Matty Woodruff
Cross-Industry Thinker · Strategist · Creator
www.mattywoodruff.com | MattyWoodruff@gmail.com
I help leaders and teams adopt new technology, untangle manual processes, and build systems that scale.
Also, I love to cook and run a small crafts studio.
Why I focus on people.
The hardest problems in a business are almost never the technology. They are the calls leaders make about people, priority, and pace, and the cost of getting those wrong.
My consulting practice exists to make those calls a little sharper, a little less lonely, and a lot more deliberate.
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 need a single conversation. Others run for quarters. I scope to your problem, not a template.
Recent Thoughts on Coaching and Consulting
Engagement Models three ways we work together
01
Advisory
A second pair of eyes on the strategic and technical calls you can't easily delegate: platform bets, technical diligence, roadmap, and the people decisions behind them. Most often startups, but useful any time you'd rather not figure it out alone.
- Technology & AI strategy advisory Evaluating platform bets, AI and vendor selection, and build-vs-buy calls before you commit budget or headcount.
- Board & investor technical diligence An independent read on the technical narrative behind a fundraise, acquisition, or board update, before it's in front of people who'll ask hard questions.
- Roadmap & architecture review A second opinion on where the platform is headed, what's actually load-bearing, and what can wait.
- Technical hiring & org advisory Screening technical hires and vendors, or sanity-checking how an engineering org is structured, before you commit to either.
02
Coaching
For leaders growing into a bigger seat, and for teams that need to make decisions together better. Confidential, practical, and grounded in what you're actually working on this week.
- Executive coaching For CEOs, founders, and senior leaders working through strategy calls, organization design, or the step up into a bigger seat.
- New-manager transition coaching For first-time and newly-promoted managers: the IC-to-leader transition, building authority without overreach, the unfamiliar shape of the work.
- Technical leadership coaching For engineering leaders growing into VP/CTO scope: shipping through others, managing managers, talking technology to non-technical stakeholders.
- Team & culture coaching Short engagements with a leadership team to sharpen how you make decisions together, useful after a reorg, an acquisition, or a rough quarter.
- 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.
03
Fractional Leadership
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 COO Tighten operations, instrument the business, turn execution from miracles into repeatable systems.
- Fractional CIO / CTO Technology leadership for organizations in transition: after a founder steps back, between searches, ahead of a funding event.
- Fractional Chief AI Officer Set the AI strategy, evaluate vendors, stand up guardrails, ship the first real wins, without hiring a full-time executive too early.
- Head of Strategy & Transformation Own the roadmap, align the organization, drive a single transformation program until it lands, then hand it off cleanly.
Offerings pieces you can order or combine
Strategy & Planning
Cross-industry pattern analysis adapted to your context. Roadmaps you'll actually use; decision frameworks for the calls only you can make.
Training
Train-your-team delivery, material development, end-user enablement, train-the-trainer. I build it, or take what you have and make it stick.
Screening Services
An independent read on candidates, contractors, and vendors before you sign; same analytical lens, applied early.
Proposal Services
Reviewing what's coming in or writing what's going out. The fine print, the win themes, the recommendation with reasoning.
Board & Investor Prep
Board materials, narrative scaffolding, and the practice runs that make the room land the way you intend.
Org & Operating Model
Designing reporting lines, decision rights, and the rituals that hold them together. Especially useful after growth or reorg.
Offerings
A complete listing of how I help. Engagement models (above) illustrate how I work:
from a fractional seat on your leadership team to a one-off contract to a completely custom engagement.
Offerings (below) are the various functions and work I can deliver; pieces you can order off the shelf or combine to meet your specific needs.
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. 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
See also: Proposal Services: the same analytical lens applied to
incoming or outgoing proposals; a natural companion for any vendor or contractor engagement.
Let's talk about your goals and opportunities to achieve them
Email
MattyWoodruff@gmail.com
Best for inquiries, project conversations, or anything that deserves a real reply.
I read every message.
LinkedIn
linkedin.com/in/mattywoodruff
For lighter-touch connection or following along with what I'm thinking.
For anything substantive, email is the move.
Let's talk about your goals and opportunities to achieve them
Coaching, advisory, a fractional seat, or just a good conversation. I read every message.
Get in touch