Meet Leslie Lee

Each week, we sit down with a marketing leader to learn more about their career, insights, and accomplishments. This week, that marketing leader is Leslie Lee, VP of Marketing at Deel. 

If there’s one constant across Leslie’s career, it’s ambiguity. From early startups to global scale-ups, Leslie has thrived as a builder, especially in environments where the rules aren’t written yet. She’s proof that generalists are true problem solvers.

Here are the need-to-knows about Leslie:

• In 2024, Leslie was recognized as one of the top 50 women leaders in Marketing by Women We Admire.

• She spent just under eight years at Atlassian, during which time the company increased revenue from $250 million to over $2.5 billion.

• She had an eight year tenure at PayPal, where one of her roles was to direct the online sales strategy, planning, operations for a +$3 billion enterprise retail vertical.

The fork in the road 

Marketing wasn’t on Leslie’s radar when she graduated from Haas School of Business at University of California Berkeley. She planned to follow the standard business school track into consulting, until a practice interview changed everything.

"I met with the founder of Plumtree, Glenn Kelman, and he said,

He convinced me to take a job at Plumtree, and I became the third marketer on a 70-person team."

Thrown into the chaos of a startup in the midst of the dot com boom, Leslie quickly learned by immersion. Her onboarding consisted of shadowing Glenn on calls with investors, customers, and the press. Then, she was sent off to figure it out herself. "It was the epitome of learning by doing."

Her role evolved with the company’s needs and she wore many hats: PR, developer marketing, customer solutions. The common thread? Diagnosing problems.

"People think marketing starts with storytelling. But there are a lot of other steps marketers take before that. You have to understand the product, the audience, the market gap, the internal dynamics first. You have to get the deepest understanding of the problem and then solve for that."

Breaking into enterprise 

After roles at two tech companies—Plumtree and Xythos Software—Leslie went over to the consumer space and joined PayPal. “Paypal was really appealing because it existed in this B2B2C realm.” 

There, Leslie helped the company expand into enterprise accounts, which represented a major shift from its small business roots. 

“Most of the revenue came from the SMB business where PayPal brought very clear value. If you’re a MrTedScrewdrivers.com, people likely weren’t super trusting of your site and were hesitant to input their credit card information. So an option like PayPal made sense.”

Leslie joined a newly formed group focused on getting large merchants to offer Paypal at checkout. “When we talk about it now, it seems funny that it was an uphill battle. But it absolutely was at the time.”

“Back then, large merchants like Macy's and Southwest Airlines were skeptical. They didn’t understand the value we offered and thought PayPal might hurt their brand.

Working within a startup-esq group at a larger company allowed Leslie to grow with plenty of resources, in a more defined environment than she’d been in during her previous days in tech.

Lessons from massive scale 

At Atlassian, Leslie stepped into one of the most formative chapters of her career. She led customer engagement and brand during a time of massive growth.

"At Atlassian, I learned a lot from the actual execution and seeing experts in their field orchestrate together across the board. But it was really the culture of the company—of openness and transparency—that helped me learn what it meant to really lead completely.”

On working at a large, matrixed organization, Leslie said relationships and trust are paramount. “We rolled out a new brand architecture at Atlassian and that took about a year. We had to have cross-functional conversations about data, products we might want to add to our portfolio in the future, future product rollouts, etc. It’s a lot more complex and things take more time.”

During her time at Atlassian, the company went from a few hundred employees to several thousand. Revenue increased by over 900%. And Leslie had climbed from Senior Director to VP of Brand and Customer Engagement. 

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A standout campaign

In her transition over to Deel about a year and a half ago, Leslie was back on a team that was extremely fast moving and fast to market. The HR tech company was in hypergrowth and there were major opportunities for her to make an impact, specifically when it came to cross-selling.

"We started as a one product company. Now, we’re at 14+ products but most of our customers are only using one or two of them. This gives us a huge opportunity to cross-sell to our existing base but we didn’t have very basic things to do that. We had to build from the ground up.”

Leslie’s team created a lead scoring model, tags in Salesforce, nurture campaigns. “Now we’re seeing a really healthy amount of leads come. We hear customers say all the time, ‘We just didn’t know you had these other products.’ It’s still nascent but it’s very exciting because we have 35,000 customers and a huge opportunity to expand them.”

Advice and takeaways

1) Curiosity as a personal brand.

Leslie credits much of her success to curiosity and investigative prowess. "Every problem will have a different set of questions. As a marketer, you need the curiosity to uncover them and the appetite to go deep."

Before you make moves, big or small, make sure you have an airtight understanding on the problem you’re solving for. Asking the right questions may lead you down a week-long deep dive into data or revenue ops or product but at the end, you’ll be able to clearly articulate the reasons behind your actions.

2) Create your own niche.

Leslie recalled looking at her peer set at Atlassian and seeing folks with 20 years in specializations like data analytics, comms, and PR. Still, she’s glad she pursued the generalist route. “My skill set is now very valuable because I built a reputation for being a problem solver.”

Set aside the traditional marketing specialization labels for a moment and consider what your personal brand is without them. What opportunities do you tend to raise your hand for? What skills do they require? And what stories or labels can you draw on based on those experiences? When you know those answers, you can speak to your reputation directly and confidently. 

3) Find your local experts.

Leslie leads a distributed team of 60+ marketers across priority markets all around the world. And she trusts them to provide expertise on their respective regions. "I tell them they’re like mini-CMOs in their markets. They are the ones that know  WhatsApp is a better channel in their market instead of email. They enable us to adapt our marketing meaningfully."

Whichever markets you’re in or expanding to, make sure you consult with someone who has local and colloquial expertise of the area. Getting their perspective on each element of your marketing—from channels to copy—can mean the difference between a success and a flop. 

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