Intro

#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

Send guest pitches and ideas to hi@exitfive.com
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

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.

Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.

Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.

On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.

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.