How to turn a job post into a contract

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I hate taking orders.

I’m not good at being compliant. From the time I was very small. Told my kindergarten teacher to f-off and ran away from class.

30 years later, I found myself sitting on Santa Monica pier staring at the ocean, wondering if I had had my life’s fill of taking orders.

The Head of Product at my company had just given me an ultimatum.

Follow my orders or move on.

Ok dude, challenge accepted. I’m so outta here. But how?

I couldn’t really afford to quit and have no work, and even though I knew I could get another job, the 8-12 week interview cycle in tech was getting real old.

But what about a contract?

It turned out to be the perfect exit plan.

It has also become my continuous fall back plan.

Today’s issue is about how to find a full time job and turn it into a contract. Perfect if you could use a little padding in your pipeline this fall!

How to turn a job post into a contract

The story

Back in 2019, I took to the job boards to find a full time role that was similar to what I wanted to do on a contract.

Tech companies were pretty used to 3 month stints from just about anyone so I knew it wasn’t going to be that hard to convince them to make this switch.

Here was the role I found (can you believe I still have this screenshot):

INSTEAD of applying, I went over to LinkedIn to look up who I knew on Gusto’s design team.

Low and behold! Vlad worked there!

I didn’t know Vlad that well. We met through the growth design community. But I sent him a DM on LinkedIn anyway—would he intro me to the hiring manager?

He said yes! This is my follow up email to him for forwarding.

From there, I did a call with Kostas, the Head of Product Design, and we were off to the races.

Here’s some details about the interview and deal process:

• Virtual meetings: 3-4 (I met with Kostas, the team and the CMO separately) and I did a portfolio review once or twice.

• In person meetings: 1 (I flew up to SF for a half day in their office—I was already speaking at a conference so it worked out well.)

• A few weeks of emails and calls: On the procurement, contract, payment details

• Deal size: $118,100 USD

By October, I had a Gusto badge and laptop and was working on a 6 month contract to lead a growth design project 🚀 

The strategy

1. Find a job that suits your skillset and sounds like a contract you’d want to do

2. Locate the hiring manager (bypass recruiters and AI)

3. DM or email them and see if they’ll talk to you about the role (“Are you open to this being a short contract role?”)

4. Decide preferred contract format (in my case, Gusto was full time for 6 months but later on, I’d do a couple part time contracts—half time or hourly)

5. Anticipate and be ready to debunk hesitations (common ones are how long you’ll stay, how much you’ll be part of the team and location/remote work)

The sticking points

Sticking point 1: I didn’t live near an office
I lived in LA and the entire team I’d be working with was in San Francisco. Gusto wasn’t that keen on remote work. I agreed to fly up to SF once a month if they paid for it (which they did.) Their SF office is stunning btw.

Sticking point 2: How they’d pay me
I wanted to invoice and be paid as a corporation (which I had newly formed and was planning on using!) but that wasn’t that easy for them. They had previously set up contractors through a staffing agency. My insistence on the invoice route would mean that I was paid late every time.

Sticking point 3: I had no contract to give them
We used their contract not mine (I didn’t have my own Master Services Agreement yet). I shared a similar scope of work from another project and that’s what went into their contract.

I didn’t have lawyers at this time but now, I have Counsel for Creators write and review most contracts (especially with bigger companies where payment comes from a department).

The hacks

• Use your LinkedIn connections: Avoid applying via the job link. Especially now, that’s filled with AI automation and recruiters. You’ll have way better luck finding a contact inside the company.

• Take an informed guess at who the hiring manager might be: Don’t know anyone? Look up the company on LinkedIn and see if you can figure out whose in charge of the role. I did this on the Winning by Design outreach (where I didn’t know anyone) and I might have even guessed their email address.

• Lead with fit, close with contract: Sell them on you first (why you!) and make sure it’s clear you’re not interested in full time and what the contract looks like in your mind.

• Be opinionated about the role: It’s “I’m perfect for this one role” not “do you have any roles.” The more confident you are, the more confident they’ll be that you’re the one.

• Have solid links to share: A website, a good LinkedIn profile, a PDF, whatever highlights your expertise. You must establish credibility fast. Send what they need to vet you!

Last tip I’ll share is from my friend Holly who years ago only wanted to work at Netflix. She told me when she applies to jobs, she’s just looking at 3 or 4, not hundreds so she can focus on getting in there.

Her method worked to get her in at Netflix and I’ve loved it ever since!

P.S. I found this hilarious photo of the Gusto team dressed as the design tool Figma for Halloween (it’s not gonna make sense.) See if you can spot me 😛