ashby

Director of Sales (Well-Oiled Operations) @ Acquisition

Chicago, IL (Remote)RemoteFull-timePosted 75 days ago

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About this role

The RoleThe 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 DoSales Leadership and Performance ArchitectureOwn 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 InfrastructureArchitect 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 ReportingOwn 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 Bring5+ 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 LikeSuccess 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 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 GreatnessBe 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 CandorHave 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 CharacterBe 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.

Skills

PortfolioWell-Oiled Operations

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Director of Sales (Well-Oiled Operations) at Acquisition | ResuMinder Jobs