VP of Operations (Well-Oiled Operations)

Acquisition.com • Chicago, IL

3d • $180,000 - $210,000

About The Position

The Role
Our portfolio company Well-Oiled Operations builds systems that scale for teams, clients, and leaders who want to grow. We’re hiring a Vice President of Operations to lead the execution engine behind that mission, ensuring the company runs with clarity, consistency, and control as we scale.
This is not a maintenance role. It’s a mandate to translate vision into systems, align every department around measurable outcomes, and turn complexity into structure that drives growth and profitability.
If you think in frameworks, thrive on accountability, and love building an organization that runs itself, keep reading.
Who You Are
A strategic operator who turns ideas into execution, outcomes into systems, and systems into scalable growth.
Experienced in leading cross-functional teams, aligning Marketing, Sales, Customer Success, Finance, and Operations under one clear operating rhythm.
Decisive, data-driven, and disciplined, with a deep understanding of how process, people, and performance interact.
A leader of leaders who builds trust through clarity, accountability, and consistent follow-through.
A builder who thrives on simplifying the complex, creating order from chaos, and executing with precision.

Requirements

• 10+ years of progressive leadership in Operations, Business Management, or Executive Execution, including 5+ years leading cross-functional teams.
• Proven success scaling multi-department organizations and driving measurable improvement in efficiency, profitability, and performance.
• Experience partnering directly with executive leadership to align company goals, people, and systems.
• Executive presence with calm, confident decision-making under pressure.
• A leadership style defined by clarity, accountability, and connection.
• Thrives in fast-paced, entrepreneurial environments that demand both structure and speed.
• Proficiency with CRM, project management, and analytics tools (e.g., HubSpot, Slack, Monday.com, or similar).
• Strong analytical, financial, and systems-design acumen.
• Ability to build reporting frameworks, design KPIs, and drive execution through data.
• Must be able to work CST hours.

Nice To Haves

• Based in the Milwaukee or Chicago area (HQ in Chicago with two live events per month).
• Occasional travel for leadership sessions and company events.

Responsibilities

• Translate Vision into Execution
• Partner with the CEO to operationalize the company’s strategic priorities into clear, measurable goals.
• Build the company’s annual and quarterly planning framework — ensuring every department is aligned and accountable.
• Lead cross-functional operating rhythms (weekly, monthly, quarterly) that drive execution and transparency.
• Connect strategy to systems, metrics, and daily actions across all teams.
• Build and Optimize Systems
• Architect scalable processes across all departments to support rapid growth without losing quality.
• Implement company-wide SOPs, reporting structures, and performance frameworks.
• Oversee the design and improvement of workflows, dashboards, and automation tools that enhance productivity.
• Continuously evaluate and refine systems for efficiency, clarity, and scalability.
• Lead and Develop the Team
• Manage and mentor department leaders across Operations, Finance, and People.
• Build an accountable leadership culture that emphasizes ownership, communication, and execution.
• Oversee recruiting, onboarding, and training systems that ensure the right people are in the right roles.
• Serve as a stabilizing force - providing clarity and calm during periods of growth or change.
• Drive Profitability and Performance
• Own company-wide efficiency, margin, and resource utilization targets.
• Collaborate with Finance on forecasting, budgeting, and performance reporting.
• Use data to identify bottlenecks, anticipate risks, and make operational decisions proactively.
• Ensure every initiative supports growth, profitability, and long-term sustainability.
• Operational Excellence and Reporting
• Establish KPI frameworks that make performance visible, actionable, and accountable.
• Build dashboards that provide real-time visibility into execution across all business units.
• Create an operating system that scales — one that leaders trust, teams understand, and data validates.
• Maintain a balance between speed and precision, ensuring decisions are both informed and executed quickly.

Benefits

• Flexible Unlimited Paid Time Off and Company-wide Holidays
• Employer sponsored Medical, Dental, & Vision plans
• $1,950 annual Employer HSA contribution
• FSA options including dependent care
• Employee assistance program and mental health resources
• Employer match program for 401(k), eligible for both Traditional and Roth accounts
• $1,200 annual wellness reimbursement through JOON that supports health, family care, pet care, fitness, and more!
• For local or visiting team members, enjoy access to a state of the art gym at our HQ in Las Vegas

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed