Chelsey Wiley — Product & Platform Executive
Building AI platforms, decision systems, and operational scale.
Product executive driving AI-powered operational transformation across healthcare, logistics, and SaaS — turning complex operational environments into automated, governed, data-driven platforms organizations can trust at scale.
Open to Director, VP, and Head of Product roles AI platforms · Decision systems · Operational SaaS · Healthtech & Logistics
1.4M+
Registered users on platforms led
500K
Active users supported
30+
Enterprise customers served
25%
Faster product delivery
70+
Cross-functional contributors led
EXECUTIVE SUMMARY
A product executive who builds the platforms that move organizations from activity to outcomes.
I specialize in building scalable digital platforms that transform complex operational environments into automated, data-driven systems. My work spans healthcare, logistics, and SaaS — shipping platforms used by 1.4M+ registered users, 500K+ active users, and 30+ enterprise customers.
My focus is the product operating model: aligning product, engineering, operations, and executive leadership around clear platform architecture and measurable business outcomes. Track record includes reducing product delivery timelines by 25%, increasing digital revenue by 20%, improving operational efficiency by 20%, and supporting enterprise digital platforms serving millions.
Today I'm leading the AI logistics automation platform at Aircon — the decision layer turning freight quoting, booking, and shipment execution into governed, AI-driven operations for enterprise forwarders. I'm exploring Director, VP, and Head of Product roles where the next stage of operational transformation is being defined — particularly in AI platforms, decision systems, healthtech, and logistics SaaS.
EXPERIENCE
Product leadership across AI logistics, healthcare scale, and enterprise SaaS.
Aircon
2024 — Present
AI · LOGISTICS
Product Strategy Lead — AI Logistics Automation
Aircon builds automation platforms for freight forwarders — quoting, booking, and shipment execution through intelligent operational systems
Lead product strategy for an AI-driven logistics platform serving ~30 enterprise freight customers and ~1,200 operational users — turning manual quoting, booking, and shipment execution into governed, automated workflows.
Architect the unified logistics automation platform — quoting, pricing governance, booking, and shipment orchestration — establishing the substrate for AI-native freight operations.
Lead development of the Admin Panel governance control plane, enabling enterprise customers to configure pricing rules, automation logic, and operational policy at scale — turning AI workflows into auditable, operator-trusted systems.
Designed system architecture for AI-driven operational agents supporting quoting, booking, and cargo tracking workflows.
Established the product operating model across executive stakeholders, product leaders, and engineering — defining rituals and governance that scale decision velocity without sacrificing platform integrity.
Helped define Aircon's market positioning as a decision platform for freight operations, aligning product strategy with marketing, sales, and executive leadership.
Baylor Scott & White Health
2022 — 2024
HEALTHCARE PLATFORM
Senior Product Lead — Digital Health Platforms
One of the largest nonprofit healthcare systems in Texas, serving 3M+ patients across hospitals, clinics, and digital platforms.
Led product strategy for enterprise digital platforms supporting 1.4M registered patient accounts and ~500K active users across the health system's digital footprint.
Directed product initiatives across 35+ product, UX, research, and product operations leaders and 30–40 engineers — coordinating 70+ cross-functional contributors against shared operational outcomes.
Reduced product delivery timelines by 25% through improved planning, governance, and cross-team coordination.
Led product initiatives that closed preventive care gaps for 4,500 patients — translating digital platform investment into measurable clinical outcomes.
Launched new patient service models including the In-Home Vaccine Program, informed by user research and front-line operational insights.
Spearheaded the Accessibility Research Program, advancing WCAG compliance and expanding platform usability across diverse patient populations.
900lbs of Creative
2021 — 2022
ENTERPRISE SAAS
Senior Product Manager
Digital product agency delivering enterprise and consumer platforms.
Improved product delivery efficiency by 20% by implementing structured planning, team norms, and quality controls across enterprise and consumer engagements.
Led competitive analysis and customer research, aligning product roadmap with operational reality and measurable customer outcomes.
Recognized with the Radical Candor Award for leadership and communication clarity.
Lifeblue
2018 — 2021
ORGANIZATIONAL LEADERSHIP
Project Manager — Enterprise Web & Application Platforms
Digital product agency delivering enterprise and consumer platforms.
Reduced departmental turnover by 30% through mentoring, onboarding redesign, and leadership development.
Led cross-functional product delivery across design, engineering, and client teams.
Championed accessibility and inclusive design as strategic practice — a recurring theme across every role since. Received the Radical Candor Award.
Balfour & Co.
2017 — 2018
DIGITAL COMMERCE
Product Manager — B2B & B2C
Led digital commerce transformation that grew online sales by 20% and lifted marketing ROI by 15% through product hierarchy optimization and disciplined A/B testing.
Independent Consulting
2010 — 2017
FOUNDATIONS
UX Design, Front-End Development & Accessibility Consulting
Independent product, design, and accessibility consulting for nonprofits and small businesses — the foundation for a career built on accessibility as strategy and measurable digital outcomes.
How I work
I lead from the operating model outward. My instinct is to find the structural reason things aren't moving — misaligned roadmaps, unclear ownership, governance that lives in someone's head instead of the platform — and fix it in a way that doesn't require me to be in the room for it to hold. I work best when product, engineering, and operations are treated as one system, not three departments handing work over a wall. I've been recognized for candor and directness, and I care as much about the conditions that produce good decisions as the decisions themselves.
SELECTED WORK
Case studies framed by what changed — not what was built.
HEALTHCARE · PLATFORM STRATEGY
Unifying a Fractured Product Landscape
How aligning multiple competing roadmaps into one strategic plan returned 62% Digital ROI and delivered preventative care to 4,500+ patients who would otherwise have missed it.
AI · DECISION SYSTEMS
Reframing AI triage as a Decision Platform
How research-led product leadership turned a misdiagnosed "symptom checker" brief into First Contact Navigation — a decision platform where 30% of users credited the EHR-integrated appointment view with their next step into care.
PLATFORM · GOVERNANCE
Governance as a Product Surface
How treating the design system as a governance surface — not a deliverable — cut rework by 30% and held MyBSWHealth's top patient-app rating through a business-wide rebrand that would otherwise have broken it.
PLATFORM STRATEGY · INCLUSIVITY
Inclusivity as product strategy
How betting on inclusivity as architecture — not a feature — turned Gold's Gym Now into a strategic asset in the brand's acquisition by RSG Group and proved platform value can extend well beyond direct revenue.
CORE EXPERTISE
The disciplines I lead from.
Product Strategy & Platform Architecture
Designed the unified logistics automation platform at Aircon and digital platform strategy across BSW's 1.4M-user health system.
AI-driven product systems
Architected AI-native agent workflows for freight quoting and cargo tracking; led First Contact Navigation, an EHR-integrated decision platform credited by 30% of users with their next care step.
Enterprise SaaS platforms
Built and governed platforms serving 500K+ active users and 30+ enterprise customers across healthcare and logistics.
Operational automation
Turned manual freight quoting and shipment execution into governed, automated workflows — reducing human-in-the-loop decisions without sacrificing operator trust.
Product governance & PMO frameworks
Built the operating models at Aircon and BSW that scaled decision velocity across 70+ cross-functional contributors without sacrificing platform integrity.
Digital transformation
Led initiatives reducing delivery timelines by 25%, growing digital revenue by 20%, and closing preventive care gaps for 4,500 patients.
Cross-functional leadership
Directed 70+ contributors across product, UX, research, engineering, and operations — coordinating execution against shared outcomes, not shared calendars.
Data-driven product development
Built measurement frameworks connecting platform investment to clinical outcomes, retention, and enterprise customer health.
Accessibility & inclusive design
Championed WCAG compliance as a strategic capability — not a compliance checkbox — across BSW, Gold's Gym, and independent consulting engagements since 2010.