Sales Executive Assistant in Brookfield, Wisconsin at Heartland Technology Group

Position Summary:

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.

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 escalate, 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. Choose HBS today!

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