In 3–4 weeks, you'll have a visual roadmap with timelines, budget ranges, and dependencies — ready for the boardroom.
WHAT THIS ENGAGEMENT IS
We take your competing priorities, technical debt, and business ambitions and turn them into a realistic 12-month plan. Not a Google Doc with bullet points — a visual, resourced roadmap that shows what gets built, in what order, by whom, at what cost, and with what dependencies.
It's the artifact your CTO presents to the board and your engineering leads use to plan quarters.
Days 1–5
We interview stakeholders across engineering, product, and business leadership to inventory every active initiative, wish-list item, and known obligation. We also review your current architecture and team capacity.
Days 6–10
We facilitate a working session with your leadership team to force-rank initiatives against business value, technical dependencies, and available capacity. This is where the hard trade-offs get made.
Days 11–18
We build the roadmap: initiative swimlanes, milestone markers, dependency chains, and quarter-by-quarter resource requirements. Each initiative gets a budget range based on scope and complexity.
Days 19–22
We present the draft roadmap for calibration. This is a working session — expect to adjust sequencing, challenge assumptions, and pressure-test timelines.
Days 23–25
We deliver the finalized roadmap package and walk through the details with whoever needs it — your board, your engineering leads, or both.
A visual roadmap with initiative swimlanes, milestones, and dependency chains. Shows what's happening, when, and how initiatives relate. You'll use it for board presentations, quarterly planning, and engineering alignment.
Learn MoreA quarter-by-quarter view of capacity needs — how many people, what skills, and whether to hire, contract, or partner. You'll use it for hiring plans, budget requests, and vendor scoping.
Learn MoreTransparent cost estimates for each initiative, broken down by phase. Presented as ranges with assumptions clearly stated. You'll use it for financial planning and board budget approval.
Learn MoreA visual map of what blocks what — technical, vendor, hiring, and decision dependencies. The things that cause mid-stream resets when discovered too late. You'll use it for risk management and proactive escalation.
Learn MoreYou only have one major initiative — just scope the project directly. The problem is execution speed, not planning. You need ongoing strategic leadership, not a one-time plan.
For a single initiative, go straight to Development + Delivery. For ongoing leadership, Fractional Strategy Leadership is the better fit.
You have more initiatives than capacity and need principled trade-offs. Your board is asking for a technology plan with real numbers. Engineering and business leadership aren't aligned on what to build next. Dependencies between initiatives are unclear.
We send over a brief engagement letter and schedule your kickoff within the week.
“The roadmap gave us a shared language between engineering and the board. For the first time, everyone understood what we were building, why, and what it would cost.”
About 8–10 hours total: stakeholder interviews, a half-day prioritization workshop, and two review sessions.
The heaviest lift is the prioritization workshop — that's where the real decisions get made. Everything else is designed to work around your team's schedule.
They will. The roadmap is built to accommodate change — it's structured so you can re-sequence without rebuilding the whole plan.
We design the roadmap as a living framework, not a rigid waterfall plan. Initiatives are modular so you can re-prioritize quarterly without losing the dependency logic or budget models.
No. We'll document what we need during discovery. Existing documentation helps but isn't required.
We'll build the architectural understanding we need through stakeholder interviews and our own technical review. If you have existing docs, great — they accelerate discovery. If not, that's part of what we deliver.
Yes. The roadmap, budget ranges, and resourcing plan are frequently used in investor materials.
They're designed to be credible with a technical audience and clear for a non-technical one. Many clients use the deliverables directly in pitch decks and board presentations.
The roadmap becomes the backlog. We staff a development engagement to start building against it.
Pair this with fractional leadership to keep the roadmap alive and accountable.
We'll send over a brief engagement letter and schedule your kickoff within the week.
