Top Tech Jobs & Startup Jobs in Chicago, IL

Lead the Customer Retention team, managing hiring, onboarding, coaching, case assignments, retention performance, concessions, commissions, and operational playbooks. Partner cross-functionally to identify churn drivers and improve customer outcomes. Develop predictive and AI-assisted outreach programs, report forecasts and results to leadership, and personally handle sensitive retention conversations. The role requires strong knowledge of retirement plan administration, negotiation, data analysis, and team leadership in financial services, fintech, or B2B SaaS.

Leads and develops a high-volume Sales Activation Coordinator team responsible for client outreach, retirement-plan document collection, intake quality, controlled-group setup, and handoff to plan design. Manages SLAs, capacity, coverage, forecasting, escalations, and performance metrics while partnering with Sales and Quality Control. Drives process improvements, SOP development, workflow automation, and technology adoption to improve conversion velocity, data integrity, and customer experience.

Support new clients and white-label partners in setting up and launching 401(k) plans. Manage activation pipelines, timelines, onboarding workflows, monthly targets, objections, escalations, and cross-functional coordination. Educate customers on retirement plan options, maintain engagement, troubleshoot software issues, and identify process improvements while delivering a high-quality customer experience.

Enable and optimize payroll integrations for clients using more than 400 payroll providers. Troubleshoot data transmission issues, evaluate discrepancies, guide clients through integration setup, and support first 401(k) contributions. Collaborate with Sales Activation, Payroll Partners, Product, Customer Success, and Operations teams. Draft procedures, account for SEC, DOL, and IRS regulations, investigate root causes, implement solutions, improve processes, and manage projects while maintaining accurate, client-focused communication.

Build and expand referral partnerships with technology, HCM, benefits, CPA, and financial advisory partners serving SMBs. Develop strategic referral networks, generate leads, establish partner goals and performance metrics, and execute go-to-market and demand-generation initiatives. Resolve partnership issues cross-functionally with Sales, Product, Marketing, Legal, and Finance while managing relationships in a quota-driven environment.

Owns strategic partnership growth for a fintech retirement platform. Sources, negotiates, structures, and closes complex distribution agreements with payroll providers, benefits brokers, financial institutions, PEOs, and embedded-fintech partners. Develops channel strategy, models partnership economics, coordinates integrations and go-to-market execution across teams, manages executive communications, and ensures effective handoff to partner management. This is an individual-contributor role focused on building new channels and delivering measurable revenue impact.

Manages assigned retirement-plan accounts as the primary client contact, providing customer service, issue resolution, plan design and document support, compliance guidance, regulatory deadline assistance, annual testing, Form 5500 coordination, and audit support. Partners cross-functionally with implementation, sales, support, marketing, and product teams while maintaining current knowledge of ERISA, IRS, and Department of Labor requirements.

Leads Human Interest’s ERISA compliance program across 401(k) operations, ensuring adherence to ERISA, DOL, and IRS requirements. The role modernizes compliance workflows, develops automated monitoring and reporting systems, manages fiduciary governance and regulatory incidents, oversees escalations and remediation, partners with Product and Technology, manages auditors and regulators, and coaches compliance managers. The director also advises executives on risk, maintains policies and training, and scales technology-enabled compliance operations.

Build and own a greenfield mobile application for iOS and Android, including architecture, features, security, accessibility, testing, telemetry, and App Store and Play Store releases. Use AI coding agents throughout development, establish CI/CD and rollout processes, solve secure fintech problems, and collaborate with Product, Design, and backend engineers. Mentor teammates and drive high-quality, reliable customer experiences.

Supports contribution trade operations by reviewing customer and account data, processing payroll contributions accurately and on time, identifying and correcting discrepancies, troubleshooting integration issues, maintaining records, responding to inquiries, and improving workflows. The role collaborates cross-functionally, provides operational insights, supports reporting and compliance, and contributes to projects that enhance efficiency and data integrity.