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VP of Operations (Well-Oiled Operations) at Acquisition.com. Remote Location: Chicago, IL (Remote). The Role. The Vice President of Operations at Well-Oiled Operations is responsible for building, running, and scaling the operating system that powers the company and reflects the exact systems we teach our clients.. 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. 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 optimize org structure to ensure the right people are in the right seats at the right time. 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. 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 adoption, 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 understands how B2B program-based businesses scale and who can build the structure, accountability, and systems 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.