Letter to a new startup CMO

Len Markidan
Dec 23, 2020
Dear new startup CMO,

Congrats on the new gig!

You’re probably excited, proud, and if you’re anything like I was, having an intense “oh, shit” moment when you realize the gravity of what you’re now responsible for.

You’re also probably looking for a playbook to follow to ensure your success.

I’ll deliver the worst news first: that playbook doesn’t exist. 

You’ll have to make thousands of decisions a month, and no existing playbook can tell you how to make all of them.

But it’s not all bad news, because as CMO, you get to write your own playbook.

And you’ll get thousands of chances a month to learn, improve, and even when things go wrong, correct them.

Three years ago, I came into my role as CMO at Podia with plenty of marketing experience, and some management experience, but this was the first time the buck truly stopped with me. 

It’s been an intense, gratifying, and amazing three years (so far…I’m not going anywhere!), and most importantly to me, I’m happy with the job I’ve done.

Without giving numbers away, the company has roughly 40x’ed revenue since my first day.

I spent a lot of time looking for that playbook when I started, and of course, I never found one. 

I wrote my own, and have learned a few things — some more painfully than others — along the way. This is my attempt to document that for you.

Every marketing leader is different, and this isn’t intended to be a comprehensive overview of all the different ways to do things.

These lessons are from just one journey: mine. 

With that caveat out of the way, here’s a collection of lessons I’ve learned, so far, in my first CMO role.

Learn from others, but contextualize everything

There’s plenty of advice out there, for those who seek it.

This letter is one example of that.

Seeking out conversations with marketers and leaders a step or three ahead of you is a valuable way to learn and become better.

And you should seek out smart people to help you with questions you have, or to help you uncover questions you don’t have but should.

But the context for almost every piece of advice you’ll get is different from what you’re facing.

Consider the person and the business the advice is coming from:

  • Were they at a different stage when they implemented this advice?
  • Are they in a different market, with different customer tastes?
  • Did they have different resources than you currently have?
  • Did it happen in a different time, with different market and cultural conditions?
  • How are their values, goals, and business different from yours?

The goal of seeking advice shouldn’t be to reproduce someone else’s approach in your business. 

The goal of seeking advice should be to better understand how other smart people think and approach similar problems, so that you can use your unique perspective to make the best decision for your business.

The times I’ve gotten the most value from advice haven’t been when I took action on the advice directly; rather, they’ve been when I used the advice to think about a problem differently, and then take action — even if not always the advised action — based on that thinking.

How to choose your first marketing channels

One of the first, and hardest, marketing questions you’ll be expected to answer is “what channels should we be pursuing to start?”.

Start with the intersection of:

  1. Where your customers are, and
  2. What and your team (if you have one) are best at

Many marketers make the decision based on only (1) or (2), but this is a mistake.

When I joined Podia, my first big undertaking was a customer research project. I interviewed dozens of customers, surveyed many more, and spent weeks exploring the market and competitive landscape.

It was clear that there were several channels we could pursue.

However, most of my marketing success and learning had been in the field of content marketing at Groove, so we started with what I knew.

I had general knowledge of channels like affiliate marketing, event marketing, and social media marketing, though I was by no means an expert there.

But I had been living and breathing content marketing for the better part of a decade prior. 

I knew how to start from nothing and build a successful program, and so that’s what we did, going all-in on content marketing.

True success in any other channel didn’t come until much later, when I had the opportunity and the bandwidth to learn much more about those channels.

Every business has a limited marketing budget, and this approach de-risks your marketing investment by focusing on what’s most likely to work.

Marketing deposits compound over time

Many of us spend our careers looking for that perfect, blow-everyone-away marketing campaign that will 10x the company’s growth.

The path to success for most marketing efforts looks very different.

Spend time thinking about those moonshots, of course, but don’t discount the importance of doing lots and lots of little things, and making small, consistent “marketing deposits” every single day.

Every email you send, every social media posting, every ad, every webinar…these are all opportunities to add to your brand equity in the marketplace, and you should ensure your team is making small deposits as frequently as possible.

Do this every day for five years, and you’ll all-but-certain to be an overnight success.

Find your first day jitters again

That way you feel now, where everything is a blank slate and you can do anything?

It’s liberating. 

Everything you try will be new and uncomfortable, so you can’t avoid the discomfort. You’ll have to push through it to get anywhere.

But when things start to work, you’ll get more comfortable.

You’ll know that what you’re going to do will work, because you’re simply doing more of what already works. It’s minimally risky, and likely to make a positive impact.

That’s a good thing, and you should certainly pour fuel on a flame that you’ve worked hard to successfully ignite, but don’t let that be all you do.

Keep taking good risks. Try new campaigns and push your team to take on new projects that are outside of your comfort zone.

Try to find those “first day jitters”, the ones that make you feel like everything is a mess and you’re in way over your head, as often as you can.

The biggest breakthroughs we’ve had have come from exactly those types of projects.

Hire to relieve pain, not to create work

Always opt to under-hire rather than over-hire. 

When staring at the blank marketing branch of your org chart, you’ll be tempted to put together a “stack” of teammates.

“We’ll need an email marketer, a social media marketer, two content writers, a partnership manager, and a marketing operations manager.“

If you’re not trying to build a VC-fueled unicorn (which the entirety of this letter assumes you’re not), then slow down.

Hire to relieve the pain of valuable work not getting done, not to create unvalidated new work that didn’t exist before.

Additionally, don’t hire for a role until either:

  1. You or someone on your team has done it (and netted positive results)
  2. You’ve hired a consultant, freelancer, or agency to do it for you first (and netted positive results)

Doing the work yourself is the best way to understand what it means to do the work well, as well as to validate whether the role is actually needed, and brings a net positive impact to your business.

The second best way, and often the only way for work that requires unique skills you may not have or can’t easily learn(e.g. data analysis or highly technical projects), is to hire someone with those skills to help you on a contract basis. While the upfront costs may seem higher than a salaried employee, the long-term costs are much lower.

Managing people is going to take more of your time than you think, and everyone you hire is someone you need to manage, and, ultimately, answer for. 

If things don’t work out, you have to let that person go, and both of you will have to deal with the fallout.

So tread carefully here.

Get stakeholder buy-in

As a leader, you have a magical weapon that can make just about anything happen: your title.

At the top of the org chart, you can pull rank and push things through, meaning that things in your head can become reality much faster than before.

Don’t get too comfortable using this weapon. In most cases, it’s the worst way to get the best results from your team.

Antoine de Saint-Exupery’s quote about teaching your team to yearn for the vast and endless sea has become management cliche, but it’s for good reason. 

People will do a much better job at things they want to do, and things that they’re invested in, than they will with things simply assigned to them.

Invest time into talking with your team regularly about the company’s vision and goals, how their projects align with those, and the impact that they’re having on your customers. And when you’re planning to assign a new project, take the time to get the team excited to work on it, get their input, and give them a reason — beyond keeping their job — to knock it out of the park.

Document everything

Treat every job you do more than once as something you’ll need to teach someone else to do, because you almost certainly will.

Document your recurring tasks with clear descriptions, screenshots, and if helpful, video walkthroughs, and keep it somewhere that everyone on the team can access (we use Slab for this).

At best, a lack of documentation will create a time-suck for you every time you need to teach a team member to do something. 

At worst, it’ll mean that you’re going to get called in while you’re on vacation to do some menial-but-urgent task that anybody could do, but only you know how to do.

Communicate often

You’ll hear legends of “entrepreneurial” employees who can be handed a project, and then go off, do the work, and come back with a finished product.

These people exist, and I’ve been fortunate to have them on my team, but this doesn’t mean, as some mistakenly believe, that you should hand off the project and wait for “the big reveal”.

The big reveal is the worst way to achieve an outcome that’s close to what you envisioned when you first decided to take on the project.

Communicate early and often throughout a project’s development, scheduling regular check-ins (at least weekly) to go through progress, and make (either macro or micro) adjustments to keep things aligned with your expectations.

Even the best team members can’t read your mind, and assuming they can will only set you both up for disappointment.

Note that communication doesn’t mean that you have to have lots and lots of meetings. Nor does it mean that people always need to be on Slack, and that you need to interrupt your team members to give you updates.

In fact, we only have one scheduled, standing meeting with the Podia team. But we’re always communicating, whether via Slack (often asynchronously), long-form Basecamp updates, or impromptu Zoom calls. 

I’ve found that the projects where we communicate least are the ones least likely to be successful, and the ones with regular, frequent communication are the ones most likely to succeed.

Manage up

I often hear marketers complaining about CEOs that don’t value marketing, or who are otherwise bad to work for.

And yes, there are some CEOs who you’ll simply never be happy reporting to.

But often, these common complaints can be resolved - and your life made so much better for it - by learning to manage up.

Your CEO doesn’t value marketing?

Show them its value.

They’re micromanaging you?

Beat them to the punch with more proactive communication, and make sure they have the answers they want before they ask you.

They’re annoyed at how long something is taking?

Figure out how long they expect it to take, why they have that expectation, and help bridge the gap between their expectation and reality.

I’m not saying that it’s necessarily your fault your CEO does these things, but complaining and waiting for things to change isn’t a winning strategy. 

Either do something about it, or leave. 

Though, I’ve known more than a few marketers who left, and then complained about similar treatment at their next job, too.

It is in your best interest to learn to manage up.

I did a 30-minute training on how to manage up for Forget the Funnel, which you can watch for free here

Manage across

Build relationships with other department leaders, outside of your all-hands leadership meetings.

Set up a monthly call with the people leading your development, support, and any other major departments within the company.

These are great for:

  1. Hearing about the challenges that the rest of the company is facing, and what they’re learning.
  2. Understanding the goals that other departments have, so you can align them with your own.
  3. Keeping everyone aligned on roadmaps and projects being led by other departments, so you can better support each other.

In many companies, when marketing needs help from engineering or support for a campaign, that’ll be the only time the CMO reaches out to the other department’s lead for help. 

This transactional approach makes these conversations an annoyance and a chore for the other party. 

But by building these relationships over time, trusting each other, and connecting regularly, the leadership team will truly feel like a team, and you’ll be happy to help each other succeed.

It also increases the number of smart people within your organization who come to you with ideas about how the company can do a better job.

It’ll never look like the ideal

You’ll hear stories about companies with picture-perfect marketing workflows, pristine data dashboards, and “levers” they pull to make the marketing engine cleanly scale up or down at will.

Oh, and their teams work in complete harmony, their code is perfect, and they haven’t sent the wrong email to the wrong segment since 1992.

Of course, when I describe it this way, it’s obvious that this doesn’t really exist, but it doesn’t stop us from comparing ourselves to companies who look like they have everything figured out so neatly.

Just like humans, every successful business is dealing with its own mess on the inside.

Strive for excellence, but don’t assume that everyone else achieves it every second of every day.

That assumption will make you both sad and risk-avoidant, both of which are bad ways to live and work.

Through partnerships and just by getting to know people there, I’ve seen the insides of some of these “ideal” companies, and I’ve almost always walked away thinking that we’re doing a lot better than I feared.

What questions do you have?

I want this to be the most useful letter every new CMO who reads it has ever gotten.

I’ll continue to update it, and if you have a question I can help answer, let me know: either leave a comment, email me, or reach out on Twitter.

Good luck. The fact that you care enough about doing a good job to search this out, and read it in its entirety, tells me that you’ll be just fine.

All the best,

1 comment

Oct 4, 2023

This is great!