Outside Sales Representative

Outside Sales Representative

TownSq 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 TownSq's structured sales methodology and pipeline governance standards. The job requires 60% of travel.

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

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

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 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%)

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

• 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