Top Remote Jobs in Madison, WI

Lead the technical direction, architecture, and development of Compass, an LLM-powered agent platform. Design multi-agent systems, MCP and A2A integrations, orchestration, evaluation, and observability infrastructure. Drive cross-team technical projects, production support, engineering quality, mentoring, and adoption of AI-assisted development practices. Partner with Product, QA, Design, Operations, and Engineering stakeholders to deliver reliable agentic systems.

Own and expand a portfolio of 15–25 enterprise accounts, generating approximately $1.2M in annual expansion quota. Prospect within existing customers, identify new departments and use cases, build executive relationships, run business and quarterly reviews, and close complex 6–12 month enterprise deals. Partner with sales engineers, customer success, and leadership while creating account plans, developing pipeline, and presenting Monte Carlo’s data and AI reliability platform to technical and executive buyers.

Own Cleo’s application and product security program across SaaS and customer-hosted products. Lead SSDLC practices, threat modeling, security tooling, vulnerability management, penetration testing, coordinated disclosure, CVE publication, and NIST CSF controls. Define product security standards, roadmap, secure defaults, access controls, and customer-facing advisories. Partner with engineering, product, architecture, and customers while guiding security engineers and consultants. Also establish protections for LLM applications, AI agents, and AI-assisted development workflows.

Owns the end-to-end redemption and fulfillment pipeline, including vendor SLAs, shipping, exceptions, customer support processes, and cost reconciliation. Manages the product catalog, sourcing, merchandising, pricing, vendor onboarding, and market data integrations. Establishes cross-functional operating rhythms, reporting, decision rights, and scalable processes while building a future fulfillment and merchandising team.

Manage commercial print partners across performance, capacity, cost, and contract compliance. Run scorecards and business reviews, audit invoices and recover overcharges, forecast capacity, enforce print and postal standards, and coordinate corrective actions. The role also qualifies new partners, supports production rerouting, and builds AI- and SQL-driven automation for audits and reporting. It requires extensive collaboration across operations, logistics, Product, Engineering, Finance, and Supply Chain, with approximately half the time spent onsite at partner facilities.

Owns the Member Services knowledge base and end-to-end member journey documentation. Establishes knowledge governance, taxonomy, review cycles, and health reporting; maps cross-functional processes and policies; partners with business and product teams to identify operational pain points and product opportunities; and ensures product changes are reflected across member-facing documentation. The role requires influencing stakeholders without direct reports and supporting both human and AI-enabled service tools.

Leads East Coast enterprise sales performance, coaching and developing quota-carrying sellers, managing complex multi-stakeholder deals, improving forecasting and pipeline discipline, recruiting talent, and driving regional go-to-market execution. Partners with senior executives and cross-functional teams to achieve predictable revenue growth across senior living and post-acute markets. Requires extensive enterprise B2B SaaS sales leadership experience, MEDDPICC expertise, and willingness to travel 40–50%.

Coordinate end-to-end interview scheduling across recruiting stages, manage calendars and reschedules, communicate logistics with candidates and interviewers, maintain accurate ATS records, protect interview capacity, and support interviewer onboarding. Partner with recruiters and hiring managers to prioritize urgent hiring needs, resolve scheduling bottlenecks, and improve recruiting operations and candidate experience.

Own QA strategy and release quality for POS, back-office, and payments products. Build automated unit, integration, API, contract, and end-to-end tests; integrate testing into GitHub Actions; validate hardware, offline modes, payment flows, and upgrades; establish release gates and test environments; monitor quality metrics; reproduce merchant issues; and coach engineers on testable design and quality practices.

Lead a hands-on engineering team building and shipping features for a modern trucking transportation management system. Partner with Product and Design to shape roadmaps, contribute to Ruby on Rails and React development, mentor engineers, maintain engineering quality, understand customer workflows, and deliver improvements quickly in a fully remote environment.