Enterprise Account Executive

Enterprise Account Executive

At Instawork, our mission is to create meaningful economic opportunities for local businesses and skilled hourly professionals in communities around the world. We're building the leading AI-powered labor marketplace—and we're looking for exceptional talent to help us scale quickly and make an even greater impact. Backed by world-class investors like Benchmark, Spark Capital, Craft Ventures, Greylock, Y Combinator, and others, we're transforming the way the world works.

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 and enterprise 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.
• Travel Expectations: 40% annually (on-site client visits, tradeshows, conferences, events)

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 and 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 CA-based applicants:

• The base salary for this position is $110,000, eligible OTE for a 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.