AI-Native Chief of Staff & Operations Architect

Herewithinc; Washington (District of Columbia); Hybrid; USD 140,000 - 210,000; Full time

Job summary

Herewith is seeking a highly organized, AI-native Chief of Staff to optimize operations, administration, and execution in a fast-moving startup. You will build scalable systems, improve processes, and enable faster, better-informed decisions with leadership.

Collaborating with product, engineering, and finance, you’ll drive cross-functional initiatives, dashboards, and strategic projects while shaping the company’s operational foundation for growth.

Qualifications

• Up to 10 years of experience in startups, operations, finance, GTM, or similar fast-paced environments.
• Strong organizational and project management skills.
• Excellent written and verbal communication.
• High attention to detail with strong follow-through.
• Comfortable managing multiple priorities with minimal direction.
• AI-native mindset using modern AI tools to automate work and improve analysis.

Responsibilities

• 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.
• 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.

Skills

Organizational skills

Project management

Analytical thinking

Written and verbal communication

Attention to detail

Multi-tasking

AI-native mindset

Job description

Herewith is seeking a highly organized, AI-native Chief of Staff to optimize operations, administration, and execution in a fast-moving startup. You will build scalable systems, improve processes, and enable faster, better-informed decisions with leadership.

Collaborating with product, engineering, and finance, you’ll drive cross-functional initiatives, dashboards, and strategic projects while shaping the company’s operational foundation for growth.