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
• (02:08) - – What Customer.io does and who they serve
• (03:08) - – Growth story: from bootstrapped to private equity-backed
• (05:08) - – Team size and breakdown of the 30-person marketing org
• (07:08) - – Balancing PLG and sales-led within one team
• (09:08) - – How the org is structured: focus teams vs. centers of excellence
• (11:08) - – Aligning team goals to sales motions and funnel stages
• (13:08) - – How Customer.io prioritizes internal marketing requests
• (15:08) - – Avoiding the “who bangs the table loudest” trap
• (16:08) - – Cross-functional alignment with sales and product
• (18:08) - – KPI vs. OKR: how Customer.io uses both
• (21:43) - – Examples of key KPIs for the business
• (23:43) - – How OKRs cascade across the org
• (25:43) - – Why structured goal setting leads to better marketing impact
• (27:43) - – What channels are working: events are back
• (28:43) - – Examples of creative event formats that build community
• (30:43) - – Building pipeline without pitching at events
• (32:43) - – How Customer.io defines and tracks long-term influence
• (35:43) - – The decline of SEO and rise of AI-influenced buying
• (37:43) - – Why positioning is more important than ever
• (39:43) - – Product and marketing alignment in a modern org
• (41:43) - – Selling both the product and the roadmap
• (42:43) - – Jason’s one wish for marketers: better customer data
• (44:43) - – Personalization, adaptability, and breaking through the noise
• (45:43) - – Closing thoughts

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