Chief Of Staff (AI)

TL;DR

Chief of Staff (AI): Serving as a strategic operator and force multiplier for the CEO and leadership team with an accent on cross-functional execution, executive communication, and AI-enabled operations. Focus on driving high-priority initiatives, managing investor relations, and building scalable AI-augmented workflows to improve organizational speed and discipline.

Location: Must be based in the USA (Fully remote)

Salary: $175,000–$225,000

Company

hirify.global is a Series A startup transforming health insurance with Dynamic Copay solutions, providing infrastructure for health insurance payors to offer simpler, high-value care.

What you will do

• Drive high-priority cross-functional initiatives including strategic partnerships and operating-process improvements.
• Own the consolidation of executive narratives for Board meetings and investor relations materials.
• Champion AI adoption by building workflows, prompts, and automations across sales, finance, and product teams.
• Partner with the VP Finance on KPI reporting, scenario analysis, and enterprise deal execution.
• Facilitate leadership team rhythms, decision logs, and company offsite planning.
• Reinforce a high-trust, high-accountability operating culture as the company scales.

Requirements

• 4–7+ years of high-performance operating experience in startups, strategy, consulting, or investment banking.
• Strong analytical skills with comfort in financial models, KPI dashboards, and pipeline analysis.
• Exceptional written and visual communication skills for Board decks and strategic memos.
• Deep hands-on AI fluency with a track record of turning recurring work into repeatable AI-assisted processes.
• Must be based in the USA.
• Healthcare experience is strongly preferred.

Culture & Benefits

• Competitive total rewards package including equity.
• Comprehensive medical, dental, and vision insurance.
• 401(k) plan with company matching.
• Unlimited PTO with a mandatory 12-day minimum.
• Computer and home office stipend provided.
• High-growth environment with significant autonomy and career development opportunities.