Middle Market Account Executive

We are seeking a results-driven Middle Market Account Executive to lead strategic B2B SaaS sales across a portfolio of regional and multi-state property management companies. In this role, you will own a dedicated territory and drive new business through account-based prospecting, consultative selling, and multi-stakeholder engagement. You will work with senior decision-makers to identify operational challenges and demonstrate how innovative technology can improve resident retention and reduce property management costs. From initial outreach and product demonstrations to pilot programs and portfolio-wide agreements, you will manage the entire sales cycle. This position offers the opportunity to influence business growth through high-value contracts and structured land-and-expand strategies. You will join a performance-oriented, remote sales environment with clear targets, modern sales tools, and attractive earning potential.

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.