My operating system for the first 90 days of go-to-market leadership, and the matrix behind the GTM Alignment Diagnostic.
Observe / Analyze / Execute is a framework for the first 90 days of GTM leadership, developed across marketing leadership roles at B2B cybersecurity companies. Days 1 to 30 are Observe: every stakeholder, customer conversation, platform and number is mapped before anything changes. Days 31 to 60 are Analyze: observation becomes a model, with the funnel worked backward from the ARR target and every function rated against what the stage requires. Days 61 to 90 are Execute: dashboards, operating cadence and the plan of record get installed. The sequence is the framework. Execute only holds up if Observe came first.
I have spent my career building and scaling B2B cybersecurity companies: marketing leadership seats inside venture and PE-backed startups, plus consulting engagements across many more. Every company was different, with a different stage, a different buyer, and a different board. But the failure pattern was always the same. Leaders under pressure act before they understand. They inherit targets built without a model, and they spend their first quarter producing activity instead of alignment.
The activity looks like progress. Campaigns ship, the website gets refreshed, a new tool gets bought. Then the quarterly number arrives and nobody can explain the gap, because no one built the math that would have predicted it. By the time the model exists, a quarter of runway is gone and the leader is defending decisions made before they had the information to make them.
This framework came from doing this repeatedly and codifying what worked.
Listen before acting. Every stakeholder, every customer conversation, every platform, every number, mapped before anything gets changed.
Turn observation into a model. Benchmarks, the funnel worked backward from the ARR target, every function rated, the budget scoped against the number.
Install the machine. Dashboards, operating cadence, the plan of record. Alignment made structural, not aspirational.
The first month is deliberately unproductive by the usual measures. Nothing launches. What happens instead is mapping: sales leadership, product, customer success, finance, and the board each get asked what they believe the GTM motion currently does and where it breaks. Customer conversations get read rather than summarized. Every platform in the stack gets opened, including the ones nobody has logged into for a year. Every number that anyone reports gets traced back to how it is calculated.
The output is not a plan. It is an accurate picture of what is actually happening, which is almost never what the reporting says is happening.
The second month turns observation into arithmetic. The funnel gets worked backward from the ARR target: required closed-won, required pipeline at the real win rate, required opportunities at the real conversion rate, required qualified leads, required spend. Every marketing function gets rated against what the company's stage actually requires rather than against a generic org chart. The budget gets scoped against the number instead of against last year plus a percentage.
This is where most disagreements get resolved, because a disagreement about strategy is usually a disagreement about a number that nobody has written down.
The third month installs the machine. Dashboards that report against company ARR rather than siloed marketing metrics. An operating cadence that puts marketing, sales, product and customer success in the same weekly conversation with the same numbers in front of them. A plan of record that names owners and dates.
Alignment made structural, not aspirational. Aspirational alignment is a slide. Structural alignment is a meeting on the calendar with a dashboard nobody can argue with.
The three phases are not equal in weight and they are not interchangeable. Observe is the one that gets skipped, because it is the one with nothing to show for it at the end of the month. It is also the one that makes the other two work. A model built on assumptions produces a plan built on assumptions, and the plan will be defended long after the assumptions are known to be wrong.
The most common version of this failure is a marketing leader who arrives with a playbook from the last company. The playbook is usually good. It is just answering a question this company has not asked.
The GTM Alignment Diagnostic is this framework made self-serve. It scores 13 alignment dimensions using 83 questions, then maps every gap it finds against the three phases, so each gap lands as an action in a specific 30-day window rather than as a general recommendation. Not a recommendation. A sequence.
A free 21-question scan runs in about seven minutes and returns an alignment score, a marketing functions coverage map, budget and funnel math computed from your targets, and a starting 30-60-90 plan. The full 83-question version adds budget and investment, team and talent, strategy and governance, leadership alignment, product alignment, and channel and advisory.
The same sequence runs underneath the How to Hire for GTM reference library, where each role's first 90 days follow the same three phases, and underneath the agentic pipeline that runs this site: signal collection is Observe, scoring and normalization are Analyze, digest and outreach are Execute. That is documented on how this site runs.
A framework for the first 90 days of go-to-market leadership: days 1 to 30 Observe, days 31 to 60 Analyze, days 61 to 90 Execute. Every stakeholder, customer, platform and number is mapped before anything changes; observation becomes a funnel model worked backward from the ARR target; then dashboards, cadence and the plan of record get installed.
Because a plan built before the model is a guess with a deadline attached. Leaders under pressure inherit targets built without a funnel model, then spend their first quarter producing activity instead of alignment. Execute only holds up if Observe came first.
The diagnostic is the framework made self-serve. It scores 13 alignment dimensions with 83 questions, then maps every gap against the three phases so each one lands as an action in a specific 30-day window. A free 21-question scan runs in about seven minutes.
No. The most common use is a new marketing leader's first quarter, but the same sequence works for a fractional engagement, a repositioning, a post-acquisition integration, or any point where the operating model has drifted from what the revenue target requires.
I did, across marketing leadership roles at venture and PE-backed cybersecurity companies including Constella Intelligence, DoControl, DuskRise, HYPR and Morphisec, plus fractional engagements. It began as a live client workshop and was later engineered into a self-serve diagnostic.