Mid-Market Account Executive

Be Part Of A High-Performing Team:

Join a fast-growing SaaS company building an SMS-based communication and operational intelligence platform for frontline and deskless workforces. The team is focused on helping organizations reach employees who may not regularly use email, desktop tools, or traditional workplace apps. This is an opportunity to join an early commercial team where Account Executives play a hands-on role in building pipeline, closing new business, and shaping a repeatable go-to-market motion as the company scales.

What’s In Store For You:

This is a full-time, direct hire opportunity with a hybrid schedule in downtown Chicago. The role is onsite Tuesday through Thursday and remote Monday and Friday. The position offers high visibility with revenue leadership, the opportunity to join an early-stage sales organization, and the ability to contribute directly to sales process development while owning a new-business quota.

How You Will Make An Impact

• Own the full sales cycle from outbound prospecting through discovery, demo, negotiation, close, and handoff.
• Build a self-sourced pipeline through cold calling, email outreach, LinkedIn prospecting, account research, and targeted outbound campaigns.
• Engage mid-market buyers and business leaders to uncover communication, workforce, and operational challenges.
• Position a SaaS platform as a clear business solution tied to measurable value, adoption, and operational impact.
• Run consultative discovery calls and product demonstrations that connect buyer pain to platform capabilities.
• Manage a high-velocity sales motion with typical deal sizes around $15K–$30K ACV and approximately 30-day sales cycles.
• Maintain strong CRM discipline, pipeline hygiene, forecasting accuracy, and clear next-step management.
• Partner closely with revenue leadership to test messaging, refine outbound strategy, and help build the repeatable AE playbook.
• Bring a proactive, ownership-driven mindset to an early-stage environment where structure is still being built.

Are you a proven SaaS seller ready to grow from outbound execution into full-cycle impact?

• 3+ years of B2B SaaS sales experience, ideally with a clear progression from SDR/BDR into an Account Executive role.
• Current or recent quota-carrying AE experience selling SaaS or technology solutions.
• Proven outbound prospecting background with comfort generating self-sourced pipeline.
• Strong track record of meeting or exceeding quota in SDR/BDR and/or AE roles.
• Experience running discovery, demos, business-value conversations, proposals, negotiation, and close.
• Ability to clearly explain personal ownership of closed deals, not just team-supported wins.
• Comfortable operating in a fast-moving startup or early-stage sales environment with limited hand-holding.
• Strong communication skills, curiosity, coachability, resilience, and ability to simplify product value for business buyers.
• Experience selling in a high-activity environment with disciplined follow-up and strong pipeline management.
• Stable work history or a clear, credible story of progression from sales development into closing roles.
• Familiarity with tools such as Salesforce, HubSpot, Salesloft, Outreach, ZoomInfo, LinkedIn Sales Navigator, Apollo, Gong, or similar sales platforms is preferred.