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What I wish I knew as first-time CMO

16 Lessons I Wish I Knew...

I went from Marketing Manager to CMO in 4 years.

And damn did I make a bunch of mistakes along the way.

I didn't realize how different the role of "good marketer" was from the role of "good marketing leader."

After some time now away from a marketing leadership role (I'm retired from being a marketing leader, don't worry) I've had some time to think back on the things I wish I knew then.

Here they are:

16 Lessons I Wish I Knew As First Time B2B Marketing Leader

  1. Forget the acronyms & best practices, use your brain. Ultimately there are only three ways to grow a business: get more new customers, increase the transaction value, increase how often people buy from you. You can get lost in the MQL PQL SQL SAL definitions and best practices. Get back to the basics and operate from first principles.
  2. You need a story to be successful in B2B. Call it a category, call it a movement. Regardless, you need a story that people can bring to their boss about why they should buy your product beyond features + benefits. HubSpot created inbound marketing. Gainsight championed customer success. Drift conversational marketing. Each led through education + expertise and showed people a new way of doing things. Sell the vision and the story.
  3. You need to sweat the "offer" - request a demo and contact sales are only going to convert for the highest intent prospects. You need other offers. HubSpot's website grader. Drift did a "test drive" to test the chatbot on your website before talking to anyone. Demandwell has a free SEO audit. Clari has a revenue leakage calculator. These are all smart ideas that are still further down the funnel than ebook but work to get qualified buyers in to eventually talk to sales.
  4. Avoid incremental thinking. You can waste so many cycles thinking that the next homepage variation or the email series is going to be the thing that gets you out of the revenue hole. Rarely does "nurturing" solve the problem. Take bigger swings.
  5. You must find a way to get on the same page as sales, no matter what. Find a way to put all the internal politics aside. You will never be successful unless you can marketing sales + marketing = revenue *together*. Find out how the VP of sales is comped and do everything in your power to get on the same page. Health teams gives bonuses based on company goals not team goals. Find out and fix it. Manage up to the CEO if needed. Life is 100% easier when sales + marketing have shared revenue goals.
  6. Make finance and ops your best friends. YOU HAVE PLENTY TO DO ON YOUR OWN, YOUR JOB IS NOT FINANCE AND OPS I PROMISE YOU!!!! But instead find a way to make them your key business partners. Same way you need to be on the same team as sales, you need to be on the same team with finance and ops. Make them your best friends - collaborate on marketing as a business function Don’t be like 28 year old Dave “I got this myself” - DON’T GET DEFENSIVE - take the help, work together.
  7. Show your work and master internal communication. Top complaint: I never know what marketing is doing. If you can’t get the people inside fired up, how will customers be? Top complaint: Marketing is doing a lot, but no idea how it fits our goals. You must always be sharing the bigger picture, related to company goals. Some systems I like: Slack: sharing screenshots, work in progress, teasers, etc. Weekly, monthly, quarterly recaps - here’s what marketing is up to . Take any opportunity to present to the company you can get. Create cross-functional check-ins with marketing, product, sales, CS, finance, ops, together. Marketing is the leadership department as Christopher Lochhead says. Make it that way. Lead by example. You're supposed to be the best communicators in the company right?
  8. You must be able to articulate what your marketing strategy is. Don’t get lost in the tactics - see too much of this today. It’s the job of the marketing leader to have a vision for HOW the company does marketing. ABM? Product led? Both? SMB? Mid Market? Enterprise? Be intentional about your approach. You cant take the peanut butter approach and spread average stuff everywhere and expect to win. FOCUS. But also what type of marketing, what brand do you want to be? Have a view on the market, have a view on how you’ll do marketing this year, have a POV on what good marketing looks like. Ex: at Privy we sold to small businesses so we knew they weren't marketing experts and our marketing had to speak to them and they didn't have a lot of time to figure it out, so we had to lead with simple + clear + educational content.
  9. You must be able to think short term and long term. Hitting today's goal is great, but what about when the plan jumps 50% next year? You need to be able to build the foundation for that now or you'll wish you did a year from now. Spend 70% of your time on today and 30% of your time on next year/tomorrow. Be disciplined about laying the groundwork for next year and beyond and it will payoff. What will your next channels be? Where can you get future growth from? Start testing and learning now before you need it. Then you can be ready to turn it on.
  10. Manage up to the CEO. She cares about two things: revenue and the story. Keep your communication + collaboration tight to those things. She doesnt need to know every detail about what's going on inside of your org and you shouldn't let her. Manage up and get help around revenue and the story. Focus your efforts there.
  11. You have to making hiring your job not your side project. People are everything. You know that. Every HBR article ever has said it. But candidates are not going to magically fall on your lap you must treat this like your own marketing program. It's not HR / recruiters job it's your job - no one will know who to hire better than you. Build a brand for yourself in the market. Get religious about sourcing via LinkedIn. Make it your full-time job. Even if you're not hiring you should always be meeting great marketers -- at least so you can model / know what great looks like. Keep a list of your dream team. Make a spreadsheet of names of great people you'd hire if you could one day. You never know.
  12. Create your own momentum. It's 2022. You dont need to wait for Gartner or Forrester to write about you. You dont need the product team to ship the one key feature. Marketing is ultimately about content. You can create your own momentum by thinking like a publishing company. Create regular marketing launches. We called them "marketable moments" this can be content, research, reports, events. And then hopefully yes you have product shipping regularly and can do regular product launches too. But stick to a monthly launch calendar. Make some noise every month on your own, no matter what ingredients you have from the company or product team. Set the dates in advance. Dates and deadlines drive action. At Drift we launched the first Tuesday of every month, regardless. It helped us create our own momentum and was a competitive advantage -- PLUS it was contagious and pushed the rest of the the company to ship more too, especially the product team. They wanted to keep up with us.
  13. Your job is to get the job done. Doesn't matter if your hire internally, agency, outsource, use an intern or your grandmother. As the marketing leader they are paying you to deliver the result. Put that above everything else especially your ego. That's the biggest difference between the marketing leader and the individual contributor. It's not necessarily your job to do it but its your job to get it DONE.
  14. Do the job internally first before hiring externally. Always test and prove - at least get some signal internally. “What should the role of events manager do?” - no idea, you find out. Ex: you think you want to hire a partner marketing person; great make it part of product marketing's role for a quarter to test and learn. Ex: you want to hire for PR. Great. Make it part of your job for a quarter. You’ll never know what good looks like, how to measure, etc. unless you test it first. You can do this for almost any role / any “job" - I've made many mistakes because I didnt do this first.
  15. Get comfortable making bets without perfect data. You will rarely have all of the data / perfect data. Ultimately marketing is about making bets. Attribution doesn’t tell you what to do, it’s an input, something to help guide you. Even in our “data driven world”, must be able to act + make a bet + make a gut decision. That’s the skill (and the fun) of this job 
  16. Spend the budget. Dont be afraid of it. Use it. That's what it's there for. 
What else would you add to this?


- Dave

New Podcast: Community Is So Hot Right Now


New this week on the podcast: I spent an hour chatting with Jake Randall - he's COO at Common Room, a B2B SaaS company that's doing something interesting in the COMMUNITY space and we talk about why "community" is such a hot topic in our world. Jake also spent a decade at Okta, so we shared some of his lessons there.

Listen on Spotify


Listen on Apple Podcasts

Have you been listening to the Exit Five podcast? I think we've been bringing the B2B marketing heat lately, but what do I know.


Shoutout to my friends at Demandwell for sponsoring the podcast. Demandwell is the best SEO solution for B2B SaaS marketers. They’ve helped customers like Lessonly drive 40% of their revenue from organic search. And they helped Terminus’s make organic search their number one source of demos. Check them out. Tell them you heard about them from Exit Five.


Find Marketing Jobs, Reach Marketing Talent


It's rocky out there right now. Every week there seems to be another B2B SaaS company you've heard of making layoffs.


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As of today there are 68 open roles, including:

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