The Marketing Millennials How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373
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Dec 10, 2025 Jason Lyman, CMO of Customer.io, shares his insights on annual planning, drawing from his extensive experience in high-growth tech. He reveals the Play to Win framework and common pitfalls like siloed marketing plans. Lyman emphasizes a balanced 70/20/10 approach to budgeting, allowing room for innovation. He discusses how AI enhances planning workflows and the importance of stress-testing strategies. Additionally, he encourages individual contributors to influence annual plans by bringing valuable insights and aligning their work with business goals.
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Use The Play To Win Framework
- Use the Play to Win framework to anchor your annual plan with five clear questions.
- Align your marketing plan to company strategy by defining aspiration, where to play, how to win, capabilities, and management systems.
Dropbox Paper Misaligned Launch
- At Dropbox, marketing misaligned with product launch resourcing for Dropbox Paper.
- The gap left insufficient promotion and PMM support, undermining the launch's impact.
Cascade Plans Into Tangible OKRs
- Cascade the annual plan into multi-level alignment with peers and direct reports.
- Translate strategy into short-term commitments (e.g., Q1 OKRs) so cross-functional partners see tangible actions.
