Outside Sales Manager

About the Role TownSq is seeking a high-performing Outside Sales Manager to drive new logo acquisition through a consultative, field-based sales approach. This role is ideal for a disciplined seller who thrives in face-to-face engagement, understands complex buying committees, and can confidently challenge prospects with insight-driven conversations. You will own the full sales cycle from territory planning and outbound prospecting to on-site presentations, executive conversations, and closed-won execution while operating within TownSq’s structured sales methodology and pipeline governance standards. The role is based in Richardson, TX with travel expected. What You'll Do

• Own and manage a defined geographic territory with full accountability for pipeline, forecast accuracy, and quota attainment
• Execute a structured territory plan that includes outbound prospecting, on-site meetings, events, and partner-driven opportunities
• Travel approximately 60% of the time to meet prospects, attend industry events, conduct demos, and build relationships
• Conduct in-person discovery meetings with property management leaders, operators, and decision-makers
• Deliver compelling on-site presentations and demos aligned to prospect business challenges
• Lead value-based, Challenger-style sales conversations that reframe problems and differentiate TownSq
• Navigate multi-stakeholder buying groups and guide prospects through structured decision processes
• Manage opportunities through defined pipeline stages with strong hygiene and documentation
• Maintain accurate, timely CRM updates in Salesforce (activities, notes, next steps, close plans)
• Build and maintain opportunity-level close plans, including stakeholders, decision criteria, timeline, and risks
• Participate in weekly pipeline reviews, forecast calls, and coaching sessions What We're Looking For
• 5+ years B2B outside/field sales experience
• Territory ownership
• Proven mid-market/enterprise closers
• Salesforce CRM proficiency
• Valid driver's license
• Ability to travel ~60%