#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
(03:15) - – What Customer.io does and who they serve(04:15) - – Growth story: from bootstrapped to private equity-backed(06:15) - – Team size and breakdown of the 30-person marketing org(08:15) - – Balancing PLG and sales-led within one team(10:15) - – How the org is structured: focus teams vs. centers of excellence(12:15) - – Aligning team goals to sales motions and funnel stages(14:15) - – How Customer.io prioritizes internal marketing requests(16:15) - – Avoiding the “who bangs the table loudest” trap(17:15) - – Cross-functional alignment with sales and product(19:15) - – KPI vs. OKR: how Customer.io uses both(22:36) - – Examples of key KPIs for the business(24:36) - – How OKRs cascade across the org(26:36) - – Why structured goal setting leads to better marketing impact(28:36) - – What channels are working: events are back(29:36) - – Examples of creative event formats that build community(31:36) - – Building pipeline without pitching at events(33:36) - – How Customer.io defines and tracks long-term influence(36:36) - – The decline of SEO and rise of AI-influenced buying(38:36) - – Why positioning is more important than ever(40:36) - – Product and marketing alignment in a modern org(42:36) - – Selling both the product and the roadmap(43:36) - – Jason’s one wish for marketers: better customer data(45:36) - – Personalization, adaptability, and breaking through the noise(46:36) - – Closing thoughtsJoin 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter
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Brought to you by:
Customer.io - An AI powered customer engagement platform that help marketers turn first-party data into engaging customer experiences across email, SMS, and push. Learn more at customer.io/exitfive.
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