Outside Sales Representative

With more than 225 branch offices across North America, Associa is building the future of community for nearly five million residents worldwide. Our 11,000+ team members lead the industry with unrivaled education, expertise, and trailblazing innovation. For more than 43 years, Associa has brought positive impact and meaningful value to communities. To learn more, visit

Town Sq is seeking a high-performing Outside Sales Representative 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 Town Sq's structured sales methodology and pipeline governance standards. This role is in office at our Richardson, Texas location and travel is expected.
This role is based in Richardson, TX - local candidates preferred. Travel is required.

• 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 Town Sq
• 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

• 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
• Experience owning a territory and managing a full sales cycle
• 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%)

• 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

• Consultative, insight-driven selling
• Strong executive presence and communication skills
• Excellent territory planning and time management
• High accountability and pipeline rigor
• Resilience, adaptability, and competitive drive

We are an equal opportunity employer and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, pregnancy, age, national origin, disability status, genetic information, protected veteran status, or any other characteristic protected by law.