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Making a new career move. The thought process behind leaving for a new job (plus where I'm headed and what we're hiring for next)

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Hi there 👋

So …

I got a new, new job.

At the start of the year, I left Buffer to join Polly, and I’ve had a wonderful time helping scale their marketing org and build their marketing engine.

Then an unmissable opportunity came my way.

I’ve joined the team at Oyster, which is a B2B SaaS product that helps companies be the very best at distributed work and helps talented people worldwide get access to great jobs no matter where they live. Fundamentally, today, Oyster helps HR teams hire, pay, and take care of their worldwide talent. But everything the company does is underpinned with a mission and purpose to close the global talent gap.

I am leading their marketing team, just as I’ve done at Buffer and at Polly.

I’ve been there a few weeks now (I was waiting for the right opportunity to tell all of you).

And already I’ve found myself in a moment. We announced our $50 million Series B funding last week, which comes just five months after the Series A funding in February of this year. The company is just 18 months old.

And we’re hiring! If you’d like to come join me — and I would be delighted if you would — there are open marketing roles for:

So with all that said, I thought I would use this week’s newsletter to explain how decisions like this happen, what elements I considered, what mistakes I made, you name it. Ask me anything, too. I’ve found over the past few months that many people are wondering when is the right time to make a move, whether it’s six years since your last one (me) or six months (me, again).

Wishing you a great week,

When opportunity knocks, should you answer? Here’s some advice that meant a lot to me …

As I was wrestling with the decision to stay with the Polly team or pursue this new opportunity at Oyster, I felt incredibly overwhelmed by the weight of it all. I was feeling all my feelings: fear, doubt, excitement, heartbreak.

I felt that a decision to go — to leave my team — would be a very selfish decision.

But I eventually came out of my spinning and realized:

It’s okay to prioritize you when it comes to your career.

Logically, the inverse would be bizarre — don’t think about yourself when making career decisions?? It’s a silly idea, but I found myself feeling guilt about putting myself ahead of many other things and especially ahead of my feelings of responsibility, commitment, and relationship. Perhaps you’ve struggled with that see-saw before, too: leaving a place that relies on you in order to go and do something different, for you.

I love the team at Polly — I had just hired some amazing teammates, which made the timing especially surprising.

But I couldn’t deny the pull of Oyster, for a few reasons:

  1. They are mission-oriented in a way that resonated deeply with me

  2. They are purpose-built with a remote culture

  3. There is huge potential for tangible growth for me personally and for the company

Here’s a bit more about how I thought of each of those areas.

Mission …

There was no one thing pushing me away from Polly, which I’ve come to realize is a very fortunate thing (many friends who have joined new companies have found that things aren’t as they were made out to be). Instead, the single biggest thing pulling me toward Oyster was mission.

I came to see it like this: At various points in my career, different things have mattered to me:

  • Buffer was a great fit for me when I highly valued security and safety in my job

  • Polly was a great next step when I came to value new experiences since it gave me exposure to areas like sales and growth

  • Oyster now makes sense as I feel called to do mission-aligned work

For those of you who’ve got to know me through this newsletter, you probably know how important remote work has been to me. It gave me access to jobs I would have never dreamed of before. It gave me precious time at home with family as my son has grown up. I have benefited so much from the gifts of remote work, and I want as many people as possible to get the same advantages.

I’ve pursued this through coaching, mentoring, etc. and through teaching at the local university. But to have a chance to leave this impact on the world through my main role?

Too good to be true.

Culture …

When you’re interviewing for a new job, I generally recommend you dig deep into a few important areas on company performance and company culture. Some questions to ask:

  • What is your acquisition, retention, and revenue performance to date? (It’s almost as important that they are willing to tell you those numbers — trust and transparency FTW — than what the numbers are)

  • What are the goals for those metrics to change? What happens when a team reaches their goals or misses their goals? (Useful for understanding culture and expectations)

  • Why do people stay? (Or, the inverse: Why do people leave?)

These questions can help reveal the culture, or lack thereof. You can also use specific datapoints that you’ve learned about the company: what is their vacation policy, what asynchronous tools do they use, is it a team with a lot of parents.

Oyster had a couple of specific culture items that I found enticing:

  • They have a Head of Remote, which tells me they care deeply about investing in a remote work culture

  • Their Notion was transparent and available so I could see the way they document their practices and the way they communicate

  • They have a social impact thesis and a pending B Corp status

  • Their company values specifically call out things like Diversity & Inclusion, which matter a lot to me

When joining a young company, you may find that in addition to building your team, you also need to build company culture. That can be exciting and fulfilling work, but it’s a lot of extra work. I realized that the work that I felt called toward — the work that I had the energy for — was evolving the culture rather than building it from scratch.

Growth …

I aspire to bring a growth mindset to my work (some days, it’s easier than others). And I have found ample opportunities to do so at Oyster:

  • Close ties to the VC firms and access to their network of mentors

  • Documented strategy across all areas of Oyster, which helps me learn lots about sales, finance, product, ops, etc.

  • A team of folks from different SaaS backgrounds, high-growth companies, worldwide perspectives (I was fortunate to have this at Polly, too)

When I made my previous move from Buffer to Polly, I wrote about my decision-making process, including a quantifiable method of comparing one job to the next using a spreadsheet and formula.

I still highly recommend this method, especially if you’re considering multiple opportunities. But a funny thing happened to my process this time around … I didn’t even consider making a spreadsheet.

The Oyster role was such a clear fit for the person I was becoming and the impact I wanted to leave with my work.

Ultimately, that’s the advice that carried me through:

It’s okay to make decisions for yourself.

It’s okay to make decisions based on where your heart is leading you.

If you feel there’s a better fit for you somewhere else, then there’s someone who’s a better fit for the role you’ve left.

Leave with honesty and care. Own your decision. You can’t own other people’s feelings (though I often try).

Make your career what you want: if you value security or experiences or mission or growth, be open when those serendipitous opportunities find you.

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. 💙

About Kevan

I’m a marketing exec who specializes in startup marketing and brand-building. I currently lead the marketing team at Oyster (we’re hiring!). I previously built brands at Buffer, Vox, and Polly.

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