Leadership in Startups: Upside Down at 150 People

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A crash course for startups on leadership, strategy, culture, team building and more (from an SVP of startup marketing).

What you’ll learn

  • Build startup leadership skills that prepare you for Dunbar’s Number
  • How to define mission, vision, and strategy at your startup
  • How to design teams, culture, and communication at your startup
  • Explain “Dunbar’s Number” and how it applies to your startup
  • Identify the early signs that your startup’s approaching Dunbar’s Number
  • Articulate the major problems startups face when they hit Dunbar’s Number
  • Start planning & implementing actual changes to the way your startup operates
  • Better empathize with leadership as your startup goes through its biggest change yet


  • Have some professional work experience (minimum 1 year)
  • Experience at startups (or fast growing companies) is helpful, but not required
  • Leadership experience is helpful, but not required


“Something weird happens to companies when they hit 150 people”. This was the title of an article I read on Quartz last year and after reading it, my reaction was:

“Yes! That’s it. Finally, someone understands what startups go through!!”

For context, my name’s Dinesh Thiru and I run marketing here at Udemy. I joined way back in 2011 when we were about 5 people and have seen us through the whole wild startup ride of ups, downs, sideways, back ups and more. It’s been incredible. The learning and leadership experience of a lifetime. But there was one time in particular that no one prepared me for…

In the summer of 2015, Udemy was 150 people… and by the end of 2016, we were 250. And that is when everything went upside down.

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All the things that used to work stopped. All the things we thought would work didn’t. And in a certain sense, we had to re-invent how we operated as a company.

And I blame it all on Robbin Dunbar.

Who’s Robbin? Why did things go upside down at 150 people? What did we learn? And how did we survive?

Well, if your startup is getting ready to pass 150 people and you’re looking for a leadership crash course on mission, vision, strategy, culture, team building, org design, goals, communication, and everything in between… please step inside!

Who this course is for:

  • Leadership of startups between 30 and 300 people
  • Team members of startups between 30 and 300 people
  • People thinking about joining startups between 30 and 300 people



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