10 Years in the Startup World (for those considering a job change)
Last year, a colleague at a growing startup and I met for coffee. We had the usual catch-up conversation talking about life, family, CAC, LTV and how they were impacting the overall growth of the company. By the end of the conversation, it became apparent that they weren’t sure if they were in the right department/position and while we parted ways with smiles on our faces, there was a lot more on their mind that didn’t come out. This person genuinely wasn’t sure how to proceed at their company or with their career.
That night, I spent some time reflecting on my 10 years in the startup world here in Boston and shared the following thoughts. Just last week, this person sent me an email telling me how many times they had re-read the below over the past year and it should be shared publicly for others feeling the same way…so here it is…
Intro:
Wanted to reiterate a few things because I know the mindset you’re in right now and I know how lucky I’ve been to have people help me during these types of times. I’ve been able to learn from some absolutely incredible bosses (including current) who were all driven to help me advance in my career from day one. We just had an open dialogue from the start that went something like “clearly Dan you want to be a marketing leader. While I hope you end up being that leader here, I’ll do everything I can to help you get there regardless.”
That’s not something most bosses will ever say. When I was a specialist, they put me on a plan to manager. When I was a manager, they put me on a plan to director, then VP, then CMO…etc. The point here is there are things I definitely wouldn’t have thought of if I hadn’t worked for some of these uncommon and high-powered professionals. The one thing I’ll say that I was extremely hard working for these people and made them real money, working at 3 AM if need, increasing numbers by hundreds of percentages and effectively managing teams. The one thing you’ll find is that if you’re willing to work harder/smarter and think about things creatively and differently than other people, you’ll keep moving ahead faster. It’s amazing how true this still is today. You’d think more people want this or understand it, but it’s not the case.
You’re asking the right question at the right time in terms of is this company/position right for you, so you shouldn’t feel bad about that or be hesitant to chat with other people including your CEO. It’s clear you love your company, have been there for years and anyone can see that, so you questioning your current career path isn’t going to be off-putting to people. If you start to become unengaged and it’s clear you’re not as productive, then I could see management taking notice of that but I don’t get the sense you’d slip. Here are a few things I’d think about (and don’t stress about any of this too much, at the end of the day your life is awesome and so privileged comparatively to the rest of the world).
1. Marketing Career Path:
You know the deal here, everyone needs a VP of Marketing and one of the reasons that there are so few CMOs in Boston is because most VPs aren’t cut out for the role or leadership doesn’t believe the marketing is a C-level role…this can be quite different from NYC/SF, but there’s a huge opportunity to be an established marketing leader within the community. The thing is, you have to know you want it. When I look at the image below, I get excited and can’t wait to build out most of these functions, how do you feel when you look at it?
While it’s going to be different at every company, this is more or less how I like to start conceptually when building out teams. If this stuff excites you, start learning what you don’t know and the more boxes you can check off the closer you are to being a head of marketing. It’s not as important that you can DO all of these things (or incorporate them all and there are plenty of things missing from this chart, it’s just a visual example) but more so that you acknowledge they exist and can hire/manage accordingly, as well as list them in order of importance for your specific company. The best marketers in Boston/anywhere are the ones that can think creatively and find new ways of doing meaningful things at scale. Quant is important but you can always hire for quant, it’s much harder to hire for creative ideas that produce revenue. Also, if you want to be a CMO, you need to be comfortable managing 10+ people at least and hopefully more.
2. Culture
I’ve accepted the fact that I’ll probably never have it as good as I had it at HubSpot. During my two years there, our team was so much fun, so hard working and we moved numbers up and to the right every week in a meaningful way. I miss that culture probably once a week. While you don’t work there, you do love your current company culture and it’s a bit of a first love for you. You need to expect a worse culture if you move on. Not saying other places don’t have great cultures but there’s something about the first great culture you experience that sticks with you, kind of like your first kiss or first date.
From what I’ve seen at your startup, you guys have such a unique culture, I’d be worried about certain people going elsewhere and not being successful because the culture is so different, and I’ve seen this a lot with other startups with unique cultures. It’s ok to go to a place with a “worse or different” culture than your current company, just know that going in and plan accordingly, don’t ignore it. They may not value marketing as much, or you, your career, data, humanity, kindness…etc…the best place for a chop shop to hide is in the spotlight, and they do exist. Also, as I said this morning if you take another startup role, expect that in 6 months it could be over, that’s just how our world works. If you move on from your current role, you’re giving up stability for an unknown amount of time, which may or may not matter to you.
3. Personal Brand
The question is, what do you want to do? If you want to stick with your current startup through an exit, then you need to impress your execs. There’s nothing wrong about staying with a great startup for 10 years. If you guys can sell for $300M and you can grab 1%, that’s huge! You’re already X years vested, you know the management team, which is critical, and you know the company. A lot of people left currently public startups early due to “career growth” and are kicking themselves in the face now. This comes down to what you want to do though. I’ve always viewed startups as harder to work for than most corporate jobs so I’m in for big equity. If I don’t have it, it’s not worth it to me. Now, if you do want to move on eventually, then at some point, you have to make a name for yourself, outside of just the brand. When companies are asking who the best marketers are in Boston, you need people to say you. You need to be public, get PR, speak at conferences, get featured on major publications, lead local workshops and grow your team and impact so that when the growth of your company is highlighted, you’re a visible part of the story for others to see. That’s the most important part.
4. Compensation
Everyone has his or her own number; the more important thing for me personally is equity. If you’re going to join an exec team or early on, think whole percentage points and make sure you have a legal expert review everything.
5. Purpose/People
Your current startup is an awesome company with a great mission. You have to ask yourself what you’re passionate about professionally when thinking about the future.
When I exited a former job and took my first official “CMO” position at another startup in Boston, I did it because I really wanted to stay in Boston, and here comes the kicker…I had a personal goal to make “CMO” by 30. What an idiot, biggest mistake of my career. I let the idea of attainment cloud my vision on every level one goes through when considering a new job. Needless to say, that experience ended fairly quickly. In the end, I’m 100% to blame because I took the role and everything in start-up world is at-will employment, it’s all risk. But, if you’re not stoked about the company, the mission and your exec team 100%, don’t do it. There are other opportunities even if you can’t see them at this exact moment. It’s better to go slow on job transitions than make abrupt choices. I consider this the most important lesson I’ve learned as a professional to date. It’s not always fun to share this stuff, but maybe it will help you avoid the same mistakes I did. In the end, as long as you learn from stuff like this, everything works out just fine J
Outro:
If you’re anything like me, you live in your head and are always questioning things. While it’s a blessing as a marketer/BD person, it can also drive you crazy from time to time so keep asking questions, go slow, sleep on things for weeks if needed. I’m genuinely interested in seeing you continue to do well according to your expectations and goals, always happy to be a sounding board.
Best,
Dan
