I am often asked by 20-something employees at my company, HubSpot, if I would recommend that they get their MBA. While I never flat out say no, I do offer my perspective about the value of learning key lessons -- while getting paid -- by working at a company that is in the process of achieving scale. Most of these learnings are simply not possible in the classroom. Recently, after one such conversation, I grabbed a whiteboard and started to list the reasons. I stopped at 51 -- I had run out of whiteboard. 

I posted the list to our internal wiki. It is one of the most commented-on posts I've written, with many veterans and young professionals offering their own lists and observations. I thought I would share it here for anyone weighing such a decision, and for managers of those employees.

My first job out of college was at PTC (back then it was known as Parametric Technology Corporation), a company with a few hundred employees and doing really well at the time. I started off as secretary for the vice president of channel sales. When I left 10 years later, I was a vice president, and PTC had thousands of employees.

Because there are so few high-tech companies -- especially in Boston, where I live -- that grow to a thousand or more, it is incredibly hard to acquire the knowledge to actually scale up a company.

Here are just some of the things I learned firsthand or by observing:

  1. How important nailing hiring criteria was in scaling.

  2. What it felt like to manage people.

  3. What it felt like to make unpopular but correct promotions.

  4. What it felt like to bet on someone smarter than me and back them.

  5. What it felt like to manage and how that felt different than leading.

  6. What it felt like to manage managers.

  7. The pain of having too many layers and having a top-heavy organization.

  8. The pain of having too few layers and having too flat an organization.

  9. The pain of having high employee turnover.

  10. How to fix the problem of high employee turnover. (Hint: Develop your people.)

  11. That to keep up with growth, you are constantly reorg-ing, and I got used to dealing with that.

  12. I got very used to constantly running out of office space.

  13. I got good at dealing with international languages.

  14. I learned how to deal with international cultures and how to bend our culture to fit, but not turn our culture inside out.

  15. I got used to the process of localizing your product and company quickly.

  16. How to mess up an acquisition.

  17. How to do an acquisition right.

  18. How the quarterly cadence of a public company feels.

  19. How important making your numbers consistently is.

  20. How painful it is to miss your numbers when you are public.

  21. How to deal with the constant stress of having a number over my head for years.

  22. What it was like to have a crap boss.

  23. What it was like to have an awesome boss.

  24. How to deal with "imposter syndrome."

  25. How important good communicators were.

  26. How to position a product.

  27. What it was like to ignore the signals of disruption.

  28. What disruption felt like from below.

  29. How to win against bigger competitors.

  30. What it felt like to work in a crappy culture.

  31. When to fire someone (usually too late).

  32. How to fire someone.

  33. How not to deal with people when they leave your company.

  34. What it felt like to work in a field office away from headquarters.

  35. How important the first person I hired in every new office was.

  36. How to open field offices.

  37. How to scale field offices.

  38. What it felt like to be in a huge headquarters.

  39. What it felt like to have an office in a city versus in the suburbs.

  40. What it is like to work with finance people and what they cared about.

  41. What it is like to work with legal people and what they cared about.

  42. What different types of marketers did.

  43. How to build a direct sales organization.

  44. How to build a channel organization.

  45. What it feels like to have channel conflict.

  46. How to sell.

  47. The value of a well-designed commission plan for a sales organization.

  48. The downside of sticking too long with the same commission plan for a sales organization.

  49. To treat customers well.

  50. The value of a platform.

  51. The old marketing playbook, which enabled me to think of the new marketing playbook.

I had planned to get an MBA while I was in my 20s, but I was learning so much at PTC that every year when it came time to do my application, I decided not to do it. I ended up waiting until I was 37 years old to get my MBA.  

The 10 years at PTC were kind of like shoots and ladders from a career perspective. I went forward fast and then I'd stay sideways awhile. I ended up staying for 10 years, and I'm sure glad I did. I wouldn't have had the personal capital in my savings account to start HubSpot, or the network to help vouch for me, or the confidence to keep going.