Top Remote Senior Level Jobs in Madison, WI

Assistant General Counsel responsible for managing litigation, disputes, arbitrations, investigations, and prelitigation matters for GuideWell and its affiliates. The role manages outside counsel, develops legal strategies, advises business leaders, drafts and reviews legal documents, serves as an external legal contact, and manages complex matters with minimal supervision.

Own the full sales cycle for new healthcare provider accounts, including prospecting, discovery, product demonstrations, negotiation, and closing. Build and manage pipeline, maintain accurate forecasts, meet revenue targets, and develop business cases for complex healthcare purchases. Collaborate with marketing, sales development, and product teams, attend industry events, and provide market feedback. The role is remote and focuses on selling to musculoskeletal provider groups and specialty clinics.

Manages complex internal business projects from inception through delivery, overseeing scope, schedules, budgets, resources, quality, stakeholders, risks, and changes. Develops project plans, status reports, meeting materials, and governance improvements. Coordinates cross-functional teams, vendors, and process changes while mentoring project management staff. Requires strong project management, process improvement, data analysis, communication, organization, and reporting skills, with proficiency in Microsoft Office tools.

Own post-underwriting risk management across live merchant portfolios. Monitor transaction activity, fraud, chargebacks, disputes, refunds, and processing trends; investigate unusual patterns; recommend reserves, holds, limits, monitoring, and remediation; and provide data-driven recommendations to Payments leadership. Improve risk alerts, workflows, dashboards, and automation while collaborating with underwriting, compliance, product, engineering, operations, and client success.

Lead the architecture and hands-on development of AI agents and autonomous storefront systems. Build agent tools, execution loops, evaluations, observability, MCP infrastructure, quality gates, and optimization workflows. Design APIs, data models, and service boundaries across TypeScript, Node.js, React, Postgres, MongoDB, and Redis. Drive AI-native engineering practices, testing, reliability, technical communication, and cross-functional technical leadership.

Leads and grows an engineering team responsible for customer-facing web, mobile, and backend products. Owns delivery, technical direction, architecture, reliability, hiring, coaching, and career development. Partners with Product and Design to prioritize work and deliver dependable releases. Establishes AI-assisted engineering practices, supports AI-powered customer experiences, and builds systems for scheduling, payments, client management, notifications, and integrations.

Manage cybersecurity for facility-related IT and OT control systems supporting U.S. Government operations on Diego Garcia. Responsibilities include system administration, network and access control, vulnerability and threat reviews, incident reporting, audit logging, certification and accreditation support, backups, recovery procedures, compliance, and system maintenance. The role advises leadership, coordinates with stakeholders, maintains security documentation, and ensures reliable operation of critical services in a remote overseas environment.

Lead product-focused data science and machine learning initiatives, including exploratory analysis, production model development, evaluation frameworks, generative AI, graph-based machine learning, recommendation systems, and personalization. Collaborate with engineering, product, and business teams to deliver high-impact solutions, influence strategy, and communicate insights to technical and non-technical stakeholders. The hybrid role requires four days per week in the Greater Boston area.

Own the post-sale customer lifecycle for enterprise software customers by driving adoption, value realization, retention, and growth. Build executive relationships, develop customer success plans, coordinate cross-functional resources, resolve complex issues, communicate product value, and support renewals through metrics gathering, pricing, quoting, negotiation, and closure.

Develop and document enterprise-grade SaaS platform functionality while improving quality and performance. Responsibilities include full-stack development, functional and unit testing, defect triage, code reviews, API and process documentation, operational support in regulated environments, and collaboration within Agile and DevOps teams. The role requires expertise in C#, ASP.NET Core, T-SQL, Entity Framework Core, web technologies, software design, debugging, distributed architectures, and high-performance APIs.

Own the technical aspects of enterprise airline deals from qualification through deployment and expansion. Design integration and cloud architectures, lead demos and proofs of concept, respond to RFPs and security questionnaires, review technical contracts, and ensure customer commitments align with engineering capabilities. Build reusable technical assets, support adoption, and communicate customer requirements to product and engineering teams.

Own global operating expense planning, forecasting, and management for personnel costs, headcount, travel and entertainment, and digital services taxes. Partner with business leaders on financial decisions, lead close and accrual processes, analyze variances, and deliver financial reporting. Improve budgeting and forecasting through automation, AI-enabled tools, dashboards, and scalable analytics. Manage headcount planning and present business reviews covering performance, risks, opportunities, and recommendations.

Owns client audit engagements, reviews and signs off on AI-generated audit work, makes evidence and risk judgments, maintains audit methodology, and defines quality standards for AI workflows. The role leads complex engagements, explains AI-generated work to clients, tracks AICPA standards, designs AI evaluations, builds technology-enabled audit modules, mentors accounting engineers, and helps determine when AI-assisted procedures are ready for client use.