Caleb Drolshagen

B.A., Political Science, University of Wisconsin-Madison. 15 years hiring/development experience includes sales reps and managers. Multiple award winner for driving performance across Retail, B2B, D2D. 15 years leading teams, target setting, coaching, scheduling, and driving performance over multiple locations and multiple industries.

Branch Manager - Bold North Roofing & Contracting

(2026-04 - 2026-05)

• Led efforts to recruit and onboard sales team to prepare for branch opening
• Built relationships and collaborated with vendors, suppliers, and manufacturers to establish presence of new branch
• Utilized Acculynx and Hail Trace to drive initial sales
• Drove Door to Door sales for temporary branch

Regional Manager - 1-800Hansons - Madison, Omaha, Sioux Falls

(2024-01 - 2026-04)

• Directed sales and operational performance across multiple territories (Madison, Omaha, Sioux Falls) including roofing, siding, windows, gutters, and bath
• Recruited, onboarded, and ensured compliance of Install Partners to support branch growth
• Opened new Madison branch and rebuilt Omaha branch, driving branch expansion and revenue growth
• Led lead planning and distribution to maximize sales opportunities and team productivity
• Developed and facilitated new hire training modules to enhance sales rep performance and accountability
• Coached and developed President's Club sales representatives, fostering a high-performance sales culture (2024, 2025)
• Achieved President's Club Award 2x (2024, 2025)
• 4.9 Branch Google Review Rating

Associate Director - AT&T - Wisconsin

(2021-08 - 2023-07)

• Managed sales and operational performance for 8 locations across Wisconsin, driving accountability across wireless and broadband sales
• Built and led diverse management team, hiring majority of store managers and assistant managers
• Coordinated outside sales (Door to Door Broadband, Business to Business phone calling) and sales events, utilizing Salesforce for lead generation and tracking
• Maintained professional documentation for coaching and performance evaluations
• Achieved market-leading audit compliance and third place in year-over-year performance in 2023
• Directed the training, development, and performance evaluation for managers, assistant managers, and sales reps

Store Manager - AT&T - Janesville & Madison, WI (Janesville, Madison East, Madison University)

(2013-08 - 2021-08)

• Summit Winner
• Hiring Circle Manager for Madison area
• Host of Tech Tuesday on NBC15 from 2017-2020
• Managed training, development, and performance evaluation for assistant managers and sales representatives
• Led prospecting and management of outside sales (Door to Door, phone calling) and sales events, leveraging Salesforce for lead generation
• Developed Assistant Manager Development Program to enhance leadership pipeline
• Achieved market-leading audit compliance and coached multiple Summit Winners and sales reps to management roles
• Created partnerships for high-impact sales events resulting in nation-leading performance

Assistant Store Manager - AT&T - Madison, WI

(2011-02 - 2013-08)

• Coached sales representatives to achieve sales targets and improve performance
• Assisted in hiring and training staff to support sales goals
• Managed prospecting and outside sales events (Door to Door, phone calling) to drive revenue growth
• Maintained documentation for coaching and performance evaluations
• Supported achievement of store sales targets across multiple product categories

B.A. - Political Science - University of Wisconsin-Madison