Executive Design Leader, Technical Project Manager & SDLC Optimizer
About
Case Studies
Home About Case StudiesWelcome,
I, Cleo Henderson, am an award-winning design leader and technical project manager specializing in turnarounds, legacy modernizations, and secure AI agent workflows.
I bridge the critical operational divide between complex software architectures and revenue-generating user experiences.
With over 20 years of experience spanning early-stage startups to publicly traded enterprises, I align the software development lifecycle (SDLC) with highly structured design systems to eliminate engineering waste, neutralize revenue leakage, and accelerate speed-to-market.
My engagement models are highly adaptive to support your current organizational needs: I am actively accepting retained full-time executive placements, dedicated part-time leadership mandates, and interim fractional/contract advisory roles.
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My Core Leadership Pillars
01. Fractional Leadership & Creative Strategy
I provide high-impact executive oversight to establish "Platform Rigor" for scaling organizations. Specializing in cross-functional alignment across product, engineering, and creative divisions, I manage the full-cycle product design strategy and help build high-performing in-house teams without the overhead of a permanent search.
02. Design Maturity & SDLC Auditing
I execute rapid, 2-week "Design-to-Conversion" audits to map your product pipeline. By identifying invisible technical and visual friction points, I show leadership teams exactly where they are suffering from user churn and developer overhead waste.
03. Technical UI/UX Architecture & AI Workflows
I specialize in designing safe, WCAG-compliant "Human-in-the-Loop" (HILT) interface systems for autonomous B2B and Generative AI agent platforms. My approach balances deep clinical, financial, or regulatory compliance constraints with frictionless frontend execution.
Selected Career Milestones
30% Codebase Rework Reduction (Mar Dat)
Standardized cross-functional SDLC practices to streamline engineering-to-design handoffs and program custom Salesforce Lightning Web Components (LWC).
$8+ Billion Scale (Steadfast Companies)
Engineered a scalable digital product foundation for a multifaceted real estate heavyweight, streamlining platform architecture across investment management and property development divisions.
Startup Acquisition Polish (Call Complete)
Scaled and redesigned the user experience for a high-velocity multi-family maintenance communication platform, aligning the product story with market positioning to prime the lean startup for a successful sale.
Southeast Hospitality Empire (Halls Chophouse)
Architected a comprehensive, decade-long digital roadmap that scaled a single legendary Charleston steakhouse into a premier Southeast hospitality powerhouse commanding a portfolio of premier dining destinations.
$21 Million Market Disruption (Active Pest Control)
Engineered and deployed a custom, zip-code-gated eCommerce platform that transformed a regional home services heavyweight’s digital footprint and automated decentralized customer acquisitions across Georgia and Texas.
Product Exit IP (Info Tycoon)
Led the UX strategy and field research for the flagship Mobile Inspection App, authoring the core intellectual property (IP) foundation that anchored the acquisition of the asset by SightPlan.
+49% Organic Traffic Growth (CoStar Group)
Directed user-centric product designs and marketing creative across the Apartments.com Network, driving a massive +49% Year-over-Year traffic increase.
$300 Million Exit (Oracle / Vitrue)
Served as frontend developer and visual UI/UX architect on the platform-wide rebranding initiative that supported Vitrue's successful acquisition by Oracle.
$360,000 Saved (RentPath)
Spearheaded the multi-family rental industry's first native applications for iOS and Android, saving $360k in developer overhead by introducing cross-platform framework strategies.
My Technical & Design Arsenal
Leadership & Ops
Agile DesignOps • Technical Project Management • Talent Acquisition & Mentorship • Multi-team Alignment • Compliance Strategy
UI/UX & Creative
Figma • Information Architecture (IA) • UI/UX Architecture • User Testing • Field Research • Wireframing & Prototyping • Adobe Creative Suite • Video Production
Dialects & Code
Lightning Web Components (LWC) • HTML5/CSS4 • JavaScript • jQuery • Bootstrap • SASS/LESS • Generative AI & Conversational Design
The Private Consulting Vault & Case Studies
When corporate partners and enterprise boards require systemized, programmatic digital transformations, they leverage my private design consultancy, AndThereWas, LLC.
To explore the detailed, full-scale SaaS exit and enterprise case studies (including my work with FlexTecs, Martonomy, and Steadfast Companies), you can access the secure case study vault below.
Publications
🗂️ Organizing Your Design Documents to Increase Productivity
⚡️ 8 Image Optimization Tips to Improve SEO & Website Experience
Awards
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🦟 Active Pest Control: Disrupting the Market with Zip-Code-Gated eCommerce -
🥩 Halls Chophouse: From One Chophouse to a Hospitality Empire – A Decade of Digital Partnership -
⚡️ Call Complete: Lightning Strikes Twice – Reuniting to Polish, Scale, and Sell -
🔦 Illuminating the Unseen: Translating Abstract Vision into Award-Winning UX -
📆 OpenHotel: Modernizing a Hospitality Titan (A 20-Year Homecoming) -
🤲 Thomas House: From Starter Site to Scalable Impact – A Digital Renovation with Zero SEO Loss -
🦑 Steadfast: A Scalable Foundation for an $8+ Billion Real Estate Company -
✨ Martonomy Solutions: A Full Stack Overhaul and Giving a Face to Enterprise AI -
🐦⬛ Crowe: High Ambition, Hard Deadline: From 0 to Live in 10 Days -
💸 FlexTecs: Redefining the Recovery Audit Industry