The First 90 Days, and the Two Years After
What I'd actually do with the role. The same Listen, Diagnose, Implement, Monitor cycle from the Story page, put into a real timeline.
Days 0-30: Listen
Why it matters: Before anything gets proposed, I need the real picture, not the version any one person tells me, but the overlap across everyone who touches the sales motion.
Who: Structured conversations across sales, marketing, leadership, and the individual contributors actually running the plays.
How: Prioritized by stakeholder influence and interest, not whoever's easiest to schedule. 20-plus conversations in a month is a full-time job on its own.
What I'm looking for: The gap between what leadership intends and what actually happens on a live call.
Grounded in data: Ramp time, win rate by segment, conversion at each pipeline stage. Not built on opinion alone.
Days 31-45: Diagnose, the Strategy Report, and the Charter
Why it matters: A low win rate could be a training problem, a messaging problem, a lead-quality problem, or a tooling problem. Jumping to a fix before telling those apart builds the wrong solution faster.
Synthesize: What came out of Listen, checked against the data.
Cross-check: What leadership sees, what reps experience, and how customers respond rarely tell the same story. The truth is in the overlap.
Land on the real problem. Written down, not implied.
Enablement Strategy Report: Ideal state, current state, the strategic initiatives that close the gap, the programs those initiatives require, what's being asked of leadership, open questions. This is what earns buy-in on direction, before a single program gets built.
Charter: The Report's highest-leverage initiatives, scoped down to one executable program, boundaries, why it matters, success criteria and metrics built in from day one. Socialized and signed off before execution starts.
Days 46-90: Begin Implementation
Why it matters: By day 90, this isn't a plan anymore, it's already underway.
Start with the highest-leverage priority, sequenced the way a customer actually moves through the funnel, not wherever's easiest to build.
Ship with a metric attached. Not bolted on after the fact.
Close the 90 days with real numbers moving, not just a document.
Year 1: Establish and Build
Why it matters: Coverage across the funnel, in the order the Charter set, not the order that's easiest.
Top-of-funnel content and process, mid-funnel qualification and discovery tools, downstream closing and retention support.
Every layer shipped with a way to measure it, not added afterward.
A recurring audit of what's already built: what's stale, what's unused, what's getting bypassed.
Closes with: A real data set, actual ramp time, actual conversion movement, actual usage numbers, and a leadership-facing report that closes the year on evidence.
Year 2: Optimize and Prove
Why it matters: The work shifts from building coverage to refining what's already there.
Year 1's data decides what gets scaled, fixed, or sunset.
Reporting shifts from activity metrics (what shipped) to revenue-impact metrics (what moved): win rate, sales velocity, quota attainment, deal size. Same terms leadership already measures the business by.
Enablement moves from reacting to requests to something leadership consults proactively.
The Cycle Doesn't Stop
Two years isn't an end point. It's where enough has been built that the cycle runs continuously instead of as one long build. A program going stale, unused content, a new gap the org's grown into, any of it goes back through the same four steps: Listen, Diagnose, Implement, Monitor. Early on, that runs at the scale of the whole function. Later, it runs in smaller, parallel loops, scoped to whatever's drifted, for as long as the function exists.