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 .

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 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