Mid-Market Account Executive - Chicago, IL

Waitwhile

1d•$88,000 - $116,900•Remote

About The Position

As a Mid Market Account Executive at Waitwhile, you’ll own the full sales cycle from prospecting and discovery to negotiation and close. You’ll focus on mid market customers across key industries like retail, finance, government, education, and healthcare, and play a key role in shaping the next stage of Waitwhile’s growth story. You’ll work closely with Marketing, Sales, and Customer Success to build pipeline, run tailored demos, and close deals that create long term value for both our customers and Waitwhile.

Requirements

4 to 6+ years of B2B SaaS sales experience with proven success closing mid market or upper SMB deals
Consistent track record of meeting or exceeding quota
Strong communication, negotiation, and storytelling skills
Experience with consultative and value based selling
Ability to navigate complex buying committees and multithread deals
Familiarity with tools like ZoomInfo, HubSpot, Chorus, and Notion
High School Diploma required, Bachelor’s degree preferred

Nice To Haves

Experience selling to retail, education, or enterprise services
Ideal candidate will live in Greater Chicago, Illinois

Responsibilities

Own the full sales cycle
Manage opportunities from first conversation to close
Focus on deals in the $30K to $150K ARR range
Build pipeline strategically
Partner with BDRs and Marketing to target the right accounts and industries
Drive pipeline through inbound opportunities and self sourced outbound
Run world class demos and presentations
Partner with sales engineers to build custom tailored demos
Tailor messaging and ROI storytelling to each buyer persona
Become an expert on Waitwhile and the value we create across industries
Negotiate and close deals
Deliver deals that create real value for customers and Waitwhile
Ensure each deal is a strong long term fit where we can keep driving impact over time
Collaborate across teams
Partner with Sales, Marketing, and RevOps to align on campaigns, handoffs, and messaging
Share insights from prospecting to inform content, targeting, and positioning
Work closely with Product and Customer Success to ensure smooth onboarding and strong outcomes
Track and forecast
Track all leads from top of funnel to close in HubSpot
Own timelines and estimated close dates across your pipeline
Contribute to data driven pipeline reviews and forecasting

Benefits

Health, dental and vision insurance coverage, helping you “be safe, be healthy”
Unlimited Paid Time Off
A commitment to your future with a 401K plan, which currently offers a 6% company match and no vesting period
Health Savings Accounts – Tax-advantaged savings account used for healthcare expenses
Flexible Spending Accounts – Tax-advantaged spending accounts for healthcare and/or dependent daycare expenses
Disability Insurance –Short-Term and Long-Term coverage, paid for by Allegion, provides income replacement for illness or injury
Life Insurance – Term life coverage with the option to purchase supplemental coverage
Tuition Reimbursement
Voluntary Wellness Program – Simply complete wellness activities and earn up to $2,000 in rewards
Employee Discounts through Perks at Work
Community involvement and opportunities to give back so you can “serve others, not yourself”
Opportunities to leverage your unique strengths through CliftonStrengths assessment & coaching