StephenKeith

Experience & Expertise

15+ years bridging human needs with enterprise technology through strategic design and digital transformation

Director of Design & DevelopmentUX StrategyInnovation LeaderDigital TransformationEnterprise Integration

Leadership

Strategic technology leadership that humanizes complex systems while driving measurable business outcomes

Design & Technology Strategy

Architecting the intersection of user needs and business value

  • Led digital transformation initiatives at McAllister , CVS Health, and FM Global
  • Established Google Developer Groups Providence chapter, fostering Art + Design + Technology community
  • Pioneered Hypothesis Driven Development methodology for maintaining sanity in creative processes
  • Architected enterprise integration strategies achieving 10-20% EBITDA improvement
Providence GDG FounderMaritime Innovation LeaderEnterprise UX Strategist

Team Building & Mentorship

Creating environments where creativity and rigor coexist

  • Built distributed teams across healthcare, finance, and maritime industries
  • Mentored 100+ designers and developers in user-centered methodologies
  • Fostered collaboration between Brown, RISD, URI, and Johnson & Wales
  • Implemented agile transformation with focus on hypothesis-driven development
Cross-functional LeadershipAcademic PartnershipsCommunity Building

Executive Leadership

Translating complex technical concepts into strategic business value

  • Director of Design & Development at McAllister (2023-Present)
  • Sr. UX Manager at CVS Health - Enterprise Design Strategy
  • Vice President of UX Design at FM Global
  • Founded PrivateLanguage.ai and co-founded Stage Zero Health
Board PresentationsP&L ImpactDigital Transformation

Technical Expertise

Deep expertise in user experience design, enterprise architecture, and emerging technologies

User Experience Design

Making enterprise software feel human

  • Service Blueprint methodology for complex system design
  • Jobs to Be Done framework for customer-centered innovation
  • HEART metrics and Key Experience Indicators (KEIs) for measuring UX impact
  • Information architecture for knowledge preservation and retrieval
HealthcareFinanceMaritimeInsurance
Service DesignJourney MappingJTBD Framework

Enterprise Integration

Unifying fragmented systems into coherent experiences

  • API-first architecture design for legacy system modernization
  • Retrieval Augmented Generation (RAG) for enterprise knowledge management
  • Robotic Process Automation (RPA) for operational efficiency
  • Digital twin implementation for maritime operations
HELM ConnectOracleDynamicsBoomi AtomSphere
10-20% EBITDA Improvement50% Admin Work ReductionReal-time Integration

Innovation & R&D

Building the future while solving today's problems

  • AI/ML implementation for predictive maintenance and route optimization
  • Autonomous vessel technology research and development
  • Compliance automation platforms reducing administrative work by 50%
  • Personalization at scale through behavioral design principles
Predictive AnalyticsIoT IntegrationProcess AutomationAI Strategy
PMaaS PlatformDigital Twin FleetAPI Sandbox

Methodological Approach

Hypothesis Driven Development (HDD)

  • Falsifiable statements aligned with business OKRs
  • Jobs to Be Done for understanding customer progress
  • Experience Blueprints mapping hypothesis to measurable signals
  • HEART metrics for validating user-centered outcomes
Discovery ResearchDesign ProcessMeasurementOptimization
Fortune 500 EngagementsStrategic DecisionsReduced Ambiguity

Innovation

Actively exploring the intersection of AI, maritime operations, and human-centered design

Current Initiatives

McAllister Innovation Lab

  • Unified Maritime Operations Platform (UMOP)
  • Predictive Maintenance as a Service (PMaaS)
  • Digital Twin Fleet Optimization
  • API sandbox for enterprise application integration
AI/MLIoTDigital TwinsRAG Systems
Maritime InnovationFleet OptimizationPredictive Analytics

Community Leadership

Google Developer Groups Providence

  • Monthly meetups on emerging technologies
  • Collaborations with local universities
  • Partnerships with businesses and government
  • Focus on practical AI implementation
BrownRISDURIJohnson & Wales
Art + Design + TechnologyAcademic PartnershipsInnovation Culture

Thought Leadership

Publications & Presentations

  • Hypothesis Driven Development methodology evangelism
  • Maritime digital transformation best practices
  • Enterprise UX in regulated industries
  • Building innovation culture in traditional businesses
HDD FrameworkHEART MetricsService Blueprints
Industry SpeakerMethodology PioneerStrategic Advisor

Work History

A progressive journey through technology leadership and innovation

Director of Design & Development

Current

McAllister

Leading digital transformation initiatives for a 160-year-old maritime company, architecting the intersection of user needs and business value through strategic R&D.

Key Achievements

  • Established Innovation Lab developing Unified Maritime Operations Platform (UMOP)
  • Architected Predictive Maintenance as a Service (PMaaS) reducing operational downtime
  • Implemented Digital Twin Fleet Optimization for real-time vessel tracking and analytics
  • Built API sandbox for enterprise application integration with HELM Connect, Oracle, and Dynamics
  • Achieved 10-20% EBITDA improvement through strategic technology initiatives

Technologies

AI/MLIoTDigital TwinsRAG SystemsHELM ConnectOracleDynamicsBoomi AtomSphere
10-20% EBITDA Improvement
50% Admin Work Reduction
Real-time Integration
Maritime Innovation Leader

Chapter Director & Founder

Current

Google Developer Groups Providence

Founded and lead Providence's premier technology community, growing to 500+ members in 6 months. Orchestrate quarterly enterprise innovation summits connecting Fortune 500 companies with emerging technologies.

Key Achievements

  • Built community of 500+ developers, designers, and innovators in 6 months
  • Secured partnerships with 4 universities (Brown, RISD, URI, Johnson & Wales) and 15+ corporate sponsors
  • Design and deliver executive AI workshops for C-suite leaders across Rhode Island
  • Created talent pipeline program connecting 50+ developers with enterprise opportunities
  • Host monthly "AI in Enterprise" sessions drawing 100+ business leaders and technologists

Technologies

AI TransformationCommunity BuildingExecutive EducationEnterprise InnovationStrategic Partnerships
500+ Members
$75K Budget
15+ Sponsors
4 Universities
50+ Talent Placements

Co-Founder & CTO

Stage Zero Health

Architected AI-driven risk assessment platform transforming cancer prevention from clinical calculators to human-centered narratives. Building AI-native platform with 30% journey completion (10x industry average).

Key Achievements

  • Architected AI-native platform orchestrating 25+ clinical models
  • Achieved 30% journey completion rate (10x industry average)
  • Designed microservices architecture enabling HIPAA-compliant data processing
  • Developed proprietary algorithm translating complex risk factors into personalized detection strategies
  • Created IP portfolio around narrative-based health engagement
  • Established partnerships with medical institutions for clinical validation

Technologies

AI/MLHealthcare TechHIPAA ComplianceMicroservicesClinical ModelsRisk Assessment
30% Journey Completion
10x Industry Average
25+ AI Models
HIPAA Compliant

Founder & Principal Consultant

PrivateLanguage.ai

AI transformation consulting firm advising Fortune 500 executives on AI adoption strategies.

Key Achievements

  • Generated $350K+ in consulting revenue through strategic AI transformations
  • Maintain 100% client retention with $50K average engagement value
  • Developed proprietary framework for AI readiness and ROI assessment
  • Coach C-suite leaders on prompt engineering, RAG systems, and AI governance
  • Built network of 200+ AI practitioners and business leaders
  • Delivered keynote presentations on AI transformation at industry conferences

Technologies

AI StrategyRAG SystemsPrompt EngineeringAI GovernanceExecutive AdvisoryDigital Transformation
$350K+ Revenue
100% Retention
$50K Avg Engagement
6-Month Duration

Sr. UX Manager - Enterprise Design Strategy

CVS Health

Led design transformation for HealthHUB, CVS's $5B retail health innovation initiative spanning 1,500+ locations. Directed team of 12 designers delivering concurrent transformation initiatives.

Key Achievements

  • Led design transformation for HealthHUB, $5B initiative across 1,500+ locations
  • Co-led strategic engagement with SY Partners (Apple Retail, IBM transformation consultancy)
  • HealthHUB transformation positioned CVS to deliver $2B in incremental revenue within 18 months
  • Personalization initiative generated $150M in incremental annual revenue
  • Homepage redesign improved customer satisfaction scores by 28 points (NPS)
  • Reduced customer service calls by 40% through improved digital self-service
  • Drove 35% increase in digital engagement through personalized content

Technologies

Service DesignDesign SystemsPersonalization at ScaleHEART MetricsHealthcare TechEnterprise UX
$5B Initiative
$2B Revenue Impact
$150M Annual Revenue
28 NPS Increase
40% Call Reduction

Fractional Director - Digital Transformation & Personalization

Edward Jones

Directed cross-functional team of 8 developers and strategists. Architected "Moments That Matter" algorithm for 7M+ client accounts enabling personalized financial planning.

Key Achievements

  • Architected "Moments That Matter" algorithm identifying 47 life events for 7M+ accounts
  • Reduced advisor preparation time by 50% through automated insight generation
  • Achieved 97% client satisfaction with 95% on-time delivery
  • Served as SAFe Agile expert bridging design thinking with scaled agile methodology
  • Mentored team of 8 in SAFe principles and design integration
  • Delivered comprehensive knowledge transfer ensuring sustainable capability

Technologies

Personalization at ScaleSAFe AgileFinancial ServicesAlgorithm DesignDesign ThinkingEnterprise Integration
7M+ Accounts
97% Client Satisfaction
95% On-time
50% Time Reduction

Associate Vice President - UX Design & Digital Transformation

FM Global

Recruited from GE Digital to establish and scale enterprise UX capability. Built design team from 3 to 19 professionals in 10 months (530% growth), managing $3.5M talent acquisition budget.

Key Achievements

  • Built design competency from 3 to 19 professionals in 10 months (530% growth)
  • Managed $3.5M talent acquisition budget and relocation program
  • Led digital transformation of core insurance platform affecting 1/3 of Fortune 1000 companies
  • Drove 45% reduction in quote-to-bind time through reimagined digital experiences
  • Delivered $12M in operational savings through process digitization and automation
  • Achieved 91% internal client satisfaction despite aggressive transformation timeline
  • Operated design team as internal consultancy with defined SLAs and success metrics

Technologies

Enterprise UXTeam ScalingDigital TransformationInsurance TechProcess AutomationProfessional Services
530% Team Growth
$12M Savings
45% Time Reduction
91% Satisfaction
$3.5M Budget

Industry Experience

Deep domain expertise across regulated and complex industries

Maritime & Logistics

3+ years

Current Focus

Healthcare

15+ years cumulative

Financial Services

6+ years cumulative

Insurance

15+ years cumulative

Let's Build Something Meaningful

Whether you need strategic design leadership, digital transformation expertise, or someone who can bridge the gap between human needs and complex technology, I bring a unique combination of creative vision and analytical rigor.

Get in TouchSchedule a Call