About Us
The Founder of AndThereWas
Cleo Henderson
Principal Transformation Consultant, Chief Design Officer & Systems Architect
Cleo Henderson is a 10+ award-winning Principal Transformation Consultant, Chief Design Officer, and Fractional Design Leader with over 20 years of experience translating highly complex technical and operational challenges into measurable business revenue.
As a versatile systems architect, Cleo has successfully navigated every phase of the corporate lifecycle:
• 0-to-1 Startups: Redesigning and scaling early-stage ventures to establish immediate market viability and secure initial traction.
• High-Growth Scale-ups: Modernizing legacy platform architectures to optimize operational margins and directly anchor high-value acquisitions.
• Massive Enterprises: Orchestrating product strategy, user-centric interfaces, and brand design networks for multi-billion-dollar corporate ecosystems.
At AndThereWas, Cleo deploys proprietary operational frameworks to help engineering-led firms build absolute “Platform Rigor”, streamline the software development lifecycle (SDLC), and eliminate the critical “design-to-deployment” handoff friction that leads to silent revenue leakage.
Proprietary Operational Methodologies
The 5 D's of Creation Framework
Designed on a “measure twice, cut once” engineering philosophy, this proprietary execution cycle ensures that strategic alignment occurs long before a single line of code is compiled, preventing wasted client capital and developer overhead:
1. Discover: Digging deep for answers and extracting raw requirements in the formless void.
2. Define: Shaping strategic intent using precise user flows, information architecture, and structural concepts.
3. Delight: Fortifying platform vision via premium brand identity and emotional user interactions.
4. Design: Applying system-wide strategy to repeatable, compliant, and componentized UI pattern libraries.
5. Deploy: Developing, testing, and launching responsive assets that exceed market and performance expectations.
The E.A.R.S. Mindset Alignment
Because scalable digital products are ultimately built and run by human teams, AndThereWas integrates the E.A.R.S. alignment process to optimize cross-functional communication and slash codebase rework by 30%:
• Empathy: Gaining context to clarify true project, user, and stakeholder expectations.
• Accountability: Defining clear ownership of deliverables and leading by direct operational example.
• Responsibility: Meticulously covering tracks and ensuring uncompromising code, documentation, and design quality.
• Support: Providing hands-on technical and design assistance to fill operational gaps in the product journey.
Core Consulting Offerings
01. Fractional Leadership (Interim CDO/CXO)
Providing high-impact executive oversight to establish organizational “Platform Rigor” and manage product design strategy. Cleo partners with technical leaders to build high-performing, in-house product teams and align cross-functional engineering, product, and design divisions without the overhead of a permanent search.
02. Design Maturity Audits
Executing a rapid, 2-week “Design-to-Conversion” pipeline audit. By mapping current development workflows, Cleo identifies and eliminates the specific friction points, visual debt, and communication gaps causing user churn and engineering waste.
03. Technical Strategy & AI Design
Designing secure, WCAG/ADA-compliant “Human-in-the-Loop” (HILT) workflows and interfaces for Agentic AI. Cleo ensures that autonomous agents, complex software architectures, and automated data object mapping systems are highly intuitive, safe, and built to scale.
Institutional Impact & Case Studies
%
Codebase Rework Reduction (Mar Dat)
Standardized cross-functional SDLC practices, aligned generative AI agent workflows, and programed custom Salesforce Lightning Web Components (LWC).
Billion USD Scale (Steadfast Companies)
Engineered a scalable digital product foundation to streamline platform architecture across investment management and property development divisions.
SEO Loss with Digital Renovation (Thomas House)
Redesigned and migrated a critical community service platform into a scalable, modern digital footprint with absolute organic search protection.
Billion USD Scale (Steadfast Companies)
Redesigned the user experience for a high-velocity multifamily maintenance communication platform to prime the lean startup for a successful sale.
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 its acquisition by SightPlan.
Million USD Market Disruption (Active Pest Control)
Engineered and deployed a custom, zip-code-gated eCommerce platform that automated decentralized customer acquisitions across Georgia and Texas.
Million USD Exit (Oracle / Vitrue)
Managed complex user flows, high-fidelity wireframes, and information architecture for the rebranding initiative that directly supported Vitrue’s successful acquisition by Oracle.
%
Organic Traffic Growth (CoStar Group)
Directed user-centric product designs and marketing creative across the Apartments.com Network, driving unprecedented Year-over-Year traffic increases.
USD Saved (Rent. / formerly RentPath)
Spearheaded the multifamily rental industry’s first native applications for iOS and Android, leveraging cross-platform framework strategies to eliminate developer salary overhead.
Sole "Award-Winning" UI/UX Architect (OpenHotel)
Designed and engineered custom SaaS application and web experiences for a CVBs and hospitality giants as the sole visual designer for 3.5 years of my 5 years, delivering responsive interface concepts on a bi-weekly deployment cycle, and winning all awards obtain by the company to date.
Looking to Embed an Executive into Your Core Team?
Cleo Henderson collaborates with scaling SaaS platforms, healthcare technology organizations, and forward-thinking venture portfolios globally.
Executive Hiring & W2 Placements
For venture capital funds, corporate recruiting managers, or founders looking to embed Cleo Henderson directly into their core leadership team as a permanent W2 executive or dedicated fractional partner, visit the private executive hiring portal:
View Cleo Henderson’s Personal Executive Profile âž”