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Welcome back!

After three years of building Chezie and multiple iterations of our team structure, we've finally found what works for us: a lean team of contractors. We've gone from full-time employees to contract developers, from US-based teams to international talent, and learned a lot of expensive lessons along the way.

Here's our team evolution story and why we ultimately decided contractors were the way to go.

Our Team Journey

Our first year was just me full-time with my sister working part-time. We built our MVP on Bubble and landed our first few customers. Then, like many founders, we got ambitious. We moved away from Bubble to build a full-stack version of our product. This kicked off a series of team changes:

Currently, we operate with two founders and a mix of contractors. Specifically, we have two developers, one designer, one VA, and two content creators. Our team is the most efficient and flexible it has ever been.

Why We Switched to Contractors

After several painful hiring and letting-go experiences, I decided we needed to be as flexible and lean as possible. Here's why contractors made sense:

1. Hiring is Really, Really Hard

Hiring full-time employees was probably the second most burned-out I've ever felt as a founder (first place goes to fundraising). It's exhausting between sifting through hundreds of irrelevant applications and fending off headhunters trying to charge 20% placement fees. It always felt like there were more jobs than available talent. When you're a startup founder, you don't have the money to invest in expensive recruiting tools, and the process ends up taking as much time as fundraising.

2. You Can't Really Judge Fit From Interviews

I've made three bad hires and'll be completely transparent about what went wrong.

Someone can look perfect on paper, ace the interviews, and even do well on take-home assignments. But there are critical things you won't discover until you're working together.

For example, we hired two incredibly intelligent people who could articulate concepts beautifully, but when it came to actual output, they lacked the bias toward action we needed. You can't assess someone's velocity or output quality through interviews alone – you need to work with them. And once you've gone through the entire process of hiring someone full-time, it's much harder to make changes if things aren't working out.

3. Flexibility is Everything

When running a startup with limited funding, your number one goal is staying alive. What is the easiest way to do that? Keep money in the bank. And the easiest way to save money is to reduce hiring costs.

With contractors, you can:

• Scale down when things are slow

• Quickly add capacity when things are busy

• Avoid expensive US salaries and benefits

• Skip payroll tax complications

A lot of founders fall in love with the idea of building a big team, but the truth is, you often don't need to. Things move quickly in startups, but not always predictably. Having the flexibility to adjust your team size and cost structure is invaluable.

Our Process for Finding and Managing Contractors

Here's my playbook for building a solid contractor team:

Finding Great Contractors

I always use Upwork, and I'm extremely detailed in job posts. We specify:

• Required skills and experience

• Our working style (daily standups, response time expectations)

• Time zone requirements

• Communication expectations

I shortlist to the top 3 candidates based on ratings and reviews, then pay attention to every interaction. If someone takes days to respond to a message, that's probably how they'll be to work with.

Here’s an example of a job posting and take-home assignment I used for our contact UX designer.

Managing Successfully

Managing contractors takes a different approach than managing full-time employees, especially when most of your team is international. I do a few things to make it work:

Regular Check-ins

The key is finding the right balance of synchronous and asynchronous communication. For our engineering team, daily standups are non-negotiable. However, weekly syncs work better for designers and content creators who work on their own schedules. These regular face-to-face meetings help maintain alignment and build relationships.

I'm particularly strict about communication during working hours. During interviews, I explicitly stated that I needed responses within 15-30 minutes when contractors were "on the clock." This might sound intense, but there's a reason: we often get urgent customer requests that need quick attention. Being upfront about this expectation helps filter out contractors who aren't comfortable with this work style. Doing this also makes it easy to let go of someone if they aren't responsive because you clarified the requirements.

Clear Communication Channels

We use Slack for most communication, and I'm very intentional about keeping things organized and transparent. Every week, I clearly outline what needs to be done in our Slack channels. This is especially important for our international team members who might be sleeping during US business hours.

Time Zone Management

All but one of our contractors are international, which presents unique challenges. We've had to be creative about scheduling and communication. For instance, with our engineers, we have set working hours that overlap with our US team. We're more flexible for other roles like design and content creation, where real-time collaboration is less critical.

Async by Default

Whenever possible, we default to asynchronous work. This means detailed documentation, clear task descriptions, and explicit deadlines. However, we've learned that even with async work, regular face time is crucial for building trust and maintaining alignment. Our weekly syncs aren't just about status updates—they're about maintaining relationships and ensuring everyone feels connected to the team.

Tips for Keeping Great Contractors Around

One challenge of working with contractors is that because they aren't full-time, they can easily leave you and switch to another role. For that reason, you need to be very intentional about what you offer them to make them want to stay. Retention is just as important for contractors as it is for your full-time hires.

If you’re looking into bringing on contractors, consider these strategies:

1. Pay Above Market - We pay about 10% above market rates. This is still cost-effective for international contractors, but it makes us a preferred client.

2. Respect Time Off - Honor local holidays and time zones. If someone is based in Mexico or Kenya, they get their public holidays off.

3. Be Transparent - Ask for openness about other projects and commitments. This helps with scheduling and availability.

If you have thoughts about working with contractors or want to share your own experience, reply to this email! Would love to hear from you 🤝

Catch you next week,

Toby