Director of Sales

Objective

The Director of Sales will lead both the Janitor Service (JS) and Complete Building Solutions (CBS) salesforces and is responsible for driving profitable revenue growth, leading and developing a high-performance sales organization, and executing a disciplined sales strategy aligned with City Wide’s mission of delivering comprehensive facility management solutions.

This leader owns top-line growth, pipeline health, sales process execution, and talent development while partnering cross-functionally with operations to ensure client retention and long-term profitability. The Director of Sales will build a culture of accountability, activity intensity, and consultative selling excellence.

Key Responsibilities

Revenue Growth & Market Expansion

·        Own and achieve annual and quarterly revenue targets.

·        Develop and execute a strategic sales plan aligned with company growth objectives.

·        Identify market expansion opportunities across verticals (Life sciences, commercial real estate, healthcare, education, industrial, etc.).

·        Monitor KPIs including pipeline value, close ratios, sales cycle length, margin performance, and customer acquisition cost.

·        Ensure consistent prospecting discipline and new business generation.

SALES LEADERSHIP & TEAM DEVELOPMENT

·        Recruit, hire, train, and coach sales executives and business development representatives.

·        Lead structured weekly pipeline reviews and Level 5 performance coaching sessions.

·        Drive accountability through performance metrics and individual development plans.

·        Establish a high-activity, high-integrity sales culture focused on consultative solutions.

·        Implement best practices in territory management and strategic account development.

Sales Process Excellence

·        Ensure consistent use of CRM and other sales enablement software for forecasting, pipeline tracking, and reporting .

·        Standardize prospecting methodologies, qualification frameworks, and closing strategies.

·        Lead formal sales meetings and business reviews.

·        Drive pricing discipline and margin protection.

·        Develop and refine value-based selling approaches.

Operational & Cross-Functional Alignment

·        Partner with operations leadership to ensure seamless client onboarding.

·        Align service delivery expectations with sales commitments.

·        Monitor client satisfaction and retention metrics.

·        Support major account renewals and contract negotiations.

Financial & performance management

·        Forecast revenue accurately and manage budget expectations.

·        Protect gross margins through a disciplined pricing strategy.

·        Analyze sales data to identify trends, gaps, and performance opportunities.

·        Provide executive-level reporting on sales performance and market dynamics.

Leadership Expectations

The director of sales is expected to:

·        Lead by example with high activity standards.

·        Foster a culture of integrity, accountability, and professionalism.

·        Develop future sales leaders within the organization.

·        Maintain a disciplined, metrics-driven approach to performance.

·        Represent City Wide in the community and marketplace with credibility and professionalism.

Measurements (Year)

Success in this role will be measured by:

·        New contracted revenue growth

·        Gross margin attainment

·        Pipeline growth and conversion rates

·        Sales team productivity metrics

·        Forecast accuracy

·        CBS client retention and satisfaction

·        Team engagement and retention

Requirements

QUALIFICATIONS

Required

• Bachelor’s degree in Business, Marketing, or related field (or equivalent experience).
• 10+ years of progressive B2B sales experience.
• 5+ years of sales leadership experience with direct team management with greater than 10 direct reports.
• Proven success managing a team responsible for $3M+ in ARR.
• Demonstrated experience in structured, process-driven sales organizations.
• Strong analytical and financial acumen.
• Proficiency with CRM platforms (Salesforce or equivalent).

Preferred

• Experience in facility services, route-based service industries, or outsourced business services.

• Experience leading sales teams in multi-service solution environments.

• Background in highly disciplined sales cultures similar to uniform, facility services, or commercial service industries.

• Experience with Microsoft Dynamics CRM

Benefits

COMPENSATION & BENEFITS

• Base salary of $140-160k DOE.
• Performance-based bonus structure with OTE of $250k.
• 3% Safe Harbor Employer 401 (k) contribution.
• $750/month company allowance towards Medical, Dental, Vision, and Life Insurance.
• $625/month vehicle allowance.
• Generous Holiday & PTO.