Middle Market Account Executive

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Middle Market Account Executive based in Brazil.

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.

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