Strategic Sales Exec Assistant | Calendar & Events Lead

HEARTLAND BUSINESS SYSTEMS LLC; Little Chute (WI); On-site; USD 70,000 - 110,000; Full time

Benefits offered by this job

Competitive compensation package

Growth opportunities

Community involvement

Personal development

Employee and family celebrations

Green initiatives

Personal time off

Work life balance

Recognition and awards

Job summary

Heartland Business Systems is seeking a Sales Executive Assistant to provide high-level administrative support to the CRO and Sales leadership. The role partners across the Sales organization and broader HBS team, handling confidential information with discretion and managing multiple priorities with precision.

You will calendar manage, plan executive meetings, coordinate complex travel, and drive process improvements using AI-enabled tools.

Qualifications

• Six plus years of administrative experience, including at least three years supporting executive leadership.
• Bachelor’s Degree or equivalent years of experience.
• Strong judgment on when to act autonomously vs. escalate, with ownership mindset.
• Exceptional organization and time-management to handle multiple high-priority requests.
• Proficiency in MS Office Suite (Outlook, Word, Excel, PowerPoint).

Responsibilities

• Serve as strategic partner to the CRO and Sales leadership, managing competing demands and supporting decision-making.
• Manage the CRO’s calendar with prioritization, scheduling, and conflict resolution.
• Coordinate internal and external meetings, leadership cadences, cross-functional initiatives, and sales forums.
• Plan and execute key sales meetings and communications, including agendas and post-meeting distribution.
• Arrange complex domestic travel (air, hotel, ground transportation) and align logistics.
• Oversee expense management for the CRO, including submission and approvals.
• Lead end-to-end event planning for executive and sales events (QBRs, Kick Offs).
• Support executive communications and social media presence with Marketing.
• Perform administrative tasks including invoicing, vacation approvals, and meeting logistics.
• Back up other administrative functions as needed.

Skills

Calendar management

Executive support

MS Office

Outlook

Travel coordination

Communication

Education

Bachelor’s Degree or equivalent

Tools

Microsoft Office Suite

Outlook

Word

Excel

PowerPoint

Job description

Heartland Business Systems is seeking a Sales Executive Assistant to provide high-level administrative support to the CRO and Sales leadership. The role partners across the Sales organization and broader HBS team, handling confidential information with discretion and managing multiple priorities with precision.

You will calendar manage, plan executive meetings, coordinate complex travel, and drive process improvements using AI-enabled tools.