#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
- (02:21) - – What Customer.io does and who they serve
- (03:21) - – Growth story: from bootstrapped to private equity-backed
- (05:21) - – Team size and breakdown of the 30-person marketing org
- (07:21) - – Balancing PLG and sales-led within one team
- (09:21) - – How the org is structured: focus teams vs. centers of excellence
- (11:21) - – Aligning team goals to sales motions and funnel stages
- (13:21) - – How Customer.io prioritizes internal marketing requests
- (15:21) - – Avoiding the “who bangs the table loudest” trap
- (16:21) - – Cross-functional alignment with sales and product
- (18:21) - – KPI vs. OKR: how Customer.io uses both
- (21:59) - – Examples of key KPIs for the business
- (23:59) - – How OKRs cascade across the org
- (25:59) - – Why structured goal setting leads to better marketing impact
- (27:59) - – What channels are working: events are back
- (28:59) - – Examples of creative event formats that build community
- (30:59) - – Building pipeline without pitching at events
- (32:59) - – How Customer.io defines and tracks long-term influence
- (35:59) - – The decline of SEO and rise of AI-influenced buying
- (37:59) - – Why positioning is more important than ever
- (39:59) - – Product and marketing alignment in a modern org
- (41:59) - – Selling both the product and the roadmap
- (42:59) - – Jason’s one wish for marketers: better customer data
- (44:59) - – Personalization, adaptability, and breaking through the noise
- (45:59) - – Closing thoughts
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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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