Mid-Market Account Executive

Be Part Of A Dynamic Team:

Join a fast-growing, Series A technology company building a communication platform for frontline and deskless workers. The company helps employers reach teams that may not use email, sit at a desk, or rely on workplace apps by enabling simple, effective communication through SMS. Serving commercial industries such as manufacturing, transportation, logistics, hospitality, retail, and other frontline-heavy environments, the platform gives organizations a practical way to improve employee communication, engagement, and operational visibility.

What’s In Store For You:

This is an opportunity to join an early revenue team during a key growth stage. The role offers direct exposure to revenue leadership, the chance to help shape a developing mid-market sales motion, and the ability to build a meaningful pipeline in a large, underpenetrated market. The position is based in Chicago with an in-office schedule Tuesday through Thursday. The company offers benefits, an uncapped commission opportunity, and equity/RSUs that will be discussed during the interview process.

How You Will Make An Impact:

• Own a high-outbound sales motion focused on creating and closing new mid-market opportunities.
• Build a pipeline through cold calling, lead generation, account research, targeted outreach, and creative prospecting.
• Run discovery conversations and demos with HR leaders, HR managers, and operational stakeholders.
• Sell a practical SaaS platform into commercial industries with large frontline or deskless employee populations.
• Manage a fast-moving sales cycle, typically around 30 days, with deal sizes commonly in the mid-market range.
• Maintain strong CRM discipline, accurate pipeline stages, clear next steps, and reliable forecasting.
• Partner with revenue leadership to refine outreach messaging, objection handling, and repeatable sales processes.
• Help expand the company’s reach across industries such as transportation, logistics, manufacturing, hospitality, and retail.

Are you a proven outbound SaaS sales professional ready to help grow a mid-market revenue team?

• Experience as an Account Executive, Business Development-oriented AE, or full-cycle SaaS seller.
• Strong outbound prospecting background, including cold calling, lead generation, and self-sourced pipeline.
• Experience selling SaaS products to HR leaders, HR managers, people teams, workforce leaders, or related operational stakeholders.
• Background selling into commercial/frontline-heavy industries such as transportation, logistics, manufacturing, hospitality, retail, or similar sectors.
• Comfort with a fast sales cycle and mid-market deal sizes.
• Ability to run discovery, deliver demos, qualify quickly, and move deals toward close.
• Strong communication, resilience, coachability, and day-to-day activity consistency.
• Comfortable working in an early-stage environment where the sales process is still being refined.
• Able to work onsite in Chicago Tuesday through Thursday.
• Familiarity with common sales tools such as CRM platforms, LinkedIn Sales Navigator, ZoomInfo, and outbound sequencing tools is helpful.