Chief of Staff

Helm Health•USA,

3h•$175,000 - $225,000•Remote

About The Position

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! 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.

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.

Nice To Haves

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.

Responsibilities

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.
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.
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.
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.
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.