In the early days of Drift, I did all the customer support until that became overwhelming on top of my full-time job. In order to manage and scale that, I began hiring outside contractors. At the time of writing this document, we’d recently hired some other full-time folks on the support team and I wanted to transition our contractor hiring and management process over to them as a career growth opportunity. I wrote this playbook out as means to make sure that they had all the context that they needed to be successful in going through this themselves.

I think the price range stuff is pretty counterintuitive. There was a tendency to just say, “How can we do this for the lowest cost possible?” But your brand is on the line, your customer experience is on the line: having bad customer support interactions can be the death of your brand in certain segments or circles if there are enough of them consistently over time.

Since we were hiring support folks to support people through our chat product, I never interviewed candidates over the phone or on Zoom. Why would I need to, when all that was important was how they interacted over text? If anything, I thought that talking to them via phone or a video call would just bias me. Hiring people directly through the channel that they’ll be using was a huge learning for me. Doing that lets you really understand how they’ll function in the role and makes it much easier and more efficient to determine if they’re the right fit.

Our training at Drift was pretty aggressive: by their second week, our contractors were taking the helm and in the fire of running support conversations. So it was really important for me to actively review their work early on. Their first few hours on the job, I’d go in the chat inbox and see the way they were responding to get a sense of whether they were just making up answers to stuff they didn’t know, rather than pinging me on the side to get clarification. You can tell pretty early on whether someone is capable of handling ambiguity well, which is something that I think is especially important for an early-stage startup like we were at the time, where the product is constantly changing and it’s hard to provide an exact playbook. As long as they were showing that they were capable of figuring things out on the fly as needed, we knew that we could feel good about continuing to invest in them.


I think really good contractors, especially in the support world, just don’t need any oversight after a couple of weeks. If I started to get things sent to me by other people on the team—whether it was, “Hey, this person answered this question weirdly” or “This customer was upset by the way they responded to their issue” or whatever—it was a quick signal that something was wrong. When it just worked and I didn’t have to think about it at all, those are the people we kept around for years, and they continued being successful in that role. We didn’t even have regular 1:1s, they just did the job and it was great and easy. I think that’s the biggest thing to keep in mind with contractors: you’re hiring these people to do a specific job, so it’s not a role where you want to be devoting time to constantly responding to things they’re doing that are off or bad


Matt Bilotti

Hiring support contractors might seem like an afterthought, but it shouldn’t be: your brand is on the line every time they interact with a user.

The playbook for finding, interviewing, hiring, and training remote support contractors

Over the past year and a half, we've hired 7 different remote support contractors to help our customers.

of them have been phenomenal ([Redacted])

of them couldn't keep up with the technical angle of things

was immediately a bad fit (this was the very first hire I made that I learned from)

This program has scaled out to give us, as of January 17th, 2018, coverage 

M-F from 3am-9pm ET, and Sat-Sun from 9am-5pm 

(who covers which hours [link redacted]).

We're relatively close to 24/7 support, which is super exciting...just a few more hires and we'll get there.


Keep an eye on volume in the success inbox...that is the leading indicator.

 If it is consistently above 7-10 open conversations during any given chunk of hours...  First check to make sure the people on chat duty are actively contributing.

 If that is the case and the remote support person is also doing great and this is consistent over the course of about two weeks, it's time to hire another person for that time block.

Reason 2 - Lots of chats are coming in during hours that the widget is offline

 If the beginning shifts (right now that's 3am M-F, and 9am on weekends) are starting with more than 30 conversations, it's time to hire somebody into those off hours (that's why we hired Jeremy...the team was consistently coming into inboxes at 9am that were 30-50 conversations.

Reason 3 - We actively want to say we provide 24/7 support to enterprise customers (has not come to be yet)

All candidates have been hired through Upwork thus far.

Here is the process I've created over the past couple years that has been successful:

Go to our Upwork account in the "My Jobs" tab

Click on the highest version of "Customer Delight Representative (and Technical Support)

Edit the section of the job description to clarify which hour time slot you're hiring for

Set the start date 2 weeks from the point you're posting this 

(you should be able to find, interview, and fill this role within 2 weeks)

Here is the job posting I've written that works well**

** Every great candidate has cited this posting and the job title as the main reason they applied:

We're looking for someone who knows how to put smiles on faces and enjoys solving puzzles. The kind of person who simply wants everybody to be happy and knows how to find answers on their own. Somebody who will go out of their way to make sure somebody has everything they need and they understand a problem entirely.

Ideally, you understand software well or are super quick at learning it (or have some kind of technical background). We're a young software company and our product is constantly changing, and we need a person who will be able to keep up with that pace of change without a ton of guidance.

At our company, we're building tools for customers to talk to their customers. And that means we use our own tools or chat and email!

We're currently offering live chat support 

Monday-Friday from 9am - 9pm Eastern Time

As we grow, we're getting more and more customers overseas (in Europe and beyond) and we want to be there to support them during their days.

For the first few weeks, you'll be working closely with myself and a few others on our team to make sure you have everything you need to be educated on the product and provide a good experience.

You won't be expected to resolve all issues - Some will be very technical and the rest of the team is here to help. Ideally you can help work through any non-code-related issues and learn all the intricate details of how our product works over time, which will allow you to be able to tackle more and more on your own.

This is a very, very important role for us. You must be a native english speaker (or close enough to it). and able to deal with people whose first language isn't English. Any previous experience with Javascript is a major, major plus for this role.

Help be one of the faces of our company - our customers need you, the smiles you can share, and your ability to problem solve alongside them!

Generally, you'll get anywhere between 25-50 applications within the first 48 or so hours.

After 24 hours of posting the job, I'll screen through all of the applications, and shortlist about 5-10 of them.

The following two days, I'll do the same process and generally end with about 15 shortlisted (a feature in Upwork) candidates.

Highly recommended guidelines based on successes and failures thus far Immediately disqualify somebody if...

If somebody is offering <$4 to do the job

I have attempted to find a great hire at this price point again and again and generally these people are only really great at scripted support jobs - not for us

If somebody is offering >$25/hour for the job

They're not going to be okay coming down to the price range in which we pay these contractors ($13/hour is the standard for this role)

If the cover letter has bad formatting/grammar/spelling mistakes

We need somebody who knows how to be great at written communication above all else

They have the same bullshit posted into the cover letter / answers to screening questions that was clearly copy+pasted

about the heart and soul of this job posting

The best they can say about their technical background is they know things like Microsoft Word and Google Docs

I promise you, these people are not going to be able to keep up with the complexity of our product

Short-list somebody if their application contains most of the following...

They have thoughtful, non-robotic responses to the screening questions 

They've had previous education and can explain that they've worked with things like Javascript or APIs in the past 

Their test scores are generally decent (at the bottom of their profile)

They have a great, unique answer as to why they're a better fit for the role than all the other applicants (a pre-screening question)

Strange things that are surprisingly great indicators of a great potential hire...

They have no previous Upwork experience. 

every single one of the great hires I've made so far had less than 100 clocked hours on Upwork projects at the time of hire.

This is a signal that this is a person who's looking for the contracting life. They're new to this and are looking for something unique. We can get them before they're jaded by the shitty bullshit jobs that are rampant on Upwork

They inject some kind of humor into their application

It shows off the bat that they're going to fit well in the "be human" culture we have

They believe their personal rate (their suggested rate) lands between $11-$14.

They're already in the ballpark of our price range and are gonna be happy with it.

Okay, now you have about 15 people shortlisted.

The next step is to interview, which you will conduct entirely via chat.

The reason for this is that if these people are going to spend 100% of their time on chat, it doesn't matter what they sound like, look like, anything at all...keep yourself from getting ANY sort of bias and focus on what matters..

Look at them again and pick the 5-7 you think are the best.

Send them a message. Below is what I usually send.

Make the turnaround for a conversation quick (AKA Setup a meeting for 24 hours after your message)

I promise you will lose out on great people if you're slow by even a few days. Great people are picked up VERY quickly on Upwork. Don't miss your chance with them.

When the candidate agrees, tell them to come to Drift.com and ask for you via the chat widget. Tell them they should check out Drift ahead of time and even sign up for the free version of the product to try it out.

Leave it at that. If they can't figure out these instructions, they're not going to be a good fit.

Thanks so much for applying to this role!

I can definitely see some potential for this to be a fit to work together. [MAYBE ADD A NOTE ABOUT A SPECIFIC ANSWER THEY GAVE]

Let's find some time to talk a bit more about this role. Are you free tomorrow at [TIME] to chat for a bit? Thanks!

Okay, so now they agreed to chat with you and they're showing up to chat.

Here's how to structure the interviews...

Have one of the customer advocates talk to them first ([redacted] and [redacted]) have done this part of the process before so loop them in)

The CA will chat with them for 30 minutes

If they're feeling like there's a good potential for a fit, hand them off in the chat to another CA for 30 more minutes

If they're feeling like there's not a good potential for fit, politely thank them for their time and part ways 

(and follow up with them a few days later letting them know you're moving forward with other candidates)

The next CA will chat with them for 30 minutes if it is a good fit.

If at this point, both CAs feel like they're a good fit, pass them off to the hiring manager (previously this has been me) for a final 30 minute chat.

(You wanna look for a thoughtful answer and not just "it's cool" or "it's pretty")

 What was it about the job description that made you want to apply?

 What are the things you think make a great support experience over chat?

 Can you tell me a bit more about the technical experience you mentioned in your application?  What are you concerned about when it comes to working with Drift?

(if they're just asking about when they start and how much we'll pay, or have no questions at all, those are bad signs)

Positive things to look out for that would flag "this one can be great":

Playbook for Hiring Remote Support Contractors at Drift

The playbook for finding, interviewing, hiring, and training remote support contractors

When to hire

Reason 1 - Volume is consistently high

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