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Director of Business Development and Sales

Winter Services Inc
Milwaukee, WI Full Time
POSTED ON 4/3/2026
AVAILABLE BEFORE 6/28/2026
The Director of Business Development is responsible for leading and scaling the Business Development function to drive sustainable pipeline growth and strategic market expansion. This role oversees the Business Development team and owns the strategy, execution, and performance of lead generation, prospecting, and early-stage deal development. The Director partners closely with Sales, Marketing, and senior leadership to align business development efforts with company growth objectives, ensuring a consistent, high-quality pipeline that supports revenue goals. This role combines strategic planning, team leadership, and hands-on optimization of processes, tools, and metrics.

Duties and responsibilities:
  • General Responsibilities
    • Oversees Business Development strategy and leads the Business Development Sales Team.
    • To report all sales results to Operations Leader and Executive Leadership Team.
    • To complete all required paperwork in a timely and efficient manner.
    • To ensure daily company sales activities are working towards achieving company KPIs which support growth and profitability benchmarks.
    • Ability to take direction from and assist Executive Leadership Team in company macro planning.
 
  • Sales Responsibilities
    • Implement a consistent new-business sales strategy process for all divisions to allow for transparency and reporting on KPI’s across brick-and-mortar branches in 6 states as well as a nationally subcontracted division.
    • Develop new business sales and individual activity KPIs to ensure maximum efficiency in the new business sales process.
    • Fully utilize all available sales tools to their fullest extent including but not limited to Salesforce, ZoomInfo, CoStar and LoopNet.
    • Partner with platform leadership, regional and branch managers to track and report on weekly sales activity and progress toward goals through Salesforce and other available tools.
    • Assist with complex RFPs and contracts to ensure verbiage is in alignment with company standards and within legal compliance for type of jobs being performed (Federal, Municipal, Local, etc…)
    • Ensure a smooth transition process for new customers to move from New Business Development to Account Management.
    • Develop and continually evaluate new business sales compensation plans to ensure consistency and market equality.
    • Prepare marketing materials and/or specific presentation materials to assist in educating customers on larger bids or future pipeline opportunities.
    • Partner with Marketing to ensure social media and other content messaging is timely and appropriate for the impending seasons by geography.

Goals and Objectives:
  • Increase overall sales while maintaining margins and profitability.
  • Attends, contributes, and participates actively in all required company meetings.
  • Manage and maintain positive relationships with team at all levels within the company.
  • Implement and enforce relevant company policies and standard operating procedures.
  • To set personnel performance goals and objectives annually.
  • Actively participate in personal self-improvement by reading and participating in self-motivation and goal setting programs.
  • To continually improve knowledge and understanding of macro company’s operations.
  • To continually improve organization and efficiency with regards to his/her responsibilities.
  • Continually maintain or improve morale of company partners.
  • Mentor partners to reinforce company culture and vision.
  • Reinforces through performance and example the company ‘mission statement’.

Qualifications:
  • Bachelor’s degree in Business, Landscape Management, Horticulture, or related field.
  • 5-7 years in sales leadership experience in the landscaping and snow industry.
  • Strong understanding of snow removal, landscape maintenance, enhancements, irrigation, and construction operations at scale.
  • Proven track record of managing Business Development teams and sales deliverables across multiple locations in both a landscaping and snow environment.
  • Strong financial acumen and associative math skills with experience in sales forecasting, budgeting, and P&L accountability.
  • Strong leadership skills with a focus on a consistent process, team development, KPIs, and process improvement.
  • Proficiency with Salesforce CRM management, ZoomInfo, CoStar and LoopNet.
  • Familiarity with industry systems such as Aspire, LMN, BOSS, Viaesys, Yeti, SitePhotos or other landscape and snow specific business management software.
  • Strong proficiency in Microsoft Office Suite (Word, Excel, PowerPoint, Outlook),
  • Ability to perform site “take-offs” and prepare complex bid responses in alignment with RFPs.
  • Creates energy and motivation in self and team with the ability to lead and participate as appropriate.
  • Confident in presentation, and able to influence and persuade others even when outside immediate area of comfort/responsibility.
  • Self-starting, self-reliant and resilient to pressure.
  • Excellent communication, collaboration, and problem-solving abilities.
  • Ability to work on the business, not just in it (strategic focus).

Salary.com Estimation for Director of Business Development and Sales in Milwaukee, WI
$184,193 to $227,357
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