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

Job Description

Job Description

Read This Before Applying

This is a high-bar leadership role.

We are not looking for a traditional COO who manages meetings and maintains existing processes.

We are looking for a builder of operational systems.

Your job is to turn Single Grain into a highly disciplined, AI-native operating company.

You will drive three outcomes simultaneously:

• Operational rigor

• Financial discipline

• AI-native organizational transformation

If your experience is primarily:

• Maintaining existing operational structures

• Managing meetings and status updates

• Acting as an internal coordinator rather than a system builder

• Avoiding AI or automation in workflows

then this role likely is not the right fit.

Strong candidates for this role typically have:

• 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

If that excites you, keep reading.

All candidates must complete the COO Operations Challenge before interview consideration.

Assessment link:
- claude/blob/main/challenges/ops -coo-009/brief.md

Build the Operating System for an AI-Native Growth Company

Single Grain is not a traditional agency. We are a digital growth company operating at the intersection of services, software, and AI.

Our portfolio includes:

Single Grain (Agency)

Enterprise digital marketing services including:

• SEO

• Paid media

• Creative

• CRO

• AI-driven growth strategy

Our clients come to us for serious, scalable growth , not basic marketing support.

ClickFlow

Our AI-powered content optimization platform.

ClickFlow helps companies unlock hidden growth from existing content by identifying high-impact SEO opportunities and improving rankings through systematic testing.

Karrot

Our AI-powered performance marketing system.

Karrot generates ads, landing pages, and campaign assets in seconds, enabling marketing teams to launch campaigns significantly faster.

We are actively evolving into a tech-enabled services company, where software, automation, and services combine to create leverage.

Our CEO Eric Siu hosts the Leveling Up podcast and co-hosts Marketing School , reaching millions of marketers every month.

But brand alone does not build great companies. Operational systems do . That’s where you come in.

The Role: AI-Native Operating Architect

This is not a traditional COO role.

This role is responsible for designing and running the operating system of the company.

You will ensure Single Grain operates with:

• Elite operational discipline

• Strong financial accountability

• High AI fluency across teams

The COO serves as the organizational integrator , connecting strategy, execution, and accountability.

Your job is to ensure the company runs predictably, efficiently, and at high velocity.

What You’ll Own Organizational Operating System

You will install and maintain the company’s operational infrastructure.

This includes:

• Company-wide operating rhythms

• Weekly operational reviews

• Quarterly planning processes

• Leadership accountability frameworks

• KPI tracking systems across teams

Execution must become systematic instead of reactive.

AI-Native Organizational Transformation

Single Grain expects AI fluency across the company.

You will 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

• Encouraging teams to build agentic workflows

The goal is simple:

AI handles repetitive work. Humans focus on strategic work.

Financial Discipline

You will enforce financial awareness and accountability across the organization.

This includes:

• Budget discipline

• Contribution margin visibility

• Revenue forecasting accuracy

• Cost control systems

Leaders must operate against clear financial scorecards.

Process Enforcement

Operational systems only work when they are followed.

You will ensure:

• Core processes are documented

• Operational standards are enforced

• Accountability mechanisms are in place

• Teams consistently follow operating procedures

The COO is responsible for execution discipline across the company.

Organizational Integration

You will act as the integrator across leadership teams.

This includes:

• Coordinating cross-department initiatives

• Resolving operational conflicts

• Removing execution bottlenecks

• Ensuring alignment between leadership teams

Your job is to ensure the company moves quickly and in the same direction.

What Success Looks Like

Within your first 12–18 months:

• ≥75% of the organization classified as adaptive AI users

• AI workflows widely adopted across departments

• Clear operational rhythms installed across the company

• SLA adherence ≥90% across delivery teams

• Improved financial visibility and budget discipline

• Faster execution across cross-functional initiatives

• Reduced operational bottlenecks

• Improved project completion rates

In short:

The company runs faster, cleaner, and more predictably because of the systems you built.

Who This Role Is Perfect For

You’ll likely thrive here if you:

• Have previously helped scale an organization

• Think in systems rather than tasks

• Are comfortable enforcing operational discipline

• Use AI tools regularly to improve workflows

• Are highly analytical and operationally rigorous

• Prefer building infrastructure over managing bureaucracy

• Have a strong bias toward execution

Who This Role Is Not For

This role is not a fit if you:

• Avoid operational conflict or enforcement

• Prefer maintaining existing systems instead of building new ones

• Avoid AI or automation

• Default to excessive meetings instead of operational clarity

• Prefer theoretical strategy over operational execution

We are looking for operators who build and run systems.

Our Hiring Process

After an initial screen, select candidates will complete an Operational Leadership Challenge.

This challenge evaluates:

• Operational system design

• AI transformation thinking

• Financial discipline frameworks

• Organizational leadership approach

• Strategic decision making

We will compare candidate responses with AI outputs for the same challenge.

Generic answers will not pass.

Ideal Candidate Signals

Strong candidates typically demonstrate:

• 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.

Benefits

• Medical, dental and vision insurance after your first month of employment

• 401k with 100% match up to 4% of your salary

• $50K life insurance policy paid 100% by the company

• 12 weeks of paid family leave after one year of employment

• Flexible unlimited PTO

• $100 utilities stipend ($50 per paycheck)

• $60 UberEats credit monthly

• MacBook, keyboard and mouse

• $500 work-from-home office reimbursement

Compensation:

• $185,000 - $225,000 DOE