---
title: 'Chief of Staff at Helm Health'
canonical: 'https://feeny.ai/job/chief-of-staff-helm-health-united-states-azn9zmvttx9b'
type: 'job'
last_seen: '2026-09-08'
---

# Chief of Staff at Helm Health

- **Company:** Helm Health
- **Location:** United States
- **Employment:** full-time
- **Work type:** remote
- **Posted:** 2026-07-02
- **Last confirmed live:** 2026-09-08
- **Apply:** https://jobs.gem.com/helm-health/am9icG9zdDrTPgJI6ur_5wseW5cpUsLK

## Job description

## About Helm Health

Helm is a Series A start-up transforming health insurance with "Dynamic Copay" – a new insurance plan that lets members see simple, upfront prices for all medical care before making decisions. Our team is building the infrastructure to power these plans for health insurance payors. With Helm, our clients offer simpler health plans to their members, helping them navigate to higher-value care.

Our team has specialized in Dynamic Copay solutions since 2020, and Helm is the only independent platform in the market. We have grown rapidly since our launch, working with clients from local health plans to the nation's largest health insurers. The market is forming around us, making it an exciting time to join!

## Role Overview

We are seeking a high-agency Chief of Staff to serve as a strategic operator and force multiplier for the CEO and leadership team. This role sits at the intersection of company strategy, executive communication, AI-enabled operations, business analytics, investor relations, and high-priority cross-functional initiatives.

You'll be responsible for connecting the dots across the organization - driving execution on critical cross-functional initiatives, creating the analysis and materials that keep the company moving forward, and ensuring leadership priorities translate into action. The scope of this role is deliberately broad: depending on company priorities in a given quarter, you might be deep in fundraising prep one month and building sales analytics the next. The common thread is leverage: you will help Helm move faster, communicate more clearly, and execute with greater discipline. If you're a generalist operator with low ego who loves crafting narratives and driving execution across every function of a Series A start-up, this role is for you.

This role reports directly to the CEO and will work closely with the executive team, Board, investors, advisors, and external partners. It is a high-growth seat with a clear path into a meaningful leadership role as the company scales.

Responsibilies Strategic Planning, Special Projects & Executive Leverage

- Drive high-priority cross-functional initiatives that require dedicated execution focus, such as strategic partnerships, advisor management, operating-process improvements, market analysis, and special projects.
- Help translate company priorities into clear plans, owners, timelines, decision points, and follow-through.
- Facilitate quarterly and annual planning with the executive team to ensure alignment on goals, milestones, and key dependencies.

Board, Investor Relations & Executive Communications

- Own the consolidation and translation of executive narrative for quarterly Board meetings into clear, compelling written and visual materials.
- Prepare investor relations materials and support future fundraising efforts.
- Draft executive updates, internal communications, and strategic memos as needed.

AI Enablement

- Champion AI adoption across Helm by identifying high-leverage use cases, piloting tools, and building workflows, prompts, internal playbooks, and lightweight automations.
- Help teams in sales, finance, operations, product, and leadership use AI to improve speed, quality, and leverage.
- Set the internal standard for thoughtful AI-augmented work, including use cases that go beyond chat-based interfaces into structured workflows, data analysis, document generation, research, coding-adjacent tools, and repeatable internal processes.
- Bring the rest of the company along, regardless of each person's technical comfort level.

Business Operations, Finance & Revenue Support

- Partner with functional leaders to improve the systems and reporting that help Helm make better operating decisions.
- Support the VP Finance on company planning, KPI reporting, forecast updates, scenario analysis, and Board/investor materials.
- Support enterprise deal execution through analysis, collateral, RFP support, meeting preparation, and follow-up tracking.

Leadership Team Coordination & Culture

- Help facilitate leadership team rhythms, including agendas, notes, decision logs, and follow-up tracking.
- Ensure important decisions, open questions, and cross-functional dependencies are captured and advanced.
- Plan and execute company offsites end-to-end, including logistics, content planning, and post-offsite follow-through.
- Help reinforce a high-trust, high-accountability operating culture as Helm scales.

## Requirements

- 4–7+ years of high-performance operating experience, ideally in a high-growth start-up, strategy, business operations, consulting, investment banking, venture capital, private equity, corporate development, strategic finance, or a similarly demanding environment.
- Strong analytical skills, including comfort with financial models, operating metrics, KPI dashboards, pipeline analysis, and decision-support analyses.
- Exceptional written and visual communication skills, especially for Board decks, investor materials, executive updates, sales narratives, and strategic memos.
- Deep hands-on AI fluency. You use AI daily to do real work - not just chat, but structured workflows, automation, data analysis, and document generation. Comfort with tools like Claude Code, Cursor, or Codex, and a track record of turning recurring work into repeatable AI-assisted processes.
- Healthcare experience is strongly preferred, especially in health insurance, benefits, payer/provider technology, digital health, or healthcare services.

## Who You Are

- High Agency: Self-directed and comfortable recommending next steps based on limited information.
- Low Ego: No work is below you. You are equally willing to shape company strategy, build a Board slide, clean up a messy tracker, or book offsite lodging.
- Discretion: Ability to handle sensitive financial and personnel information with the utmost confidentiality.
- Structured Thinker: You love turning chaos into clear processes.
- Executive Judgment: You understand the CEO's and leadership team's context, represent decisions accurately, and know when to escalate versus act independently.
- AI-Native Operator: You are constantly experimenting with new tools and workflows and naturally look for ways to make yourself and others more leveraged.
- Mission-Oriented: You are excited about Helm's product and believe in what we are building.

## Compensation

The target base salary range for this position is $175,000 - $225,000 and is part of a competitive total rewards package including equity and benefits. Individual pay may vary from the target range and is determined by several factors, including experience, skills, location, internal pay equity, and other relevant business considerations.

## Benefits/Offerings

- Bonus + equity
- Unlimited PTO (mandatory 12 days)
- Computer + home office stipend
- 401(k) + matching
- Medical, dental, and vision insurance
- Autonomy and tons of room for career growth

Occasional Travel We meet quarterly as a company.

Please note that this is a fully remote opportunity.

## About Helm Health

## Company Overview
- **One-liner**: Helm Health powers a new wave of health plans by providing a Dynamic Copay platform that brings simple, upfront prices to members and eliminates deductibles.
- **Entity Type**: Private (Seed stage)
- **Headquarters**: Columbus, Ohio, United States
- **Founded**: 2023
- **Founders**: Brodie Stone, Ross Klosterman

## Core Business
- **Primary industry**: Healthtech / Insurance technology (Embedded Software Products)
- **Target customers**: B2B – TPAs (Third-Party Administrators) and carriers who build Dynamic Copay products for their members
- **Mission or purpose statement**: “Take the confusion out of health insurance by making every service easily shoppable, upfront. Guaranteed.”

## Products & Services
- **[Dynamic Copay]**: A system that adjusts member cost share based on the value of healthcare services, aiming to provide higher benefit coverage and lower total cost of care. (SaaS platform)
- **[Copay Algorithm]**: Dynamically scores healthcare providers and assigns copay levels to them. (Algorithm/API)
- **[Copay Repricer]**: Bundles claims to match the price quoted upfront to the member. (Service/API)
- **[Shopping Tool]**: An intuitive search experience for healthcare services, used by members and navigators. (Application)
- **[Provider Finder Tool]**: Helps users find healthcare providers with regularly updated information from partners. (Informational tool)

## Market Standing
- **Valuation/Market Cap**: Not disclosed (Seed round, amount not publicly available)
- **Key Metric**: Total Funding – Seed round from 1 investor (undisclosed amount)
- **Notable Investors/Partners**: Investor not named; partners include TPAs and carriers (specific names not public)
- **Growth Signals**: Employee headcount grew 61.5% year-over-year (from ~10 to 17-19 employees); remote-first hiring across engineering, product, and executive roles; 75% of care is shopped through the platform, delivering 15% plan savings.

## Competitive Advantages
- **Dynamic Copay model** that uses upfront prices to drive member engagement and decision making, reducing plan costs.
- **Smart claim bundling** preserves provider fee-for-service reimbursement while creating simple, guaranteed prices for members.
- **Value-based coverage** based on provider cost and quality, eliminating deductibles and reducing complexity.
- **Early mover** in a niche combining health insurance transparency with algorithmic pricing.

## Strategic Focus
- **Scale the engineering team** to build out core backend infrastructure, data pipelines, and public-facing APIs.
- **Expand product capabilities** in claims monitoring, self-service configuration, and reporting.
- **Deepen partner integrations** with TPAs and carriers to drive adoption of Dynamic Copay products.
- **Maintain HIPAA compliance** and data governance as the platform grows.

## Why Work Here
- **Remote-first culture** – all current open positions are remote within the United States.
- **Early-stage impact** – join a small, growing team (17-19 employees) where engineers own significant parts of the architecture.
- **Mission-driven** – work on making healthcare pricing transparent and affordable.
- **Modern tech stack** – TypeScript, PostgreSQL, Redis, BigQuery, gRPC, and cloud infrastructure (CI/CD, DevOps).
- **Growth opportunities** – roles span senior to staff levels; company has grown headcount >60% YoY and shows strong product-market fit.
- **Notable perks** – not explicitly listed, but typical of early-stage healthtech startups: equity, flexible remote work, direct influence on product direction.

## Sources
1. [helmhealth.com](https://www.helmhealth.com/)
2. [crunchbase.com](https://www.crunchbase.com/organization/helm-health)
3. [builtin.com](https://builtin.com/company/helm-health/jobs)
4. [linkedin.com](https://linkedin.com/company/pay-with-helm)
5. [gem.com](https://jobs.gem.com/helm-health)

## Other roles at Helm Health

- [Senior Back-End Engineer: Infrastructure](https://feeny.ai/job/senior-back-end-engineer-infrastructure-helm-health-united-states-tkdnppnej5jc) — United States
- [Staff Product Manager: Admin Dashboard & Configuration Engine](https://feeny.ai/job/staff-product-manager-admin-dashboard-configuration-engine-helm-health-united-tpt3pnav91bz) — United States
- [Staff Back-End Engineer: Search APIs](https://feeny.ai/job/staff-back-end-engineer-search-apis-helm-health-united-states-8faygvtjn2mb) — United States
- [Staff Back-End Engineer: Claims Engine](https://feeny.ai/job/staff-back-end-engineer-claims-engine-helm-health-united-states-m6wtswc4zf2q) — United States
- [Staff Back-End Engineer: Data](https://feeny.ai/job/staff-back-end-engineer-data-helm-health-united-states-zmzzpt2tfqsr) — United States
- [Senior Back-End Engineer: Dynamic Copay Engine](https://feeny.ai/job/senior-back-end-engineer-dynamic-copay-engine-helm-health-united-states-c91q02392xh7) — United States
- [Senior Full-Stack Engineer I: Self-Service Configuration & Plan Design](https://feeny.ai/job/senior-full-stack-engineer-i-self-service-configuration-plan-design-helm-health-1pgam20yq0m0) — United States
- [Senior Full-Stack Engineer I: Claims Monitoring & Management](https://feeny.ai/job/senior-full-stack-engineer-i-claims-monitoring-management-helm-health-united-drz813dwn6hd) — United States
- [Senior Full-Stack Engineer I: Self-Service Reporting](https://feeny.ai/job/senior-full-stack-engineer-i-self-service-reporting-helm-health-united-states-gsv5gqc0bfsn) — United States
- [Chief of Staff](https://feeny.ai/job/chief-of-staff-bisnow-new-york-0mq8mw97mmp5) — New York, NY