Outside Sales Representative

Key Responsibilities

• 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
• Partner closely with Marketing on regional events, campaigns, and field enablement
• Coordinate with Implementation, and Client Success to ensure clean handoffs and successful onboarding
• Represent the voice of the customer back to leadership with insights from the field

Requirements

• 5+ years of B2B outside / field sales experience (SaaS or technology preferred)
• Proven success closing mid-market to enterprise deals with multi-stakeholder buying groups
• Strong comfort with in-person meetings, travel, and executive-level conversations
• CRM proficiency with Salesforce
• Valid driver’s license and ability to travel extensively (60%)

Preferred Qualifications

• Experience selling SaaS, workflow platforms, or community-based technology
• Familiarity with Challenger, SPIN, MEDDICC, or structured sales methodologies
• Experience selling to property management companies, HOAs, or adjacent markets
• Track record of consistent quota attainment and forecast accuracy