Email marketing

How to hire email marketing experts: where to look, who to court, and how to evaluate talent

Mae Rice, November 16th 2022

The last time Lisa McGovern knew she had to hire an email marketer, it was because “we didn’t have anybody supporting retention and reactivation efforts,” she says.

McGovern, a senior lifecycle marketing manager at Upwork, noticed her team’s email flows onboarded and activated Upwork clients in droves. Then…the emails dried up.

No one owned the later stages of the customer journey, and no one had time to.

“There was this whole huge opportunity from a business perspective,” McGovern says.

So she decided to hire a new email marketer—a process she knows well. At Upwork alone, McGovern has helped hire 7 email marketers, for her team and peer teams.

And of course, she’s been hired as an email marketer, too. She knows the process from both sides.

But for many marketing teams with little or no dedicated email headcount, recruiting email marketers feels mysterious. How do you know it’s time to hire?

But for many marketing teams with little or no dedicated email headcount, recruiting email marketers feels mysterious. How do you know it’s time to hire? How do you write a job description that makes sense—and avoid overpaying?

Basically, how do you act…normal?

We asked two professionals who have done it before—McGovern and Suze Dowling, co-founder and chief business officer at Pattern Brands, a family of 7 home goods brands—to walk us through their best practices for hiring an email marketing expert.

Table of contents:

When to hire an email marketing specialist

There are 3 core questions to ask yourself when you’re assessing whether or not to hire an email marketer, Dowling says:

  • Are “the wheels on the bus going around”? Or, to paraphrase Dowling—are essential transactional and promotional emails flowing seamlessly? If not, it’s time to hire.
  • What email opportunities are you passing on due to headcount? Sometimes a lean team means skimping on analytics, flow complexity, and integrations. Estimate: Could revenue from these email upgrades support a new hire? If so, full speed ahead.
  • How burnt out is your current team? If everyone is stretched thin with no end in sight, you may have outgrown your current headcount—and hiring can help you retain existing employees.

Burnout is the toughest element to estimate here. When is employee frustration a workflow or time management issue, and when is it a headcount issue?

“We actually take an agency lens,” Dowling says. She and her team estimate how long recurring tasks take by tracking team hours and deliverables completed with a tool called Toggl.

Lean on a professional to help scope out what you need, as opposed to blindly trying to figure that out.
Lisa McGovern
Senior lifecycle marketing manager, Upwork

If the email team’s to-do list takes more than the number of work hours available in a day, “that can be another data point that helps influence how you resource,” she says.

If you’re stuck on the fence about whether to hire an email marketer, you can also turn to an external email pro for advice. McGovern recommends booking a consultation call, using tools like Upwork’s new consultations feature.

You can “lean on a professional to help scope out what you need, as opposed to blindly trying to figure that out,” McGovern explains.

Would you rather: freelance, full-time, or agency?

Once you decide it’s time to hire an email marketer, you have to pick a type of talent to hire: full-time, freelance, or agency.

McGovern and Dowling—a former agency leader herself—broke down each talent type’s unique strengths and downsides when it comes to email marketing.

The pros and cons of an email marketing freelancer

Freelancers are the fastest, most flexible hires. Here are 5 pros and cons of this type of individual contributor.

  • Pro: They’re great for tests and short-term projects. If you’re trying out an experimental strategy, or doing a project that’s a “temporary large lift”—like building out flows in a new language—a freelance hire makes sense, McGovern says. “You have the opportunity to dip your toe in,” she explains, and “you and the freelancer can flex the work up and down” as needed.
  • Pro: They can quickly take on tasks that are common across many businesses or clients. In Dowling’s experience, it’s easier to engage freelancers to support work that recurs across businesses—like email creation and deployment—than idiosyncratic strategic planning.
  • Pro: They bring in fresh perspectives. Freelancers work with multiple clients, so they have broader recent experience than full-time employees, McGovern says. That can be especially generative when you’re brainstorming subject lines or copy alternatives for tests. “More brains are better than one,” Dowling says.
  • Pro: They can start this week. Through Upwork, leaders can hire freelance email marketers in just a few days, McGovern says, which comes in handy for urgent needs and fast-growing teams. At Pattern, Dowling has so far worked exclusively with freelance email copywriters, “just so that we could scale quickly.”
  • Con: They can churn quickly. It’s part of the deal—freelancers can depart after completing a single project. They’re not ideal for “ongoing continual support,” McGovern says.

The pros and cons of a full-time employee

Full-time hires hold down the fort and create continuity within your organization. But what if you want to pivot fast? Here are 5 pros and cons of an employee.

  • Pro: They live and breathe your business. Full-time employees understand your brand, your value prop, your email strategy and your big-picture roadmap (and history). Pattern has 2 full-time email marketers working across its 7 brands, because “it was very important to us that we could maintain that knowledge in-house,” Dowling explains.
  • Con: They can take months to hire. McGovern notes that full-time hiring processes can take 12 weeks—or more.
  • Pro: They’re more likely to be on call. For Pattern, having in-house email marketers has really boosted “the speed with which we can onboard new brands into Klaviyo,” Dowling says.
  • Pro: They work cross-functionally. Full-time employees understand your org chart and make cross-functional efforts easier. Pattern’s full-time email marketers have worked with paid media to create emails based on successful paid ads, and the whole marketing org has collaborated to map out user journeys across the Pattern ecosystem, Dowling says. Freelancers can also support cross-functional project work, but may typically support a single business unit.

The pros and cons of email marketing agencies

Agencies can manage bigger, more amorphous projects than an independent professional marketer or full-time employee, but you won’t always be their top-priority client. Here are 4 pros and cons of an email marketing agency.

  • Pro: They bring insights from a diverse portfolio of clients. Even more than freelancers in some cases, agencies have “broad exposure” to different businesses, Dowling says—which makes them very helpful for benchmarking performance and pointing out up-and-coming trends.
  • Pro: They boost your headcount. For lean companies with one-person email teams, like italist, an agency’s people power can help level up testing and optimizations.
  • Con: They don’t always know the ins and outs of your industry. For companies in highly regulated industries, like alcohol or healthtech, this can pose compliance problems.
  • Con: They can be slow to react. It takes advance planning to get the most out of an email marketing agency. “They’re not able to react so nimbly because they’re balancing a variety of client priorities,” Dowling explains.

How to draft an effective job description, in 2 steps

If you decide to hire a full-time marketer, your next task is to write the job description. Who are you looking for? What do you want them to do?

It’s all about prioritizing, McGovern says. Hiring managers often have a long list of traits they’re seeking.

The required skill versus the nice-to-have is super, super critical to differentiate.
Lisa McGovern
Senior lifecycle marketing manager, Upwork

“I think the required skill versus the nice-to-have is super, super critical to differentiate,” McGovern says.

Step 1: Identify your must-have skill set

Email marketing is a “very jack-of-all-trades, multi-talented type role,” McGovern says. She’s found that the function involves two core skill sets: strategic skills and execution skills.

  • Strategic skills: These are the skills it takes to conceptualize and optimize emails that drive desired business outcomes. “You’re thinking, ‘How am I acquiring new customers? How am I retaining existing customers?’” McGovern explains. Strategists know how to build an email marketing roadmap, plan tests, and iterate on strategy based on results.
  • Execution skills: Think of these as the technical and operational skills involved in “the actual email build,” McGovern says. These might include: the HTML and Figma savvy to create and customize new email templates; the SQL capabilities to launch new segmentation criteria; and the ability to flawlessly QA and schedule campaigns.

Individual contributors will usually excel at one of these facets of email marketing, but “it’s really, really hard” to find a person who can do it all, McGovern says.

To figure out which skill set you want to prioritize, think about the strengths your team already has—and what you want this role to accomplish.

  • If you don’t have in-house channel expertise, make strategic skills a top priority. With the right software, basically anyone can execute a basic email strategy.
  • If you need to execute a custom email strategy, prioritize execution skills and experience with your current tech stack. They come in handy “if things get muddy or tricky” and your CRM starts giving you error messages, McGovern says.
  • If you need both skill sets—strategic and execution skills—then you probably need multiple hires or an agency.

Next, you need to actually write the job description.

Step 2: Write a job description that gets inbound interest

Writing a job description is a tightrope walk. You want to highlight what’s unique about your company, but you also want to use common email marketing terms where appropriate, so people find your job description in search. Here’s how McGovern and Dowling recommend approaching it.

First, pick a title for the position. The most popular ones are:

  • Lifecycle marketing manager: If you’re looking for a strategy-skewing skill set, this will bring in the most relevant candidates, McGovern says. (And it’s her title, so she would know!)
  • Email marketing manager: If you’re looking for a technical or operational skill set, this title makes the most sense.

Next, sketch out the job description. Usually, this has 4 sections:

  1. A blurb about your company, which you can usually adapt from prior job descriptions or a website “About” page
  2. An overview of the specific role, including goals, KPIs, and recurring tasks involved
  3. A list of required skills and experience, which could range from HubSpot expertise to experience with ecommerce startups
  4. A list of nice-to-have skills and experience, which are relevant to the role but can be learned on the job

Dowling recommends browsing other job postings for inspiration. “Take a look at job descriptions for roles of a comparable seniority at a similar company,” she advises.

Take a look at job descriptions for roles of a comparable seniority at a similar company.
Suze Dowling
Co-founder and chief business officer, Pattern Brands

In other words, if your startup just raised a Series B, don’t look at job descriptions from Fortune 500 companies. Look at postings from other Series B startups, scanning for language you like and common keywords that feel relevant.

A couple more tips on writing your job description:

  • Don’t require a set number of years of experience, because a year is different at different companies, Dowling says. It’s OK—maybe even preferable—to have learned email marketing by crash course.
  • Use popular email marketing keywords to get strong inbound leads.
A note about the difference between full-time hires and freelancers:
Your scope of work for freelancers should be materially different from your full-time hires to avoid misclassification risks. For freelancers, you’ll want to provide timeframes for the work to be done, with expect projects already outlined.

How to find and evaluate email marketing talent

Once you’ve described the talent you’re looking for, it’s time to chat with candidates.

There are two main ways these conversations start: with inbound interest, or with proactive 1:1 outreach from the hiring team.

A great job description—promoted to your network, and via ads on job-searching platforms—can drive inbound interest from candidates.

But especially for smaller companies looking for full-time employees, 1:1 outreach is key.

5 tips for effective candidate outreach

Despite excellent inbound applicants, Pattern found both of their full-time email marketers through proactive outreach—and Dowling did most of that outreach herself. Her road-tested tips for getting responses:

  • Leverage a tool like UpWork: Freelance marketplaces like UpWork can shorten the length of time between your business need and getting someone set up and in that seat. Unlike LinkedIn, the search tools are more granular and folks are inputting all the details of their work experience so you get a more holistic view of a candidate, quickly.
  • Send a bat signal to your network. “Your network and word-of-mouth referrals is No. 1,” Dowling says. So ask for recommendations from friends, colleagues, and marketers at companies with great email marketing. This is effective for finding full-time employees and agencies.
  • Spice up your subject line. In cold outbound communications, Dowling recommends honing your subject line to spotlight the clickiest information about the opportunity, concisely. Personally, she’s seen success with the subject line “Exploratory chat for lifecycle marketing manager at Pattern Brands, a Series B-backed company.”
  • Stay in touch. Even if someone isn’t a fit for your current opening, they might know someone who is—or make a great collaborator down the line. “We always end emails with, ‘If this role isn’t a fit for you, let us know if there’s someone in your network it may be good for,’” Dowling says.

5 interview questions for individual contributors (+2 for agencies)

Once candidates start to express interest, it’s time to interview. Strategic questions can clarify a candidate’s priorities, work style, and talents.

So what should you ask, exactly? McGovern and Dowling have found that these evergreen questions differentiate the OK-fit candidates from the great ones.

  1. What brands do you think are doing really exciting stuff with email? Dowling finds this one “really telling”—it helps capture a candidate’s personal taste.
  2. Based on your observations as a consumer, what are 3 tests you’d want to explore for our brand? This one captures how well they understand your business, and how effectively they can translate hypotheses into tests.
  3. What’s a technical challenge or roadblock that you’ve worked through in the past? This helps give you a sense of their past experience, and how they solve problems.
  4. What have been your most and least successful email campaigns? McGovern likes this question because “the answers help me see what the candidate focuses on,” she says. “Are they focusing on the strategic? Are they focusing on the technical?” This is likely where they’ll focus on the job, too.
  5. How much do you expect to be paid? It’s worth getting aligned here early. “I don’t want to pay you the bare minimum that makes you feel comfortable,” McGovern explains. “I want you to be happy, engaged, and not already looking for your next opportunity.”

If you’re evaluating an agency or freelancer, the evaluation process is different—and Dowling has a couple questions she recommends for those situations, too.

  1. What are a few tactics or ideas you or your team would implement in the first month—and the first 6 months? “This shows how they’re thinking, how they work with limited information, and how quickly they’re able to activate,” Dowling explains.
  2. Can you share client case studies? These function the way personal references do in a job search, Dowling says. Ideally, these come from companies in related industries, at a similar stage of growth.

Once you find email marketing talent that meets your needs—and feels trustworthy—you’re ready to hire.

I am a firm believer that skills can be taught, but character—that can’t be.
Suze Dowling
Co-founder and chief business officer, Pattern Brands

That trust piece is key, Dowling notes. “I am a firm believer that skills can be taught, but character—that can’t be,” she says. For startups and SMBs, “these very early hires are so impactful to setting that foundational culture.”

Hiring an email marketer takes patience and grit. It’s not easy, whether you’re hiring for an SMB or a major public company like Upwork.

For Dowling, the biggest challenge has been finding someone comfortable working full-time across Pattern’s multiple brands. “That’s definitely been an interesting journey,” she says.

McGovern’s biggest challenge has been hiring for expertise that complements hers.

“I don’t have a technical background,” she says, “so it’s always challenging for me to hire for a more technical skill set, because I don’t have a strong way to pressure-test it.”

But Dowling and McGovern have both found ways to make it through and hire great email talent. It’s difficult, but doable.

Dowling has learned that Pattern’s best-fit candidates often come from agencies, or “a brand that had multiple categories or some level of multi-brand nature to it,” she says.

McGovern has learned that when she’s hiring for a job she hasn’t done herself, it helps to reach out to other email marketers, whether they’re colleagues at Upwork or contacts outside.

“Tap in your network,” she advises.

Mae Rice
Mae Rice
Mae Rice is an editor and writer covering marketing, tech, and the ways they intersect. She lives in Chicago.