Independent practice · Open to projects & the right seat

I help sellers win skeptical buyers — with proposals, enablement, and AI that actually works.

Twenty years in proposals — twelve inside Oracle's global proposal organization, where I administered the Responsive (RFPIO) platform, owned the security and AI answers enterprise buyers check hardest, and finished by shaping how the organization adopted AI. Now independent, for teams that answer RFPs and security questionnaires — whether or not they have a proposal team.

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What I do

Four questions I get asked, and what I do about them.

For teams that answer RFPs and security questionnaires — and are putting AI into that work — whether or not you have a proposal team yet. Every answer below names its source.

Response

Q · Three RFPs landed this week. Who owns them?

Answer the documents that decide deals.

Deals are rarely lost on capability. They're lost in the response — late, generic, or assembled by whoever had time. What fixes it is a motion, not heroics.

  • Map the response motion end to end — where time leaks, where quality slips, where deals stall
  • Stand up a response function where there isn't one yet: intake, owners, turnaround standards, and a library to answer from
  • Run the big ones with you — win themes, compliance matrices, executive summaries for the C-suite, customer references and orals prep

Source300+ proposals at Oracle; hundreds of customer reference sectionsReviewedOct 2026

AI adoption

Q · Half the team ignores the AI. The other half trusts it too much.

Roll out AI people trust enough to use.

AI adoption fails in two directions: people who won't touch it, and people who send whatever it writes. Both get fixed the same way — test it on your real content, write down where it may draft and where only the approved answer will do, and give every role someone to ask.

  • Test AI features against your real content before rollout — accuracy, usability, and where a person has to check
  • Design the workflows — prompts, retrieval, review steps — around how your team already answers buyers
  • Recruit a champion in every role, write the usage guidance, and train people on the features they'll actually use

SourceAI adoption work, Oracle's global proposal organization, 2025–26; role-based champions for every major platform rollout and AI initiativeReviewedOct 2026

Platforms & content

Q · We bought the platform. Why can't anyone find a current answer?

Make the platform you already bought pay off.

Platforms don't fail at purchase; they fail after go-live, in the library nobody owns. AI speeds the decay up: a bad answer becomes cheap to repeat and expensive to catch.

  • Implementation, configuration and administration support for Responsive (RFPIO) and comparable response platforms — templates, permissions, AutoFill and CRM field mapping, usage reporting
  • Library architecture and governance — owners, sources, review dates and automated reminders, so SIG, CAIQ and due-diligence answers stay current with your SMEs and your CISO, procurement and legal reviewers
  • Keep the library growing and AI-ready: harvest the best new answers from recent proposals, break long answers into passages AI search can use, and merge the duplicates, so retrieval returns the right answer, not a confident wrong one

SourceResponsive (RFPIO) administrator through Apr 2026; Qvidian implementation team; 5,000+ security and AI answers managed, 3,000+ of them from the SIG and CAIQReviewedOct 2026

Enablement

Q · The training happened. Why hasn't anything changed?

Get the team using the system — at scale.

Adoption is a production problem before it's a training problem. People use what is short, findable, and made for the job in front of them — and you only know if it worked by measuring it honestly.

  • Build the program, from zero if need be: onboarding, role-based learning paths, certifications, and video produced from storyboard to publish
  • Run the operation behind it: request intake, priorities, field communications, and a launch calendar that keeps the field from being buried
  • Measure adoption honestly — who's using it, who isn't, which searches come up empty, and what to do about it — and coach the people who make the content

Source350+ instructional videos; learning paths on an LMS I administered; Seismic & Kaltura administrationReviewedOct 2026

Track record

Twenty years. One coherent arc.

Two decades of response work — first across commercial and government procurement, then twelve years inside Oracle's global proposal organization, from proposals to enablement to AI. Through two platform rollouts, reorgs, and the messy reality of high-stakes response work.

In production, not in a demo

Responsive · Qvidian · Seismic · Kaltura

SourceResponsive (RFPIO) administrator through April 2026 · Qvidian implementation team · Seismic & Kaltura administration · CRM AutoFill mapping from Oracle Fusion Sales Cloud

  1. 2005 – 2014

    Commercial and government proposals

    State, local, federal civilian and Department of Defense buyers — including a past-performance section an Air Force source selection committee rated "Exceptional," the highest rating on the federal scale. I also designed and implemented one company's proposal workflow.

  2. 2014 – 2019

    Senior Proposal Manager, Oracle

    300+ proposals for commercial, highly regulated, and state and local government buyers, with senior ownership of the most complex. A seat on the implementation team for a 1,000-seat Qvidian rollout across North America and Europe.

  3. 2019 – 2024

    Video Enablement Producer, Oracle

    350+ instructional videos from storyboard to publish, in a video program I helped start as one of its first two people and then ran — plus Seismic and Kaltura administration and adoption reporting.

  4. 2024 – 2025

    Content Manager, SaaS Cloud Security & AI, Oracle

    Managed 5,000+ question-and-answer pairs across SaaS Cloud Security and AI, including 3,000+ SIG and CAIQ answers, inside a 30,000+ item library. Kept them current by adding the new answers solution consultants and application technologists wrote for recent proposals.

  5. 2025 – 2026

    Senior Content Strategist, AI for Proposal Automation, Oracle

    Shaped how the global proposal organization adopted AI: contributed to LLM customization and to retrieval (RAG) and small-language-model evaluation, and trained the people who would use the new features.

  6. 2026 – now

    Founder & Principal, Woodruff.Work

    An independent practice for teams that answer RFPs and security questionnaires, with or without a proposal function. It runs on the same discipline it sells.

How the practice runs

Agents do the legwork. I decide what goes out.

Four scheduled agents on Claude handle the practice's recurring work: two monitor the market, one reviews the pipeline every Monday, and one checks next actions every Thursday. Reusable skills draft tailored documents from a library of claims I've confirmed, the way a proposal team answers from its library. They follow written procedures and share their records, and nothing goes out without my review. I design them; Claude writes the code.

Agents · on a schedule

Market scanDaily
Market scanWeekly
Pipeline reviewMondays
Next-action checkThursdays

Written procedures · shared records

Me

My reviewNothing goes out without it.

Out the door

Outreach and documents
SourceThe practice's own operations, running since September 2026

And a JD from Tulane Law, so procurement terms, flow-downs and legal review cycles don't slow me down.

What Survives Review

Generation was never the bottleneck. Trust was.

AI made proposal content cheap to produce. It didn't make it true. When anyone can generate an answer in seconds, the scarce thing is knowing which answer is current, approved and defensible. Most of what's published on this comes from companies selling software. This is the view from someone who isn't.

The sweet woodruff mark, drawn in full

Woodruff.Work

Provenance beats fluency.

A proposal is a set of claims your company will be held to — in the contract, the security review, the renewal. A confident wrong answer in a questionnaire isn't a draft; it's a liability. The test isn't whether it reads well. It's whether you can stand behind it.

The library is the product.

No feature automates ownership. Someone has to know where each answer came from and when it was last true — and that someone needs a structure that makes it possible at three thousand items. Or thirty thousand.

Humans lead. Tools earn their place.

Retrieval demos beautifully on a clean corpus and behaves very differently against years of answers written by dozens of people. I've tested AI features before release and administered the platform after go-live. AI accelerates the work; people own the call on what's true enough to send.

The review cycle

Generation got fast. Every review is still a person's call.

  1. Blue TeamIs the win strategy right?
  2. Black HatWhat will the others bid?
  3. Pink TeamDoes the draft carry the strategy?
  4. Red TeamHow will a skeptical buyer score it?
  5. Green TeamDoes the price hold up?
  6. Gold TeamAre we ready to submit?
  7. White TeamIs every page clean?

The color-team reviews, in the order a pursuit runs them. AI speeds up the writing between them; people still own the call in each one.

SourceShipley's color-team reviews; White Team as the final page check; questions paraphrasedSchematicNot to scale

How we work together

Same problem. Two ways to fix it.

Bring me in from outside for a defined piece of work, or bring me on to build the function in-house. Either way it starts with a 30-minute conversation about what isn't landing.

Shape 01 · Assessment

A fast, honest read.

≈ 2–4 weeks · Fixed fee

A focused diagnostic on your response motion, answer library, platform setup or AI adoption — findings, recommendations and a clear next-step decision document, at a fee set in a one-page scope before we start. The right first step whether you have a proposal team or not.

Shape 02 · Build

Ship the change.

≈ 1–3 months · Scoped to the problem

A scoped engagement to design and stand up a specific improvement — a response function, a library rebuild, a platform rollout or rescue, an enablement program, or an AI rollout. I deliver the work and hand it to the team that owns it.

Shape 03 · Standing partner

A steady outside voice.

Ongoing · Monthly retainer

Fractional support for proposal and revenue leaders who want a thinking partner on call — for complex deals, mentoring, AI and platform decisions, and the moments when an honest outside read is worth more than another internal meeting.

Or bring me on · Full-time or contract

Building the function in-house?

I'm open to the right seat — proposal and response leadership, response platforms, AI adoption, content strategy or enablement — at a company whose buyers need proof before they sign. Available now.

Talk about a role

Let's have a 30-minute conversation.

No deck. No pitch. No software to sell you. Tell me what you're working on, what's not landing, and what'd be different if it did. If there's a fit — a project or a seat — we'll find the shape that makes sense.

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