Top Remote Senior Level Jobs in Milwaukee, WI

Lead a team managing employee benefits and leave programs (FMLA, ADA, COBRA, state leaves), ensure regulatory compliance, oversee vendor relationships, improve processes and HR systems (Workday), handle escalated cases, and coordinate with HR, payroll, legal, and finance to deliver timely, accurate, and compassionate service.

Provide commercial and corporate legal support for a fast-growing fintech: negotiate and draft contracts, translate legal terms for internal partners, advise on regulatory/compliance issues, integrate legal workflows into product and go-to-market activities, and steward vendor and partner relationships.

Lead a portfolio of middle-market self-funded employer clients as primary post-implementation contact. Manage renewals, account health, reporting, issue resolution, cross-functional coordination with implementation, sales, analytics, and third parties to drive retention, satisfaction, and growth.

Fixed-term (approx. 6 months) senior contract recruiter managing full lifecycle hiring across the US and Canada. Responsibilities include intake, sourcing (active and passive), screening, interview coordination, assessments, reference/background checks, offer support and preboarding tasks. Maintain ATS records, build pipelines for hard-to-fill roles, ensure compliance and inclusive practices, communicate with candidates and stakeholders, and provide reporting and process improvement suggestions. Remote, 20–40 hours/week.

Lead end-to-end UX/UI for a scaled dental SaaS platform, build and maintain a reusable design system, integrate AI-augmented workflows, conduct customer research with dentists, and collaborate with product and engineering to deliver accessible, technically feasible designs.

Serve as chief of staff to senior sales leadership, establish GTM cadence, optimize sales processes, analyze performance, lead territory and forecast planning, maintain CRM and revenue systems, and align cross-functional stakeholders to drive sales efficiency and growth.

Manage day-to-day administration of health and welfare benefits, 401(k), paid time off, and leave programs. Ensure regulatory compliance (FMLA, ADA, ERISA, ACA, HIPAA), reconcile vendor invoices, support open enrollment, maintain plan documents, track LOA/FMLA/ADA and workers' comp timelines, and advise managers on leave decisions.

Lead month- and year-end close, manage accounting team, maintain general ledger integrity, prepare/review journal entries and financial statements, support audits, improve accounting processes and reporting to enable business decisions.

Own and administer HubSpot and related marketing systems, manage integrations with Salesforce and other platforms, ensure data quality, design lead lifecycle and routing, build dashboards and attribution models, analyze funnel and campaign performance, automate processes, and partner with Sales and Revenue Operations to improve conversion and revenue contribution.

Lead Synapticure's full marketing function: set strategy and roadmap, manage agencies and a small internal team, launch a rebrand and website, run paid acquisition and lifecycle programs, own CAC/LTV targets and measurement with Mixpanel, develop caregiver- and partner-facing messaging, and ensure clinical and compliance alignment. Drive weekly growth rhythms, scale channels deliberately, and build internal capability to meet enrollment and partnership goals.