Account Executive

This is a high-impact role for a hunter who thrives on competition, loves to win, and wants to be part of something that matters. You will report to a Sales Manager and play a critical role in driving Instawork’s next phase of growth, on-site 5 days per week in our downtown Chicago office.

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, eligible 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:

A variety of 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

Employee health savings accounts (HSA) contribution

Flexible spending plans

401K plan

Perkspot - discount program through Lumity

#LI-Onsite

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.

#J-18808-Ljbffr