Freelancers: The secret sauce to scalable support operations

Working with freelancers is a hands-on approach to outsourcing that offers you agency, flexibility, and the potential to make great hires from a pool of folks who have on-the-job-training at your company. Outsourcing adds elasticity to your support team: it helps you flex quickly with changing support demand. Outsourcing with freelancers has the added benefit of letting you select the individuals you work with, cultivate a robust expandable (and contractable!) extension of your support team, provide the coaching, guidance, and performance feedback you want to give based on the work you see, and create a strong candidate pool for when you’re looking to hire full employees. 

I’m the Program Manager for Contractor support at Automattic, where we’ve worked with more than 125 freelancers over the past three years, and where more than 20 former freelancers are now full employees of our support team. We currently work with about 60 freelancers, who we call Happiness Contractors, who support Tumblr, WooCommerce, and WordPress.com users. 

Secret Sauce

We’ve found that freelancers are the secret sauce to scalable support operations in three main ways:

1. A hybrid of in-house support team plus freelancers allows you to scale up and down. You can identify buckets of work to outsource to freelancers in times of high volume, lean staffing, and to create space for your in-house team to focus on high-impact support and sales work, then outsource those buckets of work at different scales as needed.
2. By working with freelancers, you build relationships with individuals who are invested in your support organization, who do quality work, who have positive experiences working with you, who are often happy to rejoin for another contract later, and who have the potential to join as full employees, then give back to the program to support new freelancers.
3. Hiring part-time freelancers can let you offer levels of service your small team would otherwise be unable to. For example, we can offer an improved level of native language support for some communities because we can work with part-time people. We’d be hard-pressed to do that with a full-time, in-house team, but the flexibility of freelancers lets us improve the customer experience for those communities.

Outsourced support comes in a variety of flavors, from working with a third party vendor where you have zero interaction with the agents supporting your customers, to working with a Business Process Outsourcing (BPO) partner who provides and manages workers for you in partnership with you, to working with freelancers who you manage. Each flavor of outsourcing comes with tradeoffs. With freelancers, it’s up to you to support and manage the hiring, onboarding, quality, performance, and offboarding of every agent. While this can seem like a cost – “I have to manage more people!” – it is also a benefit. You get to work directly with the people you’re bringing into your support organization: you can pick who you hire, coach them through their work to ensure the quality you want for your customers, make decisions on who to cultivate and who’s not a good fit, build relationships and goodwill, and potentially gain great full employees that you may not have found through your traditional recruitment channels. And we’ve found that by their nature of being freelancers, most of the folks we contract with are motivated, self-starting, highly competent, and eager to learn and grow.

This post will cover some of the questions you’ll want to answer to build the infrastructure to incorporate freelancer support in your organization.

Steps to incorporate freelancers into your support organization

Feel free to download the worksheet at the bottom of this post for prompts to help you work through the following questions in more detail:

1. What is your desired outcome of outsourcing to freelancers?
2. What’s the scope of work? 
3. When do you need freelancers?
4. Who do you want to work with?
5. How will you support freelancers?
6. What are the logistics of setting them up?
7. What does success look like?

1. What’s your goal?

The most important question to ask yourself before getting started is this: what is the desired outcome of outsourcing to freelancers? Why are you thinking about working with freelancers, and what do you want to see as a result of working with freelancers? Jot this goal down. You’ll want to come back to it.

2. What’s the scope of work?

I mentioned before that the secret sauce to our contractor program is that we identified various buckets of ticket types we can pick off and give to freelancers in our times of need. We also outsource support for 7 non-English languages to language-native or fluent freelancers. The goal you outlined before will help you identify what the scope of support will be for the freelancers you want to bring on board, and the scope of support itself will determine many steps that follow, including how you route support requests, what your training will need to cover, and how you’ll handle escalations.

If you’re considering freelancers, think about high-level ideas of what you want freelancers to work on: is it a small portion of the work? Is it everything? For example:

• What ticket types would the freelancers support? (eg basic/tier 1 lets you route easier stuff to freelancers, leaving complex or higher impact work to in-house staff)
• What channel(s) will they support? (eg email, phone, live chat)
• What would you want escalated to your in-house team?

3. When do you need freelancers?

The “when” in this question is multilayered: before getting started with any outsourcing, you’ll want to think about the following: 

• whether you want to outsource work on an ongoing basis
• whether it’s seasonal
• whether there are certain times of day you need to fill in for
• whether you want freelancers to work part time or full time
• how soon you want to get started: when do you want freelancers to be trained and in the queue? 

You’ll need to answer the first four bullets before you can create your job description so that you can set expectations for the freelancers you work with; the final bullet will determine your timeline for when to start putting all the pieces in place.

4. Who do you want to work with?

If you’re thinking about freelancers, there’s a good chance you have an idea of what you’d like the freelancers to be capable of, what kind of mindset and skills you’d like to find, and when you’d like them to be available. 

For example, at Automattic we want WordPress experts who can work part-time from wherever they want in the world, and who have a mix of teamwork, writing skills, and technical knowledge to help us meet our goal to build relationships and trust with our customers. We want to work with people willing to work on 1-6 month contracts, and we re-evaluate our need and the freelancer’s performance to decide whether to renew at the end of the agreement period. To find the right people, we include an interview and a writing assessment using example support questions as part of our screening process, and we work with Upwork to find, pre-screen, and pay freelancers through.

Think about these questions as you consider who you want to work with and how you’ll find them.

• Who is your desired candidate? Think mindset, expected skills, pay range, time zone/location, when you want them to work, how many hours a week you’ll need them to work. You’ll use these qualities to write a job description.
• How will you evaluate candidates? eg resume review, interview questions, writing assignment with support questions.
• What will your contract agreement look like? Will it be open-ended, or will it have an end date? Do you need an NDA? Will you write performance expectations into the agreement (recommended)? Ask for help from your legal team if available.
• Where will you find freelancers? (eg Upwork, Fiverr, Toptal, Hubstaff, and others) Do you want a platform that pre-screens talent which you then sign off on? Do you want a platform that handles invoicing and payments? Do you want to search yourself and handle invoicing? 

5. How will you support freelancers?

Aside from picking who you want to work with, most of the other steps we’re covering are steps you’d likely need to take whether you’re outsourcing with a BPO or with freelancers. The question of how you will support those agents, though, sets freelancer outsourcing apart from working with a vendor. Rather than the BPO managing the agents, it’s up to you to support them. This support requires time, attention, and intention from your in-house team. The payoff can be big. At Automattic, we’ve found that the support from one full time Happiness Engineer can result in the output equivalent of 10 Happiness Engineers, with a high level of quality, and with the result that when we’re hiring full employees, we’ve got a pool of qualified folks familiar with our customers, who we’ve built relationships with, and who have on the job training in the way we work.

We’ve built our support structure similar to our division and team structure: we have a program manager who oversees the program, similar to a head of support for a business unit; we have Happiness Engineers (our in-house support agents) who act as Advisers to the freelancers, similar to a team lead, and who we assign up to 5 freelancers who they guide with the expectation that they’ll dedicate 1 hr per week per freelancer to support them; and we have a rotating role called the Adviser on Duty, where every two weeks, two of our in-house Happiness Engineers have dedicated time to sweep bug reports from freelancers, communicate product updates, and handle other issues that come up that that affect all freelancers. Once all the hours of our in-house team are added up, and we convert freelancer output to full time equivalencies, we aim for a ratio of the equivalent of 1 in-house team member to support freelancer equivalencies of 12 in-house agents.

Here are some things to think about for how you’ll support the freelancers:

• Who will review freelancers’ tickets, efficiency, and efficacy?
• What will the ticket review process look like?
• How will you communicate with freelancers? Eg for bugs, product updates, gathering customer insights or ticket trends
• How will you recognize and reward high performers?
• How will you make freelancers feel like part of the team? (eg swag? watercooler channels? buddies?)
• How/when will you handle performance evaluations, rate increases, and terminations?

6. What will need to happen behind the scenes to set this all up?

The first two questions we talked about here – what is the outcome you want to achieve with freelancers, and what will their scope of work be – will largely determine how you configure freelancers’ “workspace.” For example, if you want to give them a subset of customer requests, you’ll want to figure out what those request types are and how you can route them to freelancers. You’ll also want to think about:

• What security measures do you need to put in place?
• Does a queue already exist for this work?
• Do training materials exist for this work?
• What tools or access levels will freelancers need?
• What will the escalation process look like, both in terms of instructions and routing?
• When will individual freelancers be expected to work?

Once you’ve figured those things out, you can then create your training materials and figure out how long it would take someone to go through them to plug into your timeline.

7. What will success look like?

This will tie back into the original outcome you laid out in the beginning of the workshop. What will you measure to know whether you’re succeeding? Our indicators and success metrics evolve with various expansion projects, but the consistent ones are:

• Customer Satisfaction
• First reply time or SLA achievement
• Queue mitigation (ie, did we clear a backlog, did we stabilize queues during a time of lean staffing)

The main questions you’ll want to answer for this one are the following:

• How will you know if your work with freelancers is working?
• What will you measure?
• What are the thresholds for success?

Once you’ve launched, it is so much easier it is to evaluate whether things are working if you have already defined what success looks like. It’s very tempting to skip this step and think “I’ll figure it out later,” but I promise, Future you will thank you if you take the time to complete this step before starting your project.

Time to begin!

Once you have the answers to the questions above, you’re ready to put together a plan and milestones, and then execute!

Presented at Support Driven Expo, Las Vegas, Nevada. October 19, 2022.