How I accidentally became a Head of Marketing 👕

My inadvertent step onto the career ladder

May 05, 2025

👋 Hi there! You’re reading the Bonfire newsletter from Kevan Lee & Shannon Deep. Each week, we highlight brand, marketing, and creative learnings from our experience as in-house marketers turned agency owners who think a lot about creativity, our relationship to work, and how all of that impacts our identities. We’ll also feature insights from our digital community of super smart folks (come join us!).

Wishing you a great week!

Stuck climbing the career ladder? Been there, done that, lived to tell about it

I remember the exact moment I stepped onto the startup career ladder.

At the time, I was working at Buffer—a dream of a company with an awesome social media product, fantastic people, and one of the best cultures in tech. I was building our go-to-market strategy through organic content and SEO. I got to write tons of blog posts and grow a big audience. I loved it. I was getting paid to write!

Then came a pivotal moment: My boss, Buffer’s co-founder, asked me a question.

Did I want to stay on the content track as an individual contributor?

Or build a marketing team and step further into leadership?

If I stayed the course, I’d remain an expert writer and highly respected individual contributor, doing the stuff I’m really good at and helping move the business forward.

If I chose to step into marketing management, I’d hire a team, lead strategy, get a new title, and gain influence. (And have something to brag about on LinkedIn!)

It did not take me long to decide.

I chose the Head of Marketing path.

And I never wrote another blog post again!

(Kidding. Well, kind of.)

Finding your fit

My sliding doors moment at Buffer has been on my mind lately as I’ve been hearing more and more people share their stories of career design in tech. Turns out, there are a lot of different ways to have a career! This is stating the obvious, of course, but when you’re climbing the ladder, it’s hard to see beyond the next rung.

One of my favorite career storytellers happens to be a former Buffer colleague of mine, Mary Jantsch. Check out her career story here.

And, get this: Mary will be the featured guest at our next Campout event this Wednesday, May 7! The event is free for anyone to join. Mary will be sharing much more about career design, how to find your fit, and how to do more of the work that brings you most alive. We’d love to see you there!

That moment at Buffer was a fork in the road for me. I don’t have any regrets about my choice. In fact, I have a lot of gratitude for the opportunity I was given (not everyone gets such a lucky offer!) and for all the things it taught me—eventually, sometimes painfully—about how to find my fit and be myself.

To be fair to junior startup person Kevan, I had no idea about the implications of my decision at the time; I was still googling “MRR” and “what is an equity cliff.” My decision-making criteria for career moves then was largely shaped by what I thought I should be doing. Go with the more prestigious path. The one that got the title, the paycheck, the bragging rights. The one my dad would be proud of. The one that I thought everyone else would choose.

As I’ve been thinking more about career design, it’s interesting to imagine how this could have played out for me if I had chosen a different path. For instance:

I remain in my prolific content creator role at Buffer.
I build a reputation as a content expert.
I go on the speaking circuit.
I leave Buffer to start my own content business.
I write a book.
I become a shark on Shark Tank.

Or even something less publicly ambitious but still fulfilling:

I remain in my prolific content creator role at Buffer.
When the time comes, I leave Buffer to do the same work for a different company.
I change jobs again, joining a content-first company that wants me in an IC executive role (imagine that!),

(If you’re curious for a proxy of the above paths, check out Jimmy Daly and Val Geisler; they have each forged a pretty neat career journey of their own.)

And I can even imagine a world where the marketing leadership path did fit with my interests and passions, for the long haul, and I kept on climbing that ladder:

VP of Marketing at Buffer
SVP Marketing at Oyster
CMO at Rippling (where I specialize in corporate espionage PR spin)
CEO at Gusto, thanks to my HR tech career path
General Partner at the VC firm Emergence Capital, a Gusto investor

Instead, my path has been a bit of all of it, but it’s finally a path that I feel like I am choosing, creating, and enjoying, building something cool with Shannon and aligned with the kind of people we want to be and the lives we want to live:

VP of Marketing at Buffer
SVP Marketing at Oyster
Co-founder at Bonfire
[Any other role or project that I deem to be personally meaningful]
Retirement (sooner or later!)

How to navigate a creative marketing career, in hindsight

If I could have known then what I know now, I probably would have given myself the following advice:

1 - It’s okay to take your time.

For sure I felt like I owed my Buffer co-founder an answer right away. Future Heads of Marketing do not waffle when presented with the opportunity to be a Head of Marketing. Or at least the good ones don’t! (This is what I told myself.)

And pace has reared its head many other times in my career decisions where I’ve grabbed at the next “should” opportunity, the opportunity right in front of me, before giving myself the time and space to actually decide what I want and how I feel. Big decisions deserve their space. And there are fewer decisions bigger than how you design your life and your work!

(Also, yes—having time and space to make career decisions is an immense privilege!)

2 - It helps to talk to a variety of other people.

I was new to the startup game and so only knew what I had read about in business books and blog posts, which taught me to climb, climb, climb and never stop. I could have benefited greatly from seeking other perspectives. No doubt there were lots of other people out there who were charting their own path. I just didn’t know them and didn’t know where to find them.

Part of my sharing this story and part of hosting Wednesday’s event with Mary is to help everyone see that there are other ways to navigate a career with creativity and confidence. Shannon and I have chosen this path with Bonfire. We can tell you how we’re doing it and connect you with lots of people who are doing it many, many different ways, too.

3 - Know yourself better.

Therapy plug!

(Seriously, therapy is great for getting to know yourself better. So are books. So are friends.)

I would often ask my direct reports in our 1:1s, “What do you really want?” This was totally unfair because I could not answer this for myself! The closest I came was during a coaching session; when asked what I really wanted, I immediately blurted out “write fiction and retire early,” then spent the rest of the session explaining to my coach why that was impossible and ridiculous.

So maybe 3a: Know what you want—and give yourself the courage and grace to pursue it.

Want to learn more? Join us this Wednesday

Mary will be joining us live on Zoom this Wednesday for a conversation about crafting your career, discovering your identity, and aligning your work with your life. The event starts at noon Eastern time. It’s completely free to join and participate.

We hope you’ll join us on Wednesday!

Notable links, convos, and events

You can see all this and more in the Campout community.

ICYMI - Our latest course on brand measurement is live! This one is all about the brand impact that you actually cannot measure but still makes a difference and is well worth the investment. If you’ve got an hour to spare and want to convince your boss about the real value of brand, then this is the course for you!
Speaking of the power of brand storytelling, we were grateful to have the chance to write this essay in The CMO Club about how brand stories drive differentiation.
Community member Will Crowley has been curating this awesome list of B2B marketing goodies like books, frameworks, resources, and more. Check it out. And a big hat tip to Will!

But wait! There’s more…

Wanna be friends?

If you love this newsletter and wish it were more interactive, you’re in luck! Join us over in Campout, our digital community for creative marketers and the creative curious.

Wanna work with us?

If you need help with brand strategy and storytelling, fractional brand and marketing leadership, and bringing your brand strategy to life in impactful ways, send us an email at hello@aroundthebonfire.com to get in touch.

As always, you can find us on LinkedIn, Instagram, and Threads.