Bridgehead Advisory

Your AI is ready.
Government isn't buying.

Most AI companies build great technology and then hit a wall trying to sell it to the largest buyer on earth. I've been on the other side of that wall. $80M+ in federal software sales. Former HHS Chief Architect. I know how the machine works because I've operated it.

Book a Strategy Call See the track record →
Federal Sales Strategy ◆ AI Go-to-Market ◆ CMS / HHS / VA / DoD ◆ Procurement Navigation ◆ Enterprise Deal Architecture ◆ Revenue Operations ◆ Federal Sales Strategy ◆ AI Go-to-Market ◆ CMS / HHS / VA / DoD ◆ Procurement Navigation ◆ Enterprise Deal Architecture ◆ Revenue Operations
$80M+
Federal software sold
in a single year
800%
Quota attainment
peak year
8 yrs
Inside CMS, HHS,
VA & DoD accounts
$10M
ARR built from zero
in 12 months
The Problem

You raised a Series B. Your AI works. Your sales team is crushing it in commercial. Then someone says "we should sell to government" — and everything breaks.

The RFPs don't make sense. The sales cycles stretch to 18 months. Your reps can't find the real decision maker. Your pricing model doesn't fit procurement vehicles. And your competitors — with worse technology — keep winning because they know something you don't: how the machine actually works on the inside.

Who I Am

I was Chief Architect of the National Health Information Network at HHS — inside the agency, designing the national data exchange infrastructure. Then I spent eight years at MarkLogic where I sold the database that powered Healthcare.gov and closed $80M in a single year on a $10M quota.

I've led healthcare security at AWS, advised Confluent on government and enterprise positioning, and built multiple companies from the ground up — including one that hit $10M ARR in 12 months. I now build production AI systems daily on the Claude API and run n8n automation workflows for real business operations.

I've been the buyer. I've been the seller. I've been the architect. There is no one else in the market with this exact combination of experience. I help AI companies stop guessing about government and start closing.

What I Do
01
Federal Sales Strategy
Procurement vehicle selection. Stakeholder mapping. Agency-specific positioning. Deal architecture for CMS, HHS, VA, DoD, and state agencies — built from years of closing inside these buildings.
02
AI Go-to-Market
Your model is impressive. Government doesn't care. I translate what your technology does into what procurement officers, program managers, and agency CIOs need to hear to sign.
03
Enterprise Deal Architecture
Hands-on deal coaching for seven- and eight-figure opportunities. Multi-stakeholder alignment, technical evaluation navigation, and the political mechanics that make or break complex government deals.
04
Revenue Operations
Pipeline architecture, AI-powered outreach systems, and sales process design — built by someone who has carried a quota every year and consistently destroyed it. I don't theorize about sales. I close.
The Track Record
2024 — PRESENT

PayStreet Holdings — Co-Founder & COO

AI-powered tax credit recovery and payroll. Built WOTC screening system capturing 2-3x industry standard

2021 — 2022

Amazon Web Services — Global Healthcare Security

Led Wickr Healthcare post-acquisition. Zero-trust collaboration for enterprise health

2019 — 2021

Confluent & Code Dx — Strategic Advisor & Regional Director

Event data streaming and application security for government and enterprise buyers

2009 — 2017

MarkLogic — Director, Public Sector Healthcare

$80M+ in federal sales. Healthcare.gov infrastructure. 800% quota. MarkLogic's largest business line.

2008 — 2009

U.S. HHS — Chief Architect, National Health Information Network

Designed the national health data exchange infrastructure from inside the agency

1996 — 2008

Versant → iPlicity (Co-Founded) → IceWEB → Kapow/Kofax

Two CTO roles. Built and shipped technology from scratch. Federal systems engineering.

Stop guessing.
Start closing.

If your AI company is serious about government — and you want someone who's been in the building — let's talk.

Book a Strategy Call

Typically responds within 24 hours