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You might have guessed from the subject line that I have some news to share! I’ll get right into it below. Wishing you a great week ahead,
How to leave a job you love
They say “startup time” warps your reality of actual time.
Sometimes, a year in a startup can feel like 10 years. Sometimes it can feel like 10 minutes.
I have spent the past six-plus years working for Buffer, one of the greatest startup stories in tech. Looking back, it seems like both 60 years and 6 minutes — both gratifyingly long and incredibly short. Just yesterday, it felt like I had no idea what I was doing! (That’s both figurative — a reminisce back to my first days at Buffer — and literal to how I felt yesterday.)
After six years at Buffer, I’ve decided to move on to a new adventure.
These changes don’t happen very often for me (obviously: six years ago was my last one), so I had a lot of catching up to do on who I am, what I want out of my career, and how to navigate the unknown. The experience also brought about some tangible learnings about searching for a new job and leaving a job you love. I’m happy to share those takeaways below.
Where I’m headed: I will be leading all things marketing for Polly, a super cool future-of-work startup doing big things in the team engagement space. Polly integrates with Slack and Microsoft Teams and has 5 million+ users. I’m hoping to bring some of the Buffer magic to the Polly rocketship. 🚀
And I’m hiring!
Come work with me. I’m looking for marketing leaders in product marketing, lifecycle marketing, demand gen, and brand. Drop me a reply if you’re interested.
Lessons on leaving a job you love
Q: How do you know when it’s time to leave?
Well, I don’t know that I ever felt fully sure it was “time.” But the more I learned about opportunities, the more I felt ready to challenge myself with something new. There were a few important elements that I felt particularly compelled by when chatting with new companies:
I could tackle familiar-yet-fresh challenges … like scaling from $5M to $25M (which I’ve done), but doing it in partnership with growth and sales (which I haven’t)
I could achieve what I enjoy most at the stage I most enjoy … building marketing teams and scaling big-time brands for growth- and expansion-stage startups.
I could stretch myself, learn new things, and continue to develop as a leader … I had become great at marketing at Buffer, and I wanted the chance to be great marketing elsewhere.
I think I needed these multiple reasons all happening at once in order to seriously start picturing myself in other places. Over the past few years, I would have moments here and there where one of these factors might be true for a time — my “shields” would come down, so to speak.
Your shields drop the moment you let a glimpse of a potential different future into your mind.
But it took multiple reasons all at once for me to make the leap. When you’re at a job you love, I think it takes multiple factors: you’re seeing the same challenges again and again or you’re itching for new achievements or you can no longer picture your future growth … or maybe all three.
Q: How do you know you’re good enough to get a job elsewhere?
I had serious doubts about this. I had been doing marketing at Buffer for the past six years, but I wasn’t sure if my experiences would translate anywhere else. So I had to do a few things.
1 - Remind myself that impostor syndrome is real, and I suffer from it. Therefore, I should give myself grace. I am not as extremely out of my depth as I think I am.
2 - Turn my LinkedIn on so that I’m casually open to recruiters. Then enjoy the little dopamine rushes anytime a cold LinkedInMail arrives.
3 - Actually chat with some of the companies who want to hire. I found out through these chats that I have a ton to offer. Go figure!
Q: When should you start looking if you think you might be interested?
If you think a career move is on the horizon, give yourself at least six months to get in the groove of job hunting and interviewing.
I had my first interview in January 2020, almost a full year before I accepted the offer with Polly. (That Jan 2020 interview was with DuckDuckGo; it’s a fun story I’ll have to share here some time.)
There were two things that I learned that made me very grateful for starting when I did.
First, I wasn’t in a rush to choose any opportunity that happened my way. I could be picky and wait for a really great offer.
Second, I had a chance to refine my personal narrative. When I first started interviewing, I struggled to articulate why I might be interested in a new role or what exactly I could bring to the table. It took three or four interviews before I finally got my story down about who I was and what I could offer. My story: I helped build Buffer into one of the most-loved brands in tech. (A little hyperbole always helps.)
Q: Any other advice that was especially helpful?
1 - Make the decision as objectively as possible. (Advice from Adam G.)
2 - Your current job can be a great place to be … and a great place to be from. (Katie W.)
3 - What would you hate to NOT be doing? (Tyler W.)
4 - There is no such thing as a perfect fit. (Hema P.)
In order to make the decision as objectively as possible, I took Adam’s advice and borrowed his spreadsheet template:
This was hugely helpful to lend some measurability to a very squishy topic. With the spreadsheet, I was able to list out all the different factors that were important to me in work and then compare my current job and other jobs I was considering.
I included things like:
Work on technology that solves unique problems
Kindness and empathy are a conscious part of the culture
Boldness & risk-taking are encouraged. OK to aim big, learn from mistakes
Have space to work on teaching and personal side projects
Have the ability to use my platform for good
Earn > $200k base
Receive equity in the company
Do work that increases my future job prospects & earning potential
Have a title that represents my experience and impact
Learn new things and fill gaps in my knowledge
Work somewhere over-indexed on diversity
Work on products I use or would use
See a road I can directly grow the company exponentially
Work for a company that's profitable
A company that has product / market fit
Healthy revenue trajectory in a role that's set up for success
The second and third bits of advice came from two of my Buffer teammates. (Thank you!)
And the fourth bit of advice came from the interim CMO at Polly. This was something that I found to be true again and again in my job search, and it took me awhile to embrace it. Rather than trying to be all things for the company, I needed to own the things I was great at and be excited to stretch to fill the gaps. For my Polly role, I’m a great fit for the type of brand and marketing team they want to build; I will need to stretch to work with sales and at a high-growth startup. And I can’t wait!
(Did I mention that I’m hiring? Drop me a reply if you want to join me.) 😊
Thanks for reading and have a great week,
About this newsletter …
Each week, I share playbooks, case studies, stories, and links from inside the startup marketing world. If you enjoy what’s in this newsletter, you can share some love by hitting the heart button at the top or bottom.💙
I’m a marketing exec who specializes in startup marketing and brand-building. I currently lead the marketing team at Polly (we’re hiring!). I previously built brands at Buffer and Vox.
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