4 Lessons Learned Working at HubSpot

After two great years, I left HubSpot last month.

I’m not sure what’s next, so don’t expect a forward looking just yet. Right now, I’m focused on taking stock of all the things that I learned from HubSpot, all the great folks with whom I collaborated and the new perspectives on the software business I gained. HubSpot is an incredible place — I learned a ton. Here, mostly for my own documentation, are a few of the key lessons that I either learned or were reinforced working at HubSpot.

1. Be unafraid to make aggressive changes

This is the thing I would emphasize more than any other. At HubSpot, things are generally going well. Its no secret the business is growing. I think one of the reasons it continues to grow is that leadership team is unafraid to tackle problems with big changes. They don’t save big changes for when the business is facing big, threatening problems. They are aggressive in solving the monthly/quarterly problems with bold change. It pays off.

2. Transparency empowers

I have never ever worked at a place as transparent and open as HubSpot. Virtually everything you’d want to know about the business is known and shared on the HubSpot wiki. To paraphrase Dharmesh, you need to have a really good reason to ¬†keep something a secret at HubSpot. ¬†With more people empowered with more information, better ideas are generated, millions of small decisions are better informed and the business just runs smoother. People trust each other with open transparency.

And this extended to our relationships with our customers. We were able to more effectively work through problems or changes with the product by being 100% honest with our customers at HubSpot. The more they were informed, the more our customers trusted our judgement and accepted changes to the HubSpot product.

I loathe the prospect of ever working somewhere that wasn’t as transparent and open as HubSpot.

3. The answer is always “ship it”

Hat tip to David Cancel here. As a product manager, you’re not always sure when to ship something or take the next big step. And the answer is almost always “ship it”. Should you wait for the next round of imminent improvements to the tool? Do you wait for another round of performance improvements? Do you wait for the next round of UI tweaks? Don’t wait. Ship it. Those improvements might end up being the least important thing you should be focusing on. Your priorities need to be customer focused. And if you are teetering on making something more widely available, just ship it. You’ll learn from your customers if your priorities are right.

4. Use good judgement

This one comes from observing Brian Halligan. Occasionally there would be some cultural question or some HR policy debate that would bubble up. And eventually, Brian would weigh in with his “ruling”. And it would almost always be “use good judgement”. Should you come into work when you’re sick? Use good judgement. Should you come in when its snowing? Use good judgement. How should you behave on social media? Use good judgement.

If you have adults at your company (and having aged a certain number of years doesn’t mean you are an adult — I forget where I stole this idea from), trusting them and empowering them to make their own decisions ensures happy employees, and usually the right outcomes.

(Ex-)Hubspotters, what did you learn?

4 responses to “4 Lessons Learned Working at HubSpot”

  1. Peter says:

    Great, great post. I was at HS for a short time and, whilst it wasn’t necessarily the right “fit” for me at the end of it all (more on a balance level at that time of my life) I learned that to be great you have to be surrounded by greater people than you – don’t fear not being the smartest person in the room. It’s a message that should be tattooed on the walls at HS because it’s so true there.

    Similarly, I came to understand in my career that information, leadership and knowledge are all too often silod by rank in a company – i.e. “because” I am CEO, this is the way it is. No questions asked. Or questions are tepidly encouraged but never really listened to. HS taught me very clearly that whilst of course that has some resonance at various points in time, “good judgement” would also indicate that in fact decentralization of power in its most aggressive form gives rise to much more liberating discourse, conversation and ultimately personal, professional and company development. Everyone’s a winner. Where I can, I’ve attempted to apply those learnings at all phases and will continue to.

    HS remains an amazing place to say “I did that” albeit short.

  2. admin says:

    Peter, great comment.

    Stepping back from the idea of transparency and “use good judgement” is the meta concept that the culture at HubSpot empowers and distributes responsibility. The result is a greater sense of personal ownership across the board. And fewer people who are their to just execute tactical drudgery. There is very little middle management.

  3. Rob Sobers says:

    Nice post. As a relatively new HubSpot customer, I love the idea behind the product and company — tackling bold problems and having a transparent culture.

    I learned about HubSpot when I saw Dharmesh speak at Business of Software in 2009, when I was working at Fog Creek Software. I liked his metric- and honesty-drive approach at building a software company.

    The one thing I’ll take issue with, however, is #3 (Just Ship It). More than with any software product before, I’ve been burned by instability with the HubSpot software. I’m all for shipping software before it’s been polished, but if the thing you’re shipping prematurely is too slow, or too buggy, or breaks backward compatibility it can really impact your customer’s business in a bad, bad way.

    Maybe HubSpot needs to apply a bit of #4 to #3: when trying to push the envelope and ship features fast, use good judgement. If there’s a potential of hamstringing your customers’ business, do another round of QA.

    • Kris says:

      I couldn’t agree with you more about the pain and instability of the HubSpot Platform. I do wish they slow down to do more testing, because we’re constantly using the system and I often find so many bugs that I feel like I’m using a beta system more than a fully polished app. If I could leave this system, I would! But we’ve invested so much time into getting it to work that I feel like we’re stuck. I estimate it’s one phone call to tech support a week. I’ve learned not to trust the system and to verify that forms/emails/workflows that were working are continuing to do so. A shockingly high amount of the time, systems and tools simply break. It’s cost us more than I can say in staff time.

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