Case Studies

Proof: Expensive Mistakes Avoided, Execution Accelerated

Technology, commercial, and organizational leadership across federal services and regulated healthcare

$20M–$30M

Lucky Rabbit Portfolio

6+ → 2 weeks

Release Cadence

4 → 2 months

Framework Migration

15+

Agencies in TechFlow Portfolio

Lucky Rabbit LLC

Chief Technology Officer

2021 – 2025

Challenge

Modernize regulated federal technology services while balancing delivery, staffing, investment, and margin protection.

Leadership Approach

Technology and cloud-modernization strategy
Pricing models, forecasting, and resource-allocation analysis
Engineering leadership and cybersecurity governance
Capture solutioning and executive decision support

Results

Growth and Commercial Decisions

$20M–$30Mfederal technology-services portfolio led

~$1.5MMACPRO award supported by technical strategy

ImplementedFractional CTO initiative designed by Haywood

Delivery and Leadership

13–15OneMAC team built and led; broader influence across 60 people

6+ → 2 weeksrelease cadence improved

4 → 2 monthsframework migration completed while maintaining service availability

Product and Investment Judgment

10 monthsAgentVrify MVP to working product with seven people on a $10K–$15K budget

PartnershipAbundant evaluation led Lucky Rabbit to form a partnership

No-go acceptedleadership passed on a separate venture investment

TechFlow Inc

Senior Principal Architect

2013 – 2020

Challenge

Align modernization choices with investment, cost, security, resilience, and delivery feasibility across federal programs.

Leadership Approach

Cloud strategy and modernization roadmaps
Architecture and continuity frameworks
Technical and executive stakeholder alignment
Corporate SAFe transformation leadership

Results

Portfolio Context

$80M+federal contract portfolio supported by modernization advisory

15+civilian and defense agencies served

Organizational Transformation

SAFeserved on corporate transformation leadership team

Alignmentimproved planning, cross-functional coordination, and delivery predictability

Cardinal Health Pyxis

Senior New Product Development Engineer / Technical Manager

2005 – 2012

Challenge

Align medication-management product lifecycle and architecture decisions with clinical and regulatory requirements.

Leadership Approach

Systems architecture and software/hardware integration
Technical strategy for the Pyxis ecosystem
Product and regulatory diligence
International dispensing-platform IP evaluation

Results

Organizational Context

500+people in the organization where product strategy was supported

$500M+organizational revenue; context, not personal revenue attribution

Technical Diligence

4-personexecutive team evaluating an international dispensing platform

Ownershipproduct, regulatory, architecture, and technical-diligence workstreams

Selected Career Accomplishments

Delivery

•Release cadence: more than six weeks to two weeks
•Framework migration: four months to two
•First-pass penetration and security testing

Leadership

•13–15-person OneMAC organization
•Broader operational influence across a 60-person program
•Seven-person AgentVrify team

Commercial Judgment

•Pricing, margin scenarios, and forecasting
•Fractional CTO initiative implemented
•Abundant partnership formed; separate no-go accepted

Architecture and Governance

•Regulated AI and LLM governance
•AWS GovCloud and cloud modernization
•Evaluate designs, guide engineers, assess prototypes

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