Sales Executive Assistant

Heartland Business Systems, LLC.; Little Chute, Northern (WI, KY); Hybrid; USD 70,000 - 100,000; Full time

Benefits offered by this job

Competitive compensation package

Growth opportunities

Work-life balance

Paid time off

Job summary

Heartland Business Systems in Wisconsin is seeking a Sales Executive Assistant to provide high-level administrative support to the CRO and Sales leadership. You will manage a dynamic calendar, coordinate complex travel, prepare communications, and handle confidential information with discretion.

The role emphasizes strategic partnership, independent judgment, and the use of AI to optimize business processes, with responsibilities spanning meetings, expenses, and executive communications.

Qualifications

• Bachelor's Degree or equivalent years of experience.
• 6+ years of administrative experience including 3+ years supporting Executive Leadership.
• Strong judgment on autonomous action with ownership and solutioning.
• Exceptional organization and time-management for multiple high-priority requests.

Responsibilities

• Partner with the CRO and Sales leadership, managing competing demands and supporting decisions.
• Manage an executive calendar with prioritization, scheduling, and gatekeeping.
• Coordinate internal/external meetings, leadership cadences, and sales forums.
• Plan and execute key sales meetings and post-meeting distribution.
• Coordinate complex domestic travel arrangements and logistics.
• Oversee expense management and timely approvals.
• Lead end-to-end executive and sales event planning.

Skills

Executive support

Calendar management

Travel coordination

Expense management

Event planning

AI in processes

Education

Bachelor's Degree or equivalent

Tools

Microsoft Office

Outlook

Excel

PowerPoint

Job description

Description

The Sales Executive Assistant provides high-level administrative and operational support in a fast-paced, dynamic environment. This role partners closely with the CRO and Sales leadership, serving as a trusted liaison across the Sales organization and broader HBS team. This individual exercises sound judgment, communicates effectively, and manages multiple priorities with a high level of organization and attention to detail. This individual operates with a high degree of independence, handles sensitive and confidential information with discretion, and thrives under pressure while supporting a wide range of executive-level activities.

Roles and Responsibilities/ Essential Functions:

• Serve as a strategic partner to the CRO and Sales leadership, exercising independent judgment to manage competing demands, anticipate needs, and support effective decision-making.
• Manage a highly dynamic executive calendar, including prioritization, strategic scheduling, and conflict resolution; act as a gatekeeper for the CRO's time by evaluating requests and aligning meetings with business priorities.
• Coordinate internal and external meetings, including recurring leadership cadences, cross-functional initiatives, and sales forums; ensure alignment, preparation, and follow-through.
• Plan and execute key sales meetings and communications, including monthly calls, agendas, content development, and post-meeting distribution.
• Coordinate complex domestic travel arrangements (flights, hotels, ground transportation) and align logistics across designated team members to ensure seamless execution.
• Oversee expense management for the CRO, including submission, review, and approval of expenses in a timely manner.
• Lead end-to-end event planning for executive and sales-level events (e.g., Quarterly Business Reviews, Sales Kick Offs), including logistics, vendor coordination, catering, communications, and materials.
• Leverage artificial intelligence (AI) to enhance business processes, improve operational efficiency, and drive continuous improvement.
• Support executive communications and presence, including managing professional social media activity in partnership with Marketing.
• Perform a wide range of administrative and operational tasks, including invoice processing, vacation approvals, performance review coordination, and executive meeting logistics.
• Serve as a back up for other administrative functions.

Requirements

How To Qualify

• Bachelor's Degree or equivalent years of experience
• 6+ years of administrative experience to include at least 3+ years of supporting Executive Leadership
• Strong judgment in determining when to act autonomously vs. when to escalation, with a bias toward ownership and solutioning
• Exceptional organization, prioritization, and time-management skills, with the capacity to manage multiple high-priority requests simultaneously
• Computer Skills: High Proficiency in Microsoft Office Suite, specifically Outlook, Word, Excel & Power Point.
• Maintain an outcome focused mindset
• Have strong prioritization skills
• Always be a team player
• Carry a professional attitude and respectful demeanor

Why HBS?

Heartland Business Systems is one of THE LARGEST technology VARs or Value-Added Resellers in the Midwest. Anything that happens with computers - we do it! We PRIDE ourselves on our Core Values of:

Performance - HBS is driven to achieve exceptional results in all aspects of our business.

Respect - HBS Team Members demonstrate personal integrity and professionalism when dealing with all internal and external contacts.

Innovation - HBS is passionate to serve our internal and external customers with innovative solutions to enhance their success.

Development - HBS is committed to developing ourselves and each other in ways that support and improve the performance of ourselves and our business.

Excellence - HBS takes great pride in all we do and strive for excellence always.

What you can expect from HBS:

• Competitive Compensation Package (may include, but is not limited to: bonus, incentive, commission, fair wage, retirement plans, and benefits with HSA-compatible plans)
• Growth Opportunities
• Community Involvement
• Personal Development
• Employee and Family Celebrations
• Green Initiatives
• Personal Time Off
• Work Life Balance
• Recognition and Awards

Day in and day out, you will be a part of a collaborative, innovative and award-winning team that will make you a better professional.

Heartland Business Systems is an Equal Opportunity Employer - Including Disabled and Veterans.