He made his pitch over street food shared in Kuala Lumpur. Watts signed on, leaving an engineering job at Amazon.

In 2019, the two launched Shuffl, a startup offering a tool that matches and introduces people through platforms such as Slack or Microsoft Teams. Lee, who is the CEO, is based in San Francisco while Watts, the CTO, is in Seattle, where the 2-person company is headquartered.

Here’s how Shuffl works. On Slack, for example, users can find the Shuffl app on the platform’s app store. The app automatically creates a new channel for users, who decide how often and when Shuffl-mediated interactions take place. The app sends notifications on the channel and matches people for one-on-one or larger interactions, which can be assigned randomly or intentionally.

When the “Shuffl” happens, the organizer can share links for video conferences and provide icebreaker questions or articles for discussion. Through the “smart shuffl” feature, users can arrange for non-random connections, pairing a small group of employees with a company leader, for example.

About 1,000 teams have installed the app, Lee said, including groups within enterprise-size companies, university students in Germany and a public health organization in Wales. The service is free for groups of up to 50 members and $50 a month for teams of up to 1,000 people. The paid service provides additional benefits and support.

Competitors in the space include Donut, RandomCoffee and Snack. Shuffl will be seeking angel investors in the first quarter of 2021.

In addition to Amazon, Watt previously held engineering roles at Expedia, as well as Simply Measured, a social analytics firm that was acquired by Chicago-based social media management platform Sprout Social. Lee has worked in sales at companies including StreamSets, Interana, Apptio, and others.

The tool is available on Slack and being developed for Microsoft Teams. The intent is for the service to work on a variety of communication platforms.

“The best part about Shuffl is our service is not tied into companies and teams,” Lee said.

We caught up with Lee for this Startup Spotlight feature. Continue reading for his answers to our questionnaire.

What does your company do? Every week we “shuffl” people into new groups on their chat platform and help them create meaningful bonds with one another. Studies show team environments thrive when there are strong social bonds and trust between people. We go beyond randomly sorting groups and smartly shuffl people in new and fun combinations that spark joy.

Inspiration hit us when: We had a shared realization that work was most joyful when we had great relationships with our coworkers. We saw the power of how communicating outside our silos boosts happiness and productivity as individuals and as a team.

VC, Angel or Bootstrap: Bootstrap. Our focus on operating in a lean fashion on leading platforms in combination with the organic demand for our product created a perfect storm that has allowed us to grow solely through our revenue. This has demonstrated our value and allowed us to focus on product innovation and targeted outreach.

Our ‘secret sauce’ is: Our team’s fanatical response to challenges to deliver the best experience for our users. We consistently surprise each other with creative solutions to very complex problems, and our customers are the direct beneficiaries. We intentionally invest in features like smart shuffl because we believe in building game-changing solutions.

The smartest move we’ve made so far: Our early up-front investment to build and operate our whole service stack on AWS. Shuffl now leverages best-in-class services in performance scaling, reliability and security. These investments are a game-changer for our business as we can expand into additional platforms and innovate in new areas, which we’ve demonstrated by quickly adapting and delivering on emerging market trends.

The biggest mistake we’ve made so far: In a recent release, we had a lot of deliverables against aggressive timelines. At the time, we deferred bringing in design consultants. In hindsight, we could have accomplished key milestones sooner if we’d acted faster. We’re now proactive in leveraging counsel and help when needed.

Which leading entrepreneur or executive would you most want working in your corner? Microsoft co-founder and philanthropist Bill Gates. In addition to his technical expertise, we value his commitment to human-centered work. Shuffl’s founding principles center around making people’s lives better, and we admire his life’s work around compassion and empathy. We’d treasure the opportunity to learn and share our passion for building technologies valued for its positive human impact.

Our favorite team-building activity is: We love getting outdoors! We find our best creative ideas flow during our camping retreats and biking new trails.

The biggest thing we look for when hiring is: Trust. Our ability to deliver shuffls to our customers worldwide on a daily basis comes down to incredible teamwork. We believe in setting every person up for growth and success, and that comes with mutual trust and respect for each others’ responsibilities.

What’s the one piece of advice you’d give to other entrepreneurs just starting out: Finding the right co-founders by ensuring everyone shares and believes in the company’s founding principles, values and mission. The founders are the key that will dictate a team’s immediate success or struggles. Pick co-founders whose strengths fill in weaknesses of one another and cheerlead one another when the hard times roll.

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