Jordan HenningBook a call
Available for federal services delivery leadership

Mission-critical IT services, delivered at executive scale.

17 years federal IT at the Social Security Administration. As Branch Chief (2022–2025), led 12 direct reports overseeing 340 field IT staff across 170 nationwide Hearings Offices serving 7,000+ employees at 99.9% availability — $200M+ Agile IT portfolio, FAC-P/PM certified, Public Trust cleared. Then I started building the AI myself. Two production multi-agent systems, designed and operated hands-on: RFP Factory turns 40-hour federal proposal cycles into 2 hours of human review; Futures Bot trades autonomously at a 62% win rate over 500+ trades. Combat veteran (Bronze Star, Purple Heart, 101st Airborne). The executive federal contractors hire when AI capability and federal delivery discipline have to live in the same person.

Book 15 minutesDownload resumeJordanHenning32@yahoo.comGitHub
Public Trust Cleared•FAC-P/PM Certified•Bronze Star · Purple Heart•SSA Commissioner Award•MBA, Malone
Jordan Henning, executive portrait
Today
Jordan Henning
Federal Services Delivery Executive · 17+ years federal IT · Manager-of-managers across 170 offices · $200M+ portfolio · FAC-P/PM
Vision

If you can dream it, you can build it. I'm here to do both.

Technical work in 2026 demands visionaries more than ever — leaders who can hold the entire picture of a product, from first sketch to live deployment, and develop the whole arc with intent.

We're past the era when ideas were the bottleneck. The tools are here. The compute is here. The agents are here. What's scarce now is the operator who can see the end-state, build a path to it, and ship it without losing the original conviction.

I'm that operator — a federal services executive whose technical fluency makes every call sharper. Reads architecture without a translator, judges senior AI hires on instinct, sets delivery strategy that accounts for what the tech can actually do. The personal builds are how I keep the fluency real; the next role is leading the federal services organization that wins on AI capability — not being the builder for hire.

Read the full argument
Impact at a glance

Outcomes that hold up under audit.

Every number below is sourced from real federal and commercial work — not aspirations. Hover or tap any metric for the receipt.

0
Federal IT operation led
Manager-of-managers as Branch Chief: 12 direct reports + 340 field IT staff across 170 SSA Hearings Offices, serving 7,000+ employees
0
Nationwide offices unified
End-to-end IT service delivery across all SSA Hearings Offices
0.0%
System availability
Sustained for mission-critical platforms serving millions of users
0%
Downtime reduction
Through proactive monitoring, dashboards, and ITIL-driven CSI
0
Multi-agent AI systems shipped
RFP Factory and Futures Bot — designed, coded, and operating in production
$0M+
Federal IT portfolio
Multi-year Agile IT service & infrastructure programs at SSA
Career arc

From combat tours to executive IT leadership.

A 25-year arc through the 101st Airborne, federal IT delivery at scale, and now commercial growth leadership. Click any milestone for the detail.

    • Designing and shipping RFP Factory — a multi-agent proposal automation system that compresses 40-hour proposal cycles into 2 hours of human review, a 20× reduction no traditional GTM team can match.
    • Subcontracting multiple roles to Nava on CMS modernization programs — embedding Quadratic into a marquee civic-tech delivery prime that supports healthcare-focused federal modernization work.
    • Won two PA Invitation-to-Qualify (ITQ) vehicles and qualified Quadratic into the PA Small Disadvantaged Business program; pursuing capture across GSA MAS Schedule, STARS III, 8(a)/SDVOSB/HUBZone vehicles, and IDIQ/BPA structures.
    • Operates a FedRAMP-certified delivery posture — AI-services builds run alongside ATO-aligned controls so the federal compliance baseline is the starting point, not an afterthought.
    • Executing cross-sector growth strategy across federal and commercial markets — pricing architecture, solution scoping, offer-portfolio development.
    • Winning high-value strategic contracts and building executive partnerships in highly regulated environments where service delivery and AI maturity have to coexist.
    Federal ProcurementFedRAMPNava Subcontract (CMS)Multi-Agent SystemsPA ITQ ×2
Production AI builds

Built these myself. The fluency receipts behind the federal services pitch.

Production multi-agent systems Jordan designed, coded, and operates — proof the AI capability he sponsors as an executive is grounded in real working systems. The next role is leading the federal services organization that wins on AI capability: chairing the architecture reviews, judging the senior AI hires, and sponsoring agentic-delivery work without needing a translator.

RFP Factory

In production · Quadratic Digital
Multi-agent proposal automation
Outcome
40h → 2h per proposal · 20× faster

An end-to-end system that ingests federal and commercial RFP documents and produces polished, SME-ready proposal drafts. Specialized agents handle research, strategy, drafting, and compliance review in parallel — compressing a 40-hour proposal task into 2 labor hours of human review, a 20× reduction in cycle time, with a human always in the loop on the final pass.

  • Decomposes unstructured RFP packets into structured response workstreams and compliance matrices
  • Orchestrates research, strategy, drafting, and review agents concurrently
  • Routes each task to the LLM provider that performs best for it (Anthropic, OpenAI, or Gemini)
  • Persists project state in a relational store with full audit history for SME review
Architecture
9-stage pipeline · multi-provider
  1. RFP UploadPDF · DOCX
  2. Intake
    compliance_matrix · validator · metadata
    SonnetHaiku
  3. StrategyShortfall + gap analysis
    shortfall_strategist
    Opus
  4. Outline + Team
    outline_agent · team_composer
    Sonnet
  5. CostDual-pipeline market research
    market_researcher · cost_analyst · cost_reviewer
    GeminiClaudeGPT-5.5
  6. DraftPer-section with auto-resolve
    writer_team · needs_human_resolver
    SonnetHaiku
  7. Review (auto-loop, cap 4)
    reviewer_a · reviewer_b
    OpusGemini
  8. PolishCross-section consistency
    final_polish_detector · final_polish_applier
    Gemini ProSonnet
  9. Export DOCXcompile_proposal_to_docx
Python 3.14Anthropic + OpenAI + GeminiSQLAlchemy 2.0AlembicNiceGUIThreadPoolExecutorPrompt engineering

Futures Bot

Live since Feb 2026 · 24/5 · 62% win rate over ~500 trades
Autonomous multi-agent futures trading
Outcome
62% win rate · ~500 trades · net-positive PnL

A multi-agent trading system that monitors futures markets, generates signals, manages risk, and executes trades autonomously 24/5 — using proprietary strategies developed from 12 years of personal markets research. Live since February 2026: ~8 trades per day across the 24-hour cycle, 62% win rate over the first ~500 trades, net-positive PnL. Built end-to-end as a research platform for pressure-testing multi-agent design patterns under conditions where mistakes cost real money — the same composure-under-fire discipline that runs a service desk runs a trading desk.

  • Real-time futures market data ingestion and feature engineering
  • Specialized agents for signal generation, risk management, and order execution
  • Programmatic order placement with hard-coded risk guardrails
  • Runs autonomously with operator-level observability
Architecture
8-stage pipeline · 5-agent committee
  1. Market DataMES · MCL · NinjaTrader feed
  2. Regime Enginev3 classifier · transition tracking
    Deterministic
  3. Strategy Scanners10+ deterministic pattern detectors
    Breakout · Retest · ORB · RSI(2) · Liquidity Sweep · BB-RSI · Cup-Handle · BOS Order Block · AVWAP
    Deterministic
  4. Signal Rankingzone_guard · ranking
    Python
  5. 5-Agent CommitteeTwo-stage blind debate + synthesis
    Technical Analyst · Bull · Bear · Risk Manager · Devil's Advocate
    OpenAIClaudeGemini
  6. Risk GatesL2 walls · news adjacency · session · 6-tick scratch
    Python
  7. Order ExecutionProgrammatic SIM/live placement · scaled exits
  8. Causal Post-MortemEvery loss → root cause → regime params
    batch_post_mortem · causal classifier
    Haiku
PythonMulti-agent orchestrationReal-time market dataAlgorithmic executionRisk management
Competency profile

Quantified strengths, with proof on demand.

The radar reflects core executive competencies. Click any card to see the receipts — actual outcomes from federal and commercial work.

Third-party signal

Awards, retention, references — the parts I can't self-assert.

Recognitions issued by institutions. Outcomes measured by the teams I led. References available after the first conversation.

2008–2025

Public Trust Clearance

U.S. Federal Government · High Risk Tier

Held throughout 17-year SSA tenure. Federal background investigation; cleared to handle PII at the Social Security Administration. Eligible to reinstate.

2021

SSA Commissioner Award

Kilolo Kijakazi · Acting Commissioner, SSA

Awarded by SSA Acting Commissioner Kilolo Kijakazi for spearheading the emergency COVID-19 medical document upload system on MySSA — conceived, built, deployed, and adopted in weeks rather than the typical 12+ month enterprise cycle. Kept nationwide disability-claim processing alive during widespread office closures.

2006

Bronze Star

U.S. Army · 101st Airborne Division

Awarded for meritorious service in a combat zone during a tour in Iraq.

2006

Purple Heart

U.S. Army

Awarded for wounds received in action during the same tour in Iraq.

2020

FAC-P/PM Certification

Federal Acquisition Institute

Federal Acquisition Certification for Program & Project Managers — the federal government's standard credential for IT program leadership.

Team outcome
100%
Direct-report retention

Twelve direct reports across three years as Branch Chief — zero attrition. Federal IT promotion is slot-based, not performance-based, so retention is the real signal: the team I built chose to stay through a period of high federal turnover.

Team outcome
4 of 4
Mentees promoted into PM leadership

Every project manager I mentored as a senior PM at SSA went on to run their own programs successfully — the career-development outcome the org structure made possible.

References
Available after first conversation

References provided after first conversation, per professional courtesy.

  • 2 Federal CIO / Director-level
  • 2 SSA peer Branch Chiefs
  • Multiple direct reports across SSA + Quadratic Digital
Battlefield to Boardroom

The leadership the rest of the field can't replicate.

Three combat tours with the 101st Airborne — Bronze Star, Purple Heart — translated directly into how I run incident command, scale service organizations, and show up for customers under pressure.

Military
Resilience under fire

Three combat tours with the 101st Airborne. Bronze Star, Purple Heart.

IT Services Delivery
Composure in high-stakes escalations

Owns the room when production is down and millions of users are affected.

Military
Scaling teams in chaos

Led infantry units through deployment cycles where adaptability decided outcomes.

IT Services Delivery
Manager-of-managers across 170 offices

12 direct reports overseeing 340 field IT staff nationwide, serving 7,000+ Hearings Office employees.

Military
Mission-critical decisions

Trained to make irreversible calls with incomplete information, under time pressure.

IT Services Delivery
99.9% uptime SLA governance

Same decisiveness applied to incident command for regulated, 24/7 platforms.

Military
Doctrine + improvisation

Followed playbooks where they worked; rewrote them when reality demanded.

IT Services Delivery
ITIL discipline + pragmatic delivery

Operationalized ITIL where it created value, never as bureaucratic theater.

Military
Service to mission

Volunteered, served, sacrificed — and shows up the same way every shift since.

IT Services Delivery
Mission-driven service ownership

Treats every SLA, every customer outcome, every audit as a personal commitment.

3
Combat tours
★
Bronze Star
♥
Purple Heart
101st
Airborne Division
Insights

Perspectives shaping the next era of IT services.

Short, opinionated takes on the operating model behind world-class HPC, AI, and managed-services delivery. Start with the featured long-form pieces below — or click into any short take.

Featured · Playbook

The First 90 Days

How I'd Run a New VP of Federal Services Delivery Role

The real risk in a new senior role isn't moving too slow, it's moving fast on the wrong things. The first 90 days are about earning the standing to make the decisions that matter, then making them. Here's how I'd structure it.

Read the full playbook
Featured · Essay

If you can dream it, you can build it.

So why are we still hiring people who can only build?

We've been telling ourselves a story about engineering hiring for two decades: that the right way to find talent is to stress-test syntax. Whiteboard a binary tree. Reverse a string in O(n) time. Spend five hours on system design. The candidate who codes cleanest under pressure wins.

Read the essay

ITIL's core disciplines — incident, problem, change, and capacity management — still matter at HPC and AI scale, but the failure modes have shifted. A failed CI run on a 1,024-GPU job is a different kind of incident than a Tier-1 ticket. The next generation of service governance has to stitch together model performance telemetry, GPU utilization, and traditional ITSM workflows into a single operational picture. The orgs that get this right will have an unfair cost advantage; the ones that don't will burn millions on idle silicon.

Let's talk

Hiring for federal services delivery? Three ways to evaluate fit.

Paste your JD into the chatbot for a fit map · read the 90-day Playbook to see how Jordan would run the role · book a 15-minute intro below. Calendar is live, resumes are pre-tailored, chatbot is grounded in everything on this site.

Calendly
15-minute executive intro
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Currently exploring

Left SSA after 17 years to expand into the private sector and build outside the comfort zone — Quadratic Digital was the proving ground. Now exploring the role where vision, hands-on build, and operational discipline compound into the largest impact of my career — looking for platform fit, not another title.

Want a sense of how I'd run the role? Read the 90-day playbook
Where I want to play
Federal services delivery leadership

VP / Director of Service Delivery, GM of Federal AI Services, or Senior Director Federal Programs at federal primes and services firms — where 99.9% uptime, $200M+ portfolio scale, and hands-on AI capability all matter in the same role.

Federal AI services growth

GM, VP, or Practice Director at emerging federal AI services firms — where someone who can both win federal contracts and sponsor multi-agent AI delivery is the job, not a side capability.

Less of a fit

VP Product or VP Engineering at commercial tech (different level/tenure pattern) · IC engineering roles · Pre-revenue seed-stage where federal credibility doesn't carry weight · Roles where AI is a marketing layer rather than a real operational change

Work arrangement
Based in York, PA · Open to remote · Open to in-office · Has led teams in both. Optimizing for the right job fit.
Federal eligibility
Public Trust · High Risk · Held throughout 17-year SSA tenure (2008–2025) — federal background investigation. Eligible to reinstate.
Direct contact
Resume

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