Interview: The Fractional Job Search | Taylor Crane

This post originally appeared on Money Abroad - the newsletter for growing wealth while living abroad.

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INSIDE: Poker Player to Fractional Head of Product, Fractional Job Search Mistakes and Tips

Today, you'll learn:

• How Taylor Crane went from poker player to VC-backed founder to fractional head of product
• How he found his first clients as a fractional
• Strategies for maximizing take-home pay
• Biggest challenges and mistakes in fractional job searches, what to do about them, and the crucial mindset shift required to succeed

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Taylor is a 2x founder with a 10+ year background as a PM for early-stage startups. Currently he's founder of Fractional Jobs, the hiring marketplace for startups looking to hire expert fractional talent. Previously he was founder of Clubs Poker, backed by Village Global, scaled to 100k+ users, and acquired by KHK Games in 2023.

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Tell us about your career journey.

I was an online poker player in college when it was suddenly banned in the USA my senior year. I quickly switched focuses out of necessity from poker to startups after graduation (probably for the best). I spent about 10 years as a PM across a wide range of industries like mar-tech, insure-tech, prop-tech, and more.

In the second week of covid, I took a chance to start what became Clubs Poker, an online poker app for friends to play over video chat. I raised venture capital, and rode that roller coaster for a few years. We weren’t able to raise our seed round in the market downturn, and instead got acquired by KHK Games to launch a real-money poker company in the US market.

After a much-needed sabbatical in Bali, I jumped back into the game as a Fractional Head of Product for early-stage startups, the thing I know best. My experiences in the fractional world led me to start my next company way quicker than I expected, Fractional Jobs.

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Recently, you exited your last startup, Club Poker, before becoming a Fractional Head of Product for early-stage startups. What made you decide on pursuing a fractional career?

It was a direct result from building Clubs Poker and being absolutely desperate for expert-level help on the areas of the business I was less skilled at (e.g. marketing). After Clubs, it felt very natural to want to offer that expert help to startups.

I also had the intention of starting another company at some point, and felt like the flexible lifestyle and money from doing fractional work was a great way to bootstrap.

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Many professionals don’t know how to get started as a fractional operator. How did you design your first offer and find your first 2 clients?

The reality for fractional leaders right now is that 90% of our clients will come from your own network. If you don’t have a sizeable enough network to find clients from, it doesn’t matter how skilled or expert you are, doing fractional work will be quite challenging. This is also why I started Fractional Jobs, but we’ll get to that later.

I am lucky enough to have a pretty large network from my Clubs Poker journey and prior startup work. When I was ready for work, I wrote up a draft “offer” with a few bullets of what I can do, and posted it on Twitter hoping to get feedback. Instead, I got my first client that way.

Here’s that Twitter post:

My second client came a few weeks later when I was browsing a founder Slack and saw someone looking for a fractional Product expert, and I jumped on that too.

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You shared an interesting breakdown of take-home pay for W2 employee vs independent contractor on Linkedin. What are strategies that fractional operators should consider to maximize their take-home pay?

I want to preface by saying that this gets a lot more complicated, and perhaps above my paygrade, when your primary address is NOT in the USA. However, I imagine most of the principles are the same.

As I explored in that Linkedin post, W2 employees get screwed on taxes. Or said differently, the tax code is rigged in favor of business owners. The combo-move is to set up your LLC & elect to get taxed as an S-Corp. This allows you the freedom to engineer your compensation in a way that saves the most on taxes. Plus, all the deductions 🙂

The summary, assuming a US-based home address, is that a fractional leader (independent contractor) will take home about 10 - 20% more than a W2 employee, assuming the same gross pay. This is huge!

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Now you’re building FractionalJobs.io, a fractional job board platform. What are the biggest challenges you’ve observed facing fractional operators in their job search?

The core challenge, by a mile, is finding leads in the first place. I faced this myself, I met other fractionals facing this, and it’s the sole reason why I built Fractional Jobs.

A couple tips on tapping your network as you break into fractional work:

1. Start by reaching out to your network privately - former bosses, colleagues, mentors, friends, etc.

2. Once you have a tiny bit of momentum (including a more refined pitch), then engage your network in a more public way on social, with more confidence

(I actually did NOT do this, I went right to social, see above, without thinking much about it. I actually think I would have performed better if my message on social was not “hey here’s my WIP blurb”, and more “Hey look at what I’m doing now, let’s chat”)

Another common challenge is figuring out how to structure an engagement with a client. Hourly or monthly retainer? What does cancellation look like? Should you do a trial? When do invoices get paid?

And a third challenge, for those that are successfully doing fractional work already, is keeping your pipeline filled even if you’re currently filled with clients. Always be selling, as they say.

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What are the top 2-3 mistakes you’ve seen fractional operators make in their job search? What could they have done differently?

1. Terribly written bios/summaries/intro notes. You don’t need to write your entire life’s work. Instead, hit the 3-5 bullet points that you think are most relevant for the role. Short, sweet, confident.
2. Not tailoring your pitch to the needs of the company. I see so many copy/pasted pitches. Yes, it saves you time, but you will stand out if you take a few minutes to address aspects of the role that the hirer has already demonstrated they care about. I’ve even seen fractional operators starting to record quick Loom video pitches. HUGE STANDOUT!

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What counterintuitive or non-obvious advice would you give to professionals looking to start a fractional business?

You might think that to be a successful fractional operator, e.g. a Fractional CTO, your primary job is to be an excellent CTO. This is not true. You are now a business owner, and your job is to sell Fractional CTO services. Your primary job is that of a business owner, and the product you happen to sell is yourself.

Your “product” has to be great, so you DO have to be an excellent CTO. But that’s the easy part of the job. Being a successful fractional operator requires a mindset shift away from “I’m an Engineering leader” to “I’m a business owner”. And it’s a shift that I don’t see enough fractional operators make.

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Where can we go to learn more about you?

You can follow me on Linkedin & Twitter, and can subscribe to the Fractional Jobs newsletter here.

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This post originally appeared on Money Abroad - the newsletter for growing wealth while living abroad.

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