#263 Marketing Strategy | Dave is joined by Jason Lyman, CMO at Customer.io, a customer engagement platform used by over 7,500 companies. Jason has led marketing at Dropbox, BetterCloud, and now heads a 30-person team driving growth across both PLG and sales-led motions.

Dave and Jason cover:

How to structure a B2B marketing org for scale, alignment, and channel ownership
Why events are their #1 channel and how creative formats drive real pipeline
The KPI + OKR system they use to prioritize work and measure marketing’s impact

You’ll walk away with a clearer understanding of how to design your team, focus your strategy, and invest in channels that actually drive results.

Timestamps

(00:00) - – Intro
(02:34) - – What Customer.io does and who they serve
(03:34) - – Growth story: from bootstrapped to private equity-backed
(05:34) - – Team size and breakdown of the 30-person marketing org
(07:34) - – Balancing PLG and sales-led within one team
(09:34) - – How the org is structured: focus teams vs. centers of excellence
(11:34) - – Aligning team goals to sales motions and funnel stages
(13:34) - – How Customer.io prioritizes internal marketing requests
(15:34) - – Avoiding the “who bangs the table loudest” trap
(16:34) - – Cross-functional alignment with sales and product
(18:34) - – KPI vs. OKR: how Customer.io uses both
(22:50) - – Examples of key KPIs for the business
(24:50) - – How OKRs cascade across the org
(26:50) - – Why structured goal setting leads to better marketing impact
(28:50) - – What channels are working: events are back
(29:50) - – Examples of creative event formats that build community
(31:50) - – Building pipeline without pitching at events
(33:50) - – How Customer.io defines and tracks long-term influence
(36:50) - – The decline of SEO and rise of AI-influenced buying
(38:50) - – Why positioning is more important than ever
(40:50) - – Product and marketing alignment in a modern org
(42:50) - – Selling both the product and the roadmap
(43:50) - – Jason’s one wish for marketers: better customer data
(45:50) - – Personalization, adaptability, and breaking through the noise
(46:50) - – Closing thoughts

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Today’s episode is brought to you by Zuddl.

We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.

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If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025.

Head over to zuddl.com/exitfive to learn more.

Inside Customer.io’s B2B Marketing Strategy: Org, GTM, and Growth Channels with Jason Lyman

The Dave Gerhardt Show (from Exit Five)