Senior Account Executive

Instawork; Chicago (IL); On-site; USD 72,000 - 88,000; Full time

Benefits offered by this job

Medical, dental, and vision plans

Flexible paid time off

At least 8 paid company holidays

Phone stipend

Commuter stipend

401K plan

Job summary

Instawork is seeking a Senior Account Executive to drive growth in the Chicago office. This role will focus on building partnerships with major businesses including sports stadiums and e-commerce brands.

The ideal candidate has at least 3 years of B2B sales experience, excels in outbound prospecting, and is adept in tools like Salesforce. The role offers a competitive base salary of $80,000, with OTE of $160,000, along with stock options and a comprehensive benefits package.

Qualifications

• 3+ 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.
• Fluent in a robust sales stack; proficiency in Salesforce, Outreach, and ZoomInfo/Sales Navigator preferred.
• Experience selling into large hospitality or warehousing brands is a plus.

Responsibilities

• 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.
• Negotiate commercial and legal terms with confidence to get deals across the finish line.
• Collaborate with sales and operations to ensure customers experience the full power of Instawork’s platform.

Skills

B2B sales experience

Competitive mindset

Coaching inclination

Outbound prospecting

Salesforce proficiency

Negotiation skills

Communication skills

Experience in hospitality or warehousing

Tools

Salesforce

Outreach

ZoomInfo/Sales Navigator

Job description

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 like Benchmark, Spark Capital, Craft Ventures, Greylock, Y Combinator, and others, we’re looking for exceptional talent to reimagine the way the world works.

The future of hourly work has arrived, and we are looking for a top-performing Senior Account Executive to help lead the charge. Instawork is the #1 marketplace connecting businesses with skilled hourly workers, with 10M+ workers across 40+ markets in North America. Backed by Benchmark, Greylock, and other world‑class investors, we are reinventing how businesses hire, and we are just getting started.

This is your chance to sell a product that genuinely changes lives. Our AI-powered platform creates real economic opportunity for workers while solving one of the most pressing challenges businesses face: reliable, on‑demand staffing. You will be selling into an expansive and exciting total addressable market, including Major Sports Stadiums, E‑commerce brands, major universities, AI companies, and beyond.

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

• 3+ 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 $80,000, with an eligible OTE for a total of $160,000, 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

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 7M 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!

Instawork has 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.

Join our team to help us build something that matters! We’re looking for superstars who want to help us shape the future of work. With hubs in San Francisco, Bangalore, and Chicago, city offices in New York, Phoenix, and Singapore, we’re back to working together in‑person five days a week because we believe the best ideas happen when great people collaborate face‑to‑face. We also value diverse perspectives and encourage applications from candidates of all backgrounds.

Ready to make an impact? Learn more at www.instawork.com/about.