Chief of Staff

This is a fully remote position, open to applicants in United States.

📋 Description

• Lead high-priority cross-departmental initiatives, including strategic partnerships, advisor management, process enhancements, market analysis, and special projects.

• Convert company objectives into actionable plans with designated owners, timelines, decision points, and follow-through mechanisms.

• Organize quarterly and annual planning sessions with the executive team.

• Compile executive narratives for quarterly Board meetings into cohesive written and visual presentations.

• Develop investor relations materials and assist in upcoming fundraising activities.

• Create executive updates, internal communications, and strategic memoranda.

• Promote AI adoption by pinpointing use cases, piloting tools, and establishing workflows, prompts, playbooks, and automations.

• Aid sales, finance, operations, product, and leadership teams in leveraging AI to enhance efficiency, quality, and effectiveness.

• Collaborate with functional leaders to enhance operating systems and reporting structures.

• Assist in company planning, KPI reporting, forecast updates, scenario analysis, and materials for the Board/investors.

• Facilitate enterprise deal execution through analysis, collateral preparation, RFP support, meeting arrangements, and follow-up tracking.

• Coordinate leadership-team processes, including agendas, notes, decision logs, and follow-up tracking.

• Document and advance decisions, outstanding questions, and interdepartmental dependencies.

• Plan and execute company offsite events, including logistics, content development, and post-offsite follow-up.

• Foster a culture of high trust and high accountability within the organization.

• Report directly to the CEO and collaborate closely with the executive team, Board, investors, advisors, and external partners.

⛳️ Requirements

• 4–7+ years of high-performance operational experience, preferably in a high-growth startup, strategy, business operations, consulting, investment banking, venture capital, private equity, corporate development, strategic finance, or a similar demanding setting.

• Strong analytical abilities, including proficiency with financial models, operational metrics, KPI dashboards, pipeline analysis, and decision-support evaluations.

• Outstanding written and visual communication capabilities, particularly for Board presentations, investor documentation, executive updates, sales narratives, and strategic memos.

• Extensive hands-on experience with AI, including structured workflows, automation, data analysis, and document generation.

• Familiarity with tools like Claude Code, Cursor, or Codex.

• Proven track record of transforming repetitive tasks into repeatable AI-assisted processes.

• Experience in healthcare, specifically in health insurance, benefits, payer/provider technology, digital health, or healthcare services.

• Ability to manage sensitive financial and personnel information with the highest level of confidentiality.

• Self-directed judgment with the capability to recommend subsequent steps based on limited information.

• Capacity to work autonomously, accurately represent decisions, and discern when to escalate issues versus take independent action.

• Enthusiasm for Helm's product and mission.

🏝️ Benefits

• Bonus + equity

• Unlimited PTO (with a mandatory minimum of 12 days)

• Computer + home office stipend

• 401(k) + matching

• Medical, dental, and vision insurance

• Autonomy and opportunities for career advancement

• Quarterly company meetings/offsites