AMA with Devin Bramhall and Margaret Kelsey, hosts of "Don't Say Content" podcast

Jimmy Daly
September 15, 2023

Welcome to our AMA with Devin Bramhall and Margaret Kelsey, hosts of "Don't Say Content" podcast.

If you aren't already familiar with them, Devin and Margaret are each really experienced content & marketing pros. Devin created Boston Content, led content at Help Scout, was Animalz' VP of marketing and later the CEO. Margaret ran content at Invision and Appcues, then ran marketing at OpenView. They are each consulting now, and they are running a podcast together! I highly recommend checking out "Don't Say Content" podcast.

If you'd like some irreverent and refreshing takes on content, here are their websites:

If you were joining a new company as a marketing/content leader, what first few things would you do to create more alignment with the CEO/non-marketing leadership?

Devin: Start by listening. Ask questions to try and understand how they operate, think, etc. Then you can tailor future comms and reports in a way that's organic to them. Also, present your content plans in the context of business goals. Show how your efforts connect, even if it isn't direct. They need to experience YOU understanding THEM from the beginning and that will begin trust-building which will enable you to take more risks and be more creative later. Also, sometimes it's worth just proving yourself with numerical results first. Once I hit my traffic goal at Help Scout, the CEO was more willing to let me pursue my big vision.

Margaret: 100% - visibility is key, too. I always recommend sending a weekly update email to your boss (and ideally, boss's boss too) with what you've been working on this week, percentage attainment to goal, blockers, and any interesting insights you learned from experiments. It'll earn you massive trust with everyone who receives it. Most people stop if their bosses don't respond to it. Don't make that mistake! The benefit is in the consistency of updates.

I'd like to know what the heck is going in content marketing right now. 2023 has been whirlwind between ChatGPT, some economic uncertainty, pending Google + A.I. updates, etc. It's just so hard to make sense of what for so many years was a solid playbook. I won't ask you for predictions, but am curious where you think content teams should be focusing their energy right now.

Margaret: Content teams need to zoom up to think about rethinking channel/content fit. I think more and more "full funnel" content will happen natively on social channels, rather than trying to drive people from social to website and educated/convert there. That means we have to get comfy not having the precious data we've been able to have by converting on our website. Don't fight the changes, think about how to make them still work for you.

TL:DR is everything is changing, and that's ok. It's means you have to experiment rather than just execute

Devin: Lean more into media content and consider going media-first and using that to fuel written content strategy. That's a great place to start to build your own playbook for your specific company. And starting with media just helps with efficiency, since you can repurpose it via clips, transcribing into written content etc. It's also a platform for more strategic content partnerships.

This is a reference to a show we just recorded:

I recently left in-house roles (via layoff) and after a pretty miserable job search, decided to lean into freelance or fractional content work since it’s been how I’ve paid the bills the past few months. It’s been kind of on the quiet so far, and am just starting to think about taking a more active approach in filling my roster. What were the biggest challenges for you in going solo? And what advice do you have in starting to promote yourself? Any random funny stories or lessons learned about the consulting world?

Margaret: I've always thought about networking/staying in touch with people that I think of as "connectors" - people who are already talking with my target audience and can warm intro me. For me, that's been a lot of the folks I've worked with in the VC space, since they are already talking to a bunch of founders. Warm intros are SO much better than trying to go cold outbound.

My biggest challenge is that I still have a lot of guilt for how much I provide for my clients and how much I charge. I always feel like I should have done a little more for them (even if they are telling me that they are super happy). Definitely a silly brain quirk.

For promoting yourself: It all comes back to differentiation and product market fit. Where can you be flexible in ways that your target client needs you to be flexible? How do you make it work on your end still? For example, I don't lock anyone into multi-month contracts. They pay an invoice ahead of the month they want to use. Founders of startups want that flexibility. But I charge a (slightly) higher monthly retainer because of that.

Lean into that. It's a feature, not a bug of freelance life.

I'd love to get your take on. i think it hits a sweet spot of career development, soft skills, managing up that you both really get.

"I recently joined a company as the content marketing manager. For context, they reached out to me, I never applied. During my interview, I expressed that, while I wasn't looking for a new job per se, I was open to good opportunities. I was looking for something that would allow me to spread my wings and fly -- build a content strategy from the ground up, run all the content operations, and really own everything content. They were excited about this, and the pay was excellent. Long story short, I accepted.

Fast forward to now, and I report directly to the CEO. Rather than owning content operations, I've found that the CEO micromanages everything (not just content, but growth, product, and everything in between). Not only that, but they have very strong opinions about what they like and dislike, but can't pinpoint what it is that they like and dislike. Even when I've tried to dig into the root of the problem, they can't tell me exactly what they don't like, just that they don't like it.

Anyways, I've only been here for 2 months now, but this is the opposite of what I wanted. I feel like I went through a bait and switch. I have even less freedom and ownership now than I did at my previous company since the CEO needs to tear everything to shreds before approving it after 3 or 4 rounds of edits.

I'm already starting to look at new jobs, but how do I explain this in an interview without being totally negative? There will definitely be questions about why I'm leaving so soon, and I can't say "the CEO is a nightmare to work with and can't delegate for the life of them." Any advice?"

Devin: I've been in this situation before, so I relate to what you're feeling. Starting from the bottom: Put your marketing hat on and craft a 2-sentence explanation that points the interviewer at what you WANT them to think about you. Obviously, it needs to be true, but you can find a piece and just tell that. Most importantly, I suggest leaving your emotions at home. It doesn't matter how justified you are in your feelings, in the interview context it will make you look bad if you're too disparaging or seem too attached to what happened. It was a wrong-fit, the JD didn't line up with what they really needed and that became clear in the first two months. You left because the actual JTBD was lateral, and you're interested in growing your skills in X way.

If you are interested in making this work, my question to you is: have you had any conversations with your CEO about the challenges they present to you doing your job? Have you asked them (from a place of genuine curiosity, not frustration) what their challenges with you are or what they'd like to see more of? Or shown them a situation where they had lots of feedback and said "hey, i see you investing a lot in content, which i appreciate. but i also see that our current system is inefficient for you and for me. I want to improve it so we can show results faster, so I'm going to propose a new plan to you. I'd love to test it out for 1 month to see if we can increase output by x%. Will you support me in this?"

What do you think are some of the most important skills to focus on (for upskilling) as a freelancer looking to move more into content strategy for clients?

Margaret: Sales! Which I know is tough bc we went into marketing sometimes specifically because we didn't want to go into sales. But, if you're talking about specifically content strategy skills, I always think about moving up in "strategy" is just moving your focus to a longer time horizon. Execution is in the daily, weekly. Strategy is in the monthly/quarterly/yearly. What are you trying to build and why, instead of what gets done in the nearterm.

How important do you think a deep knowledge of SEO is (ya know beyond the basics) for content strategy type roles?

Margaret: Not super important. Understanding how it's working (and changing) is enough. It's just a channel - not god's gift to all things marketing and conversion. It was nice bc it showed strong signals of intent, but you can find that differently in other channels, too.

Two related questions. Context: I'm thinking about my career pathing and whether I should get more and more senior within content marketing or focus on becoming more of a generalist marketing leader.

  1. Do you think focusing on content is a career-limiting move? Obviously you're still wearing many marketing hats within a content role. But let's say trying to be a Director of Content vs. a Director of Marketing.
  2. It seems like you've both made the jump from content to more generalist leadership roles. Is there anything specific you did to prepare yourselves for that?

Margaret: IMO, focusing on content isn't career-limiting at all. IF you're focusing on full-funnel content and how it converts. Director of Marketing can seem more "senior" and "strategic" thank Director of Content, but not majorly so, esp if you can talk about how content fits into overall marketing strategy when the time comes.

I was a director of brand + content and then jumped "laterally" to director of marketing, but it felt like a promotion bc of the increase in responsibility. But, most importantly, where does your brain like to play (content-focused or broader)?

What can a content writer who’s learning content strategy (CS) and has no case studies in CS pitch to a potential client?

Margaret: You can deep dive a company's content strategy that you admire (i.e. document/write about what they are doing based on what you see and why they might be doing it). Putting together 2-3 of those might be enough to show off your content strategy chops.

Devin: Or put together a mini strategy for the company you are pitching! Send them a few low-hanging fruit opps you discovered doing a quick audit of their site. It's a way more powerful cold outreach.

What do you see as the biggest opportunities within content right now? Or related, when you’ve come into a new company / team, how do you suss out the biggest opportunities that content can support?

Devin: It depends on the circumstances of the company you're working for, the industry they operate in etc. In other words: there isn't ONE opportunity generally ever. Honestly, the most consistent opportunity is in the HOW not the WHAT, because the how involves the unique resources and talent of your specific company. And if you can convince them not to just follow playbooks that are already out there, then you are creating your own unique opportunity. For finding opp at new company: research. The space, talk to folks at the company across departments, be a listener in related communities, see what other folks are doing in that space. What relationships do your leaders have that others don't that you can leverage. Basically: the more information you gather the easier it will be to identify unique opportunity. The uniqueness is typically how your unique brain puts pieces together.

Which content calendar tool or tools do you recommend for better content management and marketing alignment?

Margaret: There are so many and they are all kind of becoming about the same. Gotta love tech becoming a commodity. That being said, I've always liked Asana for content calendars/tracking progress. And then for alignment, just plain ol' weekly update emails. The problem with project management software is the people who log in think it's great, but a lot of execs never get logins or trained on how it's set up (if they do log in). Thinking of everyone that's a stakeholder in marketing as a target audience and serving them updates in the channel that they are most active in (slack and/or email likely) is the best way to keep alignment

What have you learned from making your podcast so far? Because I am also running a content marketing podcast, i'd be curious to know how that's gone. i've been surprised at how different the medium is, and there's been a learning curve. in fact, we canned our first podcast and started over bc i felt the concept wasn't strong. it seems like you're enjoying it too. any tips for the aspiring podcaster out there? (subtext: i think more content marketers should be thinking about content beyond text)

Margaret: Content is so much more than text right now - esp as we start to see the rise in channel-specific content. I think Devin and I have had the benefit to have FUN while we're working on it, which funny enough, turns out to resonate with folks. The "vibes" as the kids say are super important in audio + video content.

Devin: Two big things that worked for us:

  1. we chose a format that fewer people are doing in our space (we don't do guests and we don't talk about basic tactics. We don't even really offer solutions, we just unpack problems and offer our perspectives)
  2. we already had strong networks, so the show sold itself. our marketing strategy was not robust. we just sent it to our friends in marketing and asked them to support).

Our network comes into play here too: Share Your Genius offered to produce for free, because:

  1. I had an existing relationship with the CEO and she saw the business benefit of suppporting us (through exposure and intros, which is working)
  2. Our show is good, so sponsors reached out to us.

The second point isn't a back pat. If you focus on making a great show that's different from all the rest via talent, format, or premise, you will attract listeners and sponsors. We have begun outbound sponsor outreach as well. More of a template for that. Quantifying size of audience across platforms, showing growth, and asking them what a successful partnership looks like to THEM. You can do all kinds of packages, from UGC that they can share, introductions, etc etc.

How do both of you personally define content strategy? I feel like it’s such a broad term and there’s many different interpretations of it. And what metrics are most important to you for measuring content success?

Margaret: I just replace the word strategy in my head for "longer term vision". So, what is content doing for the org? What is the machine that is being built, and how does that machine have business value? Documenting that is strategy. As for measurement, it completely depends on what part of the business you're trying to have impact on.

What kind of consulting work are you doing these days? And are your personal sites the best way to get in touch with you about that?

Devin: I'm doing fractional CMO work for companies, and growth advising for leaders. Website: yes!

Margaret: I advise founders and heads of marketing at b2b SaaS companies on marketing strategy and how to resource that strategy,

Best places to find me: DM me on LinkedIn or email me at

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