Account Executive

Intelligent Conversations; Milwaukee (WI); Hybrid; USD 70,000 - 100,000; Full time

Job summary

Midwest IT is seeking a high-activity sales professional with 3+ years of proven success prospecting into mid-market accounts, identifying key stakeholders, and securing initial conversations that lead to new business opportunities.

You are resilient, coachable, and detail-oriented, able to work remotely while spending 2 days a week in the market. Experience with consultative and solution selling in technical/software contexts is helpful as we grow our client base.

Qualifications

• 3+ years of proven success prospecting into mid-market accounts.
• Identify key stakeholders and secure initial conversations.
• Experience with consultative or solution selling is helpful.
• Comfort with remote work and 2 days/week in-market.

Skills

Prospecting

Mid-market

Stakeholder mapping

Consultative selling

Tech/software sales

Job description

You must have 3+ years of proven success prospecting into mid-market accounts, identifying key stakeholders, and securing initial conversations that lead to new business opportunities. You are resilient, coachable, and consistent in your outreach activity. You understand that solid research and thoughtful questions lead to great sales opportunities—and you love the challenge of finding creative ways to engage the market and start new conversations.

You are a self-starter, accountable, driven, detail oriented, ethical, hard-working, personable, rejection proof, and work well independently. You are comfortable on the phone, structured and organized, persistent without being pushy, and able to communicate value with clarity and confidence. Your ideal next position is with a company that values your development, invests in your success, and provides a competitive compensation package for someone who loves the art of prospecting.

This high-activity, top-of-funnel role is key to our growth strategy. Experience with consultative selling, solution selling and technical/software sales experience is helpful. Please note that while this role works remotely, you will spend 2 days a week prospecting in the market.

Midwest IT has been empowering small to mid-size businesses with exceptional IT services since 2005. With a deep commitment to long-term partnerships, they’ve built a reputation for trust, technical expertise, and delivering real business results. The team thrives on being proactive advisers in today’s fast-moving tech landscape, offering top-tier support and robust cybersecurity solutions that evolve with the threats their clients face.