Delivery Support Specialist

Heartland Business Systems; Little Chute (WI); On-site; USD 45,000 - 65,000; Full time

Job summary

Heartland Business Systems in Wisconsin is seeking a Delivery Support Specialist to help coordinate day-to-day delivery team activities, schedule resources, and progress opportunities with multiple team leads and stakeholders.

The role emphasizes collaboration with Inside Sales, AR, and finance to monitor service intake, quote services, ensure accurate billing, and assist with SOWs and forecasting.

Qualifications

• 2+ years admin/office support incl. scheduling.

Responsibilities

• Collaborate with Inside Sales and AR to monitor service intake boards and new engagements.
• Monitor requests for presales support and assist delivery with resource assignment and scheduling.
• Quote services sold/supported by business units with accurate margins and descriptions.
• Monitor contract and license expirations and coordinate renewals or modifications.
• Create Statements of Work (SOW) per guidelines and assist with customization.
• Assist with quoting, forecasting and opportunity analysis to improve scheduling and planning.
• Troubleshoot billing issues and ensure accurate credits/rebills with AR.

Skills

Administrative support

Scheduling

Customer service

Communication

Organized

Team coordination

Education

Bachelor's degree or equivalent

Tools

ConnectWise Service Module

Job description

Position Summary

The Delivery Support Specialist role is primarily responsible for ensuring efficient and smooth day‑to‑day operations of the delivery team processes and projects. This individual works closely with multiple Team Leads, Solutions Consultants, and business units to schedule, coordinate, and help progress opportunities.

Job Type

Full‑time

Roles and Responsibilities / Essential Functions

• Collaborate with Inside Sales and Accounts Receivable (AR) departments to monitor the business unit service intake boards and new delivery service engagements.
• Monitor and respond to requests for presales support and work with the delivery team to assign resources. Provide scheduling and collaboration support.
• Quote services sold/supported by business units, where appropriate. Ensure accurate margin, pricing, and descriptions of product when quoting to clients.
• Monitor contract and license expiration dates sold/supported by delivery service team and coordinate with Sales to facilitate timely renewals, cancellations or service modifications.
• Create Statements of Work (SOW) that fit established guidelines and provide specialized support for SOWs needing customization or deeper technical scoping.
• Assist Business Unit Leaders with quoting, opportunity analysis and forecasting to improve resource scheduling and project planning.
• Troubleshoot billing errors and ensure accurate client‑facing credits and/or rebills with AR Team, as needed.
• Support accounting on service agreement setup and invoicing.
• Review accounting agreements for accuracy, where appropriate.
• Collaborate effectively with colleagues in Sales, Finance, and other business units.
• Provide innovative ideas on sales support process improvements and development of services.
• Assist with marketing activities and special projects as defined by the Operations Manager.
• Perform and support activities related to business‑unit–specific processes.
• Monitor weekly business unit timesheets for timely submission and accuracy. Assist in troubleshooting any issues or discrepancies that prevent proper submission.
• Participate in scheduled meetings with Leadership, as requested.
• Provide administrative or clerical support, as needed, for team.
• Attend team educational events to maintain a high‑level understanding of the technologies and services offered by the delivery teams.
• Cross‑train with other team members supporting different business units.

Requirements

Competencies

• Accountability: Accountability looks at the extent to which an individual is willing to accept responsibility.
• Communication: Ability to promote understanding through exceptional written, oral, interpersonal, and presentation skills.
• Customer Oriented: Customer orientation implies a desire to serve both external and internal clients by focusing effort on meeting the clients’ needs, understanding their concerns, and seeking to build trust.
• Energetic: Energy looks at how much force or stamina the individual can bring to the position.
• Friendly: Friendliness looks at the ability of the individual to behave in a beneficial, amicable, or favorable manner toward someone.
• Interpersonal: Interpersonal skills look at the ability of the individual to develop and maintain relationships with others.
• Organized: Organizational skills looks at the ability of the individual to be structured and methodical in working skills.
• Relationship Building: Relationship building looks at the ability of the individual to establish and maintain a good rapport and cooperative relationship with customers and co‑workers.

Required Experience

• 2+ years of administrative and/or office support experience including scheduling, planning, etc.
• 1+ years of experience utilizing a ticketing or service management platform to manage scheduling, assign tasks, monitor work progress, produce reports, and support operational research.

Preferred Experience

• 2+ years working as an inside sales representative, project manager/coordinator or business analyst.
• 1+ years in a customer service role.

Required Skills, Education and/or Certifications

• Bachelor’s Degree or equivalent experience.
• Proficiency in the use of Microsoft products including Outlook, Word, Excel, and PowerPoint.
• Effective communication skills for collaborating across teams and supporting operational alignment.

Preferred Skills, Education and/or Certifications

• Exceptional organizational and time‑management skills.
• Understanding of general accounting and profitability/margins.
• ConnectWise Service Module Certification.

Equal Opportunity Employer

Including Disabled and Veterans