Top Tech Jobs & Startup Jobs in Chicago, IL

Leads consultative sales of PayPal Payouts solutions across new and existing accounts. Partners with Account Management and cross-functional teams to conduct discovery, design solutions, develop competitive positioning, construct pricing, and build quantified business cases. Owns opportunity targets, pipeline development, merchant activation, and profitable transaction volume. Uses data and AI tools to prioritize opportunities, supports pricing decisions, influences senior stakeholders, and provides product feedback. Travel is up to 10%.

Lead cloud infrastructure and network engineering teams supporting PayPal Credit lending platforms across AWS, on-premises environments, and GCP modernization initiatives. Own DevEx platform roadmaps, architecture, automation, connectivity, resiliency, security, compliance, vendor relationships, budgets, and cost optimization. Translate business and developer priorities into technical backlogs, partner with security and audit teams, and recruit, coach, and develop infrastructure engineers.

Leads second-line oversight of PayPal’s global payment network and partner compliance programs. Responsibilities include independent challenge, partner due diligence, monitoring, risk identification, issue escalation, remediation, regulatory and network information requests, and executive advisory support. The role partners across Legal, Product, Risk, Sales, Partnerships, and Compliance to improve governance, automate workflows, and ensure adherence to Visa, Mastercard, regulatory, and contractual obligations.

Provides executive administrative support to two Vice Presidents and one Senior Director in PayPal’s Legal organization. Responsibilities include calendar and meeting management, travel coordination, expense reporting, purchase orders, events, office administration, visitor support, onboarding, confidential communications, and special projects. The role requires strong judgment, organization, communication, discretion, and proficiency with Microsoft Office and SharePoint.

Leads complex risk management projects and resolution efforts, identifies and analyzes operational and asset risks, develops mitigation and compliance strategies, evaluates business trends, and drives global process improvements through project management and stakeholder engagement.

Leads PayPal’s specialized sales organization across the Americas, owning revenue growth, sales strategy, pipeline forecasting, account coverage, and adoption of branded checkout, payments, and BNPL solutions. Builds and develops a team of approximately 25 sales specialists, oversees complex sales cycles, partners cross-functionally on commercial opportunities, and represents field insights to Product, Finance, Legal, Marketing, and Sales Enablement. Requires strong sales leadership, strategic account management, forecasting, coaching, and organizational skills.

Manages operational relationships with global merchant accounts, addresses customer needs, supports strategic account initiatives, coordinates onboarding and technical integration, drives prospecting and new business, and monitors account health, adoption, satisfaction, retention, and growth. The role requires collaboration with account managers, onboarding teams, solutions architects, engineering, and support functions.

Owns customer acquisition CRM marketing strategies focused on incentives, merchant offers, product launches, and core value propositions. Responsibilities include coordinating media agencies and creative teams, executing co-branding campaigns, developing and monitoring experiments, optimizing campaign performance, evaluating customer experiences, and managing agency and incentive budgets. Success is measured through account sign-ups, activations, and customer habituation.

Lead technical product strategy for PayPal Ads partner integrations across advertising, payments, identity, privacy, and data platforms. Define APIs, data contracts, event schemas, SLAs, launch controls, measurement capabilities, and operational standards. Partner with Engineering, Data Science, Privacy, Legal, Compliance, InfoSec, sales, and finance to deliver secure, scalable advertising products, improve integration speed and reliability, ensure regulatory compliance, and grow measurable revenue. Mentor product managers and guide cross-functional technical decisions.

Provides product legal and regulatory counsel for PayPal checkout products across the Americas. Advises on consumer financial, privacy, and consumer protection laws; supports product design, disclosures, risk mitigation, compliance, and complex issue resolution. Partners with product, business, and international legal teams, manages legal risks, develops guidance and frameworks, and escalates high-stakes matters. The role requires an experienced payments or fintech attorney comfortable with ambiguity, emerging technologies, and fast-paced global collaboration.