About this role.
PadSplit is seeking a Boston-focused Account Executive to recruit property owners and real estate investors as marketplace Hosts. The role centers on prospecting, cold outreach, discovery, consultative presentations, financial modeling, objection handling, and closing host onboarding agreements. The AE will use Salesforce, HubSpot, and sales enablement tools to manage pipeline activity and conversion metrics while collaborating with marketing and onboarding teams. Success requires real estate or property-management sales familiarity, strong relationship-building, and the ability to work independently in a fast-paced remote startup environment. The position contributes directly to expanding affordable shared-housing supply in the Boston market.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
4/5Pace & Pressure
4/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
Skills and capabilities most closely associated with this opportunity.
Sample interview questions
I would define an ideal property profile using location, unit count, ownership structure, rental history, and local compliance considerations. I would combine public property records, investor networks, referrals, targeted outbound campaigns, and local real estate events, then prioritize accounts based on likely revenue impact and readiness to convert.
I would first understand the owner's current rental model, income goals, and specific concerns. I would then tailor the discussion around potential revenue, management simplification, onboarding support, and compliance considerations, using a transparent financial comparison and clear next steps rather than relying on a generic pitch.
I would acknowledge that traditional leasing can be familiar and dependable, then ask what outcomes matter most, such as income stability, occupancy, management time, or risk. Using those priorities, I would present a fact-based comparison of the two approaches, address perceived tradeoffs directly, and determine whether a pilot property or follow-up analysis is appropriate.
I would monitor leading indicators including target accounts researched, outreach volume, connection rate, discovery calls held, qualified opportunities created, and follow-up completion. I would also track conversion through each funnel stage, sales-cycle length, forecast accuracy, signed hosts, and ultimately the quality and activation of onboarded properties.
In a strong example, I would outline how I translated a revenue goal into weekly activity and conversion targets, organized my territory in a CRM, tested messaging, and reviewed results consistently. I would emphasize how I adjusted outreach based on data, engaged internal partners when needed, and maintained momentum through rejection until I achieved the target.
The Role That We Need:
PadSplit is hiring for an Account Executive to expand our marketplace by engaging traditional property owners to become PadSplit Hosts. This role is critical in helping homeowners unlock additional income by listing their properties, while addressing housing affordability by creating more shared housing opportunities in the Boston, MA market.
The Person We Are Looking For:
We are seeking a driven and personable Account Executive with experience in sales or real estate who excels at building relationships with property owners and real estate investors. This role involves delivering a tailored value pitch on how the PadSplit model and technology consistently drive superior rental income compared to traditional single-family rentals. The ideal candidate thrives in a remote environment, demonstrates strong communication skills, and wants to have an impact on the affordable housing crisis – one room at a time.
Here’s what you’ll do day-to-day:
- Prospect and Qualify Leads: Research and identify potential property owners who might be interested in becoming PadSplit Hosts and qualify them based on suitability.
- Conduct Outreach: Execute outreach strategies, including cold calling, emailing, and networking, to connect with traditional property owners.
- Host Discovery Calls and Meetings: Engage property owners in initial conversations to understand their needs, goals, and potential barriers to joining PadSplit.
- Deliver Value Propositions: Clearly articulate the benefits of PadSplit’s model, such as increased revenue potential, simplified management, and societal impact.
- Build and Nurture Relationships: Develop trust-based relationships with property owners, acting as a trusted advisor to address concerns and highlight opportunities.
- Tailor Solutions: Customize hosting solutions based on the unique circumstances of property owners, including financial modeling, property suitability, and compliance requirements.
- Close Deals: Guide property owners through the decision-making process, negotiate terms, and finalize agreements for onboarding as PadSplit Hosts.
- Collaborate with Onboarding Teams: Coordinate with internal teams to ensure smooth onboarding for new Hosts, providing accurate property details and expectations.
- Track and Report Metrics: Maintain detailed records in CRM systems, tracking outreach activities, conversion rates, and other key performance indicators.
- Stay Updated on Market Trends: Monitor the real estate market, competitive landscape, and legislative changes to refine outreach and value propositions effectively.
- Host Educational Sessions: Organize webinars or in-person sessions to educate property owners on PadSplit’s benefits and address common misconceptions.
Here’s what you’ll need to be successful:
- Sales Experience: Proven success in B2B or B2C sales, particularly in the real estate or property management sectors, with a track record of meeting or exceeding sales targets.
- Relationship-Building Skills: Strong interpersonal and communication abilities to build trust and long-term relationships with property owners.
- Self-Motivation and Independence: High level of self-discipline and motivation to thrive in a remote, fast-paced startup environment with minimal supervision.
- Adaptability and Problem-Solving: Ability to think on their feet, overcome objections, and tailor solutions to meet the unique needs of property owners.
- Knowledge of Real Estate Markets: Familiarity with the dynamics of real estate investing, rental markets, and property management is highly desirable.
- Tech Proficiency: Comfortable using CRM systems (we use Salesforce and Hubspot), sales enablement tools, and virtual communication platforms for outreach and reporting.
- Strong Presentation Skills: Ability to confidently present PadSplit’s value proposition through virtual meetings, calls, or live presentations.
- Analytical Skills: Capable of interpreting market data, calculating ROI, and presenting financial benefits to potential Hosts.
- Team Collaboration: Effective at collaborating with cross-functional teams, such as marketing and onboarding, to ensure a seamless experience for new Hosts.
- Entrepreneurial Mindset: Resilience and resourcefulness to tackle challenges and drive results in a rapidly changing startup environment.
- PadSplit Core Values: Consistently demonstrate our values of compassionate directness, high integrity, optimism, intellectual curiosity, strong work ethic, empathy, self-awareness.
The Interview Process:
- Your application will be reviewed for possible next steps by the Hiring Manager.
- If you meet eligibility requirements, the next step would be a phone call with a member of the PeopleOps team for about thirty (30) minutes.
- If warranted, the next step would be a video interview with one of our Head of Sales for forty-five (45) minutes.
- If warranted, the next step would be a video interview with a small panel of key stakeholders for one-and-a-half (1.5) hours. For this interview, a candidate would present a short case study to the panel for discussion.
- If warranted, the final step would be an in-person meeting with a member of the PadSplit leadership team (we come to you).
- If warranted, then we move to offer!
Compensation
Compensation is based on the role’s scope, market benchmarks, the person’s expertise and experience, and the impact of their contributions to our business goals. In addition to the base salary, there is a commission component with an opportunity to make at least double your base.
The base salary for an AE in Boston is $65,000 a year with attainable commission structure.
The annual commission target for an AE is set at $180,000.
To achieve this target, an AE is expected to onboard approximately 80 new hosts annually, with 10 hosts reaching 25 units each year.
Additional Information
Notice to Applicants:
PadSplit participates in E-Verify. All new employees are required to complete an I-9 form and be authorized to work in the United States. Employment is contingent upon successful completion of the E-Verify process.
PadSplit is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or status as a protected veteran.
Upload your resume now
- To unlock remote work opportunities and be discovered by global employers.
This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content.
