Account Executive - Waukesha, Wisconsin

Job Description

Job Description

THE COMPANY

Our client is a growing managed IT services provider helping small and mid-sized businesses strengthen their technology, improve cybersecurity, and operate more efficiently.

Serving companies throughout the Greater Milwaukee area, the team acts as a long-term outsourced IT partner, delivering proactive IT support, cloud solutions, cybersecurity services, and strategic technology guidance. The company is known for building lasting client relationships and helping businesses stay secure, productive, and ahead of evolving technology needs.

THE JOB

The Account Executive will be responsible for generating new business and building a book of clients from the ground up. This is a true hunter role focused on local networking, relationship building, outbound prospecting, and face-to-face sales.

You’ll spend significant time in the Milwaukee business community developing relationships with business owners and senior decision-makers, identifying technology challenges, and converting those relationships into recurring managed service agreements. This is a highly autonomous opportunity for someone who enjoys being in the field, creating their own opportunities, and building a territory rather than inheriting an established book of business.

Key Responsibilities

• Build new business through local networking, referrals, cold outreach, and targeted prospecting
• Attend networking events, business associations, and other local community events
• Develop relationships with business owners, executives, and senior decision-makers
• Conduct discovery conversations around IT infrastructure, cybersecurity, cloud, and business technology needs
• Coordinate on-site IT and cybersecurity assessments
• Present customized managed service solutions and recommendations
• Manage opportunities from initial outreach through proposal and close
• Close recurring monthly managed service agreements
• Build and maintain a healthy pipeline of qualified opportunities

THE QUALIFICATIONS

• 2+ years of face-to-face B2B sales experience
• Proven success generating net-new business and developing a territory
• Experience building pipeline through networking, referrals, and outbound prospecting
• Confidence selling directly to business owners and senior-level decision-makers
• Comfortable attending frequent in-person networking and business events
• Ability to independently manage the full sales cycle
• Strong closing skills and confidence asking for meetings, commitments, and next steps
• Located within a reasonable distance of the Greater Milwaukee area

Preferred backgrounds include:

• Managed IT services / MSP sales
• Telecom or managed communications
• Managed print services
• Cybersecurity or cloud solutions
• Other recurring, service-based B2B solutions
• Experience selling to small and mid-sized businesses is strongly preferred

 THE BENEFITS

• Base salary: $50,000–$75,000, depending on experience
• Year 1 OTE: $85,000–$90,000
• Year 2 earning potential: $115,000–$125,000+
• Uncapped commission
• Company vehicle provided
• Medical, dental, and vision insurance
• 401(k)
• 15 days of paid time off
• Company-funded sales tools
• Paid networking memberships and business development expenses