Wingman Operations Advisory
Reid Mason, founder of Wingman Operations Advisory

Wingman Operations Advisory

Bringing
Calm to Chaos

Growth outran your operating system. Meetings multiply, priorities blur, and the owner is still the bottleneck. Wingman starts where every good mission starts — in the room, with a workshop.

The Path

Workshop. Assess. Execute.

A deliberate sequence. Every step earns the next one.

01

Start With a Workshop

Every engagement opens in the room. Two to three days with your leadership team to surface the real problems and align on a direction.

02

Operational Assessment

A full-business health score across 15 areas — so the roadmap is driven by evidence, not opinion.

03

Fix or Do

A focused sprint or reset to fix what's broken — or a fractional executive embedded with your team to run it.

04

Advise

An ongoing advisory seat at your table, so the plan stays alive and the calm outlasts the engagement.

The Entry Point

Start With a Workshop

Facilitated, high-intensity sessions that turn chaos into a clear plan. You bring the people who run the business; we bring the structure.

01

Wingman Waypoint

COMPASS Strategic Planning Workshop

A 1–3 year COMPASS plan: priorities cross-referenced to metrics and owners, phase-tagged tasks, and a Waypoint follow-up schedule.

02

Wingman War Room

Operational Excellence / Kaizen Workshop

A prioritized improvement backlog with quick wins already in motion.

03

Wingman Command Center

Executive Operating System Workshop

A working operating system: cadence, scorecard, and accountability map.

04

Wingman Formation

Leadership & Team Alignment Workshop

An aligned leadership team flying in formation, not as solo pilots.

After the Workshop

Plan. Do. Fix. Advise.

Four tracks after the workshop, depending on how deep the problem runs.

Plan

  • Operational Assessment

    3–4 weeks

  • Strategic Planning & Roadmap

    4–6 weeks

Do

  • Fractional COO

    Engagement-based

  • Fractional Chief Transformation Officer

    Engagement-based

Fix

  • Operational Breakthrough Sprint

    4–12 weeks

  • Wingman Operational Reset

    6 months

Advise

  • Executive Advisory

    Monthly retainer

$20M+

In Documented Cost Savings

40+

Executive Workshops Facilitated

30+

Core Processes Improved

24

Years Leading in the U.S. Navy

Initial Indicator · 90 Seconds

What's Your Chaos Score?

This brief check uses eight questions to flag where operational friction may be hiding. It is an initial indicator — not the full 15-area Operational Assessment or a diagnosis.

Interactive · Three Questions

Which Workshop Do You Need?

Tell us where the chaos lives and we'll point you at the right room.

Ready When You Are

Book the Workshop. Bring the Chaos.