Technology Road-Mapping Session – align IT projects and investments with your actual growth plans.
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Roadmap • Priorities • Business Alignment

Technology Road-Mapping Session

Too many IT projects happen in isolation: a bit of cloud here, a security tool there, a rushed upgrade when something breaks. This session helps you turn all of that into a clear 12–24 month roadmap aligned with your growth plans.

See What’s Included Book Roadmap Intro Call

Typical investment: from $3,450 USD for a virtual session with follow-up summary.

Why CEOs use this session
  • ✔Turn scattered IT ideas into a coherent plan.
  • ✔Sequence projects in a sane order that supports growth.
  • ✔Get a roadmap you can show to boards, lenders and staff.
  • ✔Stop “random acts of IT” and focus on the highest-value moves.

We don’t sell software or hardware. This is about clarity, priority and timing from your side of the table.

What you get from the Road-Mapping Session

The goal is a simple, defensible technology roadmap that makes sense to non-technical leadership, and gives IT and vendors a clear direction.

  • ✔ Pre-session discovery – current systems, projects, constraints and ideas.
  • ✔ Facilitated workshop with CEO, leadership and key IT stakeholders.
  • ✔ Prioritization of initiatives by impact, risk and effort.
  • ✔ A clear 12–24 month roadmap grouped into phases and themes.
  • ✔ Identification of dependencies and pre-requisites that often derail projects.
  • ✔ Short list of “do now / do later / don’t bother” items.

You walk away with a roadmap document and summary you can use for internal planning, budgeting, and board updates.

Format & pricing

Typical format:

  • ✔Pre-work questionnaire and document review
  • ✔Half-day or full-day virtual workshop
  • ✔Draft roadmap + feedback cycle
  • ✔Final 12–24 month roadmap and summary

From $3,450 USD for a virtual session, depending on complexity and number of initiatives.

On-site facilitation is available on request, with travel capped and agreed in advance.

Schedule Roadmap Discovery Call

How the Road-Mapping Session works

1

Intake

We gather context: your business goals, growth plans, current IT landscape and any “must-do” projects already in motion.

2

Workshop

In a structured session, we map initiatives, dependencies and risk, then prioritize and group them into logical phases.

3

Roadmap & follow-up

You receive a documented roadmap, plus a short follow-up call to clarify questions and plan next steps.

Is this road-mapping session right for you?

Good fit if:

  • ✔You have multiple competing IT ideas and projects but no clear sequence.
  • ✔You’re unsure how to align IT moves with hiring, expansion or M&A plans.
  • ✔You need a simple 12–24 month view to support budgeting and board conversations.
  • ✔You want an independent, vendor-neutral view of priorities.

Probably not a fit if:

  • You are only looking for a single tactical project (e.g., “just migrate email”).
  • You already have a well-maintained roadmap that leadership trusts and uses.

Common questions

Do you replace our CIO or IT leader?

No. We complement your existing IT leadership and MSP by giving you a neutral, CEO-focused roadmap and rationale. They remain key stakeholders in the process.

Will this lock us into any specific vendor?

No. We do not resell software or hardware. The roadmap talks about outcomes and capabilities, not just specific products. You can use it with current or future vendors.

Can we revisit or update the roadmap later?

Yes. Many CEOs choose an annual or semi-annual Roadmap Refresh as part of a broader engagement or club membership when circumstances change.

Give your IT plans a clear, executive-ready shape.

One focused session can turn scattered projects into a roadmap you’re comfortable showing to boards, lenders and your own team.

Book Road-Mapping Intro Call
Looking for a more ongoing relationship? Explore the Executive IT Strategy Club or our broader Executive IT Engagements catalog.