Top Tech Jobs & Startup Jobs in Chicago, IL

Provides Canadian payroll tax services for assigned customers, managing daily cases, customer communications, tax remittances, and year-end T4, T4A, Releve 1, and Releve 2 activities. Researches and resolves multi-jurisdiction payroll tax issues, supports escalations, maintains service-level and quality targets, safeguards confidential data, and collaborates with internal teams to stabilize service delivery.

Performs daily, monthly, and quarterly payroll tax reconciliations across U.S. jurisdictions. Researches and resolves tax discrepancies, analyzes employer and employee payroll data, performs calculations, ensures compliance with federal, state, and local tax requirements, and communicates findings and corrective actions to customers. The role supports multiple customers in a fast-paced outsourcing environment.

Owns the design, documentation, launch, and continuous improvement of post-sale customer journeys and experience programs. The role uses customer metrics such as NPS, effort, retention, expansion, and adoption to improve customer success, time to value, and revenue retention. Responsibilities include cross-functional collaboration, customer advocacy, change management, journey mapping, workflow integration, stakeholder alignment, and program measurement across varied customer segments.

Manage high-volume commercial contracts and complex procurement transactions. Draft, review, and negotiate customer and vendor agreements, including MSAs, SaaS and subscription agreements, data processing agreements, SOWs, and NDAs. Resolve routine and moderately complex contract issues independently, escalating novel or high-risk matters. Partner with Sales, Product, and Technology to align contract terms with business strategy and risk tolerance.

Serve as the organization's internal payroll tax authority: advise product, sales, and implementation on complex multi-jurisdictional tax configurations, resolve escalated technical/tax issues, contribute to product roadmap and UAT, and convert deep tax knowledge into training, guides, and customer-facing advisory work to scale team expertise.

The Tax Data Specialist maintains tax profile data, processes update requests from customers, manages cases, and ensures accurate data input into multiple systems.

Own relationships with an assigned portfolio of strategic and referral partners, drive co-sell pipeline and partner-influenced revenue, manage PRM entries, co-facilitate partner meetings, enable internal GTM stakeholders, collect partner materials, recommend program improvements, and represent OSV at partner events (~20% travel).