Remote Middle Market Account Executive

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Job Title: Remote Middle Market Account Executive (

100% Work From Home) Location:

Remote from Latin America

Position Type:

Full-time

Salary : $1,900 USD/month base salary + closed deal commissions/bonuses ($150 – $300 USD per closed deal, targeting ~$72K ARR added monthly)

Schedule:

Full-time (US business hours overlap required for power dialing and client demos)

Job Overview

Our Client is a fast-growing property technology (PropTech) enterprise offering an innovative, resident-led event, app, and engagement platform tailored for residential multi-family communities. Dedicated to driving resident retention, reducing turnover costs, and saving operational hours for property management teams across North America, they deliver software and event solutions built to scale. Operating on an account-based growth strategy, they rely on seasoned, multi-threaded B2B sales professionals to secure portfolio-level agreements across mid-market operators.

The Role

Our Client is seeking a strategic, research-driven Middle Market Account Executive to own and expand a named territory of 150–250 regional and multi-state property management companies (managing 20 to 200 apartment communities / 5,000–50,000 units). Moving beyond single-community transactional sales, this professional will execute account-based outbound outreach, conduct strategic discovery sessions, deliver high-impact demos, run structured pilot programs, and navigate multi-stakeholder buying groups (VPs of Operations, Regional Managers, Marketing Directors). This role is ideal for an experienced B2B SaaS Account Executive who excels at building ROI business cases and executing land-and-expand sales motions.

Key Responsibilities

Account-Based Prospecting & Multi-Threaded Outreach

Owns a named territory of 150–250 middle-market property management companies, conducting account mapping (portfolio size, current engagement stack, key decision-makers) to prioritize quarterly targets.

Executes 50–60 tailored outbound touches daily across calls, emails, and LinkedIn, sequencing outreach across at least 3 distinct stakeholders per account (Operations, Marketing, Regional Leadership, Ownership).

Leverages referenceable client success stories, industry conference networking, and portfolio-level ROI messaging to secure high-level discovery calls.

Consultative Discovery, Demos & Business Case Development

Conducts 10–12 discovery calls and product demonstrations per month with multi-property decision-makers, diagnosing core business challenges (resident renewal rates, staff bandwidth, event spend).

Quantifies business impact, building customized financial proposals that tie platform adoption directly to renewal lift and cost savings per community.

Manages multi-stakeholder buying groups through 45–90 day sales cycles, navigating procurement, legal review, and contract negotiations for multi-property deals ($36K–$72K ARR).

Pilot-to-Portfolio Expansion & Pipeline Hygiene

Structures trial pilots with defined success metrics and clear expansion triggers to systematically convert initial community wins into full portfolio rollouts.

Collaborates with Customer Success during pilot check-ins to monitor adoption signals and drive community expansion targets.

Maintains strict CRM hygiene in HubSpot—logging detailed org maps, community counts, meeting notes, and maintaining accurate weekly pipeline forecasts.

Performance Metrics & Conversions Benchmarks

Candidates will be evaluated against clear operational benchmarks, including:

Daily Output:

50–60 Outbound Touches (30–40 Dials) | 5–7 Connects | 4–6 Decision-Maker Conversations | 3–5 New Accounts Researched.

Monthly Output:

1,000–1,200 Touches | 600–800 Dials | 100–120 Conversations | 12+ Meetings Set | 10–12 Demos Held | 5–6 Proposals/Pilots Proposed | 2 New Logos Closed (~20–25 Communities Added / ~$72K ARR Added Monthly).

Conversion Benchmarks:

Dial-to-Connect (12–18%) | Demo-to-Proposal (40–50%) | Proposal-to-Closed Won (30–40%) | Pilot-to-Portfolio Expansion (50%+ within 2 quarters).

Primary Success Benchmark:

2 new middle-market logos closed per month and ~$72K in new ARR added monthly, with at least 50% of signed pilots expanding across broader portfolios.

Qualifications, Skills, and Key Competencies

Required Qualifications

B2B