10 mistakes I made in my first head of marketing job

Candidly sharing some of the mistakes I made early in my leadership career so you can avoid them.

Hello, I’m Hema, and welcome to my newsletter First Impression. Each month, I write an in-depth post on marketing for early-stage startups. Join startup founders, GTM leaders, and practitioners, and subscribe to get the newsletter in your inbox.

My last post was about why your CMO wants to quit your startup, and I’d be remiss if I didn’t write about the mistakes I made in my first leadership role.

👉🏽 TL;DR If you are skimming, every mistake has a quick TL;DR at the bottom 😊.

Mistake # 1: Too focused on being an interviewee and not interviewing the startup.

When I started interviewing for VP of Marketing roles, I was so focused on doing all my homework on the startup and its product that I did not think hard enough about interviewing the founders and the leadership to ensure they were the best fit for me.

Of course, I asked the big questions: What’s your vision? Growth strategy? Goals and objectives? etc., but I did not dig into the sticky, challenging questions. Here are a few I’ve learned to ask now:

• What projects/ideas have you recently said “no” to and why?

  • Helps you get a sense of their priorities and whether they are chasing shiny objects.

• What does the leadership team disagree on the most and why?

  • No one will admit to the skeletons in their closet, but they certainly have them. This is one way to get at them.

• What was the most recent hard choice the business had to make?

  • Are they honest? Was it really a “hard” choice or are they doing too many things?

• Why did the last VP of marketing quit?

  • Ask everyone in the leadership team this question and observe how aligned or misaligned the responses are. It speaks volumes about their culture.

👉🏽 TL;DR Interview the startup as much as they interview you and make sure they are a fit for you!

Mistake # 2: Believing that I needed to be an expert in all aspects of marketing.

I was strong in strategy, brand, product, and customer lifecycle marketing. I was decent at partnership marketing. I was not an expert at paid advertising or SEO. But I assumed I had to be great in all aspects of marketing to be a leader.

After sweating it out for a few months and spending way too much time with SEOmoz, I realized I would never be great at it. Finally, I found a fantastic SEO expert and an amazing demand generation lead. I learned a lot from those two hires.

👉🏽 TL;DR You don’t have to be an expert in all aspects of marketing, but you do need to understand how they work together and see the right signals when something isn’t working. Don’t wait to hire for your weakness.

Mistake # 3: Letting the product team get between me and the customer.

Startups can’t afford big research teams. Typically, there’s one user research or a designer on the product team who does research. This sometimes creates the unintended consequence of all customer research going through this team.

This was the case in the startup I joined. I was frustrated by this gating, and instead of fighting for what I believed in — marketing should be having direct conversations with customers— I worked around it.

👉🏽 TL;DR Never let sales, customer success, or product teams stop you from talking to customers. If you are responsible for driving revenue, you must talk to customers, period.

Mistake # 4: Feeling too ashamed to say, “I don’t know.”

In retrospect, this particular mistake embarrasses me the most. I'm sure some of it had to do with my upbringing, but a lot of it was working for leaders who never admitted they were wrong or that they didn’t have the answer. As a leader, I assumed I needed to know the business and my functional area inside and out.

When I didn’t, I felt that something was wrong with me. I didn’t deserve to be the VP of Marketing. And worse, I expected the same out of my team, which put unnecessary pressure on them. That was really stupid.

With time and the guidance of a good coach, I learned to say, “I don’t know the answer to that, but I can find out.” It not only set a good example for my team but taught me to find the answer and thereby learn something new.

👉🏽 TL;DR There is zero shame in not knowing something. Everyone knows it’s your first rodeo. You have the job because they wanted you. Remember that. And remember, you can always find the answer.

Mistake # 5: Not staying flexible to market changes.

I’m a planner, and I worked with my team to build marketing plans well ahead of the quarter. One quarter, a key competitor launched a massively disruptive campaign we couldn’t ignore. I was completely blindsided, and I had not built any flexibility into our marketing plans.

I resisted responding to this event in a scattershot way, but at the same time, we needed to completely overhaul our plans. It caused a lot of anxiety and stress until we put a new plan in place.

This experience taught me to only lock in forty percent of my quarterly spend, so I have the resources to pivot if I need to respond to changing market conditions.

👉🏽 TL;DR Set aside some budget for the unexpected and stay open to modifying your plans in response to what’s happening in the market landscape.

Mistake # 6: Not managing up as effectively as I was managing down.

Classic rookie mistake, and I made it. I was so focused on building my team and managing my function that I wasn’t paying as much attention to building a solid working relationship with the founders and other leaders in the organization.

Part of the job as a VP of marketing, especially in tech, is continuously educating those around you on what marketing is, what it does, and, more importantly, what it cannot do. You must establish a strong partnership with product and sales leaders to be effective.

👉🏽 TL;DR Relationship matters. Don’t ignore it. Manage up, manage down, and manage sideways too. Good relationships can aid in solving intractable problems.

Mistake # 7: Not sharing both wins and flops.

When initiatives fizzled out, or tests failed to prove the hypothesis, I shied away from sharing those results. I took things way too personally. I thought every failed test reflected my poor judgment. Here are the consequences of not sharing flops:

• It didn’t encourage failure, and it discouraged rapid testing. The whole point of testing is to find winners. To have a winner, there must be a few failures, at least!

• People wondered what happened to all those things we said we would do at the beginning of the quarter. Did we do them or what?

• The organization didn’t benefit from the lessons we’d learned from all those failed tests. They couldn’t see that it made us better marketers.

👉🏽 TL;DR Sharing wins and flops, funnily enough, takes the pressure off you. It shows that you’re experimenting continuously and always learning. What’s not to like about that?

Mistake # 8: Being a hero and not asking for help.

This is another mistake that makes me cringe. Once, a rockstar in my team quit to join a competitor, and another was battling a life-threatening illness. Their work fell to me. No one on the team understood their function well enough to do it. So, I did it, in addition to doing my job. I was doing three jobs.

Instead of managing up (mistake # 4!) and telling my boss that our priorities needed to shift because the team was down by a third, or requesting his help or asking for additional budget to hire contractors, I pushed myself. Not a great example to set for my team.

👉🏽 TL;DR Don’t be a hero. No one hired you because you are invincible. Asking for help when you need it does not mean you are weak or incompetent.

Mistake # 9: Not paying enough attention to optics.

If you are the head of marketing at a ten-person startup, you are part of a close-knit team. It’s wonderful. It’s magic. But when that ten-person startup grows to fifty or two hundred with a bigger leadership team, worldwide offices, etc., not everyone knows who you are or what you do.

Sometimes, I was too focused on hitting my OKRs and managing my team. I didn’t proactively manage how I or my team was perceived. I didn’t proactively showcase their work or do a lunch-and-learn session to share my knowledge.

👉🏽 TL;DR Optics matter. Some people are natural at this. They have a keen sense of their brand image. But if you are like me, remind yourself to pay attention to what’s changing around the startup.

Mistake # 10: Waiting far too long to call out the elephant in the room.

A few weeks into my first VP of Marketing role, I knew we had an onboarding and user engagement problem. The product was not providing a guided experience, and users were not finishing what they had started. The product team prioritized “cool features” over obvious usability problems that could help engagement and reduce churn.

The product team (led by a founder) had such clout and power at that startup that I waited far too long to call out the elephant in the room — there were serious problems with how we were building the product. There was little to no user research, user testing, or any feedback loop.

Even now, when advising or working with startups, I notice new VPs of Marketing skirting critical problems to avoid founder confrontation. But the longer you wait, the harder the problem gets.

Here are a few ways in which I’ve tackled this challenge:

• State the problem as a hypothesis and use data to illuminate it.

• Enroll an objective 3rd party (an advisor, a product or GTM operator) to help you make the case.

• Share case studies, best practices, blog posts, etc., to help bring the team together to discuss the problem.

• Don’t finger-point. Blaming is not going to make you any friends. Instead, focus on enrollment and education. It’ll take longer, but you’ll bring everyone with you.

👉🏽 TL;DR Use your first 90 days to establish your credibility and identify obstacles to growth, even if they fall outside your scope of responsibility. Ultimately, if it impacts revenue, it impacts you!

Finally, if you are a first-time head of marketing, take advantage of resources like Reforge and Pavilion to augment your skillset. I wish I’d had these when I did my first rodeo!

What mistakes did you make in your first marketing leadership role? Share in the comments section below. Wrapping up this post with a little wisdom from Calvin & Hobbes 🐯 👋🏽.