Senior Enterprise Account Executive at Instawork

Chicago, Illinois, United States

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Not SpecifiedCompensation

Senior (5 to 8 years)Experience Level

Full TimeJob Type

UnknownVisa

Technology, StaffingIndustries

Requirements

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

Responsibilities

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)

Skills

Key technologies and capabilities for this role

SalesforceCRMPipeline ManagementSales ForecastingSales ReportingContract NegotiationMulti-threaded SalesExecutive PresentationDeal ClosingEnterprise Sales

Questions & Answers

Common questions about this position

What experience level is required for the Senior Enterprise Account Executive role?

The role requires 7+ years of enterprise sales experience, including leading end-to-end sales cycles, closing complex high-value deals of $200K+, and multi-threaded sales strategies.

What are the key skills needed for this position?

Key skills include strong executive presence with exceptional communication, negotiation, and presentation skills, proficiency with CRM tools like Salesforce, and a self-starter mentality to work autonomously in a fast-paced environment.

Is travel required in this role?

Yes, the role involves travel, as indicated in the responsibilities.

What does the company culture look like at Instawork?

Instawork has a fast-paced, high-growth environment that values passionate, driven, and highly motivated sales professionals who are self-starters able to work autonomously.

What makes a strong candidate for this Senior Enterprise Account Executive position?

A strong candidate has 7+ years of enterprise sales experience closing $200K+ deals, multi-threaded sales expertise, strong executive presence, and proficiency with CRM tools like Salesforce.

Instawork

Connects businesses with vetted hourly workers

About Instawork

Instawork connects businesses with over 5 million vetted short-term, seasonal, and temp-to-hire workers through its online platform. It primarily serves companies looking for hourly workers, offering a solution that is more efficient than traditional staffing agencies. The platform features an intelligent matching system that pairs businesses with suitable workers from its extensive database, supported by a rigorous vetting process to ensure reliability. This has led to a high demand for Instawork's workers, with 93% of businesses wanting them to return and a low 2% no-show rate. Businesses can view worker profiles and experience before they pick up shifts, and those looking for full-time employees can also search and hire from the database. Instawork generates revenue by charging businesses for connecting them with workers, and its importance grew during the pandemic, solidifying its market position.

San Francisco, CaliforniaHeadquarters

2015Year Founded

$144MTotal Funding

SERIES_DCompany Stage

Consulting, Consumer SoftwareIndustries

1,001-5,000Employees