I meet with lots of CEOs who want to pick my brain on the journey from starting to scaling HubSpot as its CEO. It was indeed a long strange trip, but one I learned a lot on. Here are some of the things that I learned that I hope might help some of you CEOs out there or potential CEOs out there who want to scale your business.

Keep your head in the sky and your feet on the ground: I “think” Eleanor Roosevelt was the person who dropped this great piece of CEO advice. You need to paint a compelling vision of a terrific future for your company while at the very same time dealing head on with the very real problems you have today. Toggling between those two realities is a delicate dance that takes some practice. …Btw, if you give your investor the line that you “focused on the future and not to worry too much about this quarter’s numbers,” prepare for them to vomit on your sneakers.

You’re being watched 10x more closely than you think: I often hear from HubSpotters about something I said 10 years ago in a hallway conversation that I had long forgotten. It may not seem like your team pays any attention to you (it seemed that way to me), but they are very closely observing what you say and your body language. This can be a super-power or kryptonite for you.

Watch the competition, but never follow them: I got this line from Arnoldo Hax, my strategy professor at Sloan and said it over and over and over again such that it is ingrained in HubSpot’s DNA. It is relatively obvious at this point that HubSpot competes with Salesforce.com (a formidable competitor). We very carefully watch them, but try not to “follow” them – see next lesson.

When everyone is zigging, you should zag: Regardless of what you think of Peter Theil’s politics, he wrote a really good book on startups called Zero To One. In there he talks about how you need to be right about something that everyone thinks you are wrong about for a long time. This type of “zagging” worked for HubSpot three times. First, we decided to focus on SMB (more M than S, btw) and stuck with it when everyone and their brother thought we should move to the enterprise. Second, we decided we would move from a marketing application company to a CRM platform company, competing with Salesforce, when everyone and their sister told us we were crazy to try because they were too formidable to compete with. Third, we decided we would “build” our CRM in house as opposed to acquire our way there when everyone and their cousin told us that we needed to follow ye olde CRM M&A franken-playbook.

“Don’t trash talk”: I just watched the brilliant Wimbledon finals and I always appreciate how respectful the players are toward each other and their predecessors and how they express it. I feel the same way about Salesforce, they are a very good company that is hard to compete with and no good comes in “poking the bear.” [credit to my co-founder Dharmesh for coming up with the “poke the bear” analogy and many other brilliant things.]

Times change, teams change: Our original management team at HubSpot was brilliant and I just assumed it would be the same crew we’d be in the trenches with for the whole run. That turned out not to be true and if you step back, you’d see that we are probably on our third or fourth management team. People kind of self-select for stage. Those early leaders we had were super risk seeking and really well suited to that phase and have all gone on to do awesome stuff in that early stage. I’m super proud of them. …I guess my advice is not to sweat it too much if you need to rotate leaders on your team as you grow. The company and the leader are likely both better off.

Treat your culture as your second product: Lots of ink has been spilled on this topic re HubSpot, but it’s worth spilling some more. We have two products, one we sell to our customers (HubSpot’s CRM) and one we sell to our employees (HubSpot’s culture). Like your product, you need your culture to be unique relative to the competition (for talent) and you want your culture to be very valuable. Like your product, when it is unique and valuable, your company turns into a magnet that attracts and retains terrific talent. And also like your product, it’s never done – it needs continued interation.

1 back, 2 forward, 1 back, 2 forward: From the outside, HubSpot might seem like a smoothe up and to the right story. It belies what actually goes on inside. The best way I’d describe HubSpot is two steps forward followed by one step back followed by two steps forward followed by one step back etc. As the CEO, you need to be steady in the good times and bad – there will be ample helpings of both. …Also, you shouldn’t wait for a 10 step forward moment. For us, it never happened. We never signed a customer that changed the game, made a hire that changed the game, formed a partnership that changed the game. It was grinding those two steps out at a time.

Never waste a good crisis: See previous steps back. There were plenty of problems and crises along the way. One of the things that served HubSpot particularly well is we recognized the crises when they were happening and were very explicit about trying to take advantage of them to learn and get better. Ironically, one of the best “crises” that happened to us was a long outage on the last day of the first quarter in 2019. It led us to make wholesale changes to the way we built/delivered products and enabled us to move the culture to becoming even more customer centric after experiencing that crisis.

Recruit from companies just a few years ahead of you: I’ve found this applies to board members and executives. When we hire folks from companies that are several orders of magnitude larger than HubSpot, there is an impedance mismatch. They are dealing with different issues at a different scale. We’ve had good luck with hiring folks who are at companies we admire that are just a few steps ahead of us.

A truly independent board member is worth her weight in gold: We have had several along the way from companies that were ahead of us in size, but still growing fast. Along the way, they helped us avoid untold landmines as they had “already seen the movie.” The other benefit of a truly independent board member is she is typically a good balance with your venture capitalists. Btw, in the early days, this was Gail Goodman from Constant Contact and later it was Jay Simons from Atlassian.

Feedback is the breakfast of champions: Once a year we had my co-founder, , do a 360 review for me that was like pure gold. His method is highly replicable. He basically gave an NPS survey to about 25 folks up and down the org asking two questions: (a) “Your likelihood to recommend Brian as the CEO of HubSpot” & (b) “Why?” He took the answers to those questions and put together a 20 page document for me. He found the themes in the feedback (people wrote novellas) and grouped them together with example quotes to back up the theme. For example, “Brian is good at setting and selling the vision for HubSpot” would be the theme and then he’d pick out 6 or 7 direct quotes that backed this up. …Now, not all the themes were positive like that one. The first 10 pages were my “feature” themes and the back 10 pages were my “bug” themes. I was convinced I was the world’s best CEO after page 10 and the world’s worst CEO after page 20! I shared the feedback with the company and board in a document that was my own “performance plan.”

Transparency builds trust: We were always very transparent with employees (see previous), customers, partners, and investors. When new execs would come in they would always be surprised at our level of transparency and a little uncomfortable at first. …I think that transparency builds trust. I think that trust ended up working both ways.

Your greatest strength turns into your greatest weakness: Like a lot of founder/CEO types, I like to make decisions and control things. This tendency works great when you are 10 people and can work up to 50 people, but after that, it turns into a giant disaster for your organization and yourself. Every year you need to delegate more and more – this was very unnatural for me and I suspect for many scaling CEOs. …This lack of delegation had lots of frequent flier miles on my previously mentioned annual reviews.

Make a large pie & take a bite along the way: One thing Sequoia did in our Series D round was allow us to sell some of our common shares to them as part of the round. This turned out to be a great idea for me and Sequoia. It “stiffened” our backbone when it came to acquisition interest and kept us focused on building a company our grandkids would be proud of. This had the added benefit of aligning our interests very well with our investors. …In retrospect, it was likely one of the worst financial decisions I’ve ever made, but I don’t regret it as it did the trick in the moment and the pie’s plenty big.

The IPO is the starting line: The day of the IPO was one of the best days in HubSpot’s history – lots of laughter and a lots of tears as well. In the years leading up to the IPO, I repeated the line “the IPO is the starting line” hundreds of times and I can’t say for sure, but I think it kinda worked. I wanted folks focused on building something special that ultimately our grandkids would be proud of. …The other thing I did is I never talked about the stock price and would ask folks around me to stop talking about it whenever I heard those conversations. Focusing on the price will drive one bonkers – it has a lot to do with our performance, but has a lot to do with many things out of our control.

Know when to hand over the keys: One day in 2021 I had a very bad snowmobile accident that nearly took my life. Lying in the snow badly injured, I had some time for introspection while waiting for 911 to arrive. I basically decided while lying there that I didn’t want to be CEO of HubSpot anymore. I wasn’t getting the joy out of it I once did and I didn’t think the next phase of bringing HubSpot from $2 billion in revenue to $10 billion in revenue suited my skills very well. I stewed on that for awhile and then when I recovered about 6 months later, I handed over the keys and became chairperson of HubSpot.

Pick your successor carefully: I ended up handing those keys to who has done a terrific job. There are a few reasons she was a good fit. First, we worked together for a while and I got to know her – we promoted her from within. Second, prior to HubSpot, she worked at Dropbox and Workday, two companies that at the time, were “a few steps ahead of us.” Third, while I was out on medical leave, she did a terrific job of running the company on my behalf. …I hope none of you CEOs have to go through a near death experience to decide to step down, but I might encourage some introspection on when that right time might be for you. Most wait too long, imho.

Chairpeople don’t drive: Once I took on the chairperson role, I talked to several other founders who have gone through similar CEO transitions and taken on chairperson roles. The one thing I heard from everyone was to “let go of the steering wheel.” The failure case is that the chairperson has to go back in and be CEO again a la Howard Shultz at Starbucks.

Being CEO is overrated: A lot of people want to become a CEO, including me 18 years ago. I’d just tell you that it is an overrated job. You work for everyone, including your customers, partners, employees, and investors. It’s not the other way around. You are on call to them at all times. Be careful what you wish for!

Let me know if these were helpful. If folks would like, I could deep dive on a few of these with examples and such.