← Back

Exit Five Newsletter

Exit Five Email Banner (2 Paper Airplanes)

Hello and welcome to this week’s edition of the Exit Five Weekly Email, a weekly note with B2B marketing lessons & observations, fueled by the community at Exit Five (a private community of ~3,500 marketing pros).

Join us at exitfive.com if you're not already a member.


Sponsored by Storyblok

As a marketer you know:

  1. Content is king. 
  2. Speed to market matters.

But quality content takes more time to research, craft and edit. More budget. More cooks in the kitchen (UX designers, illustrators, editors, video teams…)

Now look at your inbox. There’s an avalanche of emails hawking generative AI, CTV platforms and the latest in MarTech. Which of these can help you create better content and go to market faster than your competitors?

What about your CMS?

Teams at Netflix, Spendesk and Adidas use Storyblok’s CMS to improve customer engagement and reduce publishing time. Storyblok makes it easier for all of the teams involved in content to collaborate with an intuitive visual editor and single-source management of content. In fact, Forrester conducted a study to see what happens with teams after switching to Storyblok and calculated an ROI of 582% over three years. 

Check out the report here to see how Storyblok can help you build better content experiences, faster.


The Blessing and The Challenge of Reporting Directly to the CEO (And How To Do It Well) 

It’s the goal of many marketers to report directly to the CEO. I highly recommend it, with a caveat. If you're in it for the glamor or the glory, steer clear, that's not what it's about or like.

Jason Lemkin has a great article about reporting to the CEO for the first time. His perspective is spot-on IMO. It can be one of the greatest opportunities of your career, and it can also be the most uncomfortable job you’ve ever had. 

His main takeaways: If it’s your first time reporting to a CEO, thicken your skin up a bit. Expect to always have to deliver, even if it doesn’t always seem fair. 


  1. Turbocharged learning 
  2. Accelerated decisions, more impact, will make you way better
  3. Lifetime relationship
  4. More rewarding 


  1. Feedback can be too direct 
  2. Appreciates only results (IMO see pro #2…this is what makes you great) 
  3. Not available enough 
  4. You need to grow (IMO a pro if you have the right mindset, the source of much discomfort if not) 

You learn so much, you get to be a stakeholder, your responsibilities and influence accelerate at an unprecedented rate.  But it’s also hard.  You don’t get credit for “Best Efforts” or “Trying” or “Doing The Best You Could by 5pm.”  You also don’t always get the kudos and appreciations you are used to. You get them. But not always how and where you are used to.

If you’re good, you’ll start to get pulled into things outside of your job description. Embrace this. The CEO’s job description doesn’t actually have clear boundaries or limits, and they might expect the same of you. This is the beauty and the challenge, and you have to be up for it. 

Reporting to CEO tweet

Reporting to the CEO is a pressure cooker, that will more rewarding and accelerate your career 

I held marketing leadership roles twice (VP Marketing / Chief Brand Officer at Drift, and CMO at Privy) where I reported directly to the CEO. 

Off the top of my head here are some of the things I learned about reporting to the CEO:

1.  When you meet with the CEO, come prepared

A leadership coach once told me, planning ahead is the difference between seeming junior and seeming like an executive. My thoughts are - it can get you a lot of the way there, even if you don't quite have the experience to back it up. 

You don't need to have all the answers but you need to think things all the way through, and pull the CEO into the things you're unsure about.

If you show up to a 1:1 or discussion about marketing without being prepared, you will get either run over, or the conversation will not help you move forward with your marketing goals. 

Unpreparedness invites them to take over, which is the wedge in the door for the CEO having to manage you. I love the note from Marissa below: Micromanagement (or micro curiosity) comes from a lack of confidence in your management.

I kept a Google Doc (use whatever notes app you want) where during the week I would keep notes/bullets of things I wanted to discuss with the CEO in our 1:1.

The CEO has 1731 other things going on, so pinging her on Slack or writing late night emails almost never helps. Instead, unless it was extremely urgent, I would file questions away and save them for our 1:1. Then during the 1:1 I could drive the agenda, and go through my list of questions. This could be anything from things I was stuck on, to going deeper on a comment they made earlier, to questions about strategy, hiring, tactics, whatever it was. Keep the file. Don’t bother the CEO with all the questions during the week when they are context switching all day. Save them for your time.

micro-curiosity prepare for 1-1s

2. Keep them out of the weeds

You need to keep the CEO out of the weeds. The highest ROI of the CEO’s time with you will not come from you telling her about the laundry list of marketing activities the team is working on.

The CEO can easily be distracted and of COURSE she WILL have an opinion on everything, but don’t let her get in the weeds with you. Focus on the big rocks. The high level strategy and operational questions you have. The big blockers. The marketing strategy. The ICP. The product roadmap. The challenge with the VP of Product you’re having. That one Director on your team who you can’t get with the program and need help. Those items. Not blog post headlines..

3. Use non-real time communication to show all the work marketing is doing

… but the time to show all those other marketing activities and the “in the weeds” stuff is in some form of a weekly email / weekly wiki post / weekly marketing update. Something that can be easily found by the CEO whenever they want to see it. 

Even if no one reads this, I love this exercise as it’s a way to show the CEO and the rest of the org what marketing is doing, and get them to see that you are, in fact, in control of ALL the things in marketing.

I like to write a weekly update that covers: 

  • Progress toward goals
  • What the team got done this week
  • What the team is working on next week
  • Any wins/highlights
  • Any challenges/places you’re stuck or need help

Sending this out weekly is the best way to keep the CEO from wondering what marketing is doing (I’d share this with the whole company too so everyone can see). 

Sharing publicly opens you up to the wisdom of the crowd (and the feedback...don't let this deter you!)

Smart leaders across the company and people in the org will be able to help you get unstuck if they know what's going on in your world. I can’t tell you how many times a random engineer or product manager or VP from another team would comment on an internal wiki post with one of my marketing updates and either offer to help or provide an idea or solution to a place I was stuck.

Show your work and good things will happen.

4. Don’t hide from missed goals or bad results. Admit your mistakes. End excuses.

CEOs do not expect perfection. They deal with people all the time and understand mistakes are part of the game. The best thing you can do is share them, immediately and transparently, along with what caused the miss, and what you’re doing to make sure the mistake doesn’t happen again. Great is: someone who takes ownership, shares the most important information, and course corrects for the future. 

It is so easy to just talk about the good stuff and/or get defensive about your misses in marketing with the CEO. Don’t do that. They know better, and know somewhere inside your team something is off/broken/behind. 

The CEO should never hear about a marketing-related mistake or a missed goal from someone other than you, and it should never come as a surprise.

We used to have weekly leadership team meetings with the CEO, founders, and all functional VPs. If I had to present bad news to that group and it was the first time the CEO was hearing about it, it would never, ever go well. BUT if I had a 1:1 with the CEO earlier in the week and in private was able to share the update, the sting wears off (and surprisingly they react much more positively than being surprised by the news in a group setting). Bring the CEO in early.

As Dave Kellogg said on the Exit Five podcast, you must be a cold presenter of the facts and the truth and share bad news early. Especially before the management meeting…

Lose CEO trust

5) When you bring a problem, make sure you also bring a solution.

There is real value to surfacing issues (in marketing like #4, but also across the biz) to the CEO. Others may be scared to mention issues to the CEO. But for a CEO, having eyes on the ground that will be honest with them is hugely valuable. 

That said - if you bring an issue to the CEO, you need to have thoughts on how to solve it. This doesn’t mean that you need to solve every problem… but bringing ideas for how to tackle, who should be involved in tackling, and on what timeline makes you a partner vs direct report. 

Tips here - not every problem is created equal. So over time, gut check how important things are w the ceo (this can be an open conversation i.e. “this seems medium urgent to me, what’s your read?”)

1-1 prep and bring solutions

Hope you are having a productive week.

- Dave

PS. if you read these notes, can you reply back and say hey? I love getting responses from Exit Five newsletter readers.


🎧 Podcast #93: My Story From Marketing Manager to CMO, Building Exit Five, and Life Beyond Marketing (Interview with Dave and GTMfund's Scott Barker)


Ok turning the tables on this one - I am the guest on this episode, chatting with GTMFund's Scott Barker for their GTM podcast. Scott is a Partner and Co-Founder at GTMfund and formerly head of partnerships at Sales Hacker and through their acquisition by Outreach. We discuss: 
  • Behind Dave's career story and starting Exit Five
  • Some personal philosophies and current goals and the different chapters of life
  • Dave's systems, does he have an assistant or VA? How does he run his business today?
  • How to successfully set yourself up as a one person team
  • Evolving your strategy and goals as your companies goals change
  • How to nail your companies messaging
  • Effectively building a founder brand
  • The importance of niching down to drive growth

Listen To The Episode Now On Spotify


Join the Exit Five Community

Please join us in the new home for Exit Five (and our dedicated iOS + Android app). We have officially moved our community to Circle - our own private community on the web, with a dedicated mobile app for iOS and Android. It's bumping over there already and I've been loving the feedback from members so far.

Here's a video overview from me breaking down the new Exit Five community. You can join the community right now for free with a 7 day free trial and then choose monthly or annual billing (or to not join) after your trial. Hope to see you in there.

DW_2color_horizontal_light_bkgrnd 1 (1)

Thanks to the 2023 Exit Five presenting sponsors Demandwell (SEO) and Zapier (Automation).


Want to sponsor a future newsletter or learn more about other sponsorship opportunities with Exit Five? Reply back to this email and tell us more about your business.

If this email was forwarded to you, sign up here to get the newsletter every week.

← Back