Enterprise Account Executive

We're looking for passionate, driven, and highly motivated sales professionals to help us scale our enterprise partnerships and continue our rapid growth across the U.S. As an Enterprise Account Executive, you will be responsible for acquiring key enterprise accounts and forming channel partnerships. You will work closely with mid-market to large businesses to understand their staffing needs and provide tailored solutions that meet their workforce requirements. This role requires a strategic thinker with a passion for building lasting business relationships and a strong ability to close deals.

What You'll Do

• Identify, engage, and win enterprise-level clients through a multi-threaded prospecting approach, building relationships across multiple functions and levels within target organizations.
• Build and manage a robust pipeline of qualified opportunities through proactive outreach, targeted research, and industry networking.
• Lead end-to-end sales cycles—from initial discovery, executive alignment, and contract negotiation—ensuring a seamless transition to onboarding and implementation.
• Engage C-suite and senior decision-makers with a consultative sales approach focused on solving critical workforce challenges.
• Consistently achieve or exceed quarterly and annual revenue targets aligned to a $200K+ average deal size, averaging 10 net-new logos per year. 
• Foster long-term client relationships post-sale, identifying opportunities for expansion and continued partnership.
  Stay informed on industry trends, market dynamics, and Instawork’s evolving value proposition to position our solutions effectively.

What We're Looking For

• 5+ years of enterprise sales experience, leading end-to-end sales cycles—from initial discovery, executive alignment, and contract negotiation—ensuring a seamless transition to onboarding and implementation.
• Proven track record of closing complex, high-value deals ($200K+) over extended sales cycles (6–12 months).
• Deep experience with multi-threaded sales strategies, developing relationships across various departments and leadership levels.
• Strong executive presence with exceptional communication, negotiation, and presentation skills.
• Self-starter mentality with the ability to work autonomously and adapt quickly in a fast-paced, high-growth environment.
• Proficiency with CRM tools (e.g., Salesforce) for pipeline management, forecasting, and sales reporting.
• Bachelor’s degree in Business, Marketing, or a related field is preferred but not required.

For IL based applicants:

• The base salary for this position is $110,000 eligible OTE for total of $230k and uncapped commissions
• 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
• Home office stipend
• 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

A variety of factors are considered when determining someone’s compensation including a candidate’s professional background, experience, and location.  Final offer amounts may vary from the amounts listed above.

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 2015, 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. 

At Instawork, we constantly evaluate how to build an optimal work environment for success. Currently we operate on a hybrid model, but we remain open to adapting our policies to meet the needs of our evolving business and team dynamics. As we continue to grow, we're seeking candidates who are excited about contributing to our in-person culture and open to the idea of working in-office up to 5 days a week.

For more information visit www.instawork.com

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: https://info.instawork.com/about

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