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Heartland Business Systems
Heartland Business Systems
501 – 1,000 Employees
ConsultingEducationHealthcare
Heartland Business Systems is an IT consulting and cybersecurity provider that helps organizations connect technology decisions with business priorities. Its services span cloud solutions, data center management, managed IT, application development, AI and analytics, and cybersecurity risk assessments. HBS works with clients across consulting, healthcare, and education to modernize operations, support collaboration, improve resilience, and protect critical data, systems, and people through tailored technology programs.
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Executive Assistant to CRO and Sales Leadership

Provide high-level administrative and operational support to the CRO and Sales leadership team at Heartland Business Systems, a Midwest technology value-added reseller. Coordinate calendars, meetings, travel, expenses, communications, and sales events.

USUnited StatesWIWisconsinHybridFull-timeMiddleSeniorEnglish RequiredSales

Description

  • Partner strategically with the CRO and Sales leadership team
  • Own the CRO’s executive calendar, including prioritization, scheduling, conflict resolution, and access management
  • Coordinate internal and external meetings, leadership routines, cross-functional initiatives, and sales forums
  • Organize monthly sales meetings and related communications, including agendas, content preparation, and follow-up distribution
  • Arrange complex domestic travel, including air travel, accommodations, and ground transportation
  • Manage the CRO’s expense process from submission through review and approval
  • Direct end-to-end logistics for executive and sales events, including vendors, catering, communications, and materials
  • Apply artificial intelligence tools to improve business processes and operational efficiency
  • Assist Marketing with executive communications and professional social media activities
  • Handle administrative and operational responsibilities such as invoice processing, vacation approvals, performance review coordination, and executive meeting logistics
  • Provide coverage for additional administrative functions as needed

Requirements

  • Bachelor’s degree or equivalent professional experience
  • At least six years of administrative experience, including three or more years supporting executive leaders
  • Sound judgment when deciding whether to act independently or escalate an issue
  • Exceptional organizational, prioritization, and time-management abilities
  • Capacity to manage several high-priority requests at once
  • Advanced proficiency with Microsoft Office, especially Outlook, Word, Excel, and PowerPoint
  • Results-oriented approach to work
  • Strong ability to prioritize competing demands
  • Collaborative, team-oriented mindset
  • Professional and respectful demeanor

Benefits

  • Competitive compensation package that may include bonuses, incentives, commissions, fair wages, retirement plans, and HSA-compatible benefits
  • Opportunities for career growth
  • Community involvement opportunities
  • Personal development support
  • Employee and family celebrations
  • Green initiatives
  • Paid time off
  • Work-life balance
  • Recognition and awards
  • Collaborative, innovative, award-winning team environment

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