Jobs at Sidecar Health

The Vice President of Finance will lead FP&A, budgeting, forecasting, financial modeling, capital planning, reporting, and IPO readiness. The role partners with executive leadership, oversees financial systems and controls, supports fundraising and investor relations, manages financial risk, and builds a high-performing finance organization. This leader will strengthen scalable infrastructure, ensure GAAP-compliant reporting, guide capital allocation, and provide strategic financial insights for a rapidly growing healthcare company.

Lead product strategy and roadmap for claims automation, defining where AI and deterministic logic apply. Design human-in-the-loop workflows, audit trails, evaluation frameworks, and metrics. Lead cross-functional teams to deliver integrations, migrations, and AI-powered features while navigating regulatory constraints and measuring performance with data-driven experiments.

Design, deliver, and maintain end-to-end training programs for Claims operations including onboarding, refresher/upskilling courses, e-learning and simulations, LMS/KM administration, SME coordination, and evaluation of training effectiveness to ensure floor readiness.

Lead B2B marketing initiatives at Sidecar Health, focusing on demand generation, paid media, content strategy, and team development to drive growth and revenue.

As a Senior SDET, you will design and maintain test automation frameworks, embed with product teams to ensure quality, and implement AI-powered testing solutions.

Act as primary liaison for existing employer groups, drive satisfaction and retention, attend virtual and in-person meetings across Texas, lead renewals and negotiate pricing, provide enrollment education and support, resolve escalations, and collaborate with internal teams to ensure successful implementation and group outcomes.

The Head of Enterprise Sales will lead the sales strategy, drive growth, secure national client accounts, and collaborate with internal teams at Sidecar Health.