The Role

The Director of Sales at Well-Oiled Operations is responsible for scaling a high-performance B2B sales engine that drives predictable, sustainable revenue growth.

You will lead and develop a healthy and effective sales team, partner with leadership to align sales strategy to business goals, optimize and continuously evolve the sales infrastructure, own and drive sales targets, and leverage technology to increase output per rep, improve forecast accuracy, and create scalable enablement across the organization.

You carry the number. You improve the machine.

What You’ll Do

Sales Leadership and Performance Architecture

• Own sales targets, forecasting accuracy, and overall sales performance

• Lead and develop sales managers and frontline contributors within a disciplined, high-accountability culture

• Design and scale onboarding, enablement, and performance systems that reduce ramp time and increase revenue per rep

• Standardize and continuously evolve playbooks, scripts, scorecards, and feedback loops using performance data

• Set quotas, manage capacity planning, address underperformance decisively, and ensure strong alignment between incentives and revenue outcomes

Sales Systems and Infrastructure

• Architect and continuously improve the end-to-end sales system across qualification, closing, partnerships, forecasting, and reporting

• Leverage technology to increase efficiency, improve decision-making, and drive higher revenue per rep

• Own CRM structure, pipeline hygiene, reporting integrity, and funnel diagnostics

• Build forecasting and capacity models leadership can rely on

• Identify and eliminate system bottlenecks that constrain growth

Performance Metrics and Reporting

• Own sales performance metrics, executive reporting, and KPI visibility across all sales teams

• Track and communicate core indicators including conversion rates, pipeline health, quota attainment, productivity, and revenue per rep

• Operate within a disciplined leadership cadence that includes weekly performance reporting, structured one-on-ones, executive communication, and active participation in company planning

What You Bring

• 5+ years of senior sales leadership experience at the Director level or above, with full ownership of revenue targets

• Demonstrated success building and scaling high-performing B2B sales teams while improving revenue per rep through systems and process innovation

• Strong command of forecasting, capacity planning, and performance management, with the ability to translate data into decisive action

• Experience implementing and optimizing sales infrastructure, including CRM systems, reporting frameworks, and technology-driven workflow improvements

• Executive-level communication skills with the ability to influence cross-functionally and drive clarity in a fast-paced growth environment

What Success Looks Like

Success in this role is measured by revenue performance and system maturity. Key indicators include:

• Consistent achievement or exceedance of revenue targets

• Increased revenue per rep without proportional headcount growth

• Improved conversion rates and measurable gains across key funnel stages

• High forecast accuracy and reliable, executive-ready reporting

• Strong quota attainment across managers and frontline contributors

• A disciplined, high-performance sales culture with strong engagement and retention

Compensation and Culture

• $200K+ OTE with uncapped earning potential and performance-based commission structure

• High-accountability, results-driven culture

• Opportunity to own and scale a critical growth function

We are looking for a systems-oriented sales leader who knows how to engineer performance, develop people, and turn pipeline into predictable revenue. If you bring operational rigor, strategic clarity, and a bias for leverage, 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