Note: The job is a remote job and is open to candidates in USA. TownSq is seeking a high-performing Outside Sales Manager to drive new logo acquisition through a consultative, field-based sales approach. The role owns the full sales cycle across a Western market territory, including prospecting, in-person presentations, executive conversations, pipeline management, forecasting, and cross-functional coordination.
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
- 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
- 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
Skills
- 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
- SaaS or finance
- 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
Benefits
- Remote Outside Sales Manager position supporting the Western market
Company Overview