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.

What you'll do:

• 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

Who you are:

• 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

If you have read up to this point, we hope you are excited about this opportunity to work at Wonolo! Even if your experience does not check every bullet point, we still highly encourage you to apply. The best hires do not always check off every box of a job description.

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.

Pay Range:

The expected pay range for this position is $115,000 OTE (base of $80,500 and target variable of $34,500). Please note that individual total compensation for this position will be determined at the Company's sole discretion and may vary based on several factors, including but not limited to, location, skill level, and years and depth of relevant experience. Additionally, this role is currently eligible to participate in Wonolo's equity plan as well as a range of health and wellbeing, retirement savings, and other benefits within a holistic total rewards offering.

Benefits and Perks:

• 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!