Retail Enterprise Account Executive

4 days ago


Chicago, Illinois, United States Instawork Full time

At Instawork, we're driven by our vision to create economic opportunity for local businesses and skilled hourly professionals in communities around the world. With a growing number of hub cities across the world in the U.S., Canada, India, and beyond, we're looking for top talent to help rapidly scale our high-tech and high-touch labor marketplace. Our accomplished and dedicated team is passionate about our mission and committed to crafting revolutionary products, all with the backing of our world-class investors, including Benchmark, Spark Capital, Craft Ventures, Greylock Capital, Y Combinator, and more


We have an immediate opening for a Retail Enterprise Account Executive with a proven track record of success to join our rapidly growing team. Reporting to the VP of Partnerships, this role serves as a critical member of the sales team and is responsible for establishing a collaborative business relationship between Instawork and enterprise retail/merchandising organizations. This role requires experience in mid-market or enterprise sales, including pursuits that include multiple buyers and stages. This is a results-driven position that requires a track record of success – consistently exceeding quota.

The primary responsibility of the Retail Enterprise Account Executive is to target businesses in the Retail industry that use contingent/flex labor in large quantities. You'll have a defined prospect list, but you'll also build relationships with both regional businesses and larger national players in the retail space.
This is a high-energy, client-facing sales role requiring proven sales ability and a passion for closing deals and growing accounts. The ideal candidate understands and anticipates how decisions are made, and you will persistently uncover your prospects' needs and decision-making criteria. Your goal is to create more raving fanatics of Instawork and ensure that we become the staffing and hiring solution of choice for our clients. Above all, you will be responsible for hitting your revenue targets.
What You'll Do:

  • Establish a collaborative business relationship between Instawork and retail enterprise companies, merchandising companies, and other companies that have large staffing and hiring needs.
  • Executing the sales strategy for our B2B mobile marketplace app.
  • Reaching out to executives and key decision makers across multiple verticals in the retail sector to download and use Instawork as a primary hiring tool.
  • Utilize a consultative sales process to demonstrate how Instawork is a faster, more convenient, and cost-effective solution compared to the status quo.
  • Ensure a top-notch first experience with Instawork, and obsess over growing the account in the first months as a customer.
  • Strategically work an assigned account list focusing on net new client acquisition closing new business with a combination of in-person or Zoom calls.
  • Provide accurate weekly forecasts and sales plans.
  • Work collaboratively with the VP of Partnerships, additional Retail Account Executives and cross functional teams to drive revenue growth with new customers.
  • Provide actionable product feedback to our supporting teams in order to help iterate on our value offering.
  • Utilize our technology tools and maintain great Salesforce hygiene.

Who You Are:

  • 5+ years experience in enterprise sales, including pursuits that include multiple buyers and stages
  • A track record of success – consistently exceeding quota
  • Competitive Mentality with an innate desire to be at the top of the leaderboard
  • Experience – You follow a sales process and methodology (Solutions selling, Challenger, or other)
  • You have successfully sold into national retail businesses and have an understanding of the retail landscape
  • Willingness to work hard and go fast in a high growth startup environment
  • Proficient in Powerpoint, Excel, Google Docs and Salesforce
  • Willingness to travel 20% of the time (in-person meetings, conferences, company events, etc)

Instawork Values

  • Bias for Action -- We are a growing team and an evolving product. We want a team of do'ers to drive the company forward, even if it means making decisions with incomplete information or being wrong.
  • Act Like an Owner -- Treat this company as though it is your own. Execute on the fundamentals, and act creatively to drive growth. Your ability to drive impact in any part of our company is only limited by your courage and conviction, not your job title.
  • Always Be Learning -- We are changing an entire industry. We strive to learn from each other and get better each day, week, and month, so that our team's learnings can compound and we can all improve, together.
  • Empathy, Trust, Candor -- Empathy for our business partners and professionals means we put ourselves in their shoes. Empathy for our colleagues means we are always upfront and honest with each other, which comes from trust.

About Instawork

Founded in 2016, Instawork is the leading flexible work app for local, hourly professionals. Its digital marketplace connects thousands of businesses and more than five million workers, filling a critical role in local economies. Instawork has been featured on CBS News, the Wall Street Journal, The Washington Post, Associated Press, and more. In 2022, Instawork was ranked among the country's top 10% of fastest-growing companies by Inc. 5000 and was included in the Forbes Next Billion Dollar Startup list. Instawork was also named the 2022 ACE Award recipient for "Best Innovation" and one of the "Best Business Apps" by Business Insider. Instawork helps businesses in the food & beverage, hospitality, and warehouse/logistics industries fill temporary and permanent job opportunities in more than 25 markets across the U.S. and Canada.

For more information visit

We value diversity on our team and firmly believe Instawork is stronger when we hire people who make their own unique contributions to our culture. We welcome all applicants and encourage candidates from underrepresented backgrounds to apply.

To learn more about our company values, please visit:
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