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.

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 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.

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.

Support and scale recruiting for provider partnerships and clinical support teams. Source, screen, and advance candidates; manage interview scheduling and candidate communications; partner with hiring managers; build recruiting systems and templates; grow into full-cycle recruiting and hire and develop other recruiters.

Drive new client acquisition and revenue through high-volume lead outreach, sales strategy, CRM pipeline management, client pitches, stakeholder engagement, pricing analysis, and cross-functional collaboration to meet sales targets.