Junior Sales Executive - Milwaukee, WI (Great Lakes Region)

About the position

We're building a sales team that turns prospects into evangelists. By leveraging AI for administrative tasks, we focus on what matters: genuine human connection with people who create unforgettable experiences. As we scale, we're hiring strategically in markets where you can meet prospects in their backyard, tap into established communities, and travel to nearby trade shows. We need competitive collaborators - salespeople who win by lifting others up, who understand that delivering value always pays off, just a matter of when. You'll own the full cycle: from qualification to close to advocacy. Success means hitting revenue targets while building compound growth through community presence and customer advocacy that makes your pipeline increasingly valuable.

Responsibilities

• Own full sales cycle, ramp to quota within 2 quarters, build self-sustaining pipeline through events and vertical relationships
• Source 25% of pipeline through strategic outbound, referrals, and AI workflows while qualifying with DRIVE methodology
• Optimize demo-to-close rates, manage disciplined pipeline, deliver accurate forecasts
• Develop deep knowledge in 2-3 event verticals, leverage AI tools to maximize relationship-building time

Requirements

• 1-3 years sales experience (SDR to early AE or career changer with transferable skills)
• Competitive nature: Seeks measured, recognized, rewarded performance
• Change-driven: Excited by new tools and processes, not frustrated
• Clear communicator: Matches tone from first-time owners to seasoned operators
• Well-traveled: Navigates new cities independently, seeks strangers to connect with, maintains distant relationships
• AI-native: Uses AI as thinking partner, not just writing assistant

Nice-to-haves

• HubSpot, Claude, or automation tool mastery
• Events/hospitality background
• SMB or vertical SaaS experience
• Trade show and hybrid selling experience
• Track record of 12+ months at/above quota

Benefits

• Fully covered health/dental/vision
• 401k match
• Commuter benefits
• Unlimited PTO
• 10 holidays
• Paid family leave