Mastering Marketing in 2025: What you need to know from 14 of the best

The last 10 years has seen an insane whipsaw when it comes to go-to-market strategies. The rise of SaaS, data-driven marketing, virtual conferencing and call recordings – then the pandemic boom times when everything was easy and companies were buying any and all tools – followed by the downturn, belt-tightening, and revenue slippage. 

This year, we’ve had the pleasure of speaking with leaders who’ve helped some of the best companies play the infinite game of GTM Frogger and come out stronger and triumphant at the end of the road. I’m sharing the best secrets, tactics, and learnings from these conversations… but first, a quick intro to our distinguished go-to-market experts:

• Sterling Snow - Former CRO of Divvy, scaled the company from inception to a $2.5 billion exit in just four years
• Jon Miller - CMO of Demandbase, co-founder of Marketo and Engagio, with over two decades of B2B marketing expertise
• Carol Meyers - Former CMO of Rapid7, drove 10x revenue growth over eight years and led four successful IPOs
• Udi Ledergor - Chief Evangelist and former CMO at Gong, grew the company's marketing from zero to hundreds of millions in revenue
• Tricia Gellman - CMO Box, former CMO Drift, Checkr and master at GTM team alignment and data-driven marketing
• Jason Grunberg - CMO of Bluecore, previous marketing leadership roles at Sailthru and Oracle
• Puja Rios - Chief Revenue Officer of Frame.io, who helped scale the company from $19 million to over $100 million ARR in 2.4 years
• Alex Rosemblat - Former CMO of Datadog, who scaled marketing from Series A through post-IPO hyper-growth
• Lauren Vaccarello - Former CMO of Salesloft, previous executive marketing roles at Salesforce, AdRoll, and Box
• Greg Kogan - VP of Marketing and Growth at Pinecone, an engineer turned marketer who coined the term “vector database”
• Jessica Gilmartin - CMO of Calendly, previously CMO of Honor and Lighthouse AI
• Bernd Leger - CMO of Cornerstone OnDemand, over two decades of B2B marketing experience
• Andrea Kayal - CRO Help Scout, Dean of Pavilion CMO School and former CMO of Electric, Upserv, and Signpost
• Amandine Servain - VP of Marketing at Wunderkind, previous executive roles at Experian and Cheetah Digital

These folks have seen it all. They’ve had to deal with nearly every complex go-to-market challenge. They’ve seen every stage of company growth. They’ve built, grown, sometimes shrank, and nurtured teams. Here are some top learnings that you can immediately apply to your company and GTM motion. 

Riding the Wave of Rapid Growth and Change

Remember when your biggest worry was getting that one perfect Facebook ad out? Those were simpler times. Now, as companies scale at breakneck speeds, marketing teams are often left feeling like they're trying to build a plane while flying it.

Take it from Carol Meyers, former CMO of Rapid7, who saw the company skyrocket from $30 million to over $330 million in revenue. Her secret sauce? Adaptability and a laser focus on what truly matters."You have to have a great vision for marketing," Carol emphasizes. "It spans across brand and the softer things, as well as to revenue, pipeline, alignment to sales, and the overall goals of the company."

But it's not just about having a vision, it's about breaking it down into actionable steps. Carol suggests, "Break that down into the key things that you need to do so everyone understands what are they individually are doing and how that actually layers up."

This approach ensures that every team member, from the creative genius to the ops wizard, understands how their work contributes to the bigger picture. It's about creating a cohesive unit that can pivot and adapt as the company grows.

Lauren Vaccarello, former CMO of Salesloft, echoes this sentiment. She stresses the importance of aligning marketing efforts with sales incentives. "If marketing initiatives do not resonate with sales goals, they are likely to fail," Lauren warns. It's a reminder that as we scale, we can't lose sight of the end game - driving revenue.

But how do you maintain this alignment as your team grows from a handful to hundreds? Jason Grunberg, CMO of Bluecore, offers a practical tip: "Define your audiences and be mindful about who we target with our product, with our content, with sales, and so on. You can align teams and save sales a ton of time if marketing focuses on interested people who aren't ready to act anytime soon and let them focus on the ones who are."

The Content Conundrum of Balancing Quality and Quantity

Churning out SEO content like a factory used to be the name of the game. Now, it's time to take a more thoughtful approach to the content engine. Greg Kogan, VP of Marketing and Growth at Pinecone, puts it bluntly: "I put a lot of emphasis on substance in all our materials. I want more materials going out faster all the time but it has to have substance." Greg introduces a principle he calls "WABL" - Would Anything Be Lost. Before publishing any piece of content, ask yourself, "Would anything of value be lost if this were removed?" It's a simple yet powerful filter to ensure your content isn't just noise in an already crowded space.

So what makes good content in 2025? Udi Ledergor, Chief Evangelist and former CMO at Gong, has a refreshing take: "The days of the 40 page white papers have been over for a while in case nobody got the memo. Nobody except your competition is gonna read those." Instead, Udi advocates for creating content that's "immediately digestible and immediately applicable." It's about giving your audience something they can use right away, not just information to file away for later.

This shift towards quality over quantity doesn't mean slowing down your content production. It's about being smarter with how you create and distribute content. Jessica Gilmartin, CMO of Calendly, shares a practical tip on using information from customer interviews in their blog posts. This approach not only ensures the content is relevant but also authentic. It's the voice of the customer speaking directly to potential customers - and that's marketing gold.

But in this age of AI and content generation tools, how do we maintain this focus on quality? Alex Rosemblat, former CMO of Datadog, cautions against relying too heavily on AI for content creation. "You're going to have to find some other differentiator soon because a year from now everything will have AI underneath it." The key, according to Alex, is to use AI as a tool to enhance human creativity, not replace it. It's about finding that sweet spot where technology amplifies your team's abilities and thoughts rather than diminishes them or devolves into sea of sameness.

Aligning Marketing with Sales to Create the Revenue Dream Team

Gone are the days when marketing could live in its own little bubble, tossing leads over the fence and hoping sales would catch them. Now it's all about team alignment and shared goals and KPIs. Sterling Snow, former Chief Revenue Officer of Divvy discussed the importance of structuring incentives correctly. At Divvy, they held every function accountable for one stage later in the sales funnel than they have direct control over. For example, Marketing should not only be responsible for demand generation, but also on closed-won business. Implementation should also be measured on retention - what happens after the first 60 days when a customer is onboarded. This makes sure all functions work together.

Jon Miller, CMO of Demandbase, takes this alignment a step further with his concept of a "unified revenue team." He advocates for a structure where marketing is accountable for closed business, fostering collaboration between departments. This approach ensures that marketing isn't just focused on top-of-funnel metrics but is invested in the entire customer journey.

But how do we actually make this alignment happen? Puja Kuja, Chief Revenue Officer of Frame.io, shares a practical approach: "We have the business connection and built the trust so that we can have real candor between each other when things weren't working. But at the end of the week, we also remember that we're just people." Puja's strategy involves regular check-ins between marketing and sales leaders, not just to discuss numbers but to build genuine relationships. It's about creating a space where both teams can be candid about challenges and collaborate on solutions.

On a tactical front, Andrea Kayal, Chief Revenue Officer of Help Scout, suggests looking beyond traditional marketing metrics. While revenue is a lagging indicator, leading indicators such as New Monthly Recurring Revenue (MRR), New Annual Recurring Revenue (ARR), and net expansion often offer more valuable insights.

Bernd Leger, Chief Marketing Officer of Cornerstone On Demand, brings up an interesting point about the evolution of marketing and sales roles: "The power of marketing is derived through experimentation." He suggests that the future might see a blend of traditional marketing and sales roles, with AI taking over some of the more repetitive tasks. This evolution doesn't mean replacing humans, but rather freeing up time for both marketing and sales teams to focus on what they do best - building relationships and crafting personalized experiences for customers.

How to Think about AI as Marketing Leaders

Speaking of AI, it's the elephant in the room that our marketing leaders couldn't ignore. But far from seeing it as a threat, many are embracing AI as a powerful tool in their marketing arsenal.

Jason Grunberg of Bluecore is particularly excited about AI's potential in personalization: "Maybe what we've been talking about in marketing for the last 15 years -- the segment of one, one-to-one personalization, whatever you want to call it, is now finally possible. It's not just the content of an email, it's about the totality of your journey that is completely customized to you.." However, Jason also cautions against relying too heavily on AI-generated content: "AI is designed to pump out very generic content." The key, he suggests, is to use AI to enhance and scale existing marketing efforts rather than replace human creativity entirely.

Udi Ledergor from Gong echoes this sentiment: "I think what we saw across the room in 2024 is that more and more marketers are using AI as an assistant and an editing tool than as a content generation tool." Udi emphasizes the importance of maintaining a human touch, especially when it comes to understanding customer needs and crafting compelling narratives. But AI isn't just about content creation. Greg Kogan from Pinecone sees immense potential in AI for data analysis and customer insights: "You can mine social media feeds to see what people are talking about. Any data stream you can get access to you can now mine it for all kinds of information."

Lauren Vaccarello, formerly of Salesloft, offers a practical perspective on AI adoption: "I think there's a host of tools that B2B organizations use to better understand their prospect and the context in which they're existing but there's such a pressure that's put on the traditional outbound team or the marketing team to move with speed." Lauren suggests that AI tools can help alleviate this pressure by streamlining research and personalization processes, allowing marketing teams to move faster without sacrificing quality.

But amidst all this AI excitement, Alex Rosemblat from Datadog offers a reminder about where AI works well vs not: "I think that for close-ended data sets it works really well. A buddy of mine is the CEO of a company that does a lot of AI stuff for legal documents and with legal documents there's certain standards and language - it is a close-ended set and AI works fantastic on that stuff." Alex's point is crucial - AI isn't a one-size-fits-all solution. It's about finding the right applications where AI can truly add value to your marketing efforts, rather than trying to force it into every aspect of your strategy.

The Human Side of Marketing

While technology and strategies may differ, our marketing leaders all agree on one thing: your team is your most valuable asset. But how do you build and lead a high-performing marketing team, especially going into 2025? Jessica Gilmartin from Calendly emphasizes the importance of building a team with a diverse and specialized skill sets: "We have demand gen, we've got product and solution marketing, we've got brand, we've got comms. And these teams have shared goals between PLG and SLG." Effective collaboration across these specialties allow you to meet the customer where they’re at and manage effective sales and product-led motions. It's about creating an aligned team that's adaptable and can pivot as the company's needs evolve.

Divvy had a unique culture and way of building teams. Their culture was crazy obsessed with winning. As a result it wasn’t great for those who wanted more work-life balance. That being said, it gave younger leaders outsized rewards for great performance. Every company and team has to figure out what they care most about and hire for people who align with those elements.

Greg Kogan from Pinecone also takes a unique approach to team building, starting with developer advocacy: "Our first hire was a Dev Advocate who was himself a an ML engineer before joining Pinecone.  You have developers teaching developers how to build amazing things. What's not to love there." This strategy of hiring subject matter experts who can speak directly to your target audience can be a game-changer, especially for companies in technical fields.

But building a great team isn't just about hiring the right people - it's about fostering the right culture. Alex Rosemblat from Datadog stresses the importance of creating an environment where experimentation is encouraged. It's important for marketing leaders to create a safe space for their teams to take risks and try new things. This was how they discovered trade shows as their number one demand gen channel that served them from Series A through IPO.

Practical Tips from the Pros

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Let's distill their wisdom into some practical tips you can apply to your own marketing efforts:

1. Embrace adaptability: Carol Meyers advises, "You have to have a great vision for marketing... Break that down into like the key things that you need to do so everyone understands what are they doing and how does that actually layer up."

2. Focus on quality content: Greg Kogan suggests using the "WABL" principle - "Would Anything Be Lost" if this content were removed?

3. Align marketing with sales: Jon Miller advocates for a "unified revenue team" structure where marketing is accountable for closed business.

4. Use AI wisely: Jason Grunberg recommends using AI to enhance and scale existing marketing efforts, not replace human creativity.

5. Build diverse teams: Jessica Gilmartin emphasizes the importance of having a mix of skills on your marketing team.

6. Encourage experimentation: Alex Rosemblat stresses the need to create an environment where teams feel safe to try new things.

7. Invest in your team's growth: Lauren Vaccarello highlights how a positive work environment can turn employees into brand advocates.

8. Prioritize customer understanding: Udi Ledergor suggests starting with developer advocacy to create content that truly resonates with your audience.

9. Balance innovation with responsibility: Carol Meyers reminds us to consider ethical implications, especially when it comes to data usage in AI.

10. Measure what matters: Andrea Kayal advises looking beyond traditional metrics to track engagement and revenue impact.

One key takeaway for me? There's no one-size-fits-all approach to marketing success. What worked for one company might not work for another. But by staying adaptable, focusing on quality, aligning with sales, embracing new technologies wisely, and investing in your team, you're setting yourself up for success.

Remember, marketing isn't just about the latest tools or the flashiest campaigns. At its core, it's about understanding your audience, creating value, and building relationships. 

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