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:

https://github.com/ericosiu/beat-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

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