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

Goodshuffle; Chicago (IL); On-site; USD 80,000 - 110,000; Full time

Benefits offered by this job

Health benefits

401k match

Commuter benefits

Unlimited PTO

10 holidays

Paid family leave

Job summary

Goodshuffle is expanding its sales team in the United States with a role that covers the full cycle from qualification to close and ongoing advocacy. You will build a self-sustaining pipeline through events and strategic outbound while leveraging AI tools to optimize administrative tasks and relationship-building with wedding and events professionals.

The ideal candidate has 1–3 years of sales experience, strong communication, and a willingness to travel to nearby trade shows.

Qualifications

• 1-3 years sales experience (SDR to early AE)
• Excellent communication and relationship-building skills
• Comfort with AI-assisted workflows and tools
• Willingness to travel to local trade shows and events

Responsibilities

• Own full sales cycle from qualification to close and advocacy
• Source 25% of pipeline through strategic outbound and referrals
• Improve demo-to-close rates and maintain a disciplined pipeline
• Develop deep knowledge in 2–3 event verticals and leverage AI for efficiency

Skills

Sales experience

Strong communication

AI tools familiarity

Networking at events

Tools

HubSpot

Claude

Automation tools

Job description

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.

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 your 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