Junior Sales Executive - Chicago, IL (Great Lakes Region)
Goodshufflepro is dedicated to transforming the events industry by providing innovative tools for small businesses. The Junior Sales Executive will own the full sales cycle, focusing on building relationships and hitting revenue targets while leveraging AI for efficiency.
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
Skills
- 1-3 years sales experience (SDR to early AE or career changer with transferable skills)
- Seeks measured, recognized, rewarded performance
- Excited by new tools and processes, not frustrated
- Matches tone from first-time owners to seasoned operators
- Navigates new cities independently, seeks strangers to connect with, maintains distant relationships
- Uses AI as thinking partner, not just writing assistant
- 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
Company Overview