Account Executive - Waukesha, Wisconsin

Account Executive

Our client is a growing managed IT services provider helping small and mid-sized businesses improve their technology, strengthen cybersecurity, and modernize their operations. The company serves as a long-term outsourced IT partner, providing proactive support, cloud solutions, cybersecurity services, and strategic guidance to businesses across the Greater Milwaukee area.

The Account Executive is responsible for generating new business and building a book of clients from the ground up. This is a true hunter role centered around local networking, relationship building, outbound prospecting, and face-to-face sales. You will spend significant time in the Milwaukee business community, developing relationships with owners and senior decision-makers and converting those relationships into new managed service agreements.

This is a highly autonomous opportunity for someone who is entrepreneurial, confident in the field, and motivated by building a territory rather than inheriting an existing book of business.

You will own the full sales cycle, including:

• Attending local networking and business events
• Prospecting through phone, email, referrals, and outbound campaigns
• Building relationships with business owners and senior leaders
• Conducting discovery conversations to understand technology and cybersecurity needs
• Coordinating on-site IT and cybersecurity assessments
• Presenting customized managed service solutions
• Closing recurring monthly service agreements
• Building and managing a healthy pipeline of qualified opportunities

The qualifications:

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

Preferred backgrounds include:

• Managed IT services or 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–$90,000K
• 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