Meet Greg Gsell

Each week, we sit down with a marketing leader to learn more about their career, insights, and accomplishments. This week, that marketing leader is Greg Gsell, VP of Product Marketing at Datadog.

Greg spent his career building product marketing teams at top tech companies. He spent the first 16 years of his career at Salesforce, joining the company when it had 1,000 employees and leaving when it had reached 85,000. From there, he landed at Attentive and then his current role at Datadog. 

Here are the need-to-knows about Greg:

• At Salesforce, Greg helped reboot the Sales Cloud product line, resulting in 30%+ YoY growth on over $4 billion in ACV.

• At Attentive, he helped evolve the brand from SMS-first to multi-channel, overseeing the launch of its email and AI products.

• Greg spent several years at Salesforce as a sales engineer; he ranked among top three sellers in commercial sales, delivering over $7m in close business in 2014.

From postcards to product marketing

Greg’s marketing career started with a pile of undeliverable mail. Fresh out of college, he was temping at Salesforce on the marketing operations team when an opportunity presented itself. “They had sent out physical mailers and there were 20 or 30 mailboxes filled with return-to-sender postcards,” he said. “Our job was to call every single person and update their contact info.”

While tackling that project over the course of a few months, Greg figured out how to actually use Salesforce. And he used it to create a dashboard that tracked what his team was doing, who they were calling, and their success rate. That initiative landed him a full-time spot on the marketing ops team as a business analyst. He built his baseline of marketing knowledge and then pivoted to sales engineering, where got to know some of the product marketers.

“I realized that in sales engineering, you're tailoring a demo to a specific prospect. In product marketing, you're tailoring a story to an entire market. The same fundamental concept exists between those two, one of them is just on a hand-by-hand basis and the other one is at a much larger scale.”

This realization made Greg apply for a product marketing role and he’s stuck with the function ever since.

Riding the Salesforce wave

Greg’s time at Salesforce coincided with explosive growth and he took full advantage of that scale.

“I was always able to find the next challenge internally,” he said. That included working on multiple acquisitions, owning keynote messaging for Dreamforce, and pitching the re-org of a mobile product to strengthen its positioning. At one point, he rebuilt a team post-acquisition, transitioned from a single product to a multi-product strategy, and introduced a unifying brand narrative. 

It was the abundance of opportunities that kept Greg at Salesforce for so long. “Whenever I got to a point where I was ready to try something new in my career, I was able to find that opportunity inside the company,” he said. “And I looked around pretty hard inside the company first before I looked externally because Salesforce was growing so quickly and people were very open to new ideas.”

“I always encourage people to look around inside your org first. As a leader now, I’d much rather hire someone internally and teach them a new skill set rather than gambling on someone externally. And personally, I was able to learn a lot by doing that.” 

Merging a challenger and a leader 

After Salesforce, Greg joined Attentive, a leader in SMS marketing, as it was coming out of the pandemic and looking at a potential IPO. Then the economic headwinds of 2022 came along and, like many others, Greg found himself on a lean team that had to be hyper-focused on efficiency. 

In his two years with the company, Greg led the launch of Attentive’s email product, a move that came with many challenges and opportunities. “For SMS, we were definitely a leader. With email, we’re the challenger against long-established companies. Then all of a sudden, we started pitching these two things together.” 

Marketing the email product took some finesse. People had long wishlists based on the legacy products they’d been using previously.  “You’d make progress, hit a wall, build more, get momentum again.” 

But thankfully, they had numbers on their side. “With an SMS-first approach plus email, you get better customer data. So if you get both phone and email, your marketing is far more effective.” That insight became a cornerstone of Attentive’s positioning and its competitive edge.

_{Free Subscriber Perk}

Your new RFP consultant is free…forever.

Tired of wasting 20 hours on agency RFPs? As a Case Studied subscriber, you have access to our agency matchmaking service, Vendry, where we’ll help you by:

1) Finding you the top agencies in your industry.
2) Gathering and vetting proposals & pricing on your behalf.
3) Connecting you on calls with only the best agencies.

Our team has helped Spotify, Magic Spoon, Upwork, Ripple and 100’s of other brands hire agency partners at no cost to them (they get paid by the agency).

From 2 products to 25

Following his time at Attentive, Greg joined Datadog, a monitoring and security platform for cloud applications that ended 2024 with $2.68 billion in revenue (a 26% increase year-over-year). In this transition, Greg went from overseeing two products at Attentive to over 25 products at Datadog. However, most of the company’s revenue comes from its three main products. 

“The company is growing incredibly fast. We have a huge long tail of opportunity that we’re just starting to go after now. And fortunately, the markets are all adjacent to our core buyer, which makes it even more seamless to grow out.”

Greg’s mostly focused on figuring out how his team can operate at scale across so many different products. “I think we’re operating as five fingers right across product marketing right now and we need to operate as a fist (minus the violence of that analogy).”

The main challenge is shifting from single-product marketing to multi-product marketing. “It’s very infrequent that a customer’s pain point is solved by one single product. It’s usually a combination so we’re just listening really intently to customers and figuring out how to match what we’re hearing with our product marketing effort.” 

A Standout Campaign: Revenue Cloud

One of Greg’s proudest projects was leading the rebrand of Salesforce CPQ. This product line configured price quotes for sales and later it expanded to include billing. The two tools worked well together but they were very different buyers. “The CPQ was a sales operations buyer and the billing buyer was usually someone in finance. So we have these tools that worked really well together but we weren’t able to tell that story out to the market.”

So Greg’s team decided to rebrand. They sold the idea to leadership and the entire product suite became Revenue Cloud. It combined the messaging of both CPQ and billing, positioning it as a way to unify revenue on one platform. “We were basically taking action on where the puck was going to be versus where we were.”

“It was a risk but we had a product vision. We did a lot of testing on the concepts to prove it. And then once we felt it was a justifiable risk, we felt good moving forward,” Greg said. 

The gamble certainly paid off. “That rebrand really elevated the product line from just a nice add-on product to a major pillar of Salesforce’s product strategy,” Greg said. “It was probably our fastest growing acquisition and product line at that point. It worked out well and it introduced Salesforce to a new audience that they’d never sold to: finance people.”

Advice and takeaways

1) Find growth opportunities where you are

Greg shaped his career growth—at Salesforce and his proceeding roles—by finding and taking on big challenges. He rebuilt teams, led rebrands, shifted to multi-product. To see those opportunities, he needed to keep at least one eye on the big picture. 

Make time to think beyond your quarterly goals. What actions could help you, your team, and the business as a whole? Figure out what ideas you can pursue and map out your game plan.

2) Consider the calculated risks

Rebranding CPQ and Billing to Revenue Cloud wasn’t a guaranteed win for Greg. But it was a strategic bet. It required thorough research and leadership buy-in but all that ended up paying off in a huge way. 

If you’re coming up against a persistent challenge, consider all kinds of possibilities to solve it. Listen to your audience, run some tests, and gather data. From there, share your vision and build your case, no matter how big and bold it is.

3) Be open to different approaches

Even after spending so much time at Salesforce, Greg didn’t become rigid in his approach to product marketing. “The same fundamental philosophy exists of launching products, enabling sellers on it, and building demand. But how you do it, who you hire, and how you run the team is different, depending on the company.”

Flexibility is an important skill to lean on whenever you transition to a new organization. Be open to learning new methods and approaches, and sharing learnings from your experience when it makes sense.

Make your next move: Whether you’re planning a big brand moment or rethinking your media strategy, Vendry helps you find the right agency partner to pull it off. Fast matches. Vetted talent. Zero cost. Get started.