Account Executive (Middle Market Property Management) - Independent Contractor

The Role

We are seeking a high-energy, research-driven Account Executive to lead growth within the middle market property management sector. This role involves more than just selling a platform—you’ll empower regional and multi-state operators to transform resident engagement and retention strategies.

You will be responsible for owning a named territory of portfolios ranging from 5,000 to 50,000 units, managing complex deals involving VPs of Operations, Marketing Directors, and Ownership groups. If you thrive in a full-cycle environment where you build your own pipeline and execute a sophisticated land-and-expand strategy, this opportunity is ideal for you.

Key Responsibilities

• Own and map a named list of 150–250 middle market accounts, identifying key stakeholders and resident engagement stacks before initiating contact.
• Execute a high-volume, high-quality outbound cadence (50–60 touches daily) across phone, email, and LinkedIn, building relationships with at least three stakeholders per account.
• Lead 10–12 discovery calls and demos monthly, moving beyond feature walkthroughs to diagnose challenges like resident turnover, onsite team burnout, and event spend.
• Develop compelling proposals that tie the platform to measurable ROI, including renewal lift and hours saved per community.
• Structure and close pilot agreements with clear success criteria, collaborating with Customer Success to trigger full portfolio rollouts.
• Navigate procurement and legal to close deals typically ranging from 10–20 communities ($36K–$72K ARR) within a 45–90 day cycle.
• Maintain meticulous records in HubSpot to ensure accurate weekly forecasting and territory planning.

Requirements

• 2–5 years of full-cycle B2B SaaS sales experience, including at least 1 year managing mid-market or multi-location accounts.
• A proven track record of self-sourcing pipeline; comfortable with a daily goal of 30–40 dials and personalized sequencing.
• Experience managing multi-stakeholder deals with a 45–90 day sales cycle.
• Ability to lead deep-dive conversations that uncover pain points and quantify the cost of inaction.
• Proven ability to build a business case and defend pricing based on value rather than discounts.
• Exceptional written and verbal communication skills with the ability to influence executive-level decision-makers.
• A metrics-first mindset with a commitment to accurate forecasting and CRM hygiene.

Nice-to-Haves

• Experience in Multifamily real estate, PropTech, or resident services.
• Familiarity with the NMHC Top 50 operators or regional property management structures.
• Proficiency in HubSpot, LinkedIn Sales Navigator, Apollo, or ZoomInfo.
• Experience using structured sales methodologies such as MEDDPICC or Command of the Message.
• Previous success in a land-and-expand or pilot-to-rollout sales motion.

Benefits

💰 Competitive base salary and uncapped commission

🌎 Fully remote work environment

🚀 Career growth and leadership opportunities

📈 Long-term stability in a growing market

🎯 Performance-based incentives and bonuses

🏥 Comprehensive health and wellness coverage

📚 Professional development stipend