VP of Operations (Well-Oiled Operations)
Acquisition›
📍Chicago, IL, US
Posted 2w ago · via ashby
Apply on ashby→Job Description
The Role
The Vice President of Operations at Well-Oiled Operations is responsible for building, evolving, and scaling the company-wide operating system, leadership structure, and execution model required to support the next stage of growth.
You will partner with the CEO to translate vision into execution, install clarity across every department, and ensure the business runs with precision, accountability, and efficiency.
You own how the business runs. You improve the machine.
What You’ll Do
Operational Leadership and Execution Architecture
Translate company vision into clear, measurable priorities across all departments
Install and lead the company’s execution rhythm across weekly, monthly, and quarterly cadences
Ensure every department operates with defined goals, ownership metrics, and clear performance standards
Lead and develop department heads within a high-accountability environment
Drive fast decision-making, clear communication, and consistent follow-through across the organization
Own the design and evolution of the company’s operating system, not just execution within it
Systems and Infrastructure (System Sync)
Architect and continuously improve the company’s operating system including SOPs, workflows, and automation
Build and maintain a centralized process library to ensure consistency and scalability
Implement dashboards and reporting systems that provide real-time visibility into performance
Identify and eliminate operational bottlenecks that slow execution or create confusion
Systemize core functions to reduce dependency on individuals
Team and Accountability Engine (Team Engine)
Design and evolve the organizational structure and leadership layer to support company growth
Ensure the right people are in the right seats at the right time as the business scales
Build leadership capability with clear expectations, communication standards, and accountability systems
Install KPI ownership and scorecards so every leader owns a number
Drive consistent meeting cadence and performance review rhythms across all teams
Create a culture where accountability is standard and underperformance is addressed quickly
Performance Metrics and Reporting (Precision Planning)
Own company-wide KPIs, dashboards, and performance visibility across all business units
Ensure all initiatives are directly tied to revenue, profitability, or strategic outcomes
Partner with Finance on forecasting, budgeting, and resource allocation
Use data to proactively identify risks, inefficiencies, and growth opportunities
Ensure leadership operates from clear numbers, not assumptions
Profitability and Resource Optimization
Own operational efficiency, margins, and resource allocation across the business
Ensure time, capital, and headcount are focused on highest ROI activities
Evaluate and prioritize initiatives based on impact to profit and scalability
Build a lean, high-output organization where growth does not require proportional cost increases
What You Bring
10+ years of senior leadership experience in Operations, Business Management, or Executive Execution, including 5+ years leading cross-functional teams
Proven success building and scaling operating systems across multi-department organizations
Proven experience designing and scaling a company-wide operating system, including org structure, leadership layers, and cross-functional execution
Experience operating within an 8-figure business, with direct responsibility for evolving systems, structure, and leadership through a phase of rapid growth
Strong command of planning, KPI design, forecasting, and performance management
Experience implementing SOPs, dashboards, and accountability systems that drive measurable outcomes
Business Model Experience
Experience operating in a B2B business model is required
Strong preference for experience in education, coaching, or program-based businesses with 6 to 12 month customer journeys
Experience supporting revenue models driven by webinars, events, or consultative sales processes
Experience serving SMB customers is strongly preferred
Leadership Profile
Ability to lead leaders, create clarity in complexity, and drive execution in fast-paced environments
High ownership mentality with a bias toward structure, systems, and results
Comfortable operating in growth-stage environments where speed and structure must coexist
What Success Looks Like
Success in this role is measured by execution, system maturity, and business performance. Key indicators include:
Company goals are consistently met through predictable, system-driven execution
Every department operates with clear ownership, KPIs, and accountability
Increased output and efficiency without proportional increases in headcount
Full visibility into performance through accurate, real-time dashboards
Improved margins through better prioritization and resource allocation
The business runs without constant CEO involvement, with leaders owning outcomes and systems driving execution
Compensation and Culture
$180K to $210K base salary plus performance-based compensation
High-accountability, systems-driven, results-oriented culture
Opportunity to build and scale the operating system behind a company that teaches operational excellence
We are looking for a systems-driven operator who has built and scaled operating systems at the company level, understands how B2B program-based businesses grow, and can design the structure required to support that growth. If you can turn complexity into clarity and execution into predictable results, we want to talk.
Benefits:
We offer a comprehensive, evolving benefits package designed to support your health, family, and wellbeing. Some key offerings:
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
* Benefits eligibility applies only to full-time roles.
ACQ Core Values:
Our core values are the heart and soul of this incredible company. The right person for this role will appreciate each of these values, personally subscribe to them, and understand why each is critical to having a great business.
Competitive Greatness
Be at your best when your best is needed. Enjoyment of a hard challenge. Those who have the drive to constantly improve, the superior intellect and long term commitment to see incremental improvements become compounding returns.
Sincere Candor
Have the self awareness to accurately perceive and communicate hard truths that improve others and self, the courage to do so, and the humility to accept them, even when it hurts. Nothing great can be built without feedback: internally or externally.
Unimpeachable Character
Be the type of person with whom people are always proud to associate, personally and professionally. We look for true alignment of thoughts, words, and actions towards a goal worth pursuing.
Details
- Department
- Portfolio
- Work Type
- remote
- Locations
- Chicago, IL, US
- Salary
- $180K - $210K
- Posted
- April 6, 2026
- Source
- ashby