Chief Operating Officer (COO) / General Manager - AI-Native Operator

Single Grain•Los Angeles, CA

113d•$185,000 - $225,000•Remote

About The Position

This is a high-bar leadership role focused on transforming Single Grain into a highly disciplined, AI-native operating company. The position is responsible for designing and running the company's operating system, ensuring elite operational discipline, strong financial accountability, and high AI fluency across teams. The COO will serve as the organizational integrator, connecting strategy, execution, and accountability to ensure the company runs predictably, efficiently, and at high velocity. Single Grain is a digital growth company operating at the intersection of services, software, and AI, with offerings including an agency, the AI-powered content optimization platform ClickFlow, and the AI-powered performance marketing system Karrot. The company is actively evolving into a tech-enabled services company where software, automation, and services combine to create leverage.

Requirements

Helped scale a company with meaningful revenue or team growth
Installed operational systems that improved execution velocity
Demonstrated financial discipline and margin awareness
Used AI or automation to increase organizational productivity
Enforced operational standards across multiple teams
Comfortable enforcing operational discipline
Use AI tools regularly to improve workflows
Highly analytical and operationally rigorous
Prefer building infrastructure over managing bureaucracy
Strong bias toward execution
History of operational leadership across multiple organizations
Multiple promotions or increased responsibility in previous roles
Experience installing operational systems that improved execution
Experience leading organizations through technology transformation
Track record of operational improvements tied to measurable results
Candidates who have already helped scale a company are strongly preferred.

Nice To Haves

Not a traditional COO who manages meetings and maintains existing processes
Not primarily focused on maintaining existing operational structures, managing meetings and status updates, acting as an internal coordinator rather than a system builder, or avoiding AI or automation in workflows
Prefer building infrastructure over managing bureaucracy
Prefer theoretical strategy over operational execution

Responsibilities

Install and maintain the company’s operational infrastructure, including company-wide operating rhythms, weekly operational reviews, quarterly planning processes, leadership accountability frameworks, and KPI tracking systems.
Drive the transition toward an AI-native operating environment, including AI training and adoption programs, AI-powered workflows across departments, automation of repetitive operational work, and encouraging teams to build agentic workflows.
Enforce financial awareness and accountability across the organization, including budget discipline, contribution margin visibility, revenue forecasting accuracy, and cost control systems.
Ensure core processes are documented, operational standards are enforced, accountability mechanisms are in place, and teams consistently follow operating procedures.
Act as the integrator across leadership teams, coordinating cross-department initiatives, resolving operational conflicts, removing execution bottlenecks, and ensuring alignment between leadership teams.