Outside Sales Manager

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 www.associaonline.com. Job Description 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 job requires 60% of travel. Key Responsibilities: Revenue & Territory Ownership Own and manage a defined geographic territory with full accountability for pipeline, forecast accuracy, and quota attainmentExecute a structured territory plan that includes outbound prospecting, on-site meetings, events, and partner-driven opportunitiesTravel 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-makersDeliver compelling on-site presentations and demos aligned to prospect business challengesLead value-based, Challenger-style sales conversations that reframe problems and differentiate TownSqNavigate 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 documentationMaintain 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 risksParticipate in weekly pipeline reviews, forecast calls, and coaching sessions Cross-Functional Collaboration Partner closely with Marketing on regional events, campaigns, and field enablementCoordinate with Implementation, and Client Success to ensure clean handoffs and successful onboardingRepresent 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 technology preferred)Proven success closing mid-market to enterprise deals with multi-stakeholder buying groupsExperience owning a territory and managing a full sales cycleStrong comfort with in-person meetings, travel, and executive-level conversationsCRM proficiency with SalesforceValid driver’s license and ability to travel extensively (60%) Preferred Qualifications Experience selling SaaS, workflow platforms, or community-based technologyFamiliarity with Challenger, SPIN, MEDDICC, or structured sales methodologiesExperience selling to property management companies, HOAs, or adjacent marketsTrack record of consistent quota attainment and forecast accuracy Core Competencies Consultative, insight-driven sellingStrong executive presence and communication skillsExcellent territory planning and time managementHigh accountability and pipeline rigorResilience, 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.