Kyle Lacy Wants Marketers to Color Outside the Lines

“A lot of people don’t make the move when their inner voice is telling them that it’s time to leave. Learn to listen to that voice, because you could look up one day and realize you’ve spent five years working for a company that you don’t want to work for.”

Kyle Lacy is no stranger to swinging for the fences. 

I mean, just take a look at his resume from the past decade.

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Ridiculous. 

👉 Senior Manager at ExactTarget.

👉 Director at Salesforce.

👉 VP at OpenView.

👉 CMO at Lessonly.

Now? 

After a brief sabbatical to focus solely on the “dad” part of his LinkedIn headline, Kyle recently dove headfirst into a new role as CMO at Jellyfish. 

During his break between roles, I somehow convinced Kyle to sit down with me for nearly 90 minutes. I figured the timing was fortuitous; I didn’t want his take on marketing, I wanted his take on marketing careers. 

With more than a decade of marketing gigs under his belt, not to mention a handful of books, I figured he’d have some good advice to share.

I figured right.

(That quote at the top of this article is just the tip of the iceberg.) 

We didn’t even get to half my questions, but we covered plenty of ground:

• Where marketers should put their focus
• How to identify inflection points in your career
• When (and when not) to move into management
• What processes and tools have been most helpful throughout his career
• Why “personal brand” matters for your career (and why it doesn’t always mean daily LinkedIn posts)
• How to really take a break (that’s a biggie) 

It’s a goldmine of advice from the creator of the Golden Llama himself (for those not in the know, we’ll explain shortly). Let’s dig in.

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Switch your focus to story, not tactics

As a marketer, it’s easy to get caught up in tactics, run-of-the-mill content production, and quick wins.

But if Kyle’s long career has taught him anything, it’s the importance of cultivating a deep storytelling mindset that transcends B2B and B2C barriers and gets to the heart of the user experience.

Remember that experience is king 

The experiences your prospects have is the foundation of your brand or business, full stop. 

Kyle first learned this from the book Emotional Branding by Marc Gobe, which highlights the importance of shifting focus from products to people. 

It turns out that what people want is a good experience—from design to packaging to functionality and everything in between. 

“The only thing that makes us relevant as marketers is the experience that somebody has with what you sell,” Kyle says. “For marketers looking to build their career, the experience has to be paramount.” 

Next, I asked an admittedly biased question: how important is content for any marketing career?

Kyle’s answer: very, but not in the way you might think.

“I don’t credit myself as a great writer. I don’t think I’m good at it,” Kyle says. “But I think there’s a difference between storytelling and writing. The core question is: can you tell a meaningful story in a way that’s engaging to your audience?”

In other words, if there’s a superpower to cultivate here, it’s this: How can you become such a good storyteller that you can inspire somebody in 30 seconds?

Take risks and think outside the box 

So how can marketers apply this within their own careers? 

According to Kyle, it means experimenting with coloring outside the lines and creating something new and unique within your current job.

He’s taken his own advice many times over. At ExactTarget, Kyle helped develop original, survey-based benchmark reports surrounding email marketing, social media tactics, and more. 

“There wasn’t really anyone doing ‘state of’ type reports. It was the first time that a software company had started developing research as part of a content strategy,” he says. “That allowed ExactTarget to put a stake in the ground: ‘This is what I do well.’ It got me the job at OpenView to help run their massive content engine.”

Since his time at ExactTarget, Kyle has become even more creative when it comes to unique storytelling tactics.

Case in point: Lessonly’s viral “Golden Llama” direct mail campaign, where prospects and customers were sent gold llama figurines as part of marketing efforts—most of them spray-painted, by hand, by Lacy himself.

Why send customers a box containing something so…outside of the box?

“It’s about taking a risk, making a big bet on an idea, and leading it to set the stage for what you want to do next,” Kyle says. “At Lessonly, we took big bets on the golden llama campaign. It's about telling a different story. And that's how you make inflection points in your career.”

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Look for career inflection points 

Speaking of inflection points, what are they and how do you identify them?

To risk channeling an “Eat, Pray, Love” mantra—you need to listen to your inner voice. 

“I'm a huge believer in understanding when you need to move on,” Kyle says. “A skill you have to build as a professional is understanding when you need to make the move and why.”

To get a little more concrete, Kyle says that inflection points can often boil down to the three below:

1. Burnout
2. Boredom 
3. Failure 

That said, it’s best not to jump the gun and make trigger-finger decisions.

Press pause on submitting your resignation email if you think you might be experiencing temporary burnout that could be solved with a full night’s sleep or a week of overdue PTO. 

Do listen to that inner voice and make a career change when the sense of burnout or boredom lasts for multiple months. 

“You could look up and realize you spent five years at the company that you didn't want to work for, and it's just not worth it,” Kyle says.

The same “should I or shouldn’t I” logic applies to moments of failure. 

Little failures can be good and often make up the building blocks of learning—think an A/B test that doesn’t pan out, or routine growing pains in a startup environment. It’s chronic, large-scale failures that impact your entire team that may indicate the need for change. 

In fact, hitting walls on repeat at Seismic is exactly what told Kyle it ultimately wasn’t his best-fit role. 

“I’m not against failing, but if you're in a role and you make four or five bets and you're wrong every time, there's probably something deeper that you need to think about,” Kyle says.

If in doubt, give it time

No one likes to put up with burnout, boredom, or failure. But Kyle says it’s sometimes important to sit through professional discomfort—especially if you’re early in your career. 

How much time?

“I hesitate to give blanket advice here, but I would say 12 months,” Kyle says. “I don't believe that people can learn what they need to in less than that. When you job-hop, you're learning how to be transactional in your career. And the reality is that you've got to kind of get past that in order to fully understand what a true inflection point is.” 

Moving from job to job for more money or a new title can be intoxicating, but you need to weigh the cost. If you’re not in a job long enough to fully understand the role, the product, the politics, and the opportunities, you could be cutting yourself short.

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Make management moves—or not

An inflection point could result in making a move from one company to another. But it could also mean changing roles from individual contributor to manager.

You might assume that becoming a manager is synonymous with success. 

But Kyle’s take here is that not everybody needs to become a manager. It’s a decision marked by pros and cons, just like any other major career choice. Here’s how he broke it down:

1. Managers no longer practice their craft. 

“If you really love the craft—content, digital, product-led growth—you’ve got to spend time thinking about if you want to get into the manager role. Because it changes pretty dramatically when you do that,” Kyle says.

When you make the switch, you immediately become less tactical and more of a people manager. 

2. Managers must have deep emotional intelligence.

“Once you get into management and you start building teams, it's less about your specific tactical knowledge than it is about your ability to develop people and hire the right people. And the only way that you can really do that is by being able to understand what type of team you want to build,” Kyle says. 

Surprise! Managers have to be really good at managing people. 

You’ve got to be prepared to have difficult conversations in respectful and diplomatic ways—all while waving goodbye to the hands-on work you used to do every day. 

3. Managers should put their team members first.

Still set on becoming a manager? That’s also great. 

It’s time to start binge-reading Brené Brown and learning how to nurture the team you manage so that they can excel not only while working for you, but throughout their entire careers. 

“What I always tell my team is: I care more about your career than your job. My goal is that I don't want you to have to use a resume when you leave—I want to help you develop a network and a career in a way where you are either poached from this team because you're that good, or you can leave and get a job immediately,” Kyle says.

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Build an arsenal of processes and tools

Over the years, Kyle has also built out a chest of tools that help him maximize the potential of both his own career and the team members he manages. 

To start with, he’s a big fan of personality tests and predictive index behavioral tests. 

Don’t get hung up over choosing Enneagram versus Myers-Briggs—the point is to test your entire team so that you can map things like:

• How they communicate
• What their triggers are
• How to push them in productive ways 

“As a manager, it's a directional tool. It's not truth, but it gives you an idea of how people communicate,” Kyle says. 

His other core leadership tool is having team members identify career OKRs.

Don’t confuse this with job OKRs—although those are also necessary. Career OKRs require your team members to think beyond their current role to the next phase of their careers, so that they can take tangible steps to get there.

At Lessonly, this meant that team members set a series of quarterly goals. 

“If I wanted to become account executive, I need to go meet with five people that are account executives at different companies and learn more about how they do their job,” Kyle says as an example.

From reading relevant books to attending career-boosting conferences, the key was to have employees formally write down their personal development goals in order to actively work towards them—with management support at their back.

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Navigate career growth and personal brand 

Becoming a great storyteller on behalf of your company is one thing. It’s another thing to think about how you develop your own personal brand online.

Again, Kyle says success often comes from coloring outside the lines. How do you tell your story in a way that's different—and enjoyable? 

Do what you like

It seems like there’s a new professional around every social media corner who’s building an online empire. But you can’t be everywhere at once, and nor do you have to be. 

“Choose the mediums that you're most comfortable with, and build a community of people that you care about,” Kyle says.

Personally, Kyle loves building online communities and creating content on LinkedIn. While he can’t stand the idea of regularly scheduled content, he cited professionals like Justin Welsh who take that approach and thrive. 

“Everybody does things differently. You have to understand what really drives you and fuels you,” he says. 

Put in the reps…without overextending 

Building a successful personal brand takes a certain degree of consistency.

“You can’t just try it for a couple of weeks and expect it to work, because it won't. Repetition is important,” Kyle says.

But just like lifting weights at the gym, don’t feel like you need to overdo it, either. 

If you’re responding to every online comment and offering 30-minute Zoom calls right and left, you’ll quickly burn out. 

“Even if you love doing something, you'll hurt your network because you're overextending. You don’t necessarily need to pick and choose who you talk to, but try to have some ground rules,” Kyle says.

He also cautions pouring so much time into posting on social media that your full-time job suffers.

Think beyond social media 

Finally, keep in mind that social media isn’t a requirement for success.

“I know great marketers and leaders that couldn't care less about any of the social platforms,” Kyle says. “I have friends that haven't touched Twitter, LinkedIn, or anything, and they're doing better in their business than I could ever hope to do.” 

The key is working to build a community of people who support you, whether that happens through popular online channels or not.

So if spending all day on social media makes you want to poke your eyes out, take a different approach. Attend in-person alumni events or find other ways to build a professional community that you *actually* enjoy. 

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Don’t forget to take breaks 

No matter how much you love your line of work, there are roles and tasks that zap your energy and ones that restore them.

Sometimes taking a timeout can help you identify what those things are. See: Kyle’s recent sabbatical. 

“When I thought about taking a break, it was more than giving myself space from the daily Zoom calls and stressing about a pipeline number. It was also making sure that I spent some time doing things that gave me energy,” Kyle says. 

In other words, he wasn’t lying on a beach for three months. He was taking time to gain perspective and do the kind of work that actually charged his batteries. 

“It's all about the experience,” Kyle says (sound familiar?).

“As a marketer, you've got to obsess over the experience your prospects are having. You also need to obsess about the experience you're trying to have in your career,” he says.

So whether you’re on the clock or off, don’t be afraid to pull out a blank piece of paper and see where inspiration takes you. 

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