Mid - market Account Executive

Mid-Market Account Executive

We're looking for a confident and highly driven Mid-Market Account Executive to lead outbound sales efforts into multi-location restaurant and automotive businesses (5+ locations). This role is responsible for self-generated pipeline and full-cycle sales—identifying prospects, running discovery, building ROI visibility models, and closing recurring revenue deals. If you enjoy outbound hunting, selling to operators and franchise owners, and building repeatable motions in a rapidly scaling environment, this is a high-impact role with direct visibility to executive leadership. This role is fully on-site in our Dallas office. Our Team thrives on in-office collaboration and real-time work, with standard hours Monday through Friday.

Role Responsibilities

• Own outbound prospecting into restaurant, retail automotive, and franchise groups with 5 to 50 locations
• Build and execute multi-channel outreach sequences (phone, email, LinkedIn, video, direct mail)
• Partner with SDRs to build account lists, messaging, and campaign strategy
• Run high-impact discovery focused on traffic volume, signage visibility, and revenue lift
• Deliver platform demos and coordinate scoping with Solutions Engineering
• Build ROI and traffic visibility business cases using Cirrus analytics tools
• Manage multi-stakeholder deals including owners, operators, marketing, and finance
• Guide prospects through permitting, site surveys, installation timelines, and contracting
• Maintain CRM accuracy and pipeline hygiene inside HubSpot
• Work cross-functionally with Marketing, Product, and Project Management to drive deal success
• Provide market feedback and help refine processes, messaging, and targeting
• Represent Cirrus with professionalism and ownership throughout the full sales cycle

Role Requirements

• 3+ years of full-cycle sales experience, preferably in outbound-led roles
• Familiarity with equipment financing, leasing structures, or recurring hardware models a plus
• Proven success selling into multi-location or franchise organizations
• Experience generating your own pipeline (not dependent on inbound)
• Strong consultative selling skills, including ROI and business case development
• HubSpot CRM experience strongly preferred
• Ability to run structured sales cycles with multiple stakeholders
• Excellent verbal and written communication and presentation skills
• Self-starter who thrives in a fast-moving, high-ownership environment

What Success Looks Like

• Pipeline Generation: You build and manage a healthy pipeline of qualified mid-market accounts driven primarily by outbound efforts.
• Predictable Revenue: You consistently close net-new MRR deals while maintaining clean deal stages and forecast accuracy.
• Restaurant & Automotive Expertise: You quickly become fluent in the needs, buying dynamics, and revenue impact drivers for multi-location restaurant and automotive operators.
• Efficient Sales Cycles: You run tight discovery, build business cases that move deals forward, and proactively drive next steps without internal babysitting.
• Trusted Partner: Internal teams see you as a reliable, detail-oriented seller who manages expectations, communicates proactively, and hands off deals cleanly to Project Management and Customer Success.

Cirrus Core Values: What We Look For In A Teammate

• Bring Passion: We take pride in our work and bring our BEST to all interactions with our customers and teammates. We encourage rigorous discourse to improve the customer experience each and every day.
• Quality: Quality isn't a catch-all phrase. It is an action plan that requires hard work and focus to achieve. Step by step, we strive to build quality into everyday processes and products to achieve our collective success.
• Winning Takes a Team: Show genuine commitment, be flexible, get involved, be reliable, help and support others, and move our company forward.
• Remove Friction: Eliminate roadblocks in the way of smooth operations by promoting and embracing changes geared towards making things easier. Be bold! Don't settle for "That's just the way it is."
• Respect: An individual who communicates and conducts themselves in a polite and positive manner, and encourages others around them to do the same; without judgment of peers regardless of rank, position, age, gender, or race.
• Innovate Every Day: Have the courage to challenge what is perceived as conventional or typical. Be observant of surroundings and outspoken about ideas and changes that will positively impact people.