Settlers of Catan: B2B Marketing Lessons on Thinking Beyond Your Next Move with Chief Marketing Officer at Dialpad, Jen Grant

Marketing isn’t just about tactics, it’s about strategy. And most times, the smartest move is playing the long game.

That’s the strategy behind Settlers of Catan, a board game built on resource trading, calculated risks, and thinking three steps ahead. In this episode, we’re drawing inspiration from its gameplay with our special guest, Jen Grant, Chief Marketing Officer at Dialpad.

Together, we explore what B2B marketers can learn from staying focused on their own path, anticipating competitor reactions, and building a diversified strategy that drives long-term growth. 

Because in both Settlers of Catan and marketing, the real power play is thinking beyond your next move.

About our guest, Jen Grant

Before joining Dialpad as Chief Marketing Officer in October 2024, Jen served on the Dialpad Board of Directors, held C-level positions at Cube and Appify, led Looker’s marketing, drove the rebrand of Elastic, and grew Box to an industry-leading enterprise content company. Jen holds an MBA from Wharton, a BA from Princeton, and has been recognized as one of the Top 100 Princeton Technology leaders.

What B2B Companies Can Learn From Settlers of Catan:

• Play your own game. In Catan, constantly reacting to what others are doing can leave you scrambling. The same applies in B2B marketing. Jen encourages a more grounded approach: “You do much better, sort of very quietly focusing on your own growth.” Instead of chasing competitors or mimicking market leaders, build a strategy that aligns with your own long-term vision. Because sustainable growth isn’t won through noise, but through quiet, deliberate moves.
• Always be forecasting. Winning at Catan means thinking ahead, not just about your next move, but the ones after that. Jen says,  “I actually really love the strategy part of it. Thinking about, okay, we're about to launch a particular feature. What's that gonna make the competition do?” In a competitive landscape, it’s not enough to plan for what you control; you also need to anticipate how others will react. Great marketers operate like strategic game players. 
• Don’t bet on just one road to victory. Catan punishes one-dimensional players. You can’t win by hoarding sheep alone, you need balance. Jen explains, “It is never one thing…It's all of the things at the same time, executed perfectly well.” Diversification isn’t just about spreading risk; it’s about orchestrating a full-spectrum effort that compounds over time. The most impactful marketing isn’t siloed, it’s symphonic.

Quotes

*“The thing about Catan, and other board games, this might come into play too, but you could potentially spend all of your time trying to crush the other players…And when you play a game a lot, you're like, oh, I'm gonna try this strategy this time, see what happens. And one of the things that I've definitely never seen work is if you focus all your energy on messing with other people. You do much better sort of very quietly, focusing on your own growth.”

*“ I actually think the reason I like the game so much is the game theory of thinking ahead, 2, 3, 4 steps ahead. And so you're thinking how am I gonna achieve my goals, but what are they gonna do when I do, whatever it is, buy this road. I love that part of the game. I love thinking out ahead, okay, if we do this, then what are they gonna do? And for marketing, I think we often get caught up in the fun, creative part of marketing. But I actually really love the strategy part of it, of thinking about, okay, we're about to launch a particular feature. What's that gonna make the competition do? Are they gonna freak out? Are we kind of catching up to them? And maybe we shouldn't be so loud about it 'cause we should have had this before. All of the different implications of what you do in a market and then how the comp