Services — Matty Woodruff

Leaders that make real calls. Strategies that make a difference.

Complex decisions are made by leaders and teams. I find patterns from other industries to drive success in yours. You waste less money, dodge expensive mistakes, and find the next successful move.

Why cross-industry consulting?

Most consultants go deep in one vertical. I go diagonal. The best solutions to your hardest problems have already been solved. Just in a different industry.

I find those patterns, fit them to your situation, and help you put them to work.

How I work

Every engagement starts with identifying your actual problem, not just reviewing the symptoms. I work shoulder-to-shoulder with you and your team, not from the sidelines.

Some engagements require only a single session while others are more complex. I scope to your problem, not a template.

Engagement Models

Fractional Services

An experienced operator embedded in your leadership team. Enough time to move the needle. Not so much that you're carrying a permanent cost.

Fractional Chief AI Officer Set the AI strategy, evaluate vendors, stand up guardrails, and get the first real wins shipped — without hiring a full-time executive before you're ready.
Fractional CIO / CTO Technology leadership for organizations in transition: after a founder steps back, between searches, or ahead of a funding event where the board wants a steadier hand.
Fractional COO Tighten operations, instrument the business, and turn execution from miracles into repeatable systems. Useful when growth has outpaced the seams holding things together.
Fractional Head of Strategy & Transformation Own the roadmap, align the organization, and drive a single transformation program to completion. I stay until the thing lands, then hand it off cleanly.

Coaching & Advisory

Recurring engagements for leaders working through decisions they can't easily delegate — whether you want a coach to sharpen how you think or an advisor to weigh in on what to do. Confidential, practical, and grounded in what you're actually working on.

Executive coaching For CEOs, founders, and senior leaders working through strategy calls, organization design, or the step up into a bigger seat.
Technical leadership coaching For engineering leaders growing into VP/CTO scope: shipping through others, managing managers, and talking technology to non-technical stakeholders.
AI literacy & adoption coaching Hands-on coaching for leaders and teams putting AI to work — from "what is this actually" through safe, productive day-to-day use.
Team coaching Short engagements with a leadership team to sharpen how you make decisions together — useful after a reorg, an acquisition, or a rough quarter.
Advisory A second pair of eyes on the calls you can't easily delegate — fundraises, hires, board materials, roadmap. Most often startups, but useful any time you'd rather not figure it out alone.

Contract & Freelance Work

Project-based engagements with a defined deliverable and a defined end. Best when you know what needs to ship and just need an experienced hand to do it — or to lead the team that does.

Offerings

Accessibility Audits

WCAG 2.2 AA audits of web products, with a completed VPAT (ACR) you can hand to procurement or a government buyer. Findings come with remediation guidance your engineering team can act on — not just a pile of flagged nodes.

WCAG 2.2 AA conformance audit
Automated + manual + assistive-tech testing
VPAT 2.x / ACR authored to your product
Prioritized remediation plan

AI Adoption & Implementation

Move beyond the hype. Build an AI strategy grounded in people, process, and execution — and, when your industry or your data demand it, run the whole thing on infrastructure you control.

Strategy & Implementation

An honest read on whether you're ready for AI
Workflows built around the AI, not determined by it
Build vs. buy vs. wait, decided together
A win for employees, leadership, and the company

Local AI Environment

On-prem or private-cloud deployment — no third-party providers
Model selection sized to your hardware and use cases
Identity, access, and audit logging baked in
Data isolation so prompts and outputs stay where they belong

Automation Solutions

Find the automation with the best return-on-investment and implement it. Skip the rest.

Identify where automation actually pays off in your workflows
Pick the tools and a plan to ship them
Honest ROI analysis
Train your team for successful long-term adoption & utilization

Compliance

Get audit-ready without grinding your team to a halt. Scope the effort, write the policies you'll actually follow, pick tooling that fits, and coordinate with the auditor or regulator on the other side.

Cross-Framework

Breach response and incident readiness
Annual notification and staff training that makes an impact

SOC 2

Readiness assessment and gap analysis
Control design and policy authoring
Tooling selection (GRC, logging, identity)
Auditor liaison through Type I and Type II

HIPAA

Risk analysis and Security Rule gap assessment
Policies, procedures, and BAAs that fit your stack
Safeguards mapped to real PHI flows, not theoretical ones

FERPA

Directory vs. educational record classification
Consent, disclosure, and access workflows
Vendor and EdTech data-sharing agreement reviews

Contract Management

Managing contractual obligations across their full lifecycle — from defining what "done" looks like in an SLA to tracking performance and obligations until the engagement closes.

SLAs

SLA design: the metrics that actually matter for your context, not generic uptime numbers
Negotiation support: what to push on, what to accept, what to walk away from
Monitoring and reporting frameworks so you know in real time whether commitments are being met
Remediation planning: what happens when an SLA is missed, before it is

Contract Lifecycle Management

Contract inventory: knowing what you've signed, where it lives, and when it matters
Renewal tracking: no surprises when contracts auto-renew or expire
Amendment and variation management across the engagement
Audit readiness: being able to answer "what are we committed to?" at any moment

Contract Oversight

Ongoing obligation monitoring: are both parties delivering what they committed to?
Scope change management and documentation when requirements shift
Escalation paths defined before they're needed
Exit and termination planning so the end of a contract isn't a scramble

Data Analytics & Reporting

Turn the data you already have into reports and dashboards that actually inform decisions — not just decorate slide decks.

Data audit: what you have, what you can trust, what's missing
Dashboards and reports built around the decision being made
Pipeline and warehouse design when the raw data needs work first
Hand-off so your team can extend it without me

Digital Transformation

Technology modernization isn't just about the technology; it requires organizational change. It must be considered from day one, and implemented with technology solutions your team will actually use.

A plan with the right actions in the right order
Untangling legacy systems without breaking them
Bringing the organization along, not dragging it
Knowing when to keep going and when to change course

Education Technology

More than a decade building, implementing, and advising on K–12 and higher-education technology — including the interoperability standards that make disparate EdTech platforms actually work together.

Standards & Interoperability

Ed-Fi data standard for student-information exchange and data alignment
1EdTech (IMS Global) specifications: LTI, QTI, CASE, OneRoster
SIS and LMS integration design, validation, and troubleshooting
Interoperability assessments and vendor conformance evaluation

Implementation & Advisory

EdTech product evaluation, RFP development, and vendor selection
SIS, LMS, and assessment platform rollout, migration, and training
Build-vs-buy decisions grounded in real implementation experience
Strategy and roadmapping for EdTech portfolios and modernization

Proposal Services

Whether a proposal is coming in or going out, making sure it fits your expectations and needs.

Review

Read against your goals and constraints, not the vendor's framing
Surface the assumptions, gaps, and gotchas hiding in the fine print
Flag pricing, scope, and risk language that won't age well
A recommendation with reasoning — not just a thumbs up or down

Writing

Win themes and narrative scaffolding before drafting begins
Outline mapped to the RFP or to the buyer's actual questions
Drafting and rewriting that sounds like you, not a template
Final polish and a red-team pass before you hit send

Strategy & Planning

Utilizing cross-industry pattern analysis, I work with leadership teams to identify proven strategies from other fields and adapt them to yours.

Roadmaps you'll actually use
Sharper positioning against your competition
Plays borrowed from other industries
Decision frameworks for the calls only you can make

Technical Services

Hands-on build work, either as an individual contributor or leading the team that does.

Software Engineering

Software Architecture
Software Design
System & API Design
Code Review & Refactoring
Testing Strategy & QA
DevOps, Infrastructure & Deployment

Web Development

Frontend (accessible by default)
Backend & APIs
Performance & Core Web Vitals
Third-party integrations

Training

Training your employees and end users on the tools, processes, and products they actually use. Either I build the materials from scratch, or I take what you already have and turn it into something people learn from — then I deliver the sessions.

Train-your-team delivery — in person or remote, using your existing materials as the starting point.
Training material development — facilitator guides, participant workbooks, and the exercises that make it stick.
End-user & customer enablement — onboarding curricula, certification paths, and live workshops.
Train-the-trainer — getting your internal experts ready to run the sessions themselves.

Screening Services

An independent read on the people and organizations you're about to commit to — before you sign. Same analytical lens whether the subject is a candidate, a contractor, or a vendor.

Candidate Screening

Resume and portfolio review against the actual role requirements
Interview question design and skills-assessment rubric
Debrief facilitation for consistent, defensible panel scoring
Reference check framework and question set

Contract Employee Review

SOW and contract analysis: scope, rate, risk language, assumptions
Gap analysis — what the contract doesn't cover but probably should
Red-team: what would have to go wrong for this engagement to fail?
Market benchmarking for rate and scope

Vendor Search & Review

Vendor market map: who the credible players are for your category
Evaluation rubric built around your constraints, not generic RFP boilerplate
Shortlist review with a recommendation and the reasoning behind it
Reference outreach guide: who to talk to and what to ask

Not sure which one fits?

Most engagements start with a conversation. Tell me the problem and I'll tell you honestly how I'd approach it.

Get in touch

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