Remote Windows Deployment Jobs in Chicago, IL (NOW HIRING)

Welcome to Pioneer Square Brands, a dynamic and innovative company at the forefront of the consumer goods industry. Committed to delivering high-quality products, we take pride in our dedication to excellence, creativity, and customer satisfaction. With a diverse portfolio featuring renowned brands (Brenthaven, Gumdrop, and VAULT), our mobile technology accessories ensure our customers achieve successful technology deployments. Our team comprises passionate individuals united by a shared vision to shape the future of our industry. If you are seeking a challenging and rewarding position in a fast-paced environment where your ideas are highly valued, join us at Pioneer Square Brands and become an integral part of our exciting journey.

Our Core Purpose: We ensure mobile technology works so that people can focus on what matters.

Our Core Values:

• Genuine and Respectful
• Pride in Everything We Do
• Excellence through Innovation
• Obsessed with Customer Success

Pioneer Square Brands has a global footprint with office locations in High Point, North Carolina, and Manila, Philippines.

We are actively looking for a highly motivated and energetic professional with a positive attitude who desires to be part of our growing team. Competitive salaries and benefits, including profit sharing,await the successful candidate.

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Education Territory Manager North Central

Location: Remote (resides in IL, MN, WI, or IA)

About the Role:

The Education Territory Manager is a territory-focused, individual contributor role responsible for executing sales strategies and driving revenue and profitability for Gumdrop and Brenthaven in the education market. This position does not have direct people management responsibilities but works closely with inside sales to support territory performance.

Key Responsibilities:

Territory Strategy & Pipeline Development

• Build and execute a territory plan that targets school districts, education service districts (ESDs), resellers, and state-level buying groups
• Develop a healthy pipeline by driving outbound prospecting, responding quickly to inbound leads, and coordinating with channel partners
• Identify refresh cycles, funding windows, and device adoption trends (Chromebooks, iPads, Windows devices) to prioritize high-propensity accounts
• Map out the triangle offense for each of these strategic SDs

Direct District Engagement

• Lead all district-facing sales efforts: discovery calls, needs assessments, product demos, pricing discussions, and proposal delivery
• Build strong relationships with District Tech Directors, CIOs, IT staff, curriculum leads, and procurement teams
• Provide consultative guidance on protective cases, accessories, deployment planning, warranties, and lifecycle management

Channel Partner Management

• Work collaboratively with reseller partners to drive joint pipeline creation and close deals
• Conduct partner trainings, support deal registrations, align on pricing strategy, and share competitive intel
• Ensure partners have accurate product data, samples, inventory forecasts, and promotional materials

Deal Execution & Forecasting

• Own the full sales cycle from lead creation through close
• Prepare quotes, proposals, and RFP responses with accuracy and urgency
• Maintain weekly forecast accuracy and always keep CRM data clean, current, and complete
• Coordinate with operations on pricing, inventory, shipping timelines, and deployment requirements

Territory Relationship Building

• Build trusted, long-lasting relationships with district leaders, reseller reps, state education groups, and key influencers
• Attend regional conferences, technology fairs, ESD events, and district summits to grow brand presence and generate opportunities
• Serve as the face of the company across the territoryapproachable, reliable, responsive, and customer-obsessed

Market Intelligence & Competitive Awareness

• Track competitor products, pricing changes, and channel programs
• Identify new device trends (touchscreen adoption, iPad rollouts, rugged case requirements) to inform product planning
• Report feedback from the field to Product, Marketing, and Leadership to guide roadmap and demand forecasting

Cross-Functional Collaboration

• Partner with Product, Marketing, and Operations to improve samples, messaging, demand planning, and customer experience
• Work alongside with the Sales Enablement person to drive cohesive campaigns, outbound sequences, and district touch points
• Provide input to Marketing for district success stories, case studies, and content that will help accelerate future wins

Customer Experience & Post-Sale Support

• Ensure schools have exceptional service during and after the sale: tracking, deployment assistance, issue escalation, warranty understanding
• Proactively check in with districts post-deployment to secure renewals, refresh opportunities, and long-term loyalty
• Represent the companys values every step of the way

Performance Management & Results

• Consistently hit or exceed quarterly and annual revenue goals for EDU
• Achieve KPIs: pipeline creation, deal velocity, win rate, partner engagement, and forecast accuracy
• Maintain strong discipline around time management, territory planning, weekly activity levels, and follow-through

Additional Responsibilities

• Assist with special projects as needed
• Support cross-functional teams on ad hoc assignments

Qualifications:

• At least 5 years of experience selling successfully into the education market, with deep understanding of its unique customer dynamics in K12 Hardware Technology Resellers and Distributors
• Comfortability and confidence presenting to executive leaders and influencing strategic business decisions
• Excellent communication and presentation skills, capable of inspiring and connecting with diverse audiences
• Highly organized, skilled in territory mapping, pipeline reviews, and performance management discussions
• Strong data literacy, with experience analyzing reports
• Adept in different sales strategies and methodologies
• Familiar with Salesforce or similar CRM tools to track sales progress and streamline processes.
• Energetic road warrior, highly motivated to drive results in diverse markets
• Willingness and ability to travel up to 60% to engage with customers, partners, and team members in person

Competencies:

• A collaborative, results-driven mindset with a proven ability to meet and exceed revenue goals
• Demonstrated success in sales leadership, driving team performance and business growth
• Proactive execution of company priorities with strong ownership and accountability
• The ability to build and nurture relationships across teams, customers, and partners, both internally and externally
• Exceptional planning, analytical, and reporting skills, with a knack for turning data into actionable insights
• A keen eye for detail and outstanding organizational skills that ensure accuracy and consistency in every task

Success Indicators:

• Consistently meets quarterly and annual goals
• Grows year-over-year revenue across assigned states
• Expands footprint within top target districts
• Strong CRM accuracy and predictable forecasting
• Positive customer and partner feedback