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

About the Company and Team:

Have you ever been to a wedding and really noticed everything in the space? The flowers, tables, lighting, and dance floor didn't just appear - dozens of vendors worked behind the scenes to create that magic.

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.

About the Role:

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:

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:

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-$110k (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