Middle Market Account Executive

Accountabilities: You will take ownership of the full sales cycle for a defined portfolio of middle-market accounts, building strong relationships with decision-makers and converting strategic opportunities into long-term business partnerships. Manage a named territory of 150–250 regional and multi-state property management companies, targeting organizations operating 20–200 apartment communities and managing approximately 5,000–50,000 residential units. Research and map target accounts, analyzing portfolio size, existing engagement solutions, organizational structures, and key decision-makers to prioritize sales opportunities. Execute 50–60 personalized outbound activities daily across phone calls, emails, and LinkedIn, engaging at least three stakeholders within each target account. Leverage customer success stories, industry networking, and portfolio-level ROI messaging to generate qualified discovery opportunities with senior decision-makers. Conduct 10–12 discovery calls and product demonstrations monthly, identifying operational challenges related to resident retention, staff capacity, and community engagement spending. Develop tailored financial proposals and business cases demonstrating measurable ROI, potential renewal improvements, and cost savings across residential communities. Manage complex, multi-stakeholder sales cycles lasting approximately 45–90 days, coordinating procurement, legal reviews, and contract negotiations for agreements valued at $36K–$72K in annual recurring revenue. Design structured pilot programs with clear success criteria and expansion opportunities to convert individual community agreements into portfolio-wide implementations. Partner with Customer Success teams during pilot programs to monitor adoption, evaluate results, and identify opportunities for further expansion. Maintain accurate CRM records in HubSpot, including account maps, community counts, meeting notes, and weekly pipeline forecasts. Work toward monthly performance targets, including two new customer wins, approximately 20–25 additional communities, and around $72K in new annual recurring revenue. Requirements: The ideal candidate combines strong B2B SaaS sales experience with a disciplined outbound prospecting approach, consultative selling capabilities, and the confidence to manage complex enterprise-style buying processes. 2–5 years of full-cycle B2B SaaS sales experience, including at least one year selling to mid-market, regional, or multi-location accounts. Demonstrated success generating an independent sales pipeline through structured, account-based outbound prospecting, with at least 50 daily outreach activities using dialers and sequencing tools. Experience managing complex, multi-stakeholder buying groups and navigating sales cycles of approximately 45–90 days without depending on price discounting. Advanced consultative discovery skills, with the ability to uncover operational challenges, quantify business impact, calculate ROI, and develop compelling commercial proposals. Excellent written and spoken English, with the ability to communicate confidently and professionally with C-suite executives, operations leaders, and senior property management decision-makers. Strong ownership mentality, resilience, coachability, and a metrics-driven approach to sales performance. Proven ability to maintain accurate forecasts, manage multiple opportunities simultaneously, and consistently work toward ambitious commercial targets. Additional qualifications that would be advantageous: Previous experience in PropTech, multifamily housing, real estate services, or property management operations. Familiarity with structured sales methodologies such as MEDDPICC or Command of the Message. Experience using HubSpot CRM, LinkedIn Sales Navigator, Apollo, ZoomInfo, or similar sales intelligence and prospecting platforms. Previous success executing land-and-expand strategies or selling to large regional and multi-family property management portfolios, including NMHC Top 50 operators. Benefits: Competitive Compensation: Monthly base salary of $2,000–$2,500 USD. Performance-Based Incentives: Additional commissions and bonuses of $150–$300 USD per closed deal, linked to high-value contract acquisitions. High Earning Potential: Opportunity to contribute approximately $72K in new annual recurring revenue monthly through strategic portfolio-level sales. Strategic Territory Ownership: Manage a dedicated portfolio of middle-market accounts with autonomy over prospecting, relationship development, and expansion strategies. Modern Sales Technology: Access to CRM systems, sales sequencing platforms, power dialers, and business intelligence tools. Fully Remote Work: 100% work-from-home opportunity for eligible candidates based in Latin America. Full-Time Opportunity: Stable, performance-oriented position within a growing US-based PropTech sales environment.