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Drew Singer

Drew Singer

Leading Product @ Middesk

New York, New York, United StatesFinancial Services
Company
Middesk
Title
Head of Product | Product Management & Design
Seniority
Head
Department
Product Management
Location
New York, New York, United States
Industry
Financial Services

About

I’ve spent my career building fintech products that operate at massive scale, globally. Across consumer and enterprise experiences. I’m a product operator with experience spanning B2C and B2B, Series B through public markets, and global product launches across 20+ countries. I’ve led large-scale consumer fintech products used by tens of millions of customers, while also building B2B platforms and APIs used by banks, fintechs, and software companies in regulated environments. ⇨ I’ve led Product organizations through multiple stages of scale, owning strategy, execution, and org design as companies grew, restructured, and expanded into new markets. ⇨ I’ve built and scaled products end to end — from consumer onboarding, activation, growth, and monetization to the platforms and systems required to support enterprise customers and global operations. ⇨ My work has driven material business outcomes, including rapid global product launches, profitability turnarounds, and multi-billion-dollar gr…

Experience

Head of Product | Product Management & Design

Middesk · New York, New York, United States

Present

Chief Product Officer | Product Management, Product Design, Identity & Fraud

Stash · New York, New York, United States

⇨ Orchestrated a strategic transformation that propelled the company to EBITDA profitability, while scaling to 80% gross margins, 1.5M subscribers, and $2.5B in AUM. People & Organization: ------------------------ • Revamped the Product Organization with an 80% turnover in 8 months, prioritizing the recruitment of subject matter experts to strengthen core functional areas • Hired 14 high-impact professionals from my network and previous teams to drive organizational transformation, speed, and scale. • Boosted Product Organization NPS by 91%, significantly enhancing team satisfaction and engagement • Led and designed the reorganization of the 300+ person Product Delivery team (Product, Design, Engineering) within the first 2 months, improving both the quality and velocity of product development ⇨ Team of 30 - Product Management | Product Design (UX) | Fraud Core Products (Investments & Banking), Growth (Onboarding, Activation, Engagement, and MarTech), Platforms (Trust & Safety, Money M…

Svp | Head of Product

Stash · New York, New York, United States

Vp of Product | Platforms, Loans, Credit Card, Identity & Fraud

BlockFi · New York, United States

⇨ Led Product Platforms, Credit Card, Lending, and Fraud teams, guiding BlockFi through a full organizational and technical turnaround. Scaled to $15B in AUM and 650K global clients. Recognized as the #1 fastest-growing company on the 2022 Inc. 5000 list. People & Organization: ------------------------ • Drove 400 person Product, Eng., Design team through org transformation (R&R, Levels, Promotion Criteria) • Redesigned staffing/hiring, co-location strategy, right-sizing, and defined domain ownership creating more efficient 150 person Product Delivery organization. ⇨ Team of 25 - Product Management (Platforms) | Credit Card | Lending | Fraud Authentication, Accounts, Onboarding, Fraud, Legal & Compliance, Fiat/Crypto Payments, FinOps, Business Operations, Core Banking, Data Mgmt, Credit Card, Loans, Activation & Engagement, Identity, Fraud Strategy & Data Science Key Business Outcomes: ------------------------ • Moved from monolith to service-based architecture • Organizational efficie…

Senior Director of Product Management | Global Buy Now, Pay Later (Bnpl)

PayPal

⇨ Founded and led the Buy Now, Pay Later (BNPL) team, driving strategy and building the product suite from the ground up. Scaled to over 25M customers, 150M transactions, and 280K merchants. “I would also highlight the rapid growth of our Buy Now, Pay Later functionality. Since I’ve been here, I’ve never seen a product launch with that kind of scale so quickly.” - Dan Schulman, PayPal CEO People & Organization: ------------------------ • Led team of 16 Product Managers and oversaw the strategic direction of 150+ Product Delivery organization • Started and grew cross-functional Product Delivery team - 1 -> 16 Product Managers, 60 -> 120 Engineers, 3 -> 6 UX Designers, 14 -> 20 Partner Teams Key Business Outcomes: ------------------------ • Rapid succession of 4 distinct products (Pay in 30, Pay in 3, Pay in 4, Monthly Installments) in 7 countries (US, UK, DE, FR, IT, ES, AU) in 1.5 years • Scaled to first 3 million customers using the product in less than a year • Created 15% halo effec…

Director of Product Management | Global Buy Now, Pay Later (Bnpl)

PayPal · New York, NY

Lead Product Manager | Global Business Lending

PayPal

⇨ Scaled PayPal Working Capital and Business Lending from proof of concept to global rollout. Grew loan originations from $100M to $6B in <4 years. • Drove strategy and execution which led to the complete redesign of the PayPal Working Capital experiences and underlying platforms, launching the product in 4 countries (US, UK, DE, AU) • Managed 5 product managers and drove the roadmap and resource capacity for 60+ engineers and 3 user experience designers; influence over 14+ non-dedicated development teams • Created full customer lifecycle support resulting in a 10% increase in funded accounts, 20% increases in loan pay-off and renewals, and a 10% increase in customer satisfaction / NPS scores (60+ NPS) • Complete UX overhaul, which led to application submission to money in applicants account in <9 secs • Led integration of acquisition, Swift Financial, into PayPal and the Business Lending suite

Senior Product Manager | Global Consumer Lending

PayPal · San Francisco Bay Area

⇨ Expanded PayPal Credit distribution beyond traditional point-of-sale channels, driving a 20% increase in total merchant sales, a 30% boost in PayPal adoption, and an 80% rise in applications. • Integrated the PayPal Credit product into PayPal’s P2P payment product and navigated complexity of using a credit facility outside of the traditional point-of-sale • Defined product strategy and execution for PayPal’s Upstream Presentment program (distributed advertising) implemented across 60,000 merchants, displaying 29M impressions per day, and allows merchants to merchandise financing on their website • Developed core PayPal capability to deliver credit offers within online checkout experience and provided self-service capabilities for 380k merchants to customize offer to their specific needs

Product Manager | Bill Me Later (Acquired By Paypal)

PayPal · Baltimore, Maryland Area

⇨ Led the post-acquisition expansion of the Bill Me Later product through strategic channels including eBay and PayPal. • Developed tactical plan and executed the conversion of all customer-facing communications for the Bill Me Later product to meet new requirements mandated by the FDIC, Reg Z and CARD Act • One of two leads tasked with the integration of the Bill Me Later product into eBay and PayPal channels after acquisition, increasing new account generation by 2.3 million and year-over-year growth of 199% • Provided 24/7 issues management support for the Bill Me Later product on the PayPal/eBay channels • Product Owner responsible for writing user stories and leading agile ceremonies for a team of 12 engineers

Education

Towson University

Bachelor of Science, Business Administration

University of Baltimore

Masters in Business Administration

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