Outside Sales Manager

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. We currently have two openings: Florida Arizona/California Key Responsibilities: Revenue & Territory Ownership 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 Consultative Selling & Field Execution 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 Sales Process & Pipeline Discipline 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 Cross-Functional Collaboration 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 Required Qualifications: 5+ years of B2B outside / field sales experience (SaaS or finance 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 or similar 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 Core Competencies Strong executive presence and communication skills Excellent territory planning and time management High accountability and pipeline rigor Resilience, adaptability, and competitive drive Company Description With more than 180 branch offices across North America, Associa delivers unsurpassed management and lifestyle services to nearly five million residents worldwide. Our 10,000+ team members lead the industry with unrivaled education, expertise and trailblazing innovation. For more than 40 years, Associa has provided solutions designed to help communities achieve their vision. To learn more, visit . #J-18808-Ljbffr