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.