How to Hire Your First Engineer

Drowning In Support Tickets? Maven AGI is here to help.

Maven AGI platform simplifies customer service by unifying systems, improving with every interaction, and automating up to 93% of responses. Seamlessly integrated with 50+ tools like Salesforce, Freshdesk, and Zendesk, Maven can deploy AI agents across multiple channels—text, email, web, voice, and apps—within days. Companies like Tripadvisor, ClickUp, and Rho slash response times by 60%, ensuring quicker support and exceptional customer satisfaction. Don’t let support tickets slow you down

Request a free personalized demo today.

Hey Shifters!

As a founder, I've done a lot of hard things. But two challenges stand out above all others: fundraising and recruiting.

About 50% of my writing is about fundraising, so I wanted to spend today talking about the other beast: hiring.

Specifically, let's talk about hiring your first engineer.

Why focus on engineering? For most founders, especially those who can't code, this will be your first and most crucial hire. While you can contract or outsource many aspects of building a company – design, marketing, content creation – you eventually need someone dedicated to creating your product. Unless you can code yourself, that means hiring an engineer.

Similar to fundraising, when I started to recruit, I felt utterly lost, asking myself, "Where do I even begin?"

Let me share what I've learned about this process – what worked and what I wish I'd known earlier.

What Makes Recruiting So Tough

In my experience, four things make recruiting difficult.

As a startup, you're competing with all that while offering... well, less of everything, at least on paper.

Here are the significant challenges you'll face:

Competing Against Big Tech

Big tech companies can pay their engineers astronomically well - we're talking as much as $200K for entry-level roles at companies like Meta. Plus, they offer incredible benefits, job security, and the prestige of a recognizable brand on your resume.

There are also brand recognition factors that engineers should consider when working in big tech. Think about it: would you instead spend two years at Meta, where you're guaranteed a substantial salary and a resume boost, or two years at an unknown startup that might not exist when you’re done?

That's the reality you're fighting against.

Finding the Right Talent

Staying on the thread of big tech, there is a MASSIVE difference between a startup engineer and a big tech engineer. At an established company, the ways of doing things are documented. You must follow the existing processes and ensure that things are correctly executed.

In comparison, nothing is documented at a startup. Your job is to document as you go and figure out how things should work. Even candidates who express being open to this sort of autonomy might not know what they're getting into when they step into the role.

Making the Right Choice

There is so much FOMO when recruiting. The most popular piece of advice that VCs give founders on recruiting is to ‘hire the best people.’

But how do you know this person you’re considering is the best person for the role?

Let me tell you something…

You don’t.

Extending an offer to a candidate comes with the risk of spending weeks or months of cash on them, only to realize later that they weren’t the right fit.

While all of these challenges are real, you can mitigate or even eliminate them with some creativity in your hiring process.

How I Hired Our First Engineer

Today, I have hired five people to work at Chezie. And I've gotten better about recruiting after every one.

I am super intentional about keeping playbooks for all of the processes we have at Chezie, and recruiting is no different. It's a work in progress, but here is the playbook that's worked for us and helps me mitigate some of the challenges I mentioned above.

1. Make Your Job Attractive

You can't compete with big tech on salary, so don't try. Instead, lean into what makes startups unique:

• Autonomy over management - Big tech gives you a manager and a roadmap. At a startup, you get problems to solve however you see fit. This isn't just a job – it's actual career development, not climbing a predefined ladder.

• True Equity over stock options - While big tech flashes RSUs, startups offer real ownership. If things go well, early employees can create life-changing wealth.

• Impact over bureaucracy - You're another cog in the machine at big tech. They'll fill your role the day you leave. At a startup, your presence is felt every day. You shape the company's future and leave an imprint that lasts.

All of the candidates that you talk to should understand that working at your company is an opportunity to grow 10x faster than they would at a big tech company. Be very intentional about sharing how you see them growing in the role as you recruit them.

2. Tell Your Story

I make it a point to share Chezie's founding story in every single screener interview. I talk about what inspired us to start Chezie, our background as employee resource group leaders, the glows and grows that we've had in our three years building this company, and where we see it going. This helps candidates understand what we're building and why it matters.

It also doesn’t hurt to have this NPR video to share:

Use your founder story as a differentiator. When candidates interview at Meta, they meet with a a recruiter that doesn’t have any personal connection to the company. But you can share your mission, vision, and why you're building what you're building.

3. Look in the Right Places

Think of recruiting like sales – you want to be where your potential customers (in this case, candidates) are already looking. I always use Wellfound.

Here's why Wellfound works:

• It's specifically for startup jobs, so candidates are already interested in early-stage companies

• Monthly access is affordable ($400) compared to other platforms

• You can message candidates directly through Wellfound and see who’s been actively searching the platform

One of the biggest hacks I uncovered was that with Wellfound’s paid plan, you get access to every candidate’s resume. Everyone puts their email and/or phone number on their resume. So, depending on how aggressive you want to be as a recruiter, you can contact someone directly even if they aren’t actively looking for a new role.

P.S. - if you’re looking to use Wellfound to hire, reply to this email and I can connect you with the folks there. You’ll get $500 off and I’ll get a referral bonus 🤝🏾.

4. Be Consistent

We follow the same four-step process for every hire:

1. Application: Include prompt questions to filter out mass applications. If someone won't spend 5-10 minutes on application questions, they aren’t the right person for your job.

2. Screener: 15-minute call to gauge interest and provide role details. This is where I share our founding story.

3. Assessment: Create a project that mimics the actual work they'll be doing. I could write a whole newsletter about just this (and I probably will at some point), but the assessment should take the candidate 1-2 hours to complete and you should pay them for two hours of whatever their hourly rate would be or $150 total, whichever is higher.

4. Culture Add Interview: Notice it's "culture add," not "culture fit." We want people who enhance our culture, not just match it.

5. Don't Overthink

You'll never be 100% sure you're hiring "the best" person. That's okay.

If you have a candidate who:

• Is excited about your company

• Can demonstrably do the job

• Passes your assessment

• Aligns with your values

• Has good references

Then make the offer. Don't wait for the perfect candidate who might never come. A bird in hand is worth two in the bush.

Pro-tip: To make this more objective, create a checklist of must-haves. If a candidate checks all your boxes better than other candidates you're considering, they're probably your hire.

The Bottom Line

Unlike fundraising, which some founders might choose to skip entirely, hiring is something every founder will eventually need to do. It's a crucial skill that you'll use throughout your entire journey building your company.

I can't claim to be an expert – I've only made a handful of hires at Chezie. But this process has worked for us, helping us find engineers who not only have the skills we need but also believe in what we're building. There's no perfect way to hire. You'll need to develop your own process based on your company's needs, culture, and constraints. What matters is having a systematic approach that you can refine over time.

Your first engineering hire can make or break your startup. Take the time to get it right, but don't let perfect be the enemy of good. Sometimes the best candidate isn't the one with the most impressive resume – it's the one who believes in your mission and is ready to help you build it.

Would love to hear from other founders: what's worked for you in hiring engineers or other roles? Reply to this email and let me know!

See you next week,

Toby