Senior Enterprise Account Executive, Instawork

$130-250k

OTE

$130k

BASE

+ Equity in the form of stock options and uncapped sales incentive pay

Salesforce

Senior and Expert level

Chicago

More information about location

3 days a week in office

Flexible staffing marketplace for local workforces

Be an early applicant

Flexible staffing marketplace for local workforces

1001+ employees

B2BMarketplaceRecruitmentHR

Be an early applicant

$130-250k

OTE

$130k

BASE

+ Equity in the form of stock options and uncapped sales incentive pay

Salesforce

Senior and Expert level

Chicago

More information about location

3 days a week in office

1001+ employees

B2BMarketplaceRecruitmentHR

Company mission

To offer economic opportunities for local professionals and businesses, in communities across the world.

Job

Company

Role

Who you are

7+ 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

What the job involves

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 a Senior Enterprise Account Executive, you will be responsible for acquiring key enterprise accounts and forming channel partnerships. You will work closely with 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
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)

Our take

Around 57 million workers in the U.S. work on a 'gig' basis, providing short-term and one-off employment for a range of industries. However, due to the temporary nature of gig work, workers and understaffed employers are regularly let down by cancellations.

Instawork hosts an online marketplace that connects gig workers with local businesses across a variety of sectors including healthcare, hospitality, and warehouse work. Workers are paid hourly upon completion of a gig, at which point both the employer and worker themselves can provide feedback on the experience.

Whilst the startup faces competition within this gig-work industry, Instawork holds a smart focus on providing reliable and short-notice workers for businesses that need them. Gigs can be arranged within just a few hours of notice, and any employer or employee who cancels a job will be temporarily suspended in order to improve job success rates. Instawork's 2023 Series D funding is accelerating its AI capabilities and expanding its presence within staff distribution centres for some of the American continent's largest retailers and sports stadiums.

Steph

Company Specialist at Welcome to the Jungle

Insights

Top investors

39% employee growth in 12 months

Glassdoor (3.2)

Trustpilot (3.8)

Company

Funding (last 2 of 4 rounds)

May 2023

$60m

SERIES D

Jul 2021

$60m

SERIES C

Total funding: $148m

Company benefits

Medical, Dental, and Vision
FSA and Commuter Benefits
Parental and Family Leave
Flexible Time Off
Office & Phone Plan Reimbursement
401K Retirement Savings

Company HQ

Financial District, San Francisco, CA

Leadership

Sumir Meghani

(CEO)

Previously VP of Email at Groupon and VP at Mixx.

Salary benchmarks

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