Podcast Summary: The Marketing Millennials
Episode 373: How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io
Date: December 10, 2025
Host: Daniel Murray
Guest: Jason Lyman, CMO of Customer.io
Episode Overview
In this episode, Daniel Murray sits down with Jason Lyman, Chief Marketing Officer of Customer.io, to explore the critical components of annual marketing planning—specifically, how to build, adapt, and future-proof your 2026 strategy. They discuss the major pitfalls, frameworks for planning, the role of AI, fostering cross-functional alignment, and actionable tactics that marketers at every level can use to accelerate their growth and impact. Jason draws from a rich background across tech startups and giants, sharing both stories and battle-tested approaches to effective planning.
Major Themes & Insights
1. Jason’s Background & Passion for Planning
- Jason began in strategy consulting, later moving into tech and SaaS marketing at companies like Microsoft and Dropbox.
- Experiencing disruption (e.g., the rise of streaming, iPhones, freemium models) gave him a passion for connecting strategy to execution and innovation.
- Memorable: Jason has been both a user and now the CMO of Customer.io, uniquely positioning him to understand both sides of the marketing platform.
2. The #1 Mistake in Annual Marketing Planning
Key Point: Failing to connect marketing’s strategy to the broader company strategy.
- Misalignment leads to resource gaps, mismatched priorities, and missed opportunities.
- Example: At Dropbox, a product launch floundered because the marketing effort wasn’t tied into company-wide planning—with budgets and resources not aligning (“We didn’t align early enough in our planning process to have the budget necessary…” [04:22]).
3. Jason’s "Play to Win" Framework for Annual Planning (06:42)
Framework Components:
- What’s our winning aspiration? (Set an aspirational, company-wide goal.)
- Where will we play? (Define ICP, target market, audience attributes, and geos.)
- How will we win? (Create three to five bold “strategic pillars” for the marketing team.)
- What capabilities must be in place? (Identify resources, activities, tech, and team requirements.)
- What management systems are required? (Budgeting, tools, processes, headcount.)
Quote:
"If you have alignment around those five questions, it becomes a really easy conversation with the CEO or with your peers across the organization..." – Jason [09:13]
4. Cascading Alignment: Multi-Level Buy-in
- Cross-functional alignment is critical; good CMOs ensure that marketing plans are relevant to the executive team, but also that their leaders communicate effectively with their counterparts in Product, Sales, and Finance ([10:37]).
- Individual contributors should know how their work ladders to larger business goals, fostering clarity and motivation.
Quote:
"You almost have this kind of layer cake of alignment that needs to be articulated." – Jason [11:36]
5. Building in Future Bets: The 70-20-10 Model
- Framework: 70% of efforts should be high-confidence, 20% medium-confidence, and 10% reserved for bold, unproven bets ([13:56]).
- Adopt a "zero-based" budgeting approach annually—every line item is justified from scratch, encouraging reallocation to new priorities.
Quote:
"...the only way you learn enough to really continue to augment your approach.” – Jason [15:01]
6. Balancing Rigid Plans with Flexibility
- Keep strategic pillars constant but build in monthly or quarterly checkpoints to allow agility ([17:51]).
- Distinguish between non-negotiable metrics (KPIs) and flexible goals (OKRs).
- Build strong relationships with Finance for mid-year re-forecasting when needed.
Quote:
"Pairing annual planning with a really strong either monthly or quarterly planning effort... builds in the agility that you can change things or tweak things every quarter or every month..." – Jason [18:37]
7. Leveraging AI in the Planning Process
How AI adds value:
- Rapidly synthesizes performance data and customer feedback ([21:25]).
- Helps stress-test ideas and spot conflicting assumptions.
- Assists in translating high-level decisions into operational plans and presentations.
- Customer.io uses AI to review campaign effectiveness and optimize the marketing funnel.
Quote:
"The time to collect that and synthesize that into takeaways has been kind of dramatically reduced." – Jason [21:44]
8. How to Use Customer.io for Annual Planning
- Customer.io’s own team audits customer journeys, onboarding, and retention flows at year-end.
- Their AI assistant analyzes campaign effectiveness and highlights areas for improvement ([26:20]).
- AI-generated insights feed into annual planning for better focus, resource allocation, and smarter bets.
Quote:
"We can actually query the AI assistant to look at relative performance of different campaigns and it can... let us know this is what's working and what's not working." – Jason [26:20]
9. Career Advice for ICs & Managers During Planning Season
- Bottom-up insights are as important as top-down strategy.
- ICs should present “opinionated takeaways” based on their data, articulating where to double-down and what to stop doing ([28:21]).
- Success is about linking work to key business goals and helping leaders hit their metrics.
Quotes:
"The best strategies are ones that come together through tops down thinking and bottoms up thinking." – Jason [28:21]
"If you can figure out one thing that could move your boss's needle... you’re probably going to be seen in the org." – Daniel [31:10]
10. Motivation & Execution in Q1
- Great plans are motivators. Communicate Q1 goals clearly and set aggressive, specific targets for the first 30 days to combat post-holiday slumps.
- Monitor execution closely and address areas lagging behind early ([33:33]).
Quote:
"...anchoring the team around these goals that they want to accomplish in the first 30 days ensures that people are focused, but also too, it then gives you a building block to build on." – Jason [34:26]
11. Jason’s Marketing Hill to Die On
- Overreliance on attribution models is dangerous.
- Attribution should be seen as directionally useful, but never as gospel—marketing is too multifaceted for one model to capture its full impact.
Quote:
"I lean much more towards a more pragmatic approach when it comes to attribution... attribution is a bit over overrated and I think we need to just think about it more, think about marketing strategy more holistically..." – Jason [37:34]
Timestamps for Key Segments
- Jason’s Journey & Background: [01:21–03:31]
- Biggest Annual Planning Mistake: [04:22]
- "Play to Win" Planning Framework: [06:42–09:49]
- Ensuring Cross-functional Alignment: [10:37–13:14]
- Forecasting Future Bets (70-20-10 Model): [13:56–17:08]
- Staying Flexible & Responsive: [17:51–20:48]
- Using AI in Planning & Execution: [21:22–24:33]
- How to Use Customer.io in Annual Planning: [25:05–27:05]
- ICs/Managers: Accelerating Your Career via Planning: [28:21–30:55]
- Driving Q1 Motivation & Execution: [33:07–36:44]
- Marketing "Hill to Die On" (Attribution): [36:50–38:19]
Noteworthy Quotes
- "You need to make sure that whatever marketing strategy you develop is connected to the broader company strategy and where those priorities and goals are." – Jason [04:22]
- "You almost have this kind of layer cake of alignment that needs to be articulated." – Jason [11:36]
- "The only way you learn enough to really continue to augment your approach.” – Jason [15:01]
- "Great planning is about making sure that everything feels like it ladders up from the smallest team in your department up through the company strategy and the goals that we're trying to achieve." – Jason [32:06]
- "Attribution is a bit overrated and I think we need to just think about it more, think about marketing strategy more holistically than focusing on having one attribution model being the end all, be all for all decision making..." – Jason [37:34]
Final Takeaways
- Annual planning should be deeply integrated with company-level strategy and regularly refreshed.
- Leverage frameworks and AI to surface bold, data-driven bets, but maintain flexibility to adjust as circumstances shift.
- Every marketer—from IC to CMO—should understand how their actions map to business outcomes for maximum impact and recognition.
- Use annual planning not only as a tactical roadmap, but as a rallying cry for team motivation and alignment.
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