How a Multigenerational Workforce Helped Skillshare Scale Its Team and Culture

Skillshare’s CEO shares how having an age-diverse workplace has helped the company scale both internally and externally.
Written by Olivia McClure
April 23, 2021Updated: April 28, 2021

As Gen Z begins to enter the workforce, age diversity has become increasingly common. But rather than see this as a challenge, many companies are actively pursuing it. 

In fact, according to a Deloitte study, 70 percent of organizations believe that multigenerational workforces are crucial for future progress. 

For Matt Cooper, CEO at edtech platform Skillshare, having an age-diverse workforce has played a critical role in the company’s success. This cross-generational collaboration has made it easier to scale and meet the specific needs of the workforce while supporting a global community of learners. 

“We believe diversity creates better thinking and, ultimately, a better product for our members,” Cooper said.

Built In NYC caught up with Cooper to hear how having a multigenerational workforce has helped his company remain strong, connected and competitive. 


Matt Cooper
CEO • Skillshare

Tell us how having a multigenerational workforce makes your team stronger or improves the outcome of a project.

At Skillshare, we are proud to have a diverse roster of teachers on our platform from all generations. There’s no doubt Skillshare’s students benefit from the diversity of experience and points of view available from our teachers who offer beginner, intermediate and advanced classes. The diversity of talent on Skillshare has made our community stronger and more connected.

As a company, Skillshare is lucky to have talent from multiple generations and geographies, with team members in New York and Colombia and sites throughout the Midwest, Canada, the UK, Romania and Costa Rica. We believe diversity creates better thinking and, ultimately, a better product for our members.


How do you leverage the unique strengths and skill sets of different generations within your workforce?

In scaling Skillshare, we’ve worked to ensure we are hiring individuals who can handle the specific stage of growth we're in and help us reach the next stage. A former CEO of mine used to call these phases the “jungle,” “dirt road” and “highway.”

Since Skillshare has moved beyond the jungle (seed stage), and dirt road (Series A, B, C and D funding rounds) phases, we now find ourselves on the highway. This means we have a clearly defined market and products and are building significant growth.

We wouldn’t have gotten to where we are without multigenerational talent at our company. In the early stages of startups, most employees can do a little bit of everything. But as our company has grown, we’ve needed to hire specialists to help us get where we want to go. Depth of knowledge and specialization only comes with experience.


We wouldn’t have gotten to where we are without multigenerational talent at our company.”


What steps have you taken to understand the diverse needs and values of a multigenerational workforce in order to create a company culture and offer perks and benefits that support those different needs?

We aim to offer workplace accommodations and perks that advance our mission, brand and values, and create opportunities for personal and professional development. Flexibility is a core value at Skillshare and has become even more important in the wake of the pandemic. During quarantine, we pivoted to look toward the future and reinvent our employee experience to support a globally distributed workforce at scale. As Skillshare transitioned to a fully remote company, we offered employees stipends to set up their home offices, manage wellness, secure internet connectivity and even purchase coffee.

On the management team, we understand that different employees have different needs around flexibility. Some of our team members are moving out on their own for the first time, some are raising children and some take care of aging parents. Our flexible approach to work has enabled us to recruit superstars at all phases of life.

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