Masha Sharma
Verified Expert in Product Management
Fractional CTO/CPO and Product Manager
Arlington, VA, United States
Toptal member since September 17, 2020
Masha is a fractional product and engineering executive specializing in AI-first platforms, integrations, marketplaces, and SaaS. With 20+ years of experience, she has co-founded and scaled startups, including helping build Avenue One into a $1 billion unicorn. At Groupon, she leads AI-driven transformation initiatives focused on merchant experience, automation, and next-generation platform strategy.
Project Highlights
Expertise
- Agentic AI
- CIO
- Event-driven Architecture
- Head of Product
- Marketplaces
- Model Evaluation
- Retrieval-augmented Generation (RAG)
- Value Creation
Work Experience
VP, Merchant Experience AI
Groupon
- Led AI-first transformation initiatives across Groupon’s merchant platform, focused on automation, onboarding, and marketplace optimization.
- Directed the strategy for AI-powered merchant experiences, including agentic workflows, evaluation frameworks, and operational automation.
- Scaled cross-functional AI initiatives spanning product, engineering, and data teams to modernize merchant operations and accelerate delivery.
Head of Product
Hire Bus, LLC
- Defined the AI-driven product vision and strategy to support business growth.
- Spearheaded the comprehensive redesign of the company's SaaS platform, ensuring consistent brand identity across all digital touchpoints.
- Established a comprehensive product operations framework, implementing OKRs, key metrics, and iterative feedback mechanisms to drive data-informed product development.
SVP of Product Engineering
Avenue One
- Built and led a world-class product engineering organization that was instrumental in propelling the company to achieve a remarkable $1 billion+ valuation.
- Established a world-class product engineering organization and team to architect/implement a scalable, event-driven serverless platform on AWS.
- Ensured seamless integration with 60+ distinct business events, realizing positive impacts toward a billion-dollar valuation despite significant market and pandemic challenges.
- Restructured the engineering team topology into dynamic, cross-functional pods, dramatically improving delivery efficiency and product evolution pace. Boosted productivity by 25% and uncovered opportunities to advance team functions further.
- Guided the strategy and execution for the state transition event validation engine, increasing knowledge at every opportunity with related technologies.
- Incorporated best practices for standing up the change management process, handling the release management process and PMO development, and established the architecture leadership council framework.
- Established an Agile practice and used DORA metrics to maximize delivery.
Co-founder | CTO
RealAtom
- Built up a roadmap and collaborated closely with early adopters to gather feedback and iterate on the product, successfully acquiring over 10,000 lenders and establishing RealAtom as a leading player in the industry.
- Led a SaaS-enabled marketplace product development and achieved elite 12-week retention rates of 51% to 65%.
- Helped raise $5 million in seed funding to set up platform operations.
- Wrote onboarding sequences, product guides, and product blogs.
- Gained acceptance into the 500 Startups accelerator, an early-stage venture fund and seed accelerator, with an acceptance rate of 1.5%. It was founded in 2010 by Dave McClure and Christine Tsai.
- Was chosen to become a Forbes Technology Council contributor.
- Set up an analytics infrastructure that informed customer conversion and acquisition strategies.
- Delivered a world-class SaaS net platform for commercial real estate lenders.
Batch 21 Alumna
500 Startups
- Got accepted into 500 Startups Batch 21 (typical acceptance rate is 1.5%).
- Participated in marketing hell week while running an existing startup.
- Built out a startup product, marketed the product, led the sales effort, and stood up all operational reporting.
Co-founder | Head of Product
InteractiveShares
- Collaborated with a co-founder to develop a product roadmap.
- Led the design and development of the company's lending decision engine.
- Conducted customer interviews, then analyzed and extracted insights.
CEO
TotalPass
- Built a go-to-market strategy to acquire initial customers.
- Defined the product roadmap along with detailed user journeys and user stories.
- Launched an MVP of the initial product and solicited client feedback.
Founder
CitrusWorks
- Served as an interim head of product for a social media analytics company.
- Developed product roadmaps for multiple clients in healthtech, adtech, and consumer tech industries.
- Defined user stories, managed backlogs, and solicited requirements from corporate clients.
Director of Engineering
AOL
- Managed and delivered an audience intelligence big data platform that generated $1 million in MRR.
- Trained and mentored 14 product development teams on Agile excellence.
- Project managed key DevOps initiatives to set up continuous integration and continuous delivery processes.
Senior Systems Integrator
Department of Defense (DoD)
- Provided engineering support, systems design and architecture, vendor management, and technical expertise to various defense health information management systems (DHIMS) within the DoD.
- Validated system integration specifications, which included hardware and software in-lab installs.
- Collaborated with enterprise architecture teams to ensure that security specifications were put in place.
Software Engineer | Project Manager | Senior Technical Program Manager
SiriusXM
- Assisted with the development of the first-of-its-kind streaming media player as a software engineer.
- Defined product roadmaps, scope, and functional requirements. Conducted executive stakeholder briefings and mediated and facilitated approvals.
- Performed gap, functional, technical, and financial analysis to define integration strategies.
- Served on the post-merger planning advisory committee: represented IT for all online web application properties, facilitated the process to define the business strategy and objectives, and oversaw the analysis of overall systems dependencies.
- Defined and managed the strategy for stress and load testing of online products in support of multiple TV marketing campaigns and holiday readiness efforts.
- Developed several products from the ground up, including scope, use cases, user stories, test cases, and product review presentations.
- Received a Webby for the Best Radio award and a Best Radio Website award from the Web Marketing Association.
Software Engineer | Product Manager
M23
- Defined product roadmaps for PBS, BBC America, AIDS Marathon, and Riggs Bank.
- Developed a PBS video index search algorithm to help teachers find video segments that were aligned with their teaching plans.
- Built several scalable, data-driven web applications for clients.
Project History
RealAtom | SaaS-enabled Marketplace for Commercial Real Estate Loans
Led product development of a SaaS-enabled marketplace for commercial real estate borrowers, brokers, and lenders. The product won multiple industry awards, processed over $14 billion in loans, and achieved elite retention rates of over 50%.
RealAtom is a modern, all-in-one loan management system designed specifically for the $3 billion commercial real estate lending industry. I interviewed users; built out the roadmap; defined user story maps, flows, and user stories; managed the backlog; and set up analytics to track product KPIs. In addition to the product, I was heavily involved in defining product marketing strategies to grow the userbase and increase retention.
Artist Search for Satellite Radio Listeners
http://www.siriusxm.comArchitected and developed a smart search algorithm that searched for artist names and song names against live streaming data and predicted what channel the artist was going to play on next.
XM Satellite Radio was one of the leading satellite radio companies in the United States, with millions of subscribers, hundreds of radio channels, and thousands of artists whose music was played daily.
My goal was to write a flexible search algorithm that found the artist by name even though, more than half the time, names were being misspelled. The next step was to recommend what channel that artist was going to appear on in the near future. The added challenge was tapping into streaming data to get the artist names and channel appearances.
Education
Certification in Artificial Intelligence
Massachusetts Institute of Technology (MIT) - Boston, USA
Master's Degree in Information Systems Management
George Washington University - Washington, DC, USA
Certifications
Neo4j Generative AI Fundamentals
Neo4j
Scrum Master
Scrum Alliance
CIO University Certificate
GSA CIO University
Skills
Tools
HubSpot, Looker, Slack, Asana, Jira, Confluence, Google Workspace, Zapier
Paradigms
Scrum, Agile Product Management, Agile Project Management, Requirements Analysis, Key Performance Metrics, B2B2C, Event-driven Architecture, API Architecture, Business to Business to Consumer (B2B2C), DevOps, Low Code
Platforms
Mixpanel, Oracle Database, Monday.com
Industry Expertise
Marketplaces, Commercial Real Estate, Radio, Consumer Products, Banking & Finance, Real Estate, Entertainment & Leisure
Other
Project Delivery, Product Analytics, Technical Product Management, Relational Databases, Vendor Management, User Experience (UX), Technical Project Management, Digital Transformation Program Management, Technical Program Management, Project Management, Technical Leadership, Feature Analysis, Feature Roadmaps, Web Platforms, Product Management, Product Development, SaaS, Startup Consulting, Engineering, Leadership, Vendor Selection, Product Owner, Coaching, Consulting, Mentorship & Coaching, Product Leadership, Innovation, Disruptive Innovation, Minimum Viable Product (MVP), Product Vision, Model Evaluation, Agentic AI, AI Agents, Context Engineering, Operations, Head of Product, Data Products, Databases, Lean Startups, Startup Funding, User Stories, Email Marketing, Product Marketing, FullStory, APIs, Product Design, Data Analytics, SaaS Product Management, B2B, Conversion Rate, Advertising Technology (Adtech), Oracle RDBMS, SQL, Budgeting, Marketing Automation, Growth Hacking, Search, Segment, Commercial Real Estate Finance (CREF), Relational Database Design, Customer Relationship Management (CRM), Project Budget Management, Fintech, Business Analysis, API Integration, Enterprise SaaS, Platform as a Service (PaaS), UiPath, Streaming, Generative Artificial Intelligence (GenAI), LangChain, Large Language Models (LLMs), Natural Language Processing (NLP), Learning Management Systems (LMS), Value Creation, Retrieval-augmented Generation (RAG), IT Security, Enterprise Architecture, Marketing, CIO, Notion, Airtable, Miro, User Research, Product Roadmaps, User Flows, Backlog Management, Key Performance Indicators (KPIs), Healthtech, SOC Compliance, Journey Mapping, Business Requirements Documentation (BRD), Heap, HTML, PHP, ROI, Marketing Strategy, Growth Marketing Product Manager, Media, Java, Search Infrastructure, Data Integration, Product Strategy Consultant, Tech Sales, Innovation Labs, Technology, Early-stage Startups, Integration, Strategy, Startups, Amazon Web Services (AWS), Robotic Process Automation (RPA), Product Strategy, IT Strategy, Technical Hiring, QA Automation, Artificial Intelligence (AI), Serverless Architecture, Amazon, No-code Development, React, Node.js, TypeScript, Vector Databases, Machine Learning, HR Tools, LangSmith, CrewAI, Claude Code, GraphDB
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