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

Goodshuffle Pro

• $80K — $110K *
Business Services
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 1-3 years of sales experience, preferably as a Sales Development Representative (SDR) or early Account Executive (AE)
  • Competitive nature with a focus on measured, recognized performance
  • Comfortable with adapting to new tools and processes
  • Strong verbal and written communication skills tailored to different audiences
  • Ability to travel independently and connect with strangers in new cities
  • Proficient in using AI as a strategic tool rather than just a writing assistant

Responsibilities

  • Own the full sales cycle, ramping to quota within 6 months
  • Source 25% of pipeline through strategic outbound initiatives, referrals, and AI insights
  • Optimize the demo-to-close conversion rates and manage the sales pipeline effectively
  • Develop expertise in 2-3 verticals within the event industry using AI to enhance relationship-building
  • Deliver accurate sales forecasts and ensure disciplined pipeline management

Benefits

  • Fully covered health, dental, and vision insurance
  • 401k match
  • Commuter benefits
  • Unlimited paid time off (PTO)
  • 10 paid holidays
  • Paid family leave
Full Job Description
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

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