5+ years of B2B outside/field sales experience (SaaS or technology preferred)
Proven success in closing mid-market to enterprise deals with complex buying groups
Experience in owning a territory and managing a full sales cycle
Strong comfort with in-person meetings and executive-level conversations
Proficiency in CRM tools like Salesforce
Valid driver's license and willingness to travel 60% of the time
Responsibilities
Manage a defined geographic territory with accountability for pipeline and quotas
Develop and execute a structured territory plan involving prospecting and on-site meetings
Travel approximately 60% to engage with prospects and attend industry events
Conduct in-person discovery meetings with property management leaders
Deliver compelling presentations and demos aligned with prospect's challenges
Lead insight-driven sales conversations that differentiate TownSq
Navigate complex buying processes with multiple stakeholders
Benefits
Opportunity for high-performance bonuses
Engagement in strategic sales methodologies
Collaboration with marketing and client success teams
Involvement in the decision-making process within a growing tech company
Focus on consultative selling and relationship building
Full 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. This role is in office at our Richardson, Texas location and travel is expected. This role is based in Richardson, TX - travel is required.
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
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 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
Consultative, insight-driven selling
Strong executive presence and communication skills
