Roadmap Whiplash

In many product companies, PMs complain about roadmap whiplash. Roadmap whiplash happens when written, committed, scheduled roadmap gets overridden constantly. Customer requests ARE tracked (in Slack, Linear, emails, sales notes) but there's no clear framework for saying "yes in Q3" vs "yes never" vs "yes today." Everything feels equally urgent. At some point, the roadmap becomes meaningless.

I have observed a simpler fix recently: use external marketing moments as forcing functions for internal roadmap alignment. A conference talk in 8 weeks, a customer dinner you've publicly committed to, a campaign launch with ad spend already booked—these become immovable objects that organize everything else around them. The external commitment answers the internal chaos: 'Can this wait until after Dreamforce on May 7th?'

What is roadmap whiplash?

Roadmap whiplash is what happens when your written, committed roadmap gets constantly overridden by urgent customer requests, executive pivots, and one-off sales promises. Everything feels equally urgent, so the roadmap becomes meaningless.

If you're still making fundamental product bets—still figuring out what problem you actually solve—the ideas here may not be relevant.

The common logic is that every product business should be sprinting to hit repeatability as fast as possible. So I don’t think optimising for broad-ish appeal is that lethal. You win by getting to 20+ customers with a coherent product, not by saving 5 customers with bespoke features that prevent you from ever scaling.

The marketing moment framework is really about graduating from services to product. It's the forcing function that lets you build for a market instead of for individual logos.

Why is roadmap whiplash getting worse today?

I don't know if the AI hype cycle is causing roadmap whiplash or just correlated with it. But I do know the symptoms are getting worse.

What I do know is that the competitive clock is running faster. The marginal cost of code is dropping dramatically. People are making memes about the flood of AI launches every day. Leadership sees it. Sales sees it. Suddenly your carefully planned Q3 roadmap is "too slow" and everything gets reshuffled.

To make things worse, due to all these new toys, customer expectations reset weekly. A prospect says "we need Claude/GPT integration" in January 2025. By March, they're asking about agents. By May, it's multi-modal workflows. Your 12-week build cycle is fighting a 2-week hype cycle.

The gap between planning cycles and market feedback cycles is widening. Traditional enterprise software moved on quarterly earnings cycles. AI capabilities are announced at keynotes, demoed on Twitter, and expected in your product within weeks.

From the very top as well, investors and boards are pattern-matching to "AI winners." Every board meeting includes questions about your AI strategy. Not having a ChatGPT-style demo or an "agentic" positioning feels existentially risky, even if it's not what your customers actually need this quarter.

In many cases, roadmap whiplash ripples throughout the rest of the company.

For example, marketing needs 6-8 weeks lead time for campaign development (content, design, ad buys, PR seeding). When the roadmap changes weekly, they either:

• Build campaigns for features that get deprioritized → wasted spend
• Wait for "final" confirmation that never comes → they ship nothing
• Market the vision instead of the product → generic positioning

The scramble is both cause and effect. Without planned marketing moments, sales schedules one-off demos with custom promises. Engineering scrambles to deliver. This prevents planning for the next marketing moment. The cycle continues.

The Fix? Plan your marketing moments

The change I am seeing in the market is a new framework to address urgent feature requests for an upcoming demo.

Instead of pulling engineers off current work, scrambling to ship something half-working, disrupting the roadmap, you can say: "We're launching a big new version on Dreamforce on May 7th - three weeks away. Can they wait?"

Engineering has been building significantly more product value for six weeks. You're speaking at Dreamforce, the talk title is submitted. There's no moving it. This creates urgency and a sense of mission.

Marketing is ready too. Case studies lined up, demo video done, PR outreach to three publications who've committed to coverage launch day. When you get off stage at Dreamforce, everything goes live simultaneously.

Sales now has a clear story: "We just launched this at Dreamforce, here's the coverage, here's the customers using it." They're not explaining what you don't have - they're showing what you just shipped. Way more powerful than a half baked feature. Your product story is finally coherent.

Now, engineering then gets out of permanent fire drill mode. They're building features that matter, seeing them launch properly, watching customers use them.

This is the power of the external commitment. Now let's talk about how to create these moments for yourself.

Marketing moments and how to plan them

What is a planned marketing moment? A marketing moment qualifies when: (1) You can get meaningful attention - either earned (conference talk, major publication) or bought (event sponsorship, ad campaign), (2) You have a clear target audience there, (3) The timing allows for relevant build cycles.

Examples: YC Demo Day (if you're in the batch), SaaStr Annual, AWS re:Invent for devtools, Money20/20 for fintech, hosting a dinner for 20 CIOs in your vertical, a coordinated Product Hunt launch with influencer outreach. Even with minimal resources, the principle holds—a blog post launch date, a demo at your accelerator, or a customer showcase can serve as your forcing function.

Marketing moments aren't just conferences. They can be: quarterly customer advisory board meetings, monthly product webinars, fiscal year-end (when enterprises release new budgets), campaign flight dates you've booked. The point is external-facing commitments that force internal alignment.

The cadence depends on your market. Devtools might target monthly content launches (6-week build cycles). Enterprise SaaS might target quarterly analyst/conference moments (3-4 month cycles). Consumer AI might target weekly launches (2-week sprints). The key is consistency: pick the rhythm that matches how your customers discover and evaluate products, then build your internal process around it.

In any case, plan the marketing calendar 6-12 months out (which conferences, which campaigns, which customer events). But build in 6-8 week sprints toward each moment. You're not building for 6 months straight - you're sequencing 6-8 week pushes, each timed to a specific marketing moment. The long-term plan creates the forcing function; the short sprints create shipping urgency.

You can start small. Pick ONE marketing moment 8-12 weeks out - a conference you're attending, a webinar you'll host, a campaign launch date. Commit to it publicly (submit the conference talk, book the ads, invite the customers). Work backwards to scope what can credibly ship. When disruptions arise, the external commitment becomes your shield: 'We can tackle that after Dreamforce - right now we're locked because we're on stage May 7th.'

Planning for surprises

The obvious objection: "What about truly urgent opportunities? What if a dream customer appears with a must-have feature request?"

The answer isn't to abandon the framework—it's to build flex capacity into it. Don't devote 100% of your capacity to marketing moments. Instead, split your capacity:

• A Lane: Marketing moment commitments (60-70% of capacity) - These are locked to external dates
• B Lane: Strategic flex capacity (20-30%) - Reserved for high-value customer/market opportunities that emerge
• C Lane: Technical debt / platform (~10%) - Non-negotiable investment

Don't Become a Prisoner to the Calendar

The framework is a power tool. Use it to create clarity and force prioritization. But if you learn something fundamental about your market—if a major competitive threat emerges, if customer usage patterns reveal you're building the wrong thing—the calendar doesn't override reality.

The marketing moment should force you to make hard choices about scope and priority. It shouldn't force you to ship something you don't believe in.

The real skill is knowing which stage you're at—and adjusting your rhythm accordingly:

Pre-repeatability (0-20 customers): Sprint fast, stay flexible, learn. Marketing moments aren't your forcing function yet—product-market fit is. You might announce things opportunistically, but don't let the calendar drive the roadmap.

Early repeatability (20-100 customers): 4-6 week cycles, building toward moments. This is where the framework starts to work. You have enough customers to plan around, but you're still figuring out messaging. Use marketing moments to force narrative coherence, but stay flexible on what you're building toward them.

Scaling (100-1000 customers): 6-10 week cycles, executing with adaptation. Marketing moments are now essential. You're coordinating across teams, managing multiple customer segments, and the external commitment is what keeps everyone aligned. The AI hype cycle hits hardest here—this is where you need the shield most.

Established (1000+ customers): 8-12 week cycles, locked narratives, platform + continuous releases. You're running multiple parallel tracks. Some teams ship continuously (platform, API), others work toward quarterly moments (new product lines, major features). The marketing moments become tentpoles that organize everything else.

The transition between stages isn't about company size—it's about repeatability. You move to the next stage when the previous rhythm starts creating more chaos than clarity.

This is what the other side looks like. You're not shipping less - you're shipping more. But each thing you ship has a moment, a story, a reason people should care. You've traded roadmap whiplash for coherent progress — shipping things that build on each other, with stories that compound, in a way that doesn't destroy your organization.