2020 Simple Hiring Guide for Shopify Stores | Part 2

This article is the 2nd part of our 2020 Simple Hiring Guide for Shopify Stores. Just to recap, here are the topics covered in each piece (along with links):

  • Is it really time to hire, or should I put it off? (Part 1)
  • For which roles should I hire first? (Part 1)
  • Should I hire a generalist or a specialist? (Part 2)
  • What are the upsides and downsides of remote workers? (Part 2)
  • How should I evaluate potential new hires? (Part 3)
  • What should I do to prepare for my new team member? (Part 3)
  • If I need to let somebody go, when and how should I do it? (Part 3)

Ready for Part 2? Let’s go!

How Many Hats Can One Person Wear?

“How can I possibly afford to hire all the people I need?!” you might be screaming.

You're right to ask that question. The truth is that you probably can't. So, inevitably, the question is: should you hire one person to do all the jobs, or hire a specialist.

I, and many others, err on the side of specialists more than generalists in most cases. But let’s explore each option.


For most roles within your Shopify store, hiring talented specialists is the way to go. You simply don’t want an amateur fiddling about with the backend of your site or making guesswork of the Facebook Ads dashboard. These tasks are best left to professionals.

Sure, specialists are often more expensive. What’s more, finding a real specialist can be difficult with all the snake oil salesmen out there. Perhaps that’s why it’s often easier to work with trusted agencies or experts within the Shopify community to get yourself off the ground.

Check out our interviews with Kurt Elster and Jonathan Kennedy to learn more about some of the excellent services out there for Shopify entrepreneurs.


Generalists, while often affordable and with a seemingly endless list of skills, often don't perform well on a technical or strategic level, at least at first. Yes, they might be good at wearing a few hats simultaneously, but each of those business sectors usually suffers from the generalist's lack of expertise. At best, generalists are good at filling in gaps, but only when those gaps must be filled lest the business burns down.

As such, some decent places to place generalists are:

  • Customer support
  • Product fulfillment
  • Basic content writing
  • Entry-level social media management and community engagement

There is one notable exception to this rule. Generalists that show a lot of initiative and a strong desire to grow with your brand can often outshine specialists in the long run. Perhaps not so coincidentally, that's because those types of generalists end up becoming specialists themselves, specialists who came into their own in your business.

As a former generalist myself, I can attest to this. I’ve also worked with countless other highly successful specialists who started as entry-level generalists only to go on to highly specialized and well-paid positions. Many of them are with the same company where I met them.

So, don’t overlook a good generalist. They might just be your best hire ever.

How should you hire them?

Whether you’re looking to hire a part-time contractor or full-time employee, the question of how to find and narrow down your choices may seem like a tough nut to crack. However, it’s really simple.

On Hiring Generalists

Always start with friends, family, and close acquaintances. You already know this group of people intimately. You already have rapport. They’ll often work on a flexible schedule, for less money, and with a desire to grow.

If you can't find anybody suitable in your inner circle, start in your local community. Ask around at your favorite hang-out spots and cafes. Think about the barista or the bartender with whom you love interacting. Maybe they want some extra income and would be a stellar customer service representative or could help fulfill orders for you during days or weekends.

Finally, if you're still stuck, then you can post online.

From the expensive and often poor-quality job listing sites to sifting through hundreds of useless applicants with no real sense of their quality, this really is the worst option. What's more, you start from scratch with these types of people: no relationship, no rapport, no loyalty.

On Hiring Specialists

The process for hiring specialists is the complete opposite of hiring for generalists. In other words, start online work your way toward your inner circle.

There's one excellent reason for this: we overestimate the abilities of those close to us. Sure, your cousin Greg might have built one or two websites, but is he qualified to be the CTO of your budding new Shopify empire? Likely not.

There are, of course, exceptions. But in general, look for expertise outside your inner circle first, then work your way inward.

Remote or In-house

Finally, the question that’s on everybody’s mind these days. Should you hire remote employees or work with an in-house team?

Here, I’ll make the argument for both.


There are two primary reasons to go remote.

  • Save money
  • Access new talent

If you live in the US, Canada, or much of Western Europe, the chances are that hiring talented developers and marketers can get quite expensive on the local level. By hiring remote employees in Eastern Europe or Southeast Asia, you'll save a ton of money, which you can use to help grow your business.


As a "digital nomad" myself, I meet hundreds of new location independent workers every year. The trend toward remote work isn't slowing down anytime soon. As such, some of the most talented people are going remote, simply because they can. As such, many companies have been going wholly or partly remote in recent years so that they, too, can be a part of the cool club. So, if you want access to that talent, you have to be willing to go remote also.

That said, going remote, whether as a company or an employee, definitely has its downsides. As part of multiple remote teams myself, I can attest to the drawbacks of going remote, which also happen to be the upsides of going in-house.


There are also two essential reasons to keep your team in-house:

  • Culture
  • Accountability

Culture is a set of acceptable behaviors that form when a group of people interacts over time. We have home cultures, work cultures, and cultures among our various friend groups. People tend to conform to workplace cultures rather quickly (or else quit) because they commit to spending eight or more hours each weekday interacting with their workplace peers.

In a remote company, that level of interaction mostly doesn't exist.

Maintaining a high level of interaction with a fully distributed team is incredibly difficult. Zoom or Skype calls simply don’t make up for the subtle micro-behaviors your see during in-person meetings, nor does Slack at all compensate for the chance run-ins at the coffee machine.

The irony is that one day we may perfectly replicate VR offices so that we can better interact with our remote colleagues, only to realize that we have once again trapped ourselves inside a box.


I don't care how responsible and organized your remote team members are. Lack of contact equals a lack of accountability.

It may be true that we’ve all had in-office days where we accomplished little more than reply to a few emails and watch cat videos. But were it not for being in the office, I expect those few emails would never have been handled at all.

When nobody is looking over your shoulder, it's all too easy to take a day off or otherwise be lazy, even if you are 'on the clock.'

In short, distance degrades accountability.


We'll be back with Part 3 of our 2020 Simple Hiring Guide for Shopify Stores in a few days. Be sure to follow us on Facebook and Twitter, so you don't miss out. While you're at it, you should also subscribe to our newsletter!

Ryan Chatterton

Judge.me Editor, Content Strategist, Digital Nomad, Coworking Influencer, Lover of Wine & Tacos