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For CMOs planning through uncertainty, the best route is not more frantic activity. It is sharper content, fewer better events, strategic GenAI use, expert-led buying experiences, more program spend, outside innovation, three-year planning, realistic customer journey mapping, personalization, and employee advocacy. Consider this a practical course correction for teams navigating rough water and restless executives.

When the market gets foggy, the temptation is to do more of everything: More content, more events, more dashboards, more campaigns, more Slack threads with “quick question” in the opening line. Sadly, activity volume is not a strategy. It is often just stress wearing sneakers.
In Episode 370 of Renegade Marketers Unite, Drew shared ten “dares” for B2B CMOs planning through uncertainty. The nautical metaphors in the original were enthusiastic, but the underlying advice is sturdy: Make sharper choices, build stronger ideas, and give buyers more confidence.
B2B does not mean “bland to business.” Buyers are still people. They remember stories, tension, emotion, specificity, and a point of view. They do not remember the fourth paragraph of a white paper that says your platform “empowers seamless transformation.”
Great content should make a buyer feel seen and smarter. It should help them explain a problem, make a case, or challenge a lazy assumption. That takes more than volume. It takes an idea worth repeating.
The CMO move: Raise the bar from “published” to “worth paying attention to.”
Events are expensive, exhausting, and still incredibly valuable when done well. The move is not necessarily more events. It is fewer, better, more intentional events that support brand, community, pipeline, and customer relationships.
CMOs should ask which events actually concentrate the right audience, create useful conversations, and justify the internal lift. A smaller dinner with the right customers and prospects may beat a giant booth that mostly collects badge scans and existential fatigue.
The CMO move: Design events around strategic conversations, not calendar guilt.
GenAI can help marketing teams create variations, summarize research, mine transcripts, generate hypotheses, analyze content gaps, and extend strong ideas into multiple formats. It can also produce a flood of competent sameness if teams use it as a shortcut around thinking.
The better use is to start with strong intellectual property: Research, customer insight, executive POV, proprietary data, or a fresh framework. Then use AI to explore angles, adapt for channels, and speed the first-pass work.
The CMO move: Let AI amplify strong thinking. Do not ask it to impersonate strategy.
The original line still lands:
“Millennials in particular do not want to talk to salespeople and frankly, I don’t know who does.”
Buyers often want expertise before persuasion. They want someone who understands their business, the product, the implementation reality, and the trade-offs. That may require bringing product experts, solution consultants, customer success leaders, or technical specialists earlier into the buying experience.
This does not mean Sales disappears. It means Sales needs more expert support and fewer generic pitches.
The CMO move: Help create buying experiences where expertise shows up before pressure.
Many CMOs are over-indexed on people and technology while program spend gets squeezed. The result: A powerful engine with too little fuel and a very expensive dashboard telling you so.
Rebalancing does not mean reckless cuts. It means looking honestly at underused technology, overlapping tools, low-impact roles, and programs that need enough investment to actually reach the market.
The CMO move: Protect the budget that creates external impact, not just internal capacity.
Internal teams can become trapped by what the company already believes. A strong outside strategic partner can challenge assumptions, introduce fresh thinking, and help map opportunities the team is too busy to see.
This does not have to mean a giant consulting engagement. It could be an advisor, analyst, agency, community, customer group, or operator with category experience. The key is perspective plus practical value.
The CMO move: Add outside provocation before the plan becomes a loop of last year’s thinking with new dates.
Quarterly planning is necessary. It is also a terrible horizon for building a category, reputation, community, or durable brand. CMOs need a longer view that explains how near-term actions ladder into future advantage.
A three-year plan should outline growth priorities, market position, core audiences, brand direction, demand architecture, customer strategy, talent needs, and major bets. It gives the executive team a way to understand which investments need time and consistency.
The CMO move: Use the three-year view to protect long-term growth from quarterly panic.
B2B buying journeys are rarely linear. The original described them as “the start, stop, and sideway stumbles of a drunken sailor,” which is vivid and, in many enterprise deals, uncomfortably accurate.
Mapping the journey helps executives see why single-touch attribution is silly, why Sales and Marketing both matter, and why customers may need different proof at different moments. It also reveals gaps in content, handoffs, enablement, and stakeholder coverage.
The CMO move: Map the journey to expose friction, not to decorate a strategy deck.
Personalization is powerful when it reflects real buyer context. It is creepy or useless when it merely inserts a first name into a generic message and calls itself relevance.
Use data to understand segment needs, buying stage, role, industry context, account behavior, and known preferences while respecting privacy guidelines. Then tailor the experience so buyers feel helped, not hunted.
The CMO move: Personalize around buyer usefulness, not martech capability theater.
Employees often carry the most trusted version of the brand. They know the work, the customers, the culture, and the truth behind the positioning. Marketing should equip them to share that story clearly and credibly.
That means messaging tools, social guidance, simple content, training, and enough trust that employees do not sound like they were assembled by the corporate comms department during a power outage.
The CMO move: Turn employees into confident storytellers, not reluctant distribution channels.
CMOs planning through uncertainty do not need ten more random initiatives. They need sharper moves: Better content, stronger events, smarter AI usage, expert-led buying experiences, enough program spend, outside perspective, longer planning, journey clarity, useful personalization, and employee advocacy.
The point is not to do everything at once. The point is to stop drifting.
Prioritize programs that clarify value, improve buyer experience, build trust, and protect future growth while still supporting near-term revenue.
Use GenAI to extend strong ideas, analyze gaps, summarize insights, and create useful variations. Do not let it replace distinctive strategy.
A three-year plan helps executives understand which investments need consistency, including brand, category, community, customer growth, and market position.
Employees can expand reach and credibility when Marketing equips them with clear messaging, useful content, and guidance that feels human.