Top Tech Jobs & Startup Jobs in Chicago, IL

Own Fetch’s executive operating system in partnership with the COO. Build and manage performance metrics, OKR frameworks, leadership cadences, reporting infrastructure, decision processes, and executive communications. Drive cross-functional alignment, accountability, and execution across high-priority initiatives while synthesizing complex inputs into actionable recommendations for senior leadership.

Evaluate LLM and automation outputs for accuracy, consistency, and reliability; create annotations and training datasets; research ambiguous cases; support product recognition and classification models; and use AI tools to improve operational efficiency. The role also involves maintaining model and catalog quality through mapping and classification work.

Own the Expanded Core business P&L, financial models, forecasts, reporting, and data infrastructure. Lead monthly, quarterly, and annual forecasting, variance analysis, SQL-based data validation, and strategic business analysis. Partner with leaders on investment, headcount, expense, margin, and ROI decisions, translating financial performance into narratives for executives, investors, and board forums. Mentor junior finance team members while operating independently in a fast-paced environment.

Support Fetch’s privacy and data governance program under Corporate Counsel, Privacy. Responsibilities include documenting data discovery exercises, mapping data flows, maintaining data inventories, reviewing legal and technical documentation, and communicating project updates. The three-month remote internship begins in January 2027 and requires 12–15 hours per week. The intern will gain exposure to privacy compliance, data governance, and in-house legal operations at a consumer technology company.

Lead and develop a software engineering team responsible for expanding game discovery and rewards across Fetch’s mobile and backend experiences. Own roadmap delivery, translate product goals into technical plans, guide architecture and code quality, manage dependencies, and ensure scalable, reliable, observable systems. Partner cross-functionally, communicate risks and tradeoffs, improve team processes, and support engineers in using AI-assisted development tools.

Own sales enablement for SMB and Mid-Market teams by developing segment-specific sales motions, onboarding, playbooks, training, coaching tools, and package guidance. Partner with Sales, Product Marketing, Revenue Operations, and other stakeholders to simplify offerings, improve seller readiness, and reinforce field adoption. Use performance data, call insights, Gong, Salesforce, and AI-enabled workflows to measure proficiency, identify gaps, and improve productivity, conversion, and deal velocity.

Lead product design for Fetch’s Receipt & Rewards experience, connecting receipt capture, account linking, recognition, matching, and rewards. Define design strategy for complex, AI-enabled systems; improve usability, accessibility, trust, and experience quality; and balance user needs, data quality, business goals, and technical constraints. Partner with Product, Engineering, Research, and Data Science, drive cross-functional alignment, shape multi-quarter initiatives, and mentor designers.

Lead Fetch’s U.S. benefits and wellness strategy, including healthcare, retirement, leave, accommodations, compliance, fiduciary governance, vendor management, analytics, and financial oversight. Build scalable infrastructure for a distributed workforce, advise executives on cost and coverage trade-offs, lead a benefits team, and partner with Total Rewards, Finance, Legal, Payroll, and People teams. Provide support on compensation strategy and escalations while ensuring transparent employee communications and strong regulatory controls.

Own deal desk operations for complex revenue agreements, ensuring accurate contract setup, billing, revenue recognition, compliance, and data integrity across Salesforce, NetSuite, and related systems. Partner cross-functionally with Sales, Finance, Billing, Revenue Recognition, Implementation, and Systems teams throughout the Quote to Cash lifecycle. Manage credit evaluations, operational controls, process improvements, and two offshore Order Management resources.

Lead the strategy, roadmap, and lifecycle evolution of Fetch Play, expanding rewarded gaming into non-gaming apps. Own the user journey from discovery and installation through engagement, retention, and reward payout. Define KPIs, run experiments, develop personalization and native engagement mechanics, optimize reward economics, and manage fraud and attribution risks. Align Engineering, Design, Data, Marketing, Partnerships, and senior leaders while mentoring product managers and driving scalable consumer growth.