District Sales Leader - Annapolis & Howard County

Chesapeake Beverage Co.; Annapolis, Northern (MD, KY); Hybrid; USD 80,000 - 95,000; Full time

Benefits offered by this job

3 Medical Plans

Dental

Vision

HSA with employer match

401(k) with company match

Job summary

Chesapeake Beverage Co. is seeking a District Sales Manager to lead a team of Sales Representatives across Annapolis and Howard County. This field-based leadership role focuses on coaching, growing distribution, strengthening customer relationships, and executing our priorities in the market.

You will spend time in the field with your team, analyze data to identify opportunities, and drive performance. Compensation includes $80K-$95K with commission plus a robust benefits program.

Qualifications

• 5+ years in sales with at least 2 years in leadership.
• Bachelor’s degree in Business/Marketing or related field preferred.
• Beverage alcohol industry experience strongly preferred.
• Knowledge of three-tier beverage distribution system is a plus.
• Demonstrated ability to lead, coach, and hold a sales team accountable.
• Strong business judgment and data-driven decision making.
• Excellent communication and relationship-building skills.

Responsibilities

• Lead, coach, and develop a team of Sales Representatives to achieve sales, volume, distribution, and profitability goals.
• Spend time in the field coaching alongside your team and identifying opportunities to improve execution.
• Hold regular one-on-ones and team meetings to set expectations, review results, provide feedback, and keep the team focused on priorities.
• Set performance goals and use KPIs and sales analytics to recognize successes, identify gaps, and develop action plans.
• Partner with HR in recruiting, onboarding, performance management, and development of sales talent.
• Develop and execute district sales plans, promotions, and initiatives.
• Partner with Sales Representatives to identify account opportunities, improve route strategies, and expand product distribution.
• Maintain strong relationships with key customers and identify opportunities to grow existing and new business.
• Stay current on market conditions, competitive activity, industry trends, and category opportunities.
• Step in to support open territories and ensure continuity during territory transitions.
• Build productive, long-term relationships with key accounts throughout the district.
• Conduct customer business reviews and help develop strategies that support mutual growth.
• Coordinate supplier market visits, surveys, and ride‑withs in partnership with Business Managers and other internal teams.
• Address customer concerns quickly and professionally.
• Ensure sales programs and priorities are executed consistently throughout the district.
• Review and approve timekeeping and sales compensation information accurately and on time.
• Reinforce company policies, safety expectations, and operating standards.
• Work collaboratively across Sales, Operations, HR, and other functions to solve problems and deliver results.

Skills

Leadership

Sales Management

Coaching

CRM

Microsoft Office

Driving

Education

Bachelor’s degree in Business/Marketing

Tools

CRM systems

Sales tracking systems

Job description

Chesapeake Beverage Co. is seeking a District Sales Manager to lead a team of Sales Representatives across Annapolis and Howard County. This field-based leadership role focuses on coaching, growing distribution, strengthening customer relationships, and executing our priorities in the market.

You will spend time in the field with your team, analyze data to identify opportunities, and drive performance. Compensation includes $80K-$95K with commission plus a robust benefits program.