[![Image]() Meet Jobicy Copilot — free AI autofill for job applications + remote job alerts ›](#) [All remote jobs](https://jobicy.com/jobs.md)Open role[![PadSplit logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2021/06/da525286873130ed0b95212896ef55d4.jpg)](https://jobicy.com/company/padsplit.md)Remote opportunity at[PadSplit](https://jobicy.com/company/padsplit.md) # Account Executive – Chicago, IL Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/padsplit.md)Share12 Sep 2026Published45Listing views5Application actions12 Oct 2026Apply before Opportunity details ## About this role. AI SummaryPadSplit is seeking a Chicago-focused Account Executive to recruit property owners and real estate investors as marketplace Hosts. The role centers on prospecting, cold outreach, discovery calls, consultative presentations, financial modeling, negotiation, and closing new host agreements. The successful candidate will manage activity and conversion data in Salesforce and HubSpot while coordinating closely with onboarding and marketing teams. This is a remote, fast-paced startup sales position requiring independence, resilience, strong real-estate-market knowledge, and a mission-driven approach to affordable housing. Performance expectations include onboarding approximately 80 new hosts annually, with a subset scaling to 25 units. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 4/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is a demanding consultative sales role because it requires creating pipeline through outbound prospecting and influencing property owners to adopt a nontraditional rental model. Success depends on independent execution, credible ROI discussions, objection handling, and consistent closing performance in a fast-moving startup environment. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job medianMarket rate$70,000US market range$65k–$120k0$132k AI insightThe disclosed base salary is $70,000 USD yearly, so the job compensation median is $70,000. The posting also mentions an attainable commission structure and a $180,000 annual commission target, but this is a sales-performance target rather than guaranteed salary and is excluded from the salary range. Estimated US-market base salary for a mid-level real-estate or marketplace Account Executive is approximately $65,000 to $120,000 USD annually; actual total earnings may be higher with commissions. ## Core skills Skills and capabilities most closely associated with this opportunity. [Consultative Sales](https://jobicy.com/jobs?search_keywords=Consultative%20Sales.md)[Account Management](https://jobicy.com/jobs?search_keywords=Account%20Management.md)[Outbound Prospecting](https://jobicy.com/jobs?search_keywords=Outbound%20Prospecting.md)[Cold Calling](https://jobicy.com/jobs?search_keywords=Cold%20Calling.md)[Lead Qualification](https://jobicy.com/jobs?search_keywords=Lead%20Qualification.md)[Real Estate](https://jobicy.com/jobs?search_keywords=Real%20Estate.md)[Property Management](https://jobicy.com/jobs?search_keywords=Property%20Management.md)[Salesforce](https://jobicy.com/jobs?search_keywords=Salesforce.md)[HubSpot](https://jobicy.com/jobs?search_keywords=HubSpot.md)[Financial Modeling](https://jobicy.com/jobs?search_keywords=Financial%20Modeling.md) Sample interview questionsHow would you build a pipeline of prospective PadSplit Hosts in the Chicago market?I would segment the market by property type, investor profile, neighborhood, and likely unit economics, then prioritize owners with properties suited to shared housing. I would combine public property data, referral networks, investor groups, targeted email sequences, cold calls, and local events, while measuring contact, meeting, qualification, and conversion rates in the CRM. How would you explain PadSplit's value to a skeptical owner who currently operates traditional single-family rentals? I would first understand the owner’s current income, operating concerns, management capacity, and risk tolerance. I would then present a tailored comparison of projected revenue, occupancy assumptions, management support, compliance considerations, and the social impact of creating affordable rooms, addressing concerns directly rather than relying on a generic pitch. Describe how you would handle an objection about regulatory or compliance risk. I would acknowledge the concern, clarify the specific issue, and avoid making unsupported claims. I would use approved compliance resources and partner with internal experts where needed, explain the applicable process and safeguards, and document follow-up actions so the owner receives a clear and accurate answer. What metrics would you use to manage your performance in this role? I would monitor leading indicators such as new prospects researched, outreach volume, response rate, discovery meetings, qualified opportunities, and follow-up speed. I would also track funnel conversion, time to close, hosts onboarded, units activated, pipeline coverage, and the quality of handoffs to onboarding. Tell us about a time you used financial analysis to advance a sale. In a consultative sale, I would gather the customer’s current revenue and cost assumptions, build a simple scenario model, and identify the factors most important to their return. I would clearly explain assumptions, show sensitivity ranges, and use the analysis to support a practical decision rather than overpromise results. 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 Chicago, Illinois 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 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 (1) hour. 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 our Head of Sales at a PadSplit hosted event. * If warranted, then we move to offer! ### Compensation, Benefits, and Perks: * Competitive compensation package including an equity incentive plan * National medical, dental, and vision healthcare plans * Company provided life insurance policy * Optional accidental insurances, FSA, and DCFSA benefits * Unlimited paid-time (PTO) policy with eleven (11) company-observed holidays * 401(k) plan * Twelve (12) weeks of paid time off for both eligible birth and non-birth parents * The opportunity to do what you love at a company that is at the forefront of solving the affordable housing crisis ### 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: The base salary for an AE in Chicago is $70,000 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. 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