Fractional & Interim CIO / CTO · Digital Simplicity

I help mid-market & multi-site organizations turn IT into a growth engine, through fractional executive leadership.

Nearly 30 years running technology at the executive table as CIO, CTO, and EVP, now available one to three days a week, for organizations that need the judgment without the full-time org chart.

Book a Strategy Call or call (615) 830-9345
EXECUTIVE MBA, HOWARD UNIVERSITY · B.S. INFORMATION TECHNOLOGY, AUSTIN PEAY STATE · ITIL CERTIFIED · REMOTE-FIRST, CLARKSVILLE, TN
Where I focus
Accounting & Professional Services IT Healthcare & Regulated Industries Cloud Migration: AWS / Azure / Hybrid IT Governance, Risk & Compliance Security & Business Continuity Vendor & Contract Negotiation Multi-Site Infrastructure at Scale
Alan Watson, Principal Consultant at Digital Simplicity

Why Fractional, Why Now

The gap between where your IT sits today and where it needs to be doesn't close on its own.

01 · Budget

The $200K problem

Your team is bogged down in manual workarounds and one-off fixes, but you aren't ready to carry a full-time CIO's salary, benefits, and equity.

02 · Direction

The endless contract

You need a real technology roadmap and governance your board can act on, not another agency retainer that scopes forever and finishes never.

03 · Leadership

The open seat

A CIO left, a search stalled, or a project stalled with it, and someone senior needs to own the risk today, not once the search finally closes.

How We Can Work Together

Four engagement models, sized to what your organization actually needs.

Not a one-size-fits-all retainer. The ring on each card reads left-to-right as commitment: how much of your week I hold, and whether it's ongoing or time-boxed. Below them, the Execution Sprint: the part that makes sure results actually show up.

Board / Advisory
Monthly · per-meeting

For boards and leadership teams that want an independent technical voice, without embedding a consultant full time.

  • Periodic strategy & risk briefings
  • Vendor & contract review
  • Staffing & team-structure input
Fractional Leadership
Ongoing · 1–3 days / wk

For organizations that need senior IT judgment on an ongoing basis, without adding a full-time executive line.

  • Embedded 1–3 days per week
  • Roadmap & budget tied to business goals
  • Monthly exec/board reporting
Interim Leadership
Full-time · fixed term

For a leadership transition or active CIO search that can't wait for the search to close.

  • Full-time accountable executive
  • Continuity through the transition
  • Handoff plan built in from day one
Project-Based
Scoped · fixed end date

For a defined initiative, such as a cloud migration, security assessment, or M&A IT integration, with a clear scope and end date.

  • End-to-end audit & roadmap
  • Vendor & contract negotiation
  • Governance & compliance review
12-Week Execution Sprint New
Time-boxed · 12 weeks · 20 min / wk for your team

Technology projects go live and results often don't move. The sprint fixes the second half: one goal with a real finish line, two weekly measures your team controls, a visible scoreboard, and a 20-minute weekly rhythm. On its own for owner-led businesses, or built into Fractional Leadership.

  • One goal, from X to Y by a date
  • Weekly measures the team owns
  • Coaching until the habit sticks
How the sprint works Check your execution score

The Execution Sprint is built on the principles of The 4 Disciplines of Execution (FranklinCovey). Digital Simplicity is independent and not affiliated with FranklinCovey.

A Track Record That Translates to Your Bottom Line

Results carried from the executive roles I've held, not a pitch deck.

Cost & Budget Ownership
75%
reduction in capital expenses through disciplined IT budget ownership
15%
cost reduction across all IT vendor & partner contracts, through direct negotiation
$250M
IT P&L managed with full accountability, alongside 50% lower travel and 35% lower telecom spend
Risk, Uptime & Operations
5wk → 4hr
disaster-recovery downtime, cut via new security, DR & business-continuity platforms
22,000+
end users across 180+ locations in 22 states, supported through a Citrix virtualization rollout
Delivery & Satisfaction
35%
increase in project completion rates via a Continuous Improvement Program
25%
improvement in user satisfaction from a UX-first implementation philosophy

Free Self-Assessment · 5 Minutes

Executive Health Check

Eighteen yes-or-no questions for owners, CEOs, COOs, and boards. Score your technology governance and your team's execution, and see which engagement fits where you land, right on the page.

Take the Health Check or download the printable PDF

The Guide, Not the Hero

The person behind the roadmap.

Alan Watson

I've spent nearly 30 years in the executive chair as CIO, CTO, and EVP, building and running technology for organizations from accounting and professional-services firms to multi-site healthcare and education systems. Because I've sat on executive teams with full P&L accountability, I communicate in the language of budgets, risk, and business outcomes, not just technical specifications, so your leadership and board can act on my recommendations with confidence.

Today, as Principal Consultant at Digital Simplicity, I bring that same executive-level judgment to organizations on a fractional basis: no full-time overhead, no learning curve.

Who I work best with
  • Accounting & professional-services firms modernizing their technology
  • Multi-site healthcare & education organizations in regulated, distributed environments
  • Mid-market organizations in a leadership transition or active CIO search
Book a Strategy Call (615) 830-9345