Drew Schwartz
Verified Expert in Product Management
Product Manager
Weston, CT, United States
Toptal member since May 26, 2019
Drew has expertise in developing new product strategies, launching and scaling new products, and leading product management teams of all sizes. Most recently, he was the director of digital at Elevance Health, overseeing the strategy and management of employer and broker digital products. Previously, he was the co-founder and CPO of Harness Wealth, launching its primary go-to-market product. Before this, Drew held VP product roles at Hometeam (Care Guardian), ShopKeep, Ladders, and Gust.
Project Highlights
Expertise
- Agile Product Management
- B2B2C
- Business to Business (B2B)
- Marketing Strategy
- Mobile Apps
- Product Strategy
- UX Design
- User Research
Work Experience
Head of Product
The Dental Shop
- Partnered with founders to define the vision, strategy, and roadmap for a new dental practice marketplace, transforming an early concept into a launched product within six months.
- Built and led a cross-functional team across design, engineering, and marketing to deliver the MVP, overseeing all product decisions from UX and technical architecture to go-to-market execution.
- Designed and implemented the end-to-end user experience for practices and candidates, improving onboarding efficiency and achieving over 200 active listings in the first quarter post-launch.
- Established agile workflows and product KPIs that improved iteration speed, team alignment, and investor visibility, helping secure early traction and readiness for fundraising.
Chief Product Officer
Held
- Led end-to-end design and development of Held’s product and growth strategy, defining the company’s vision across AI, UX, and game-based habit formation to drive user engagement and retention.
- Architected and implemented Held’s proprietary AI model, corpus, and design system, integrating content creation and adaptive behavior loops that form the foundation of the platform’s user experience.
- Directed a cross-functional team of UX, product, visual, animation, and development talent to bring Held from concept to probate beta (launching 2026), while establishing a culture of design excellence and creative innovation.
- Secured multimillion-dollar funding and filed patents covering Held’s AI design framework and creator-growth platform, positioning the company at the forefront of human-centered AI and content creation technology.
Managing Partner
Go Skyward, LLC
- Built and scaled Skyward’s go-to-market and growth strategy, driving expansion through account-based marketing, AI-enhanced outreach, and creative automation for B2B and B2C clients.
- Directed cross-disciplinary teams across strategy, creative, and product, aligning client goals with measurable outcomes in engagement, revenue, and brand positioning.
- Developed AI-driven marketing systems and client intelligence models that personalized sales workflows, improved pipeline accuracy, and accelerated client acquisition.
- Secured and managed multimillion-dollar client partnerships, leading Skyward’s evolution into a data-powered growth platform for mid-market and enterprise clients.
Director of Digital Employer and Broker Products
Elevance Health
- Was responsible for the leadership of all mobile and web products for employer group customers and brokers at Elevance Health.
- Increased adoption to 91% across 147,000 employer groups and 254,000 unique visitors per month, with 7.9 million transactions annually through enhanced self-service features.
- Streamlined a payment platform to save $3.2 million annually of $13.9 billion in employer group payments.
- Reduced customer support calls by 55%, with an additional 17% reduction forecasted for 2024.
- Improved broker platform scores, achieving ease of use and task completion scores of 75.3 and 82.5, and increased conversion rates by 13%.
Product Owner (via Toptal)
Elevance Health
- Led innovative product pilots at the Digital Foundry, Elevance's new product innovation team, transforming ideas into scalable solutions across the organization.
- Managed and developed a new virtual and augmented reality childbirth modeling program that allows mothers-to-be to visualize their baby's development and help them better understand the changes happening to their bodies.
- Launched a personalized health records product for over 10 million members, achieving a 5x growth in visits and a 15x growth in page views compared to the previous app.
- Directed AR/VR product development for virtual doctor visits, which led to ongoing investment and positioned Anthem as a potential leader in the field.
- Developed a digital human project, exploring digital avatar use cases in HR and healthcare.
Head of Product and Marketing
GCS Inc. (Buster.com, BusBank.com, CorporateShuttle.com)
- Oversaw the design and relaunch of key platforms at GCS Inc., driving $20 million in annual revenue through improved conversion rates and user experience.
- Led the redesign and launch of buster.com and busbank.com, which resulted in a 24% increase in conversion and an SEO ranking improvement from position 11 to 3 on core keywords.
- Developed a long-term product roadmap in collaboration with the CEO, integrating BusBank and Buster offerings while targeting critical customer segments for scalable growth.
- Established a new product team, enhancing the organization's product, design, and development capabilities.
Deputy Product Owner
Enterprise SaaS Platform (via Toptal)
- Brought on to design and launch complex, new products to support their continued expansion into enterprise and government clients.
- Designed a complete web-based form-building tool that supports complex logic, automation, and integrations to third-party platforms.
- Provided expertise in the design of a new version of their existing platform with design and brand recommendations.
Product and Project Management Advisor
Paz Communication LLC (dba MyChapterRoom)
- Brought on as both a product and project manager to help the CEO launch new products to market and optimize the development team's performance.
- Analyzed and improved the overall performance of the product development process to ensure they are fully optimized and delivering new features at the best tempo possible.
- Helped support the launch of a new product strategy to sell to enterprise-level clients. Supported with expertise in product pillars, positioning, and contracting to close the largest client to date.
- Developed a new brand strategy, made improvements to the overall marketing site, and launched a new marketing campaign to increase the conversion of visitors to their public site.
Chief Product Officer and Co-founder
Harness Wealth
- Brought in the kickstart product development at Harness Wealth, leading the launch and growth of a unified digital platform for high-net-worth clients.
- Developed and launched the initial direct-to-consumer platform, expanding the product and engineering teams from one to seven members.
- Crafted and executed the go-to-market roadmap, achieving key milestones within the first nine months.
- Oversaw product performance and strategic integrations with Plaid and HelloSign, achieving a 94% onboarding rate and ensuring compliance.
Vice President of Product Management
Vesta Healthcare
- Led the delivery an innovative, real-time healthcare management solution that identifies and tracks members' stability, improvements, and health issues over time to lower healthcare per member per month spend.
- Drove the company's shift from direct-to-consumer to enterprise healthcare, launching a platform that tracks and manages member health in real time, reducing healthcare costs.
- Led the creation of a multi-platform app and integrated care plan technology, enhancing proactive care management and transparency for members, resulting in improved health outcomes.
- Rebuilt the member onboarding experience, achieving the highest conversion rates in company history with NPS scores in the high 70s.
- Established the product and UX teams, creating a strong product development methodology that supports continuous innovation and service excellence.
Vice President of Product Management
ShopKeep (Acquired by Lightspeed)
- Served as a senior product leader at ShopKeep, driving significant growth and product innovation for a global SaaS provider serving over 25,000 retailers and restaurants.
- Led product management, doubling growth annually, achieving conversion rates over 30%, reducing churn to 1.2%, and increasing ARR from $4 million to $15 million.
- Launched a go-to-market strategy for full-service restaurants and bars, growing this segment to 18% of the customer base and increasing the number of restaurant clients by 280% year over year.
- Developed the ShopKeep pocket iOS app and integrated gift cards, which led to high merchant engagement and a 16% increase in retention within eight months.
- Designed and launched integrated gift cards, allowing for multiple programs to be utilized through our payment gateway provider. Within six months, this product had increased to 15% of the customer base and increased retention by over 16% at month eight.
Vice President of Product Management
Gust (gust.com)
- Led Gust’s global product and technology strategy and oversaw the teams responsible for the design and development of all products and services. My primary focus was to aggressively expand Gust’s footprint, develop revenue-generating product offerings that meet each segment’s particular needs, and create high-performing teams to penetrate and expand understanding and ownership of these markets.
- Identified the initial product offering to entrepreneurs and individual investors through deep market research, direct customer interviews, and collaboration with key departments.
- Hired the product, UX, design, copywriting, and web development teams from scratch to a team of 20, establishing New York City as the core product and development center. Cultivated a positive, performance-oriented, collaborative culture. Established growth plans and retention strategies that were implemented company-wide.
- Oversaw the product and architecture redesign of the core Gust platform. This re-design allowed Gust to 1) expand sales opportunities to enterprise, individual investors, and entrepreneur direct-to-consumer markets, 2) react to opportunities more effectively through rapid release cycles, 3) support full internationalization for language and currency, and, 4) establish viral acquisition strategies to decrease marketing spend where possible.
Director of Product Management
TheLadders (theladders.com)
- Held senior management responsibility for the strategic product roadmap for the recruit.theladders.com and theladders.co.uk with a primary focus developing solutions to help HR professionals and recruiters find and place candidates for senior positions.
- Delivered the first-to-market launch of a new social recruiting product called “My Pipeline” that allowed recruiters to instantly deliver job-related content to a talent pool of candidates who have signed up to receive hiring updates. This product established a new communications channel for customers delivering an open rate of 44% on the messages and increased brand exposure for corporations.
- Designed and launched the first US and UK recruitment eCommerce sites leading to $1+ million top-line revenue in its first 9 months. Through detailed data/usage analysis and usability testing, optimized conversion for forecasted growth to over $3.5 million exceeding projections by over 52%.
- Increased search product usage by developing a new search platform that delivered an increase in search results, better zero results handling, and improved accuracy of results leading to an 81% first-page click-through rate, 75% increase in searches run by recruiter per session, and a less than 5% abandonment rate on search results.
Senior User Experience Lead
Starwood Hotels and Resorts Worldwide
- Led the full site redesign efforts for various top tier hotel brands in Starwood’s $1.8 billion Global Web Services division supported by strong partnerships with critical technical and brand leadership.
- Led the user experience for the full site redesign efforts of Aloft and Element Hotel websites with primarily responsibility implementing user research, information architecture, prototyping, and user testing.
- Managed and designed Starwood’s first fully-dedicated travel professional website, StarwoodPro.com, by conducting user research, wireframes development, stakeholder interviews, and other UX methodologies.
- Led user experience design for Microsoft Surface application projects with Sheraton Hotels. We were one of only three companies engaged with Microsoft in this technology.
Vice President of Strategic Initiatives
Ellery Homestyles
- Managed the system design, development, and implementation of enterprise-wide corporate restructuring and knowledge management systems driving increased revenue from $30 million to $100 million without increased overhead within 2 years.
Project History
Leading Fintech Platform Connecting Consumers to Top Advisors
http://www.harnesswealth.comOversaw the development of the entire initial platform from the ground up, including the product, design, and engineering.
Brought in to jumpstart the product to get it up and running. I collaborated with the CEO for over a year. During that time, I oversaw the development of the entire initial platform, guiding the product and engineering teams in the development of the processes and culture, which I grew from one to seven during that time. I also coordinated the initial beta and friends and family stealth product launches and early iterations to step the business up for continued growth.
I crafted the go-to-market product experience and roadmap, which was achieved over the business’s first nine months of operations. I built and managed product, design, and engineering teams supporting all front-end, back-end, data strategy, and product design with a culture focused on tight collaboration, transparency, and mentoring within the work hard/have fun framework. I also oversaw the performance of the initial Harness Wealth products with onboarding rates over 94%. I led strategic integrations into Plaid and HelloSign to support compliance and financial reporting.
Innovative Health Monitoring Care Management Mobile Platform
Led the product identification, design, and launch of the mobile-integrated platform, increasing revenue from $8 to $50 million.
Led the identification and transformation of Hometeam’s product portfolio and team to enter the enterprise healthcare market to deliver an innovative real-time healthcare management solution that identifies and tracks members’ stability, improvements, and health issues over time and provides the new ability to intervene before issues turn into emergencies to lower healthcare per member per month spend.
Industry-leading Mobile POS Platform Growth for Restaurants
http://shopkeep.comLed the product strategy/launch for new market expansion into full-service restaurants/bars, which led to $15 million in annual revenue growth.
Launched the 1st go-to-market product strategy and ongoing roadmap to penetrate the full-service restaurants and bars market, building from a 10% to a 23% conversion rate, 280% growth in the number of restaurants YoY, and achieving growth to 18% (April 2015) of total customer base within one year of launch.
Mobile Family Health Records Explorer
Led the design, prototyping, testing, and ultimately successful launch of My Health Records. This mobile and web-based application allows Anthem members to explore, download, connect, and share their medical information.
My Health Records is an integrated application that pulls in data from internal and external integrations to build a unified picture of a member’s health, medication conditions, medications, lab results, and other key insights with the ultimate goal of increased engagement, satisfaction with access to their data and further educational awareness of a member’s health.
This project proved to be highly successful, blowing the expectations out of the water on engagement by 17x.
Education
Master's Degree in Art and Design
Pratt Institute - Brooklyn, NY
Bachelor's Degree in Graphic Design
Skidmore College - Saratoga Springs, NY
Certifications
Pragmatic Marketing
Pragmatic
Skills
Tools
Sketch, Photoshop CS5, Google Docs, SketchUp Pro, Jira, Claude, Sketch 4, Asana, n8n
Paradigms
Agile, Kanban, Conversion Rate Optimization (CRO), Data-informed Visual Design, Design Thinking, Agile Product Management, Agile Workflow, B2C, B2B2C, Agile Project Management, Business to Business to Consumer (B2B2C), Marketplace Platforms, Gamification, Requirements Analysis, Model View Presenter (MVP), API Architecture, Rapid Prototyping, User Testing, Augmented Reality (AR)
Platforms
Apple Watch, iOS 11, Shopify, Mixpanel, Metaverse, AppsFlyer, Enterprise Resource Planning (ERP)
Industry Expertise
Marketplaces, Product Ideation, Healthcare, Financial Services, Consumer Products, Hospitality, Health & Wellness, Event Ticketing, Logistics, Real Estate, Psychology & Mental Health, Asset Management, Pharmaceuticals
Other
Certified Scrum Product Owner (CSPO), Product Ownership, iOS, Enterprise SaaS, Consumer Services, Mobile Apps, Content Strategy, UX Design, App Design, Product Management, Digital Product Design, Digital Product Management, Focus Groups, User Research, Executive Reporting, Growth Strategy, Product Strategy, SaaS, Platform as a Service (PaaS), User Journey Maps, User Flows, Team Leadership, Team Building, Mentorship & Coaching, Product Evangelism, Product Marketing, Lean Canvas, Lean Startups, Lean Development, Lean Product Development, On-demand Services, Point of Sale, Business Analysis, Freelancing, Digital, Coaching, Growth, Contract, Requirements, Product Roadmaps, Go-to-market Plans, Business Models, Product Design, Product Frameworks, Innovation, Product Discovery, Product Delivery, SaaS Product Management, Product Coach, Project Management, Cross-functional Team Leadership, Remote Team Leadership, Medical Product Manager, Healthcare Product Manager, Mobile Prototypes, Mobile Applications, Product-market Fit, Prototyping, Strategy, User Experience (UX), Brand Design, Branding, B2B, eCommerce, Go-to-market (GTM) Strategy, Business to Business (B2B), Customer Analysis, Marketing Strategy, Communication, Digital Transformation, Vendor Management, App Development, Cross-functional Collaboration, Minimum Viable Product (MVP), Project Budget Management, Project Planning, Proof of Concept (POC), Continuous Improvement, Feasibility Studies, Project Management & Work Tracking Tools, Technical Product Management, Team Management, Product Owner, Ideation, Ideation Workshops, Validation, Agile Project Management, Jira, Confluence, Program Management, Data Analysis, Consumer Insights, Web Design, Conversion-driven UX, Creative Problem Solving, Funnel Optimization, Sales Funnel, User Conversion, Feasibility, User Journeys, Roadmaps, Wireframing, Mobile, Feature Planning, Feature Roadmaps, Estimation & Planning, Project Estimation, Direct to Consumer (D2C), Startups, Technical Project Management, Backlog Management, Stakeholder Interviews, User Stories, Scrum Master, Cost Estimation, Vendor Selection, Monetization, Monetization Models, Subscription Pricing, Pricing Strategy, Software as a Service (SaaS), B2B Product Management, Key Performance Indicators (KPIs), Entrepreneurship, Web Platforms, Subscriptions, Web Applications, Business Requirements, Agile Product Delivery, Product Research, Feature Backlog Prioritization, Product Planning, Software Development, Dating Apps, Competitive Analysis, Competitive Intelligence, Market Strategy and Research Product Manager, Product Lifecycle Management (PLM), Estimations, Process Flows, Mobile UX Design, UX Audits, Dashboards, Platforms, Digital Payments, Staffing, Digital Marketing, Chief Product Officer (CPO), Customer Experience, B2B Marketing, Customer Experience Management, Backlog Grooming, User Acceptance Testing (UAT), Story Mapping, App UX, eCommerce UX, Web UI, Business Process Management (BPM), Process Mapping, Product Requirements Documentation (PRD), Stakeholder Management, Booking Apps, Booking Systems, Software Deployment, Enterprise Analytics, Product Consultant, Web & Mobile Applications, Messaging, Automation, Profit Optimization, Business Strategy, Documentation, Go-to-market (GTM) Strategy, Marketing Strategy, eCommerce, Early-stage Startups, Two-sided Marketplaces, MVP Design, Feature Prioritization, Product Analytics, User Interface (UI), Execution, Engineering Management, Growth Marketing, Growth Hacking, Market Research & Analysis, Creative Strategy, Creative Direction, React Native, Native Mobile Apps, Machine Learning, Multi-channel, Process Documentation, Healthcare IT, Project Reporting, Project Timelines, Project Management, Procurement, Healthcare, Healthtech, Design, Fintech, Artificial Intelligence (AI), Generative Artificial Intelligence (GenAI), Translation, Pricing, Data Visualization, API Integration, Market Research, Medical Software, Market Intelligence, Project Scoping, Web Scraping, Mobile Payments, Android, Healthtech, Scalability, Software Development Lifecycle (SDLC), AI Design, AI Product Management, Process Automation, Online Auctions, ERP Implementation, Financial Software, Financial Reporting, Gaming Platforms, Interim CPO, Finance Product Manager, Healthcare Software, AI Integration, AI Agents, Workflow Automation & System Integration, Conversational AI, Chatbots, Algorithms, Psychology, Angel Investing, Big Data, Collaborative Design, New Product Rollout, Innovation Games, Virtual Reality (VR), Business, WordPress, Finance, Data Analytics, Payment Gateways, Agile Coaching, Manufacturing, Product Launch, 3D Modeling, 2D Modeling, Databases, Patents, Amplitude, Social Media, Resource Management, Data Centers, Commercial Strategy, Motorsports, Cars, Life Science, Data Security, AI Product Strategy, Growth leadership, Fundraising, Executive Leadership, Strategic Design, Data Strategy, Applied AI, AI Ethics, UX Strategy, Interaction Design (IxD), Game Design, Behavioral Design, Beta Testing, Cognitive Computing, Marketing, Local SEO, Large Language Models (LLMs), Account-based Marketing (ABM), Agentic Frameworks, Retrieval-augmented Generation (RAG), Engineering, NotebookLM, Crowdfunding
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