SMB Account Executive - Chicago, IL (Great Lakes Region)

Sales Representative

The events industry Goodshuffle powers runs on passion and determination. These small businesses have managed operations with spreadsheets at best, memory at worst. We believe they deserve tools that match their dedication to creating life's most memorable moments.

Our mission: bring joy to the business of events.

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.

Core responsibilities include:

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

Non-negotiables include:

• Early career: 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

You'll have an edge with:

• 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

You might thrive elsewhere if you:

• Prefer formal sales cultures or complex enterprise deals
• Want to specialize in hunting or farming, not both
• Want to be the 50th rep, not the 5th
• Work best in isolation
• Clock in/out rather than own outcomes
• Save feedback for annual reviews

Compensation:

• OTE: $80k-$120k (60-75% base / 25-40% variable)
• Geography and experience determine the final offer

Benefits: Fully covered health/dental/vision, 401k match, commuter benefits, unlimited PTO, 10 holidays, paid family leave