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After spending more than a decade as a marketer at companies like Google, Square and Cover, Arielle Jackson has assembled a collection of tested strategies and essential advice in her marketing toolkit. And luckily for the readers of the Review, she isn’t afraid to share the goods, whether it’s a simple, but powerful framework for positioning or a set of essential brand building exercises.

As First Round’s Marketing Expert in Residence, Jackson works directly with early-stage founders on a wide range of marketing projects, from shaping how they’ll talk about their products to crafting an effective launch strategy. But as her working sessions and deliverables start to stack up, the same question eventually crops up: Is it time for the startup to hire a full-time marketer of its own?

And even after more of these first marketing hire conversations than she’d care to admit, Jackson still finds herself surprised by just how quickly they can go off the rails.

“I've heard founders say, ‘I need to hire a marketer to handle our launch in two weeks.’ I’ve read job descriptions that include everything from running social media to spearheading pricing, all in one role. Multiple folks have told me they were looking for a VP, and when I point out that someone like that may be too senior for the work they need done, they start talking about hiring an intern instead,” says Jackson.

As she navigates these discussions to level-set expectations and help more technical founders course-correct to find the right marketer for their startup, Jackson finds that she’s often repeating the same advice — so much so that she set up a canned response in Gmail — and figured others could benefit from similar guidance as they look to fill this important role.

In this exclusive interview, Jackson gives early-stage founders a playbook for nabbing their first marketer, sharing strategies for sidestepping common timing pitfalls and approaching the hiring process more thoughtfully. She offers a crash course on the essential elements of marketing to help founders figure out what kind of marketer they need, as well as five candidate profiles and helpful vetting tactics to use during the later stages of the hiring process.

THE WHEN AND THE WHY: GETTING THE TIMING (AND THE RATIONALE) RIGHT

The right time to add a marketer depends on whether your go-to-market strategy is more marketing- or sales-intensive. “If you're trying to create a consumer brand or your primary path to conversion is a marketing-driven event — organic, paid, PR, content, and so on — then it makes sense to bring on a marketer sooner, somewhere around the time you hit 10 people,” she says.

It’s different with an enterprise SaaS product. “Typically, you want to get a repeatable sales model in place first and then layer on marketing to crisp up the story and start using new channels to drive leads,” says Jackson. “Usually that’s around the same time you’ve solidified the go-to-market motion and started looking for a sales leader to take over for the founder.”

To further fine-tune the timing, startups should rely on these guiding questions before kicking off the search for a marketing hire:

Do you have multiple marketing challenges that you as the founder cannot tackle well?

First, consider whether there are enough marketing problems to solve — and whether not hiring someone is in fact the better move. “Founders don’t always have a great answer for why they need a marketer. Often they say it’s because they want to ‘grow’ or because a board member or investor recommended it. It can be a knee-jerk reaction,” says Jackson. "You need to think through the actual issues this hire would tackle."

Another consideration is whether those marketing challenges warrant full-time help. As a general rule of thumb, if you have a discrete marketing activity or a project with a clear scope, it makes more sense to hire a freelancer or an agency, whether it’s running an online ad tests or something as fundamental as coming up with a company name. “Some founders are totally comfortable with naming or they happened upon a name and that's great. If you do want help, you don’t have to hire someone for a one-time activity like this when an expert can come in on a project basis,” Jackson says. “Yes, a naming firm may cost $25,000, but that’s cheaper and more turnkey than hiring a full-time marketer.”

But keep an eye on how these projects start to multiply. "Managing all these freelancers can become a huge time suck — and it might get close to or exceed the salary for someone to take on some of that work in-house and handle it for you,” she says. “Plus, you don’t want your marketing efforts to look uncoordinated because you worked with five different freelancers who weren’t talking to each other.”

Is marketing going to play a major role in the success of your launch?

Whether a launch is epic or understated, there are best practices for releasing new products and the early-stage team needs to figure out how marketing fits into the equation.

“Companies building a physical product should start thinking about this earlier, especially if you're dealing with hardware that has a high price point and requires distribution partnerships, packaging, pricing and more before launch,” Jackson says. “Founders focused on getting the product right don't have the bandwidth to manage this marketing work themselves.”

As a prime example of the power of bringing a marketer on board pre-launch, Jackson points to Rylo, one of the companies she’s advised. “While I was helping them with their initial messaging, I wrote down the full list of everything that needed to happen before launch, and when I gave it to the founders, they were like, "Oh shit, you're right. We’ve got to hire someone ASAP,’” she says.

If your consumer hardware product is launching in a month, you needed a marketer yesterday. If you have a sales-driven enterprise startup, then take the time to lay that go-to-market foundation first before hiring anyone.

Does your headcount budget line up with your marketing budget?

Remember that hiring a marketer isn’t just about headcount dollars, but overall marketing budget as well. It’s critical to make sure your planned marketing spend matches the candidate’s expectations. “If someone’s used to running a 15-person team and a $50 million marketing budget and your startup offers no team and no budget, that's a hard sell at best and a recipe for disaster at worst,” says Jackson.

Especially in the arena of paid marketing, Jackson encourages founders to ensure that they’re putting their dollars to good use. “When a founder tells me they want to hire someone to run $10,000 worth of Facebook ads, I push back. You're going to take on the costs of a full-time hire just to spend $10,000 on a few tests? Think about your working and non-working dollars. It doesn’t make any sense,” she says. A better case for hiring? Leveraging early learnings from these ad tests to experiment with three to five other channels such as direct mail and podcast advertising — and having the budget to do so.

Jackson is quick to note that a small budget doesn't necessarily rule out the possibility of bringing on a full-time marketer. If marketing efforts will be centered around content or community, then it can make sense to hire even before you have a lot to spend. She points to Imperfect Produce as an example.

“I haven’t worked with them, I’m just a customer, but it seemed like they had a marketer fairly early on, working on the website, running their social channels, doing local community engagement. That’s similar to how it was back when I worked on Gmail,” says Jackson. “Right after we opened sign-ups, we had a very small budget for advertising. We focused on engaging power users, writing for the blog and running cross-promotions with other Google products. These efforts take time and skill, but they’re not as budget intensive as something like paid marketing.”

Are you willing to spend the time it takes to find the right person?

“In my experience, unless you’re nabbing a friend or former colleague with whom you have a strong established relationship, hiring the first marketer at an early-stage startup takes about three to six months,” says Jackson. “Not everyone accounts for this — I’ve had founders in November say that they want a full-time marketer to start before the end of the year, which is crazy. If your marketing needs are truly that pressing and immediate, working with a freelancer or an agency as a stop-gap might be a better route.”

THE WHAT: END THE SEARCH FOR A UNICORN BY UNCOVERING WHAT MARKETERS ACTUALLY DO

The next step is to spell out what this first person to don the marketing hat would do at your startup.

“When someone tells me they want to hire a marketer, I always ask them, ‘What do you want them to do?’ And more times than not, the answer is ‘Uh, I don't really know,’” says Jackson. “That doesn’t end up working out all that well. What if you hire someone who's really good at paid acquisition, but what you really needed was brand strategy?”

Too many times a startup’s first marketing hire ends up not working out because he wasn’t the right kind of marketer. You wouldn’t hire a back-end engineer who specializes in scaling systems to build you a beautiful front-end UI, so don’t make that mistake in marketing.

From finding the right PR firm and shaping a story to investing in product marketing, working out a pricing strategy, and fine-tuning the growth funnel, there’s a lot a first marketer could potentially take on — but not a lot of understanding around that fact.

“Marketers are pretty bad at ‘marketing’ marketing,” says Jackson. “Part of the problem is that marketing is a super broad field that covers so many different kinds of activities that the day-to-day of what we do can be entirely different.”

To provide a quick crash course that helps founders narrow in on the particular flavor their startup needs, Jackson organizes essential marketing work into four main groups (noting areas of overlap):

“Founders looking at this list may recognize tasks they’ve already taken care of and maybe didn’t consider to be marketing: defining the audience you’re serving, writing an email about your product to a prospective customer, hiring a designer to make your logo, approaching a partner,” says Jackson.

But even with a lay of the land and an understanding of the broad swaths marketing can cover, when it comes to deciding what to order from this marketing menu, there are still other traps founders can fall into.

Here are Jackson’s tips for spotting — and avoiding — three common mistakes:

Mistake #1: Seeking a unicorn.

“Often times when I look at a founder’s initial marketing job description, it’s a laundry list of almost everything on that list of activities. And I know very, very few people who are strong across all of those buckets,” says Jackson.

Most marketers who aren't new to the field specialize in either the so-called “soft” or “hard” sides of marketing, focusing more on brand and communications or growth, analytics, and channel optimization. “Even CMO-level candidates typically tilt more heavily in one direction,” she says. “I’m not sure where this desire to have it all in one package comes from — you wouldn’t expect an engineer to be amazing at front-end and back-end, but unfortunately this expectation exists for marketers.”

The marketing hire who’s equally proficient in product, performance, creative and comms is a rare sighting. If you find one, great. But it’s more likely that you’ll need to trim your job description and start prioritizing.

That’s why ruthless prioritization is key to crafting a job description that attracts the right species of marketer.

“One of the forcing functions for thinking through the job description is the ‘If you had to choose’ game. Yes, if you can find someone who's truly great at everything, more power to you,” says Jackson. “But let’s assume you can’t. If you had to prioritize one area of marketing over the other, how would you stack rank them? And they can’t all be equally important because that’s almost never true. Remember that the first marketing hire can always supplement their skills in other categories by eventually hiring people (either above or below) and working with external agencies or consultants.”

To rein in a marketing job description, Jackson recommends digging deeper into what the startup needs and how to frame it. “When I worked with Alma, for example, the creative side ended up being more important. That didn’t mean the other areas didn’t matter — we wanted someone who could use a spreadsheet or figure out how to run an Instagram ad,” she says. “But those skills were secondary to what really mattered, which was great storytelling chops, experience working with designers and an ability to write really well.”

Mistake #2: Putting the cart before the horse.

Another issue Jackson frequently sees is job descriptions that put the cart before the horse, focusing on the wrong specific set of responsibilities prematurely. “Often times you think you need something, but you really need the thing that comes before it,” says Jackson.

“If you say you want PR, but can’t answer questions about what you want your ideal headline to be, what kind of reporters would be interested in telling your story, then you won’t get press,” she says. “That’s because you don’t need someone skilled in media relations yet, you need positioning, messaging and product marketing first, which means you need a different breed of marketer to help you set the foundation before you start talking to reporters.”

Mistake #3: Setting the wrong seniority level.

When advising founders on how to determine the number of years to jot down in the job description, Jackson often runs into the VP-versus-intern debate she mentioned earlier.

“There's an option between these two extremes,” she says. “Founders are tempted to hire someone really senior. But marketing work at an early-stage startup is frequently down in the weeds, a place a VP-level candidate hasn’t visited for a long time — they aren’t always going to want to write copy or get into the mechanics of setting up an ad campaign, for example.”

If you’re wondering whether you need a VP or an intern for your first marketing hire, that’s a sign you haven’t put enough thought into the role.

The interview is the place to get a sense of whether a candidate has the right level of experience — and hunger — for a startup. “I interviewed a head of marketing candidate with about 20 years of experience for one of the startups I was advising recently. In these cases, I make sure to ask things like ‘When’s the last time you did X?’” says Jackson. “Communicate that you’ll need them to do some pretty tactical stuff and see how they respond, asking follow-up questions such as ‘How do you feel about doing that? Walk me through how you’d approach it.’”

Another flag is if a more senior candidate focuses too much on future plans to scale the function. “There was another candidate who had been VP of Marketing at a relatively late-stage company, and she spent a good part of the interview talking about how she structured her team, which is certainly something the startup would eventually need if they end up being very successful, but it wasn’t relevant at their very early-stage,” says Jackson.

Being the first marketing hire at a startup isn’t about building a team right away — it’s single player. It’s a hard job. If a candidate was the first marketer elsewhere, make sure she still has the appetite to start back at square one.

There’s also risk in hiring too junior of a marketer. “If a candidate’s resume says ‘Drove growth by XXY% using Y channel,’ dig a little deeper and figure out which part of that they were responsible for. Because if it turns out that they just wrote ad copy and they don't know how to actually run a campaign, that might not be the person who can own that channel end-to-end for you,” says Jackson.

Generally, Jackson advises startups to look for someone with around five to eight years of experience for the first marketing hire. “They’re still going to dive into the weeds without question, but they’ve also probably become an expert at the one or two areas of marketing you need the most help with,” she says. “A great candidate at this level will uplevel your company right now, while they grow their own skill-set and potentially rise into a VP-level role in the future. If they end up not being ready for that step, you can still hire someone over them when the time comes.”

As for assigning the appropriate title, Jackson favors “Head of Marketing” to start. “‘Director’ is fine too. If you give out the VP title too early, that can be a little limiting,” she says. “You want someone who is an up-and-comer and not super hung up on getting that fancy title now, but knows they still have a shot at earning it if they kick ass over the next couple years.”

Arielle Jackson, First Round's marketing Expert In Residence

THE WHO: PROFILES IN MARKETING TO HELP YOU FIND THE RIGHT FIT

After determining the type and level of marketing work the first hire will be focused on, the next task for the early-stage founder is find the exact person who fits the bill. To help narrow in on the best match for your startup, Jackson identifies a handful of personas that might work well, depending on what you’re looking for your first marketing hire to do.

All five of the anonymized profiles below are representative of marketers she knows personally, and provide a sense of the broad skills and backgrounds that can lead to the makings of a successful startup marketer.

The Big Tech turned startup marketer

For Jackson, learning the ropes in smaller roles at bigger companies is a great way to work up to bigger roles at smaller companies. “This is where I fit in. I started at Google, where I went through the Associate Product Marketing Manager program, then to Square, and then to a tiny startup,” she says. “People with this kind of background are probably the safest choice for a startup’s first marketing hire — they are well-versed in tech, they know how to work cross-functionally and they’ve held multiple roles across different sized companies. And probably most importantly, they understand big company fundamentals but thrive in the ‘get your hands dirty’ type of startup environment — otherwise they would have stayed on at a bigger company.”

Jackson notes that founders should be wary of candidates that have only worked in Big Tech. “You don’t want someone who’s only comfortable and familiar with staying in their lane, so that’s something to tease out in the interview and reference process,” she says.

The classically trained CPG marketer

Consumer brands, companies with physical products, and startups that rely on retail and distribution partners may want to explore hiring someone straight out of a consumer packaged goods (CPG) company that’s hoping to make their way into tech.

“I love this background,” Jackson says. “Early in my career I spent some time at Procter & Gamble in their associate brand manager training as part of an exchange program sponsored by Google. I learned more about fundamental brand strategy in those days than I did in years in tech product marketing,” says Jackson.

In her experience, these candidates tend to be more brand than acquisition oriented, but they know how to use both sides of their brains. “Of course, they’ll have to learn tech, which often moves faster than where they’ve been, but if they’re passionate about it, then it’s a reasonable bet to make,” she says.

The right hand

“I love seeing someone who learned the ropes working for a stellar marketer and now wants to go do their boss' job,” says Jackson.

“Two acquisition marketers I know from Square fit this profile. One of them started off as the second in command, working for the excellent head of user acquisition who had mastered the field at Netflix. When she left, he took on her role and the guy who worked for him moved up to become his right hand man. Now both of these former right hands run paid marketing at different companies.”

The banker/consultant turned marketer

“I wouldn’t hire someone straight out of consulting or banking as your first marketing hire,” says Jackson. “Look for someone who took on those roles earlier in their career and then pivoted to tech. They tend to be more on the left brain side than right brain, so they might be a better fit for roles focused on the performance side of marketing, but these people typically work incredibly hard.”

The agency convert

“Agency life provides great training ground for marketers since you get to work on a variety of projects for different clients. Agencies use very different titles, so a basic understanding of how their job titles map to tech marketing roles can be helpful,” says Jackson.

"For example, what the agency world calls ‘strategists’ are probably closest to brand or product marketers. Media buyers might offer a parallel to paid marketers or channel marketers in tech, but aren't always direct response oriented."

THE HOW: TACTICS FOR FINDING AND VETTING YOUR FIRST MARKETER

With a defined role, crisp job description, and profiles in mind, it can be tempting to think the bulk of the work is done. But at this stage, Jackson always reminds the founders that there’s still plenty to do. “Don’t put up a job description and hope the right candidate finds you. This is the time to lean on your network and invest in a LinkedIn premium subscription,” she says.

Here are four of her tips for supercharging the rest of your search:

I wouldn’t trust myself to assess engineering talent, so why do so many technical founders trust themselves to evaluate marketing talent? Pull in an advisor or a friend with a marketing background before you extend an offer to get a sanity check.

“Part of the issue is that marketing skills, such as analysis or writing, are more accessible so everyone has an opinion, whether it’s on ad copy or a specific marketing candidate,” says Jackson. “Something like Javascript is more binary. You either know it or you don’t, and as a marketer, I can’t really evaluate an engineer on that front. With marketing, it’s easy to fall into the trap of assuming you know what to look for, but all too often founders hire the wrong person and it doesn’t work out.

These mismatches can make it easier for CEOs to discount the value of the function as a whole — an issue that persists across companies of all sizes and stages, as research shows that CMOs have the highest turnover in the C-suite. But Jackson prefers to focus on the opportunity.

“With an early-stage startup, you have a clean slate to set marketing up for success from the start and avoid a revolving door,” she says. “If you can pinpoint your marketing challenges, define the scope of the role, find the right person and vet them properly, you’ll save yourself from painful headaches down the line — and start reaping marketing’s value much more quickly.”

Photography by Bonnie Rae Mills.

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