#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
  


• (03:07 ) - – What Customer.io does and who they serve
  


• (04:07 ) - – Growth story: from bootstrapped to private equity-backed
  


• (06:07 ) - – Team size and breakdown of the 30-person marketing org
  


• (08:07 ) - – Balancing PLG and sales-led within one team
  


• (10:07 ) - – How the org is structured: focus teams vs. centers of excellence
  


• (12:07 ) - – Aligning team goals to sales motions and funnel stages
  


• (14:07 ) - – How Customer.io prioritizes internal marketing requests
  


• (16:07 ) - – Avoiding the “who bangs the table loudest” trap
  


• (17:07 ) - – Cross-functional alignment with sales and product
  


• (19:07 ) - – KPI vs. OKR: how Customer.io uses both
  


• (22:53 ) - – Examples of key KPIs for the business
  


• (24:53 ) - – How OKRs cascade across the org
  


• (26:53 ) - – Why structured goal setting leads to better marketing impact
  


• (28:53 ) - – What channels are working: events are back
  


• (29:53 ) - – Examples of creative event formats that build community
  


• (31:53 ) - – Building pipeline without pitching at events
  


• (33:53 ) - – How Customer.io defines and tracks long-term influence
  


• (36:53 ) - – The decline of SEO and rise of AI-influenced buying
  


• (38:53 ) - – Why positioning is more important than ever
  


• (40:53 ) - – Product and marketing alignment in a modern org
  


• (42:53 ) - – Selling both the product and the roadmap
  


• (43:53 ) - – Jason’s one wish for marketers: better customer data
  


• (45:53 ) - – Personalization, adaptability, and breaking through the noise
  


• (46:53 ) - – Closing thoughts

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