On-Site Strategy Day – align IT roadmap, spend and risk with your real business plans.
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On-Site • CEO & Leadership • Vendor-Neutral

On-Site IT Strategy Day
for CEOs & leadership teams

One day on-site with your CEO, leadership team and key IT stakeholders to align roadmap, spend and risk with your actual business plans – in one room, at one time.

See What’s Included Book Intro Call

Often paired with a membership tier or follow-up advisory to maintain momentum.

Situations where a Strategy Day works well
  • ✔ You’re planning a 12–24 month growth, consolidation or M&A phase.
  • ✔ IT feels fragmented and no one has the full picture.
  • ✔ You want IT spend tied back to clear outcomes and priorities.
  • ✔ You want to build buy-in across finance, operations and IT in one day.

From $5,250 USD plus travel (capped).

Travel costs are pre-approved and capped in writing.

Who should attend

  • ✔ CEO / Owner / MD
  • ✔ CFO / Finance leadership
  • ✔ Key operations / line-of-business leaders
  • ✔ Internal IT lead and/or MSP representative (by agreement)

What we’re aiming for

  • ✔ A shared, non-technical view of current IT posture and spend.
  • ✔ A small number of clearly sequenced priorities for the next 12–18 months.
  • ✔ Alignment between leadership, finance and IT on what “good enough” looks like.

What you receive

Pre-session discovery

Short calls and/or questionnaires to capture your current state, goals and constraints. We arrive on-site prepared, not cold.

Full-day on-site facilitation

A structured but flexible day of facilitated discussions, whiteboarding and prioritization, keeping conversation anchored in business outcomes.

Written summary & 90-day outline

A concise written summary and 90-day action outline to maintain momentum after the day.

Typical agenda flow

Morning – Current state & realities

  • ✔ Business goals, constraints and risk appetite.
  • ✔ High-level view of existing systems, providers and spend.
  • ✔ Key pain points from leadership and IT.

Afternoon – Priorities & sequencing

  • ✔ Identify the few initiatives that genuinely matter most.
  • ✔ Sequence them around cash, capacity and risk windows.
  • ✔ Agree on next 90-day actions and owners.

Pricing & travel

Strategy Days are intentionally limited in number and scheduled to avoid “fly-in, fly-out” stress. Pricing always includes a clear cap on travel and expenses.

From $5,250 USD + capped travel

Exact pricing is confirmed in writing based on location, team size and any follow-on support.

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