Top Tech Jobs & Startup Jobs in Chicago, IL

Leads payroll connection and integration operations, managing managers and frontline teams while driving throughput, SLA performance, quality, compliance, and customer experience. Partners with payroll providers and internal Product, Engineering, Sales, and Customer Success teams to resolve integration issues, improve processes, manage risk, and influence product roadmaps. Uses operational data, capacity modeling, root-cause analysis, and automation to scale teams and deliver strategic initiatives.

Own full-cycle recruiting for Sales and Go-To-Market teams, hiring roles from SDRs and Account Executives to leadership. Advise revenue leaders, source passive candidates, manage candidate experience, negotiate offers, track recruiting metrics, and improve hiring processes using Greenhouse, BrightHire, and LinkedIn Recruiter. Lead initiatives involving employer branding, DEI sourcing, and recruiting process optimization in a remote, high-growth environment.

Designs and delivers scalable learning and talent development programs, including e-learning, microlearning, training materials, workshops, and leadership development. Conducts needs assessments, facilitates virtual and in-person sessions, administers the Docebo LMS, documents resources in Confluence, and uses AI tools to accelerate content creation. The role manages cross-functional People Team projects, gathers learner feedback, and continuously improves learning solutions aligned with organizational goals.

Leads Human Interest’s strategic partnerships function, expanding distribution through payroll providers, benefits brokers, accountants, financial institutions, PEOs, and fintech partners. Responsibilities include team leadership, partnership strategy, sourcing and closing complex agreements, deal structuring, performance management, cross-functional coordination, executive communication, and market intelligence. The role requires building scalable processes, personally managing high-value negotiations, and driving measurable revenue growth across the retirement and financial-services ecosystem.

Leads multiple Operations Manager teams responsible for accurate, compliant, and timely money movement transactions. Translates organizational strategy into operational plans, manages performance metrics, mitigates risk, improves processes, and strengthens client experience. Partners with Product, Engineering, Data, Legal, Sales, and Customer Success leadership while developing managers, scaling transaction operations, driving automation, and leading organizational change in a regulated fintech environment.

Lead and build a mobile engineering team from the ground up, overseeing hiring, mentorship, architecture, product execution, release governance, QA infrastructure, app-store deployments, telemetry, and cross-functional collaboration. The role manages iOS, Android, and cross-platform development while ensuring reliable, secure, high-quality mobile experiences for employees and retirement-plan administrators.

Supports GTM FP&A through revenue forecasting, scenario modeling, variance analysis, budgeting, KPI monitoring, and financial reporting. The role provides data-driven insights to Sales, Partnerships, Marketing, and Customer Onboarding leadership; prepares board and investor materials; improves forecasting accuracy; and develops scalable finance processes for a high-growth SaaS business.

Leads technical program planning and execution for money movement systems, coordinating design, product, and engineering teams. Responsibilities include managing schedules, milestones, risks, blockers, reporting, roadmaps, resourcing, cost management, and process optimization. The role supports reliable deposits and withdrawals, accurate financial tracking, and self-service capabilities for administrators, participants, and operations teams.

Manage full-cycle sales from demonstrations through contract close, including prospecting, pipeline development, product demonstrations, negotiation, and sales activity documentation in Salesforce. The role requires exceeding quotas, supporting small-business customers, navigating high-velocity sales cycles, using sales technology, and communicating product value effectively.

Build and manage referral partnerships with technology, HCM, benefits, accounting, and financial advisory partners serving SMBs. Develop referral networks, identify partnership opportunities, resolve issues cross-functionally, support partner marketing initiatives, and establish sales goals and performance metrics. Execute go-to-market and demand-generation strategies while managing relationships independently in a quota-driven environment. The role requires being in the field three days per week and living in The Bronx.