Company Overview
Glassman Technology Group (GTG) is not a market-facing company — their web presence is intentionally kept simple. GTG is a material outsource provider for a large, multinational healthcare, property and casualty insurance company with a 25-year track record delivering value to their client and client's customers.
GTG operates at the intersection of engineering, process design, and business transformation — merging strategic business acumen with deep domain expertise to deliver both strategically and tactically. Their mission centers on enabling operational transformations that scale, connecting people to complete workflows through web-based portal systems, optimizing processes for efficiency and scalability, and protecting data integrity through strong governance and validation.
GTG has built an engineering culture that thrives on clarity, ownership, and outcomes — intentionally designing teams, processes, and platforms to scale not necessarily in size, but in capability and competency.
My Role — Product Lead, Strategic Platform Development
As Product Lead at GTG, I orchestrated comprehensive product strategy and execution across multiple platform ecosystems, directly supporting the company's mission to deliver scalable operational transformations. I developed and communicated multi-year product roadmaps for three existing platforms while creating value stream mapping to optimize development flow and enhance stakeholder value delivery.
A key achievement was architecting the strategic vision for ClaimExchange.io — GTG's new provider portal — and supporting the broader migration strategy moving users and functionality from Bravo (Health.HelloCGI.com) into HelloCGI.com and ClaimExchange.io. This modernization positions GTG as a two-sided marketplace solution, enabling them to expand beyond their primary client relationship by offering white-labeled clearinghouse services for claim processing to other organizations.
Given the lean team structure, I wore multiple hats beyond traditional product strategy — leading end-to-end quality testing protocols, change management processes for feature releases, and cross-functional collaboration with engineering and business transformation teams. I also established quarterly business reviews and key performance indicators to measure both product outcomes and team performance.
Platform Scope
GTG's product portfolio spans three platforms in an active migration state. Bravo — operated as Health.HelloCGI.com — is the legacy platform still handling Group Admin onboarding and Provider workflows. HelloCGI.com has taken over customer-facing and post-onboarding group workflows, while ClaimExchange.io is being built out to fully replace the provider-facing side of Health.HelloCGI.com once complete.
Product Strategy & Operations
Upon joining GTG, I identified foundational gaps in how product work was structured, prioritized, and tracked. Before feature delivery could scale, the organization needed infrastructure — a request management system, a clear feature inventory, a unified roadmap, and cross-portal UX research.
Designed and implemented a Linear-based workflow for tracking customer requests (hotfixes, support issues, ad-hoc requests), creating visibility into unplanned engineering work and establishing accountability loops between Customer Service and Engineering. Built the data foundation for future capacity planning and automation.
Conducted a comprehensive feature inventory across three platforms (Bravo, HelloCGI, and ClaimExchange.io) serving five user types, creating the foundational mapping needed for strategic product planning and migration decisions. Identified redundancies between Bravo and HelloCGI, critical gaps that could impact user experience during migration, and opportunities where consolidated platforms could exceed original functionality.
Developed a comprehensive product strategy framework including organizational vision, mission, and a Now-Next-Later roadmap spanning both engineering and data infrastructure teams. Structured around three strategic themes — Decomplexify, Streamline, and Digital Transformation — to transition GTG from reactive development to proactive product management.
Investigated recurring registration failures affecting Property & Casualty customers across Caribbean markets. Traced the root cause to a multi-portal UX breakdown involving identical visual design between separate portals, geographic misrouting, and absent cross-portal account linking. Delivered immediate fixes, strategic recommendations, and a portal consolidation roadmap.
Feature Delivery
Alongside strategic work, I owned end-to-end delivery of three significant product features — each shipped within a lean engineering environment requiring close collaboration across product, engineering, legal, and client stakeholders.
Replaced manual document distribution with a centralized, permission-based repository enabling CG Staff to share and manage documents with Group Admins across multiple jurisdictions. Delivered within one month of joining the organization.
Led a comprehensive multi-factor authentication initiative across all portal environments and user types at the CISO's direction — email verification, authenticator app integration, and a new administrative support queue for managing MFA resets.
Transformed an entirely paper-based excess life insurance application process into a digital system covering both non-medical and paramedical paths, a health history wizard, underwriting review tools, and a full status management workflow.
Deep-Dive Case Studies
Two major platform initiatives from this engagement are documented in full — covering methodology, design artifacts, stakeholder decisions, and outcomes.
A 4-month comprehensive redesign of the ClaimExchange.io provider portal — 100+ screens, a new design system, process flow diagrams, and a complete navigation and permissions architecture for healthcare claims management.
A cross-portal MFA rollout and a structured vendor evaluation of five customer support platforms (Zendesk, Freshdesk, Help Scout, Intercom, Front) — using a weighted C&E Matrix methodology to drive an evidence-based platform selection decision.
