Account Executive (Central)

Wonolo • Chicago, IL

1d • Onsite

About The Position

Wonolo is disrupting the $140BN temporary staffing industry. Founded in 2014, Wonolo's mission is to help people find consistent work. Through our two-sided tech marketplace, we connect hundreds of businesses in need of front-line workers with 2 million underemployed workers in local markets across the United States, within minutes. Wonolo has raised over $200M in funding which will continue to help us empower the in-demand workforce by democratizing access to flexible work, opportunities to learn new skills, a living wage, and comprehensive portable benefits and perks.

Wonolo is looking for a Regional Account Executive to help drive new customer growth across the Central Region, with Chicago as the primary home-base market. This role is ideal for someone who enjoys building relationships, developing local markets, and creating new business opportunities through a mix of proactive outreach, customer engagement, and in-market presence.

As the Central Region’s dedicated Account Executive, you will help identify and develop new opportunities across warehousing, distribution, manufacturing, production, hospitality, and other labor-intensive environments. You will play a key role in helping Wonolo expand our local presence, build regional density, and create new pathways for customer growth.

This role blends regional market development, consultative selling, and cross-functional partnership. You will work closely with Wonolo’s Partnerships Managers, Regional Managers, Engagement Managers, Account Managers, and Operations teams to identify high-potential opportunities, create local momentum, and help convert new customer relationships into long-term growth.

We welcome qualified candidates located anywhere in the Chicago, IL, area and willing to be onsite.

Requirements

• Experience in B2B sales, business development, staffing, logistics, HR services, hospitality, facilities services, or a similar customer-facing growth role
• A proactive new business mindset with motivation to build pipelines and open doors from the ground up
• Local market orientation and genuine curiosity about how businesses operate and where opportunities exist
• Effective discovery and communication skills with clear articulation regarding how Wonolo can help
• Ability to build credibility with Operations, HR, and site-level stakeholders
• Comfort working cross-functionally and coordinating with internal partners to move deals forward
• Self-direction, discipline, and strong follow-through on pipeline management and activity
• Coachability and a growth mindset with openness to feedback and excitement to help build something still evolving
• Chicago-based presence with the ability to spend regular time in market with customers and prospects

Nice To Haves

• Experience in staffing, HR services, workforce solutions, or labor-related businesses.
• Experience selling into light industrial, warehousing, distribution, manufacturing, production, logistics, or hospitality environments.
• Prior territory sales, field sales, or local market development experience.
• Familiarity with the Chicago business community or Central Region customer base.
• Experience supporting customers with multi-site or multi-market growth potential.

Responsibilities

• Build and manage a pipeline of new customer opportunities across the Central Region, with a strong focus on Chicago and surrounding markets
• Develop a local-first go-to-market approach by building relationships with prospective customers and uncovering workforce needs Wonolo can solve
• Proactively identify and qualify companies that may benefit from Wonolo's tech-enabled staffing solution, including assessing fit based on labor needs and operational priorities
• Collaborate and partner with cross-functional teams to progress and close qualified opportunities
• Collaborate with Regional Managers, Engagement Managers, Account Managers, and Operations teams to ensure new customers are set up for a strong experience from first conversation through activation
• Share market insights, customer feedback, and competitive intelligence to help refine our regional go-to-market strategy

Benefits

• The opportunity for growth in a mission-driven and well-funded start-up
• Meaningful equity
• We pay 100% of the medical/dental/vision insurance premiums for you
• Generous parental leave plan
• Cell phone reimbursement and company laptop
• Retirement plans as well as life and disability insurance
• Access to no-cost on-demand mental health support, including counselling, mindfulness and meditation, and wellbeing courses
• We encourage a healthy work-life balance and offer flexible schedules, and an open vacation policy
• Team outings, happy hours, company off-sites, and more!

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed