Top Tech Jobs & Startup Jobs in Chicago, IL

Leads sales coaching and field excellence for an insurance distribution team. Builds competency models, coaching cadences, learning pathways, onboarding programs, and performance feedback systems. Provides direct coaching through call reviews, ride-alongs, and group sessions, integrates agent and competitive insights, manages a growing coaching team, and partners with Marketing, Product, Enablement, and Distribution leadership on launches and agency onboarding.

Full-cycle enterprise sales role responsible for prospecting, developing, qualifying, and closing deals with large, multi-stakeholder organizations. The position sells FacilitiesLink, a facilities information platform for planning, building, and operating large-scale campus environments. Compensation includes 50% commission, a $20-per-hour guaranteed draw, and on-target earnings starting at $150,000 annually. Flexible work arrangements are available, with occasional travel required.

Owns executive relationships and revenue growth for 2–4 high-value enterprise accounts. Develops multi-year account plans, expands product adoption, identifies cross-sell and upsell opportunities, leads renewals and contract negotiations, and coordinates Product, Marketing, Client Success, and Solutions teams. The role also conducts strategic business reviews, represents the company with senior stakeholders, and drives profitable long-term partnerships across Roadside Assistance and Accident Management offerings.

Leads OppFi’s lifecycle and brand marketing strategy across acquisition, retention, repayment, servicing, and collections. Owns omnichannel communications through Braze, lifecycle KPIs, brand standards, creative direction, customer insights, and go-to-market strategy. Manages and mentors lifecycle marketing, design, and marketing technology teams while partnering cross-functionally with Product, Data, Engineering, Operations, Legal, Finance, and executives. Drives experimentation, optimization, customer experience, and responsible marketing within a regulated FinTech environment.

Own end-to-end onboarding for high-revenue customers, partnering with Account Executives and internal teams to guide data migration, payments setup, website configuration, team permissions, and product enablement. Serve as the primary customer contact, manage timelines and risks, conduct walkthroughs, resolve technical issues, document progress in CRM tools, and share feedback to improve onboarding processes.

Leads enterprise sales and strategic customer relationships for RigUp’s downstream energy solutions. Responsibilities include prospecting, pipeline management, proposals, negotiations, onboarding, account growth, market development, and cross-functional coordination with Operations, Product, Marketing, and Leadership. The role requires deep downstream oil and gas expertise, C-suite relationship development, complex RFP ownership, frequent client travel, AI-enabled sales workflows, and mentorship of account team members.

Build and lead GC AI’s revenue operations function from the ground up. Develop go-to-market processes, hire and manage a high-performing team, select and implement operational technology, align Sales, Marketing, Product, Customer Success, and Partnerships, and optimize pipeline, forecasting, retention, deal velocity, win rates, and revenue performance through data-driven KPIs.

Own and scale enterprise healthcare accounts, focusing on proactive pipeline generation, consultative sales, and closing large provider deals. Manage relationship mapping, diagnostics, pricing strategy, executive alignment, and market presence. Continue owning client relationships through pilot implementations and full rollouts, coordinating cross-functional teams and ensuring customer adoption. The role requires strong healthcare private equity, RCM or clinical operations knowledge and a relationship-driven, full-cycle sales approach.

Own client implementation projects from contract signing through go-live. Build and maintain project plans, track risks and blockers, coordinate internal and client stakeholders, manage communication and expectations, secure required documents and approvals, escalate delays, and improve implementation processes. Serve as the client’s primary point of contact while coordinating technical and account teams without owning technical decisions or commercial relationships.

Build and expand fintech and payment systems using Go, microservices, databases, and cloud technologies. Design production APIs and tooling, diagnose customer issues, manage full release lifecycles, document systems, and mentor engineers. Collaborate with product and business teams while guiding AI agents to produce maintainable, observable, testable code that meets engineering standards. Work independently in a high-availability environment and contribute to next-generation financial products.