Michael Waxman
Michael Waxman

Director of Product

Actively looking · Member since 7 Sep 2026
Message
Location
Southern Shores, United States
Desired salary
Confidential
Work preference
Remote Only / Full Time, Part Time, Contract, Freelance
Experience level
Lead

About

Professional summary

I am an AI-native product leader with more than 15 years of experience building, scaling, and operating digital products at platform scale. My background spans telehealth, cannabis technology, defense and government contracting, powersports, automotive, and enterprise SaaS.

I have held director, principal product management, digital transformation, and CTO roles, with responsibility for product vision, roadmaps, P&L, GTM strategy, operational execution, and cross-functional leadership. I specialize in taking products from 0-to-1 and scaling them into durable revenue-generating platforms.

Most recently, I led product for a telehealth medical-card business, owning its largest revenue line and launching subscription, clinical consultation, and discount marketplace products. I have led distributed engineering, QA, design, DevOps, DBA, clinical, and partner teams across multiple countries.

I build AI-enabled product organizations and production agentic AI workflows. My work includes Claude Code, OpenAI Codex, Hermes Agent, MCP infrastructure, AI-assisted documentation, code review workflows, and integrations with GitHub, Jira, Confluence, and analytics platforms.

I am experienced in enterprise modernization, data products, headless commerce, API integrations, digital transformation, analytics, and regulated industries. I am authorized to work in the United States without sponsorship and am open to remote opportunities.

Skills

36 capabilities

Tech stack & tools

Working toolkit

Experience

Career history

Director of Product Leafwell

Owned the telehealth medical-card line, Leafwell's largest revenue product, with P&L responsibility. Set portfolio vision, product strategy, OKRs, go-to-market plans, and delivery priorities while launching membership subscriptions, clinical care consultations, and a dispensary discount marketplace from 0-to-1.

Built subscription entitlements and pricing flows and normalized revenue recognition to monthly MRR. Led a distributed cross-functional organization including approximately 20 engineers in Portugal and Romania, DBAs, DevOps, QA, and design, establishing operating cadence, roadmap governance, and clinical and partner stakeholder alignment.

Designed and deployed agentic AI development workflows using Claude Code, OpenAI Codex, Hermes Agent, and MCP infrastructure. Built AI tooling integrations across GitHub, Jira, Confluence, and Metabase, and led customer research through in-person patient events, recorded usability sessions, and PostHog behavioral analysis.

Telemedicine Product Manager Leafwell

Led product delivery for telehealth services, coordinating clinical, partner, engineering, and operational stakeholders. Supported the medical-card product line and contributed to new product development across subscriptions, clinical consults, and patient-facing marketplace offerings.

Conducted customer interviews and task-based usability testing at patient events. Used PostHog session replays, event streams, heatmaps, and cohort analysis to evaluate product behavior and identify opportunities to improve patient experiences and product outcomes.

Co-Founder & Chief Technology Officer Rishi

Co-founded Rishi and served as Chief Technology Officer, with an advisory role since 2024. Led technology and product development for customer-facing products and internal operations.

Pioneered launch and scaled the business from concept to a 100-person team operating across California, Arizona, and Michigan. Hired and built the organization from zero, surpassed $2 million in annual revenue for more than 2.5 years, and managed more than 1,000 marketing events per month for 50 major cannabis brands.

Designed and developed MVPs for internal tooling and customer-facing products using Microsoft Power Platform. Built an operational toolset spanning communications, scheduling, CRM, ERP, finance, payroll, and HR, and architected a multi-state expansion roadmap.

Principal Digital Product Manager ADS, Inc.

Managed the software portfolio for a $2 billion-revenue defense and government contracting distributor. Oversaw Oracle ERP, Salesforce CRM, custom internal tools, supplier and customer portals, a custom CPQ application, EDI, e-commerce sites, API development, and systems integrations.

Defined product strategy and features through business and customer requirements, data insights, market research, and competitive analysis. Designed a self-service, extensible headless commerce architecture that replaced 17 legacy commerce solutions and migrated $200 million in annual revenue to self-service, reducing manual order-building and accelerating contract closure.

Formalized an enterprise API integration layer to improve interoperability and future scalability. Partnered across business and technical functions to align product design and execution with customer and organizational objectives.

Digital Transformation Manager ADS, Inc.

Led vision, strategy, and execution for corporate digital development and executive-sponsored transformation initiatives across operations. Established digital strategic direction that reduced operational costs by 70% while improving the customer experience.

Implemented automated data pipelines, reporting, and dashboard visualizations, increasing data-driven decision-making by 25%. Defined team OKRs and KPIs and maintained leadership responsibility for business analysts, project managers, software developers, and data analysts.

Data Product Manager DX1, LLC (Dominion Enterprises)

Established the company's first formal technology roadmap and agile framework, improving product-development discipline and resource management. Redesigned ETL processes to automate product-data operations for millions of products while meeting complex legal and regulatory requirements.

Developed and shipped an industry-first data product for powersports and automotive parts fitment, covering 28 million parts across 60 manufacturers and distributors. Owned roadmap, backlog, data governance, and a $750,000 monthly budget for the parts-data platform.

Managed a global team of 50 ETL developers, business analysts, DBAs, and web developers. Implemented data governance, a migration engine, and a roadmap that transitioned 2,000 dealers from legacy platforms to DX1, while reducing actionable-insight timelines by 50%.

President & Executive Director Eastern NC Travel Baseball (ENCTB) / Revenge Baseball

Founded and operate a 501(c)(3) nonprofit serving more than 50 youth athletes across 12 counties in Eastern North Carolina. Built the organization from concept through IRS tax-exempt determination and established a cost-coverage model to reduce financial barriers for underserved families.

Manage a $30,000 annual operating budget supported by more than 10 corporate sponsors, secured grants, and a tiered donor program. Scaled operations across North Carolina and South Carolina, coordinating 16 tournaments per season and earning a Cooperstown Dreams Park invitation in the second year.

Education

Learning history

Loyola University Maryland, Sellinger School of Business

MBA

Towson University

Bachelor of Business Administration, Business Administration

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