Making Your First Hire in a Web Design Agency

December 28th


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When is the right time to make your first hire to grow your web design agency?

When we were making our first hire, it was a tough process.

We didn’t really know what we were doing. We’d never hired anyone before.

But, by now, having been through the process, and having hired many people since, we’ve learned a few lessons to share.

What’s in this article:

Proper Expectations

From the beginning you’ll need the right expectations, or you will never see anyone as a perfect fit for the job.

At first, when you bring someone on, you are going to spend a lot of time training them, so much that you might be thinking, “Is it worth it?”

It’s taking awhile to get them up to speed.

You’ll be falling behind in your other tasks.

Things will start piling up and you’ll have more work to do than ever.

Now, you might be able to do something in 1/3 the time it takes to show someone else how to do it.

But, without dedicating the time to training someone, no one else will be able to work for you, and you will never be able to scale.

If you want to scale, you can’t be the entire process forever.

So, be mindful of this, and be patient.

When Are You Ready to Make Your First Hire in a Web Design Agency?

The answer to this question is tough.

With our agency, we knew we were ready to hire when we had consistent cash flow that could pay their salary, we had a need for someone to take on a specific position, and, we thought we should’ve hired someone a few months earlier.

That’s how we knew.

And to this day, that’s still kind of my barometer.

I don’t hire when I think I could have enough work for someone.

I only hire when our team is at or nearing our capacity, and there is enough cash flow to pay for the new hire.

The alternative – hiring someone hoping they’ll alleviate your stresses so you can get the finances back on track – is a bad idea.

You may not get the return on investment you’re looking for.

Training and onboarding takes time.

The Role You Need

Hopefully when it’s time for you to make the first hire, you know exactly what it is you’ll need.

You shouldn’t hire someone for the sake of hiring someone, but because there’s work to be done.

The Easiest Hires

In my experience, hiring designers and creatives are the easiest to bring on to your team.

They have the raw skills needed, which you don’t have to teach. They can easily work remote and manage their projects.

They can also easily be working for you on a contractor basis.

Also, designers and creatives are easy to evaluate – you can tell if their work product is good-quality, if they manage their time well, and stick to deadlines.

The Hardest Hires

In our experience, sales roles are by far the hardest to fill.

In my experience, one challenge is that salespeople tend to interview very well, whether they are a good or bad salesperson. Because sales people “sell”, they also sell themselves very well.

In fact, I find that sales candidates are the most impressive interviewees.

Of course, I’ve found that it’s hard to find a good salesperson.

Junior-level sales roles are easier, and less expensive, to fill. But they also have significantly less experience.

More senior salespeople will command a very high salary, with both base salary and commission.

Oh, that reminds me.


You need to figure out commission.

In my agency, we did a mix of a percentage of the up-front and the ongoing charge.

Other ways I’ve seen it done – you do a portion of the upfront with a one-time payment for like one month’s recurring revenue.

Contractors or Full-Timers?

We’ve hired in different ways for different roles in the past.

Developers and designers we’ve usually started out with on a contractor basis – giving them work as-needed. But, at a certain point it makes more sense to bring them on full-time.

Salespeople should always be hired in-house and on a full-time basis, in my recommendation.


Salespeople need extensive training.

They can’t learn your service and your pitch, and improve upon it as well remotely. Some may disagree. But this is my experience.

Having a salesperson training with you face-to-face, listening in on your sales calls, having you to listen to their sales calls, and provide real-time feedback, helps them get up-to-speed a lot quicker.

The Difference Between Contractors and W-2 Hires

The easiest way to add someone to your team is as a contractor.

Legally speaking (and also very generally) a contractor is someone who works with you but has their own autonomy and independence. There’s more nuance to it, but I don’t want to get into a whole post on the legalities of it.

Contractors can be paid hourly or flat fees for projects.

The employer pays them directly for their services, but does not pay their employer taxes. The employer of a contractor does not provide any benefits like health insurance, disability, or unemployment.

Contractors are responsible for finding their own insurance and paying all of their own taxes.

Compare this to a W-2 employee (in the United States).

Someone working at your office, with set hours, under your supervision, should generally be employed as a W-2 employee. As a W-2, the employer pays taxes on the employee’s wages, and can offer benefits like health insurance, and 401k.

Being a W-2 employer is more of a headache, because it requires that the employer have a regular payroll.

Onboarding our first W-2 meant that we needed to file documents with our state, get unemployment, disability, and workers compensation insurance, and there was a lot to it.

Thankfully, we used software called Gusto that took care of all of this for us.

It streamlined and automated onboarding and payroll.

Gusto connects to your business bank account, calculates payroll taxes, and can pay employees either via check or direct deposit. Gusto also files all tax documents with the appropriate states. Even with a contractor, Gusto takes care of their annual 1099, a requirement for any contractor paid more than $600 in a calendar year.

Very easy to use.

If you are ever planning to hire a full-time W2 employee, or even a contractor, I would strongly recommend checking out Gusto.

If we were to do manually what Gusto does automatically, it would have taken dozens of hours.

Now, payroll is taken care of automatically for us.

The Job Listing

Writing the job listing can be tricky.

When you’re thinking about the job listing itself, come at it with this mindset: The job listing is partially to sell potential hires on why they should want to work with your company, and also ensure that only qualified people get in touch with you.

One piece of advice – don’t require too much.

The more requirements you put in, the fewer people respond.

You might be afraid of sifting through tons of unqualified applicants. But heres a secret: You will get underqualified applicants no matter what’s in your job description. Some people just barely skim the requirements.

I have a “hack” for job listings that weed out some unqualified people, and I’ll share that below.

But, if you ask for too much of your applicants, good candidates will not reply to your job ad.

Over the years I’ve created a lot of job ads.

My first job ad was terrible, in retrospect.

The ad read like I needed to hire a NASA engineer for a graphic designer position.

And because of that, we barely got any applicants.

Whatever skills you can teach, and plan to teach in the onboarding, don’t need to be a requirement. There are always “nice-to-haves” – skills that you might want someone to possess. But, you might not need everything.

Also, don’t forget to sell your position in the ad. People viewing the ad should be excited to apply to your position. The ad helps you weed out bad applicants, but also helps people choose where they’re going to apply.

Why would I want to work for your company?

Do I get to work on interesting projects?

Will I get to grow my skill set?

Will I get to take on greater responsibilities?

Is there potential for this to become a leadership role eventually?

Before you post, have someone else look at the listing.

Share it with a colleague. Someone who will give you honest feedback.

Asking for Referrals

One way I’ve found success with hiring a few people by this point is by referral.

Post on Facebook or LinkedIn.

Say, “Hey, my awesome company is looking to hire for this role. Please share with anyone you think would be a good fit.”

Your contacts will then refer qualified applicants.

Typically, I’ve found referrals to be the best quality candidates because your contacts will only refer people they think would be a good fit.

Think of it this way – no one is going to recommend a bad candidate.

If you were to hire them and it doesn’t work out, it reflects bad on that person who referred them. “Hey Max, you recommended Alex and it was terrible! They had no experience at all, and were late to work every day. You said you worked with them before?”

Yeah. No one is going to refer a bad candidate.

I’ve also done this internally.

Let your team know that you’re hiring for a new role. Offer a small bonus if they recommend a candidate who ultimately gets hired.

Your employees will only refer you if: 1) they like working with you; and 2) they have someone in mind who they would want to work with.

So, that’s a win.


My Hiring “Hack”

How to find the right candidate…

This next tip is my secret sauce. Don’t tell anyone.

Okay, so here’s what you do:

First, set up a Google Form with a few screening questions.

Create a question that’s relevant to the job. Something that someone with the skills you’re looking for can answer to demonstrate their knowledge.

In the past we’ve used questions like “What would you change about this website design ([insert url])” or “If you’re cold-calling a company, how do you get past the gate-keeper?”

You should also require a name, email address, phone (obviously), and have a question field for someone to share their resume. What I like to do is say, “Please share your resume via a Google Drive or Dropbox link”. This is a simple technical hurdle that ensures the people who apply have some basic computer skills.

Make the form “Public” viewable and save the link to the form.

Next, create an alias email address, and a filter in your email account.

I recommend Gmail / G-Suite for this.

In your admin panel, you can create an alias email.

Create an alias email for “[email protected][your-url]”.

Then, in your email client, create a filter for emails sent to “[email protected][your-url]” with the subject line “I like web design” (or “I like [job position]”.

I promise you, there is a method to this madness. Stay with me!

Next, create an automation in IFTTT.

IFTTT or “If this, then that” is a free automation app. Basically, if some event triggers, it actions something else to happen.

Create a free account and connect your email app.

Your “trigger” is going to be an email to “[email protected][your-url]” with the subject line “I like web design.”

The subsequent “action” is going to be to send an email back to the recipient.

The email should say, “Thank you for applying for the [job title] position at [your company]. To complete your application, please visit [questionnaire link].”

Then, create the job posting.

In the posting, do not let people apply by replying to the posting.

Instead, in big letters, say “TO APPLY FOR THIS POSITION, PLEASE EMAIL [email protected][your-url] WITH THE SUBJECT LINE “I LIKE WEB DESIGN.”

Last, test the automation sequence.

From another email address you have, test the automation. Send an email to that “[email protected]” email address.

If everything is set up right, you should then get an email back asking you to fill out that questionnaire.

Then, fill it out and submit it.

You should then see that applicant logged in your form results.

I know this seems like a big process for hiring, but it is 100% worth it.

So, this ultimately does a few things:

  1. This weeds out people who don’t follow instructions. It forces them to follow your instructions to submit their application.
  2. It requires some basic technical ability. Applicants have to know how to use Dropbox or Drive, create a public item, and share that link

The candidates you get from this have put in the effort, and this process weeds out people who would just waste your time.

Hiring people is expensive.

It’s a big time and cost investment for you.

You can spend dozens of hours reviewing applicants, interviewing, hiring, and training new hires. You want to make sure you get it right the first time.

So, this process helps.

The Interview

For your interview, I have some recommendations.

First, write out your questions ahead of time. Use the same questions with all interviewees, and take notes, so you can compare them later.

Start out the interview light. You can progress the questions to get more difficult or technical.

But, start out light, to ease them into the interview.

And, hopefully, let their guard down a bit.

“How was it getting here?”

“How’s your day going?”

Hopefully you can get past their “interview filter” and learn about them to get a sense of what it would be like to really work with them.

I had a candidate once who, after we started chatting (before we really got into the meat of the interview), kept swearing constantly. Like all $h!ts and F*cks thrown in to their casual conversation. Just, nonstop, maximum swearing. Yes, really. This happened.

Now, I don’t have a problem with swearing.

But, I do have a problem with swearing in an interview.

Especially if it’s for a customer-facing position.

If this is you on your “best behavior”, this does not bode well for the future…

Usually, I get a good feel for who I want to hire during the interviews. But I always take notes and compare them because I want to make sure that I’m not biased, or as unbiased as possible.

That’s something important to touch on, actually.


We all have unconscious biases.

People typically want to work with other people who remind them of themselves.

Be mindful.

Look at your interview notes.

Try and do what you can to take your personal preferences out of this.

Round 2 Interviews

I usually interview someone I’m going to hire at least twice before I make the decision.

I like the Round 2 because I want to make sure I wasn’t just in a good mood at a particular interview time.

Or, if I was having a string of bad interviews, an okay candidate can seem like a perfect candidate.

At our second meeting, I can generally get confirmation that I had the right instinct, or on a fresh evaluation, I realize that we wouldn’t be a good fit. By the second time we meet, I’ve already established some rapport with the candidate.

If you can, and if you’re interviewing in-person, use your Round 2 to take the candidate to lunch.

Not joking.

Take them to lunch.

In the lunch setting, you can ask some interview-like questions without the “pressure” of being in an office interview. You’re more likely to get more candid responses.

Making the Job Offer

So, now you’ve found a candidate.

Now, you need to make them an offer.

Before sending an email offer, call them first.

Tell them you were happy to meet them and that you’ll be sending them the job offer via email shortly. You can take the time to now to talk through the onboarding process with them, discuss what documentation you might need, and so on.

Next, send them an email with everything written out:

  • Job description
  • Hours
  • Salary and Benefits
  • Company holidays and paid time off
  • Goals for their 60-day probationary period (will discuss in further detail next in Onboarding)
  • Signature line at the end for them to sign acknowledging and accepting the position

Also, separately you should send a confidentiality & non-solicitation agreement.

This agreement should lay out a few things (and you can find samples online):

  • The new hire will be exposed to company trade secrets, proprietary knowledge and know-how, client lists and client-related information, and other things the company wants to be held secret
  • The new hire will keep all of this confidential and not share or distribute any information that should be confidential
  • The new hire will also not solicit any clients for any other business (this is in the event a new hire leaves to do their own thing, they don’t try to take the clients with them) 


Day 1 – what will they be doing?

My best advice here is to write out a curriculum. Ahead of time, know how you are going to train them. Otherwise, new hires take forever to get up to speed and providing a return on your investment.

For your processes – have everything written out from start to finish.

I know that you might know your processes in and out, but you should have checklists for everything.

A completely new hire should be able to read your process checklists and, provided they have the basic skills required for the position, know exactly what to do.

At my agency, we wrote out all our processes.

  • What steps go into designing a website?
  • What steps go into onboarding a new client?
  • How does sales and billing work?

Ideally, you should have everything about your business so well-documented that someone else could run it. That’s how you know you’ve done a good job.

And eventually, with all of this process documentation, you can “replace” yourself.

Meaning, you have an agency that is running without you needing to be running everything. With this, eventually you can take a few days off or take a vacation, without having to worry that everything will fall apart.

So, document everything.

As part of the new hire onboarding process, have your new hires go through your processes.

See what they get right, what they get wrong, and update your documentation as needed.

This is one of the biggest keys to getting a new hire up to speed quicker.

Importantly, if someone is doing something wrong, you have the documentation to point to.

I’ve made mistakes in the past by not having crystal-clear documentation.

And it’s slowed new hires from onboarding well.

You need to make no assumptions here.

Write out, and get screenshots, of every step.

Documentation will set you free.

The 60-Day Review

On Day 1, your new hire needs to know that they are in a probationary period, and that in 60 days you will be doing a 60-day review at which point you’ll be discussing next steps – if they’ll be staying on long-term or if they’re not a good fit.

Write out concrete objectives.

For example,

  • “Within 4 weeks, be able to design a client website from start to finish”
  • “Within 8 weeks, be able to take a new client from onboard to launch without help”
  • “Within 6 weeks, be able to make a sales call without help”

Tangible, achievable metrics are important because it creates goals to be accountable to.

It also makes your decision easier whether to keep them on or not.

You may like someone as a person, but if they aren’t able to get up to speed and are not a great fit for the position, you might need to let them go and look elsewhere.

At the 60-day mark, review their progress with them. Let them know how they did in relation to their 60-day objectives.

If they’re going to be a good fit, great. If not, now’s when you part ways.

Periodic Reviews – Quarterly and Annual

60-day reviews are great, but you should also make sure to have ongoing reviews once a quarter.

Each quarter your hires should have goals that can be achieved and reviewed, so you have a way to measure their progress. Same as the 60-day review, but more long-term.

And at their yearly anniversary, do an annual review.

Same structure as a quarterly review.

But the annual review should come with a pay raise and/or promotion.


Well, this is basically everything you need to know about hiring.

We’ve covered everything from knowing when you’re ready, to the role, to the job posting and interview process, to onboarding and the early reviews.

So take this knowledge with you, and scale your web design agency!

And, please feel free to share your experiences in the comments section below. I’d love to hear if you have any particular stories or insights from hiring in your web design agency.

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