Sidecar Health

Sidecar Health is an InsurTech company that offers a health insurance platform and medical coverage to businesses.

101-250 employees

Founded 2018

$165M series d

Health Insurance

Private Company

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Health Insurance InsurTech Insurance Health Care FinTech

Open Positions10

Transform healthcare in the United StatesFull-TimeHealth InsurancePosted

Senior Director of Account Management

Define the vision and operating model for Account Management across mid-market employer groups (up to 10,000 employees).
Create a strategic roadmap for transitioning from manual to scalable, automated systems.
Partner with C-levels to align account management strategy with company growth.
Architect the organizational structure and hiring plan.
Develop tools, playbooks, and processes for efficient account management.
Drive automation and self-service capabilities in partnership with product and tech teams.
Serve as a senior client-facing leader for key broker partners and HR decision-makers.
Own retention, growth, and satisfaction targets across the mid-market book.

Account ManagementRelationship managementCustomer Success

Showing 1 of 10 positions

About Sidecar Health

Sidecar Health is transforming health insurance in the United States. You know healthcare is complex and costly. This company built an insurtech platform that makes medical costs transparent. You can choose any licensed provider and see pricing upfront. Their unique model lets you pay for care directly with a Sidecar Health Visa card. If you find lower-cost options, you keep half of the savings. Sidecar Health serves employers with 51+ employees, offering major medical plans. The company has secured $328M in funding, achieving unicorn status with a $1B valuation. They empower you to take control of your healthcare spending.

How We Work

Sidecar Health champions a fully flexible work model. This means you have autonomy in building your daily work schedule. They prioritize transparent and asynchronous communication across their distributed team. You will join passionate problem-solvers who take ownership and act with a bias for action. The culture focuses on making a significant impact. You will work with empathy at the core of your approach.

Engineering at Sidecar Health

As an engineer here, you will solve complex healthcare data and workflow challenges. You will build scalable backend services, APIs, and robust data pipelines. The team emphasizes end-to-end ownership, from design through deployment. You will frequently optimize database queries and data models for performance. Sidecar Health actively integrates AI tools and agentic coding patterns into engineering workflows. This means you will use tools like Claude or Cursor as a core part of your daily process. You will make architectural decisions that ensure systems are fast and reliable at scale. You will deploy to AWS, using services like EC2, Lambda, RDS, and S3. Expect to contribute to engineering standards through code reviews and technical discussions.

Why Join Us

Drive meaningful impact by transforming a broken healthcare system.
Own complex problems from architecture to production, shaping the platform.
Work in a flexible, remote-first environment with autonomy over your schedule.
Engage with cutting-edge AI tools and agentic coding practices daily.
Join a well-funded, high-growth company backed by $328M in funding.

Benefits & Perks

Competitive salary, bonus opportunities, and equity packages.
Comprehensive medical, dental, and vision benefits, with fully paid premiums for employees and families on the signature plan.
A 401k retirement plan to support your future.
Paid vacation, company holidays, and global recharge days.
Mental health resources through Ginger.
Home-office stipend for remote employees.

Tech Stack

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