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  1. The Marketing Millennials
  2. How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373
How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373

How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373

The Marketing Millennials · Dec 10, 2025

Customer.io CMO Jason Lyman shares a framework for annual marketing planning that aligns strategy with company goals and drives growth.

Marketing Plans Fail When They Are Siloed From Broader Company Strategy

The number one mistake in annual planning is creating a marketing strategy in a vacuum. A plan disconnected from company-wide goals, such as a major product launch, results in resource misalignment, budget shortfalls, and missed growth opportunities.

How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373 thumbnail

How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373

The Marketing Millennials·2 months ago

Effective Annual Plans Require a "Layer Cake" of Cross-Functional Alignment

True organizational buy-in isn't just a C-level activity. It's a "layer cake" where leaders at each level—from the CMO to ICs—have tailored conversations with their cross-functional partners to ensure shared understanding and commitment to the plan.

How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373 thumbnail

How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373

The Marketing Millennials·2 months ago

Individual Contributors Best Influence Strategy by Identifying What to Stop Doing

ICs are closest to the day-to-day execution. They provide immense strategic value by using these "bottoms-up" insights to make opinionated recommendations on what initiatives to cut. This helps leadership make necessary trade-offs and avoid spreading resources too thin.

How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373 thumbnail

How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373

The Marketing Millennials·2 months ago

Build Plan Flexibility by Keeping Strategic Pillars Fixed While Tactics Remain Agile

To prevent rigid plans that break, maintain consistency in your high-level strategic pillars for the year. However, build in flexibility by allowing the specific tactics used to achieve those pillars to change quarterly based on performance and new learnings.

How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373 thumbnail

How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373

The Marketing Millennials·2 months ago

Drive Q1 Momentum By Setting 30-Day Goals for January, Not Just Quarterly OKRs

Combat the tendency for teams to ease into the new year by anchoring them around what must be completed in the first month. This creates a "fast start," builds early conviction in the annual plan, and prevents playing catch-up in February and March.

How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373 thumbnail

How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373

The Marketing Millennials·2 months ago

CMOs Can Structure Annual Plans Using the 5-Question "Play to Win" Framework

This framework provides a structured approach to planning by answering five questions: What's our aspiration? Where will we play (ICP)? How will we win (pillars)? What capabilities do we need? And what management systems (budget, headcount) are required?

How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373 thumbnail

How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373

The Marketing Millennials·2 months ago

Balance Your Marketing Plan's Risk Profile Using the 70-20-10 Budget Framework

To balance execution with innovation, allocate 70% of resources to high-confidence initiatives, 20% to medium-confidence bets with significant upside, and 10% to low-confidence, "game-changing" experiments. This ensures delivery on core goals while pursuing high-growth opportunities.

How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373 thumbnail

How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373

The Marketing Millennials·2 months ago

Use AI as a "Validator" to Stress-Test Assumptions and Harden Marketing Strategy

Go beyond using AI for data synthesis. Leverage it as a critical partner to stress-test your strategic opinions and assumptions. AI can challenge your thinking, identify conflicts in your data, and help you refine your point of view, ultimately hardening your final plan.

How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373 thumbnail

How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373

The Marketing Millennials·2 months ago