Top Remote Jobs in Madison, WI

Build and lead Headway's procurement function: define procurement strategy and policy, manage vendor lifecycle, drive cost optimization and strategic sourcing, implement procurement tooling and reporting, advise leadership on governance and risk, and hire and develop a high-impact procurement team.

Provide strategic regulatory counsel to Clinical, Product, Engineering, and Operations teams on telehealth, clinical practice, and multi-state healthcare compliance. Draft policy, support audits and remediation, translate complex regulations into practical guidance, anticipate regulatory risks, and enable compliant product innovation while partnering cross-functionally.

Lead operational readiness for new product introductions: develop service readiness plans, training, knowledge base and processes; collaborate with product, engineering, and customer success; resolve operational and escalation issues; monitor KPIs and customer feedback to drive post-launch improvements.

Investigate and respond to confirmed endpoint compromises for MDR customers using EDR tools. Analyze, contain, and remediate threats, produce technical reports, improve response strategies, and collaborate with Detection, Threat Hunting, Intel, and Product teams. Participate in a monthly 24x7 on-call rotation and work Monday–Friday 8:00am–4:00pm MT.

Partner with the CEO to drive strategic initiatives, manage the CEO's office operations, coordinate cross-functional execution (OKRs, org design, M&A), prepare executive briefings, oversee communications and investor/board relations, and implement automation and AI tools to increase efficiency. Manage calendar, travel, and high-visibility events while acting as a trusted proxy and connector across the organization.

Own end-to-end lending products (origination, underwriting, servicing) and roadmap. Lead integrations with sponsor banks, credit bureaus, and loan management software. Collaborate with engineering, design, risk, data science, compliance to build underwriting, decisioning, and servicing experiences; run A/B tests and document underwriting logic to meet regulatory requirements.

Lead design and implementation of secure global network infrastructure. Architect security standards, conduct threat modeling and network assessments, build security automation and tooling, integrate controls with SDN/BGP/MPLS platforms, support incident response, and mentor engineering teams to maintain resilient, observable network security posture.

Lead the design and roadmap for global Active Directory and identity infrastructure, implement Identity-as-Code and GitOps automation, own incident escalation and observability, define delegation/tiered administration, integrate applications with Okta and cloud identity, mentor teams, and publish identity architecture and security best practices.

Lead evaluation and data strategy for advanced AI, vision, and perception systems. Define metrics, build evaluation frameworks, audit artifacts, prioritize fixes, and translate model behavior into product decisions and data-improvement loops to ensure production readiness and downstream usefulness.

Lead planning and execution of regional brand activations across the Western U.S., including venue sourcing, vendor coordination, on-site logistics, budget management, localizing national campaigns, building partner relationships, and serving as primary regional stakeholder contact. Significant in-market travel required to support activations and ensure ROI and consistent execution.

Lead planning and execution of regional brand activations across the South Central region: source venues, coordinate vendors and staffing, manage on-site logistics and day-of execution, localize national campaigns, manage regional budget and ROI, build local partnerships, serve as primary regional stakeholder contact, and travel frequently (~50-60%) to support activations. Based in Dallas.

Lead planning and execution of regional brand activations across the Southeast: venue sourcing, vendor coordination, on-site logistics, budget management, partner relationships, localizing national campaigns, and serving as primary regional stakeholder contact while traveling frequently to support events.

Provide Tier-1 client support for the Sky Road product suite: support and onboard trade workflows, templates, funds, permissions and application layouts; document workflows and permission models; escalate issues to development; coordinate with project managers for client onboarding and testing.

Provide tax preparation, planning, and advisory services for individuals and businesses holding bitcoin and digital assets. Prepare and file tax returns, calculate cost basis and gains/losses, advise on mining/staking/airdrop income, collaborate with advisors and estate planners, maintain compliance documentation, and contribute thought leadership through articles and webinars.