Top Tech Jobs & Startup Jobs in Chicago, IL

Own QuinStreet’s AI communications strategy, including launch planning, press relations, thought leadership, proprietary research, executive content, and B2B communications for insurance and insurtech audiences. Lead the askpond.com launch, promote AI-agent platform integrations, manage PR agencies and media channels, and ensure communications comply with legal, regulatory, and partner requirements.

Lead strategy, roadmap, and execution for AI-powered conversational products connecting homeowners with contractors through ChatGPT, WhatsApp, RCS, and other assistants. Own MCP capabilities, APIs, LLM-powered qualification and matching, messaging journeys, compliance, contractor-system integrations, product KPIs, and revenue growth. Partner with Engineering, Marketing, Legal, and platform partners on a zero-to-one product initiative.

Manage health and Medicare insurance client portfolios as a strategic advisor. Drive revenue growth, optimize lead, call, and click campaigns, monitor ROAS and KPIs, analyze performance data, create reports, and communicate insights. Collaborate with media buying, affiliate, and analytics teams while maintaining CMS marketing compliance and independently managing multiple client accounts in a fully remote environment.

Own the contractor-experience roadmap for the 360Finance point-of-sale financing platform. Define product strategy, KPIs, and priorities; lead initiatives from onboarding through document signing; create PRDs; partner with engineering, design, operations, and account management; and improve contractor adoption. Design and analyze A/B tests, build Heap analytics dashboards, conduct market research, engage contractor clients, and use AI tools to prototype solutions and automate workflows.

Manage and optimize paid search, paid social, and programmatic display campaigns for multiple clients. Develop digital marketing strategies, monitor budgets and bidding, analyze performance and down-funnel data, create client reports, identify growth opportunities, and collaborate with creative, account management, and clients to improve ROI. The role also requires staying current on AI, advertising platforms, emerging digital techniques, and paid media best practices.

Leads business development for the Credit Cards category, expanding QuinStreet’s small-business publisher and partner network. Responsibilities include prospecting, qualifying, negotiating, and launching scalable partnerships across SMB-focused platforms and services. The role evaluates traffic quality, commercial potential, compliance, and scalability; manages a prioritized pipeline; develops creative distribution models; collaborates with internal teams; provides market intelligence; and represents the company at conferences and partner meetings.

Designs, evaluates, and improves ranking and recommendation systems through experimentation, feature engineering, and production machine learning. Builds reliable data and feature pipelines, incorporates multimodal signals, manages uncertainty, calibration, and model drift, and monitors system performance. Partners cross-functionally with Engineering, Product, Business, and Analytics to deliver scalable, latency-sensitive solutions with measurable business impact.

Prospect and engage mid-market customers, manage the full sales cycle from outreach through contract execution, conduct consultative discovery, communicate ROI, maintain CRM pipeline records, and achieve activity and revenue goals. The role involves building relationships with business decision-makers, developing industry expertise, collaborating cross-functionally, and growing a recurring book of business through outbound sales and closing activities.

Leads B2B inbound marketing strategy for the home services vertical, driving MQLs, pipeline, and revenue. Oversees inbound acquisition, events, marketing operations, reporting, attribution, and Salesforce data integrity. Develops unified marketing plans, analyzes funnel performance, improves processes, partners cross-functionally, and provides data-driven recommendations. Manages, coaches, and develops a remote marketing team while balancing strategic leadership with hands-on execution.

The Director of Client Sales is responsible for driving partnerships in the insurance industries, managing the full sales cycle, and executing strategic deals while ensuring client success.