Build and run the weekly, biweekly, monthly, and quarterly operating rhythm across the leadership team.
Design and maintain dashboards, trackers, reporting structures, and workflows within ClickUp and HubSpot that create visibility into priorities, deliverables, deadlines, ownership, and execution risk.
Ensure alignment between marketing strategy and daily execution; GTM planning and outbound sales activity; delivery operations and account management; AI practice development and technical initiatives; and leadership priorities and operational follow-through.
Own the structure and facilitation of leadership meetings, cross-functional syncs, and operational reviews.
Drive high-priority initiatives from planning through execution.

5+ years in a Chief of Staff, operations, program management, or senior project management role, ideally in a technology services, SaaS, consulting, agency, or professional services environment.
Demonstrated success building and running operating cadences within founder-led organizations, including daily and weekly syncs, OKR tracking, and quarterly planning cycles.
Advanced proficiency with ClickUp (or equivalent platforms such as Asana or Monday with a willingness to adopt ClickUp.
Working proficiency in HubSpot CRM.
Experience with n8n or similar workflow automation tools preferred.
Experience coordinating distributed, outsourced, or fractional team members alongside full-time staff.
Strong written and verbal communication skills. You can draft a client email, prepare a board briefing, or write a meeting recap with equal fluency.

Chief of Staff

Key skills