Mid-Market Account Executive — Founding Sales Team #3627465

Join an early-stage, high-growth technology company building an SMS-based communication platform designed for frontline and deskless workers. The company serves organizations across industries such as manufacturing, construction, hospitality, transportation, warehousing, retail, healthcare, and real estate by helping them reach employees who may not use email or workplace apps. With strong product-market fit, recent Series A funding, and a new AI-native frontline intelligence capability, the team is entering a major scale phase and building a category around real-time workforce communication and operational insight.

This is a founding sales team opportunity with significant ownership, visibility, and growth potential. The role offers the chance to help shape the go-to-market playbook, build pipeline from the ground up, and sell a differentiated platform into a large and expanding market. The position is full-time and based in Chicago, IL, with an in-office schedule Tuesday through Thursday. Stock options/RSUs are available, and benefits include medical, dental, and vision coverage. Travel is expected for events and customer meetings.

• Own the full sales cycle from prospecting through close, with responsibility for building and managing your own pipeline.
• Self-source the majority of opportunities through outbound prospecting, account research, targeted outreach, and creative sales motions.
• Run a high-activity sales motion, including consistent weekly meetings focused on both new opportunity creation and pipeline advancement.
• Navigate complex, multi-stakeholder B2B sales cycles involving HR, IT, Operations, and Internal Communications leaders.
• Build relationships with economic buyers and decision-makers to land initial locations and expand into broader enterprise opportunities.
• Maintain a disciplined, accurate pipeline with clear stages, next steps, close dates, and deal strategy.
• Help shape the sales process, messaging, and repeatable playbook as part of a growing founding revenue team.
• Sell into industries with large frontline workforces where communication, engagement, and operational visibility are critical.

• 2–4 years of full-cycle B2B sales experience, ideally in an early-stage or high-growth technology company.
• Demonstrated track record of meeting or exceeding sales targets.
• Strong ability to self-source pipeline and show examples of opportunities built from cold outbound or proactive prospecting.
• Experience selling into mid-market or complex B2B accounts with multiple stakeholders.
• Proven ability to multi-thread across business, technical, and operational buyers.
• Strong comfort selling in ambiguous, fast-moving environments without a fully built playbook.
• Entrepreneurial mindset with high ownership, resilience, coachability, and consistency.
• Ability to challenge prospects thoughtfully, hold value-based conversations, and navigate executive-level discussions.
• Experience selling to HR buyers is a plus.
• Experience selling into manufacturing, hospitality, construction, transportation, warehousing, retail, real estate, or healthcare is a plus.
• Familiarity with sales tools such as HubSpot, LinkedIn Sales Navigator, Clay, ZoomInfo, Zoom, and call recording/notetaking platforms is helpful.