Director of Sales

The Role

The Director of Sales at Well-Oiled Operations, an portfolio company, is a senior sales leader responsible for building, leading, and scaling a high performing sales organization that delivers predictable revenue growth. This role translates executive level goals into executable sales strategies, develops strong frontline leaders, and ensures disciplined execution across the entire sales funnel.

This is a hands-on leadership role suited for a growth stage organization. The Director of Sales owns team performance, sales execution, and operating rigor while partnering closely with Operations, Marketing, and Finance to ensure alignment, accountability, and scalability.

Who You Are

The ideal candidate is both a people leader and an operator. They are comfortable coaching managers, diagnosing performance gaps, implementing process improvements, and communicating clearly with executive leadership.

What You'll Do

Sales Leadership and Team Development

• Build, lead, and retain a high performing sales organization, including setters (SDRs) and closers (Business Consultants)
• Hire, onboard, train, and develop sales managers and individual contributors
• Establish clear expectations, performance standards, and accountability across the team
• Foster a collaborative, professional, and values aligned sales culture
• Provide consistent coaching and feedback through regular one on ones and performance reviews

Sales Strategy and Execution

• Translate executive level revenue goals into actionable sales plans and execution strategies
• Set and manage quotas, targets, and capacity planning across sales teams
• Ensure consistent execution of sales processes, scripts, and best practices
• Continuously evaluate and optimize the sales funnel to improve conversion, efficiency, and revenue predictability
• Conduct regular call audits and quality reviews to ensure sales excellence and adherence to standards

Performance Management and Metrics

• Own sales performance metrics and reporting across all sales teams
• Track, analyze, and communicate key KPIs including conversion rates, quota attainment, pipeline health, and productivity
• Ensure timely submission of weekly sales performance reports to executive leadership
• Partner with managers to address underperformance through coaching, redeployment, or corrective action when necessary

Cross-Functional Collaboration

• Partner with Marketing to align lead generation strategy, funnel quality, and campaign performance
• Collaborate with Operations and Finance on forecasting, headcount planning, and capacity modeling
• Maintain a strong understanding of customer needs, objections, and buying behavior and ensure insights flow throughout the organization

Compensation and Incentives

• Partner with Operations and Finance to manage and administer sales compensation plans
• Ensure accurate tracking and validation of commissions and incentives
• Provide performance insights and recommendations related to compensation effectiveness

Strategic Partnerships

• Oversee the Strategic Partnerships function and manage the partnerships sales representative
• Ensure partnerships are aligned with revenue objectives and operational priorities
• Track performance and ROI of partnership driven opportunities

Communication and Operating Cadence

Daily

• High priority sales issues communicated via Slack with the VP of Operations

Weekly

• Submission of end of week sales performance report by end of week
• Weekly one on one with the VP of Operations, prepared with insights and updates
• Weekly one on ones with direct reports

Ongoing

• Participation in weekly, monthly, quarterly, and annual leadership meetings as required

What You Bring

Required

• 4 plus years of senior sales leadership experience at the Director level or equivalent
• Proven experience building and managing high performing sales teams
• At least 2 years of B2B sales experience
• Strong understanding of sales metrics, forecasting, and performance management
• Excellent communication skills with the ability to influence across departments
• Experience working with remote or distributed sales teams
• Comfort operating in a fast paced, results driven environment

Preferred

• Experience in a growth stage or scaling organization
• Strong operational discipline with the ability to balance strategy and execution
• Ability to lead through ambiguity and drive clarity for others
• High ownership mindset with strong judgment and decision making skills

What Success Looks Like

Success in this role is measured by outcomes, not activity alone. Key indicators include:

• Consistent achievement or exceedance of revenue targets
• Sales managers meeting or exceeding performance expectations
• High percentage of sales team members achieving quota
• Improved conversion rates across key funnel stages
• Strong sales team engagement, retention, and cultural alignment
• Accurate, timely, and actionable sales reporting to leadership

Compensation and Culture

• $125K base with $200K+ OTE and uncapped earning potential with commissions structure
• High-accountability, results-driven culture
• Opportunity to own and scale a critical growth function