Building and Scaling Udemy's Team and Culture

Note: Ensemble Managing Partner Conrad Shang was an investor in Udemy’s Series C while at Norwest Venture Partners.

On the heels of the Udemy IPO, we chat with former Udemy CEO and Ensemble VC Advisor, Dennis Yang to talk culture, priorities, and solving hard problems

By Conrad Shang

Today, Udemy is a learning powerhouse: 180,000 online courses in 75 languages, 65,000 video instructors, and over 44 million global learners. Similarly, Dennis Yang is regarded as an effective leader and experienced operator that led Udemy during its foundational period of immense company and organizational growth.

Combined with laying the organizational foundation and setting the company culture, many of the strategic decisions made during this time set the course for the company, including early international expansion and founding Udemy for Business. The company now boasts a multi-billion dollar valuation and is heralded as a Silicon Valley success story.

However, the path to get here was far from obvious.

When Dennis joined in 2012, Udemy had raised a very small amount of money compared to today’s funding environment and had built an initial product. The early team – like every other startup – was trying to figure out everything else.

Every month, the bank balance dropped closer to zero. They were still far from the fabled product-market fit.

“The company had raised a $1M seed round and $3M Series A, which were respectable numbers back then. But the modest funding meant we had a short amount of time to figure it all out.” –Dennis Yang, former CEO of Udemy

In this Q&A, we talk to Dennis Yang about Udemy’s pivotal period from 2012 to 2017.

What is your advice to startups that have yet to fully demonstrate product-market fit? How should they prioritize objectives?

First on my list is figuring out how to sharpen our lens of focus. In our situation, it was figuring out the Series B right away and what we needed to prove to raise this next round.

In the early days, you’re trying to jump from lily pad to lily pad to make sure you have enough funding. It can be useful if you work backwards to figure out what you need to accomplish with the funding that you have.

Ask yourself how much money you need to raise in your next round, what things you need to learn and prove in the business, what KPIs justify that raise, and what initiatives need to be completed to hit those KPIs.

Many startups suffer from “shiny new toy syndrome”. 

They want to chase after new errant customer requests or explore new marketing channels. They jump around from idea to idea, not giving a single tactic time to materialize which results in a lot of false negative results on your efforts.

Instead, you want to push in a single direction. I'd often ask the Udemy team: “What are the 1-2 initiatives that the whole company can get behind that will drive us forward?”

How do you recruit and retain the best talent?

In general, people over-index on brand when it comes to recruiting. Brand pedigree is not always a great signal. If you find people who are really curious and bright and have a very high potential, they will do well given the right environment. These are the types of people that you want to keep giving more challenges and responsibilities.

I’m proud that we supported career paths that led to interns and entry-level employees growing into bigger and bigger roles.

Over a 5-year period, we had people growing from being an early individual contributor to leading large teams at the executive level. Other people on the team see that and get excited about that opportunity for themselves and to replicate that success.

Importantly, we also mixed raw talent with experienced leaders. Raw talent will break more glass, but will have a higher ceiling. Anchor them with people with more years of experience and different perspectives.

Your job as a leader is to architect diversity of thought. You should push for culture, values, and practical behaviors. At the end of the day, your culture ultimately reflects who you celebrate, hire, promote, and who you fire.

At Udemy, we had a lot of success pushing responsibility and authority as far down the organization as possible. The key was giving people responsibility and authority to make decisions. This led to very fast progress and happy employees. 

We optimized for speed and autonomy, which created an ownership mentality.

Looking back, what did Udemy do best during this period? What are you particularly proud of?

I joined Udemy in 2012 when there were fewer than 15 people and we had about $150,000 in revenue the month I joined. When I left Udemy in 2017, we were approximately 300 people, $150 million in revenue, had built out international operations, and had proven out and scaled Udemy for Business.

At the time, it was not obvious to expand internationally so early or to begin investing in a B2B platform which would allow businesses to benefit from our learning platform. Today, those two things proved to be vital to Udemy’s scale and success.

More than any of that, I am proud of the awesome culture of Udemy. People legitimately loved working there. And I loved working there. 

When I run into former Udemy team members, they never talk about the financial success. They almost always comment on the culture and company experience – many calling it the “highlight of their professional careers” and how proud they are to have been part of it.

There can be a lot of noise in the startup ecosystem. But remember, there are only two inputs for a business: financial capital and human capital. 

Bringing on the right team members and the right investors, at the right time, in a high-trust environment is the difference between success and failure.