Mid-Market Account Executive - Chicago, IL

Who we are💙

Here at Waitwhile we're on a mission to eliminate the 1 trillion hours people spend waiting in lines every year. Our platform combines virtual waitlists, scheduling, real-time updates, messaging, and analytics to make access to places, services, and events seamless, online or in person. Trusted by 10,000+ companies, Waitwhile has already helped over 150 million people enjoy a radically better waiting experience.

Our clients include IKEA, Chanel, Costco, Google, Delta Airlines, and thousands more. We’re just getting started, and we need your help.

At Waitwhile, we recognize that great talent and breakthrough ideas can come from anywhere. That’s why this position offers a flexible remote work arrangement, with occasional on‑site visits as needed based on the role. Whether you’re working remotely or collaborating in person, we’re committed to providing the tools, support, and dynamic environment you need to succeed.

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.

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 Rev Ops 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 Hub Spot

• Own timelines and estimated close dates across your pipeline

• Contribute to data‑driven pipeline reviews and forecasting

• 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 Zoom Info, Hub Spot, Chorus, and Notion

• High School Diploma required, Bachelor’s degree preferred

It´s a plus if you have:

• Experience selling to retail, education, or enterprise services

• Ideal candidate will live in Greater Chicago, Illinois

We want Waitwhile to be an incredible place to work. We offer great benefits and perks, flexible working hours and lots of interesting challenges. We believe in making work fun and rewarding and care about your development and are committed to your success. Join Waitwhile at this exciting stage and help shape both our future and your own.

Waitwhile has a positive, diverse, and supportive culture – we look for people who are curious, inventive, and work to be a little better every single day. We aim to be smart, humble, hardworking and, above all, collaborative. If this sounds like a good fit for you, what are you waiting for? Apply for this job!

What You’ll Get from Us:

• 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…