Account Executive

Instawork is on a mission to create meaningful economic opportunities for skilled hourly professionals in communities around the globe. Our AI‑powered labor marketplace helps local businesses scale and enables global technology companies to push the frontiers of robotics and AI. Backed by world‑class investors such as Benchmark, Spark Capital, Craft Ventures, Greylock, Y Combinator, and others, we are looking for exceptional talent to reimagine the way the world works.

We are seeking an Account Executive to lead the charge in selling our platform to major clients such as sports stadiums, e‑commerce brands, universities, AI companies, and more. This high‑impact, high‑competition role is for a hunter who loves to win and wants to be part of something that matters. The position is on site, five days a week, in our downtown Chicago office, reporting to a Sales Manager.

Who You Are

2+ years of B2B sales experience with a proven, consistent track record of exceeding quota

A relentless competitor who lives at the top of the leaderboard and will not settle for anything less

Energized by coaching and obsessed with leveling up your craft

A true hunter who thrives in fast‑paced environments and knows how to build pipeline from scratch through outbound prospecting

Fluent in a robust sales stack; proficiency in Salesforce, Outreach, and ZoomInfo/Sales Navigator preferred

Sharp negotiator with experience navigating commercial and legal terms to close

Passionate about selling a product that creates real economic opportunity and changes people’s lives

An exceptional communicator who is compelling on the phone, polished on video, and persuasive in person

Experience selling into large hospitality or warehousing brands is a plus

What You’ll Do

Own your territory and build high‑value partnerships with top partners across Major Sports Stadiums, E‑commerce brands, universities, AI companies, and more

Drive aggressive outbound prospecting to generate your own pipeline through cold calls, targeted sequences, and creative outreach

Reach executives and key decision makers, delivering compelling and tailored presentations that win

Use a consultative sales approach to show prospects exactly why Instawork is the faster, smarter alternative to legacy staffing solutions

Close new business over the phone, video, and in‑person, then obsess over expanding those accounts from day one

Negotiate commercial and legal terms with confidence to get deals across the finish line

Deliver accurate weekly forecasts and own your number

Collaborate with sales and operations to ensure customers experience the full power of Instawork’s platform

Keep a sharp, healthy Salesforce pipeline and leverage our full sales stack to stay ahead

For IL‑Based Applicants

The base salary for this position is $70,000, with an OTE for a total of $140,000 and uncapped earning potential

This position is eligible for equity in the form of stock options

This position is eligible for Instawork benefits, including:

Medical, dental, and vision plans with coverage beginning on the date of hire

Flexible paid time off

At least 8 paid company holidays annually

Phone stipend

Commuter stipend

Supplemental pay on qualified leaves

HSA contribution

Flexible spending plans

401(k) plan

Perkspot discount program via Lumity

Our Values

Empathy, Trust & Candor

– We put ourselves in the shoes of our colleagues and customers and don’t shy away from uncomfortable conversations, instead building trust through honest and direct feedback.

Bias for Action

– We practice high‑velocity decision‑making, clear‑eyed that we often operate with incomplete information. Growing quickly means it’s OK to be wrong, so long as we learn from our mistakes and course‑correct!

Always Be Learning

– We’re a curious bunch, and with AI transforming our workplace we encourage everyone to learn from each other, compounding our knowledge and experience to help us change an entire industry.

Act Like an Owner

– We work long, hard, and smart, building products that delight our users and drive growth. Your ability to impact Instawork is limited only by your courage and conviction, not your job description.

About Instawork
Founded in 2015, Instawork is the nation’s leading online labor marketplace for food services, hospitality, light industry, and logistics, connecting more than 7 M skilled workers with local restaurants, hotels, warehouses, stadiums, and more. Our AI‑powered platform serves thousands of businesses across more than 50 major markets in the United States and Canada. We’re not just helping fill shifts, we’re supporting local economies—and we’re just getting started!

We have been featured by CBS News, The Wall Street Journal, The Washington Post, and the Associated Press. Forbes included us on their Next Billion Dollar Startups list; RetailTech Breakthrough named us Workforce Hiring Solution of the Year for 2025; and Inc. 5000 recognized us as one of the country’s top 10% fastest‑growing companies two years in a row. But what matters most is our impact. We’re solving real problems for real people, and we’re doing it at scale.

We’re building a team that embraces diverse perspectives and encourages applications from candidates of all backgrounds.

#LI-Onsite

Equal Employment Opportunity Statement

– As set forth in Instawork’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

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