Chief of Staff

Location: Hybrid (DC, VA, MD)

About Herewith

Herewith is reimagining care through technology and improved care. We build technology that helps families, caregivers, and healthcare organizations deliver better outcomes while making care more accessible and affordable.

We're looking for a highly organized, AI-native Chief of Staff who enjoys building systems, improving operations, and driving execution. This role will initially focus on business operations and company administration while gradually expanding to lead strategic initiatives across the business.

Working closely with the investor and leadership team, you'll help ensure the company operates efficiently while enabling faster, better-informed decisions.

What You'll Do

Business Operations & Administration 

• Own day-to-day business operations and administrative functions.


• Manage vendor relationships, contracts, renewals, and procurement.


• Coordinate invoices, payments, and expense tracking with finance partners.


• Oversee relationships with payroll, benefits, legal, accounting, and other external service providers.


• Track company budgets and spending, providing regular visibility into operating expenses and key financial metrics.


• Improve internal processes, documentation, and operating cadence.


• Ensure important company initiatives stay organized and on schedule.

Strategy & Execution

• Lead high-impact cross-functional initiatives from planning through execution.


• Build executive dashboards, KPIs, board materials, business updates, and operating reviews.


• Use AI and data to analyze business performance and identify opportunities for improvement.


• Support GTM initiatives through market research, customer insights, pipeline analysis, and operational improvements.


• Partner with leaders across product, engineering, customer success, and operations to remove blockers and drive execution.


• Own special projects including partnerships, fundraising support, pricing analysis, and competitive research.

What We're Looking For

• Up to 10 years of experience in startups, operations, finance, GTM, product, or similar fast-paced environments.


• Experienced in organizational and project management skills.


• Strong analytical and problem-solving abilities.


• Excellent written and verbal communication.


• High attention to detail and strong follow-through.


• Comfortable managing multiple priorities with minimal direction.


• AI-native mindset, using modern AI tools to automate work, improve analysis, and increase productivity.


• Experience working with contracts, budgets, vendors, or business operations is a strong plus.

You'll Thrive Here If You

• Enjoy building order from ambiguity.


• Take ownership without waiting to be asked.


• Love improving how businesses operate.


• Balance strategic thinking with hands-on execution.


• Are excited to grow alongside a fast-moving startup.

Why Join Herewith

• Work directly with the leadership on the company's highest-priority initiatives.


• Build the operational foundation of a rapidly growing AI company.


• Gain exposure across operations, finance, GTM, product, and strategy.


• Accelerate your career through broad ownership and meaningful impact.