SMB Account Executive - Chicago, IL (Great Lakes Region)
Goodshuffle Pro
$80,000 - $120,000 / year
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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.
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-$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
Benefits
- 401(k)
- paid time off
About this role
Goodshuffle Pro is looking for a Junior Account Executive to build their sales presence in the Chicago and Great Lakes region, selling software that helps event vendors manage their operations. You'd own the complete sales cycle—from finding prospects through outbound work and community events to closing deals and turning customers into advocates—with a goal of hitting quota within your first two quarters.
The role suits someone with one to three years of sales experience who thrives on competition, enjoys travel to trade shows and client sites, and gets energized by new tools and processes rather than intimidated by them. You'd need to develop expertise in two or three event verticals, source about a quarter of your pipeline through strategic outreach, and balance both hunting and farming. The company emphasizes genuine relationship-building over transactional selling, and they're explicit about what won't work here: if you prefer formal enterprise sales structures, want to specialize in only one part of the cycle, or work best in isolation, this isn't the fit.
The compensation is $80k–$110k OTE with a 60–75% base and 25–40% variable split, plus standard benefits including health coverage, 401k match, unlimited PTO, and paid family leave. This is a hybrid role in Chicago, and success depends on your willingness to travel independently, build relationships in a new market, and use AI as a genuine thinking partner.
This role's local market on JobMinglr
Pay for this role
$80,000 to $120,000 per year
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