Case Study

From Strategist to Strategist-Builder

Building Eighty Six Strategies: A product experimentation lab that bridges strategy and technical execution through hands-on learning and systematic problem-solving.

Focus: Product Development
Timeline: 2025 — Ongoing
Role: Founder & Builder
The Challenge

Strategy Without Execution Capabilities

After more than a decade inside complex healthcare organizations — CVS Health, Blue Cross Blue Shield of Rhode Island, and RxBenefits — I developed a strong instinct for diagnosing operational problems. I could quickly identify where processes broke down, where teams misaligned, and where small structural changes could unlock meaningful outcomes.

What I could not do was build the solution myself. Turning ideas into reality meant handing them off to analysts, developers, or external vendors. Those handoffs introduced friction: context was lost, priorities shifted, and the final product often solved the specification rather than the underlying problem.

The gap between diagnosis and execution was the bottleneck.

Strategic Approach

Learning Through Building

Practical Learning Environment

Launched Eighty Six Strategies as an experimentation lab to develop hands-on fluency with modern development workflows. Intentionally narrow initial scope: landing pages, automated lead funnels, and operational dashboards. Curiosity drove the rest—each project exposed new constraints that pulled deeper into the systems behind the tools.

Technical Systems Development

Instead of following a traditional curriculum, the stack expanded organically through the friction of building real solutions for real problems.

  • Web Development: Component-based architecture, conversion-optimized systems
  • AI-Assisted Development: Structured prompting, code generation, iterative workflows
  • Automation & Data: Lead capture pipelines, operational dashboards, workflow automation

Systems-Thinking Application

Each build reinforced the same principle: when the person diagnosing the problem can also prototype the solution, iteration speeds up dramatically. This shifted thinking from recommendations to systems—things that can be built, tested, and improved in real time.

The Framework

Diagnose → Build → Optimize

01

Diagnose

Identified the core gap: strategy expertise without execution capability. Mapped every friction point in the handoff between diagnosis and implementation — lost context, shifted priorities, solutions that addressed specs rather than root problems.

02

Build

Created Eighty Six Strategies as a hands-on lab. Started with landing pages and lead funnels, then expanded organically — each project surfaced new constraints that pulled deeper into web development, AI-assisted workflows, and automation infrastructure.

03

Optimize

Compounded each iteration. Skills from one project accelerated the next. What started as basic page builds evolved into full-stack systems — automated pipelines, data dashboards, and AI-driven qualification workflows that run autonomously.

Capabilities

What I Built

Web Systems

Component-based sites built for conversion, speed, and organic visibility

SEO & Demand

Intent-based content architecture that compounds organic traffic over time

Automation

SMS + CRM workflows that qualify leads and trigger follow-ups autonomously

Data & Dashboards

Operational reporting that transforms raw data into executive-ready narratives

Outcomes

Strategy Meets Execution

Technical Fluency Without Traditional Training

Developed practical competency in web development, AI-assisted workflows, and automation systems through project-driven learning.

Rapid Iteration Capability

Removed the feedback loop lag between strategy and execution. Ideas can now be prototyped, tested, and refined in days rather than weeks or months.

Strategic Foundation for Future Work

Shifted from pure strategy work to systems thinking. Now approaches product marketing, go-to-market strategy, and operational problem-solving as buildable, testable systems.

Key Insight

Strategists Who Build Execute Better

The best strategic decisions come from hands-on understanding of systems. When you're responsible for both diagnosis and implementation, the quality of thinking improves. Friction is eliminated. Iteration becomes immediate. This shift — from pure strategist to strategist-builder — is becoming the foundation of how value is created in complex environments.

Skills Demonstrated

Systems ThinkingTechnical Learning AgilityAI-Assisted DevelopmentProduct ExperimentationRapid PrototypingFull-Stack Problem Solving