Top Tech Jobs & Startup Jobs in Chicago, IL

Own and architect the global Total Rewards function, including compensation strategy, salary structures, pay equity, benchmarking, benefits design, leave-of-absence policies, and people analytics. Partner with People Operations, Finance, Talent, and senior leaders to deliver insights, workforce planning support, compliant programs, and compensation recommendations. Lead through influence and oversee strategy while execution is supported by specialists.

Provide first-line customer support through phone, text, and email. Become an expert in Clair’s signup, earned wage advance, and repayment products; resolve financial questions; and deliver an exceptional user experience. Collaborate with product, technology, and partner teams to investigate issues and improve support. The role requires strong communication, numerical aptitude, Zendesk experience, and enthusiasm for fintech and supporting hourly workers.

Leads the AWS practice across architecture, staffing, delivery, DevSecOps, compliance automation, AI engineering, team development, AWS partnerships, and proposal solutioning. Establishes Terraform, CI/CD, GitOps, security, monitoring, and continuous authorization standards for federal environments. Provides technical authority on AWS architecture, mentors cloud engineering teams, supports AWS partner programs, and contributes to federal capture and proposal activities.

Leads Professional Development scheduling operations, supervising scheduling staff and coordinating authors, associates, sales, contracting, finance, and operations teams. Oversees workshop submissions, complex scheduling requests, master schedules, deadline adherence, contract alignment, and issue resolution. Monitors scheduling KPIs, reports on performance, and improves workflows to increase efficiency, accuracy, responsiveness, and timely customer delivery.

Designs, optimizes, and scales business systems and operational processes across Salesforce, HubSpot, and related technologies. Translates stakeholder needs into requirements, process maps, solution designs, data models, integrations, and acceptance criteria. Leads cross-functional systems initiatives, supports release validation and change management, improves data quality and reporting, and establishes governance and documentation standards. Partners with Revenue Operations, Sales, Customer Success, Marketing, Finance, Product, Engineering, QA, and platform administrators.

Owns complex international technical programs from pre-sale and proof of concept through deployment and ongoing support. Responsibilities include managing scope, schedules, budgets, risks, contracts, deliverables, invoicing, compliance, customer relationships, partners, and cross-functional stakeholders. The role supports international sales opportunities, builds governance and reporting frameworks, resolves blockers, and ensures programs are delivered on time across multiple countries, time zones, and regulatory environments. International travel is required as customer relationships and program milestones demand.

Leads enterprise financial planning and analysis across multiple divisions, overseeing operating plans, forecasts, P&Ls, profitability analysis, cash management, KPIs, and executive reporting. Partners with division leaders and executives to improve accountability, identify risks and opportunities, and guide operating decisions. Also performs delegated Deputy CFO responsibilities, including financial controls, risk management, and leadership continuity. Federal government contracting, indirect-rate management, FAR/CAS, DCAA, and Deltek Costpoint experience are strongly preferred.

Identify and qualify new MSP sales opportunities, present and demonstrate BCDR solutions, build partner relationships, collaborate with internal teams to meet sales targets, monitor industry trends, and manage sales-related expenses and reporting.

Supports US warranty insurance product development and carrier operations. Responsibilities include analyzing product performance, managing pricing and coverage modules, maintaining policy documentation, coordinating carrier reporting and reconciliations, supporting carrier relationships, responding to audits and due diligence requests, identifying compliance risks, and collaborating with Legal, Actuarial, Finance, and Technology teams. The role also assists with product submissions and capacity requests while developing expertise in insurance product design and commercial terms.

Manage social media campaigns for television projects by posting content, engaging communities, writing creative copy, maintaining content calendars, reporting consumer sentiment, and developing social content ideas. The role requires platform expertise across TikTok, Instagram, Facebook, Twitter/X, and Reddit, along with strong collaboration, communication, and deadline-management skills. Occasional nights and weekends may be required.