Account Executive - Chicago

About Us

sunday is building the fastest, simplest way to pay in restaurants. With a quick scan of a QR code, diners can pay, tip, and leave in about 10 seconds. We believe great products should feel obvious, not complicated, and we focus relentlessly on keeping things simple while earning trust from restaurants and guests at every interaction. Today, sunday powers payments in thousands of restaurants across the US, UK, and France, helping operators turn tables faster, increase tips, and unlock valuable insights. We push ourselves to go beyond what’s expected, building with ownership, moving fast, and scaling with ambition as we tackle our biggest growth opportunity in the US.

About the Role

This isn’t your typical sales role, you'll be joining our Chicago team to accelerate our growth in a key U.S. market. We’re looking for a bold, strategic, and entrepreneurial Account Executive who’s ready to make an outsized impact.

Whether you're coming from a top consulting firm and ready to get your hands dirty in the startup world, or a high-growth sales environment where you've built something from zero to one, you’ll thrive here if you’re hungry to own a market, build deep partnerships, and drive real innovation.

You’ll be responsible for dramatically growing the Chicago portfolio by building upon our existing foundation, working directly with top-tier restaurants, refining and executing our local go-to-market playbook, and shaping the way diners and operators experience payments. Join early, grow fast, and shape the journey!

Key Responsibilities

1. Lead Market Expansion: own Chicago from day one, identify, pitch, and close the best restaurants in town.

2. Build Relationships: leverage your network and hustle to connect with decision-makers and industry tastemakers.

3. Drive Strategic Sales: navigate complex sales cycles, negotiate win-win deals, and help restaurants see the full value of sunday.

4. Shape Our Future: collaborate cross-functionally to improve our product and processes based on real customer feedback.

5. Think Like a Founder: you’re not just selling, you’re building a business.

About You

• 3-5 years in sales, business development, or strategic consulting (consulting alumni welcome!)

• Entrepreneurial spirit with the drive to lead a market launch from zero

• Deep knowledge or passion for the restaurant industry

• Natural communicator and storyteller who builds trust quickly

• Confident, organized, and execution-focused, you thrive with autonomy

• Experience selling to SMBs or enterprise hospitality clients is a plus

• Familiarity with tools like Salesforce, Microsoft Suite, and Slack

What We Offer

• $120,000 to $180,000 OTE

• A great office in the heart of Chicago, Illinois with a balance of in-person and remote work (in-field with restaurant partners) hybrid work setting

• Stock options from day one

• Company performance bonus

• Unlimited PTO + 100% health coverage (you & your kids)

• Freedom, trust, and ownership from day one

• 401K

• Free Vacation Policy

• 100% Employer-Covered Health Insurance

Interview Process

• Share your story: Application with resume

• Let's get to know each other through a phone screen interview

• Meet with the hiring manager

• Impress your future colleagues with a case study

• Meet with people from other departments and understand our culture

• 3 reference checks from past managers

• Offer: we want you

Thank you for taking the time to apply, and looking forward to getting to know you!

sunday is an equal opportunity employer and does not discriminate and all qualified applicants will receive consideration for employment without regard to race, creed, color, sex, affectional or sexual orientation, gender identity or expression, gender, ethnicity, religion, national origin, ancestry, nationality, age, disability, marital status, veteran status, genetic information, or on any other basis prohibited by law (except where an attribute is a bona fide occupational qualification).