Account Executive - Chicago, IL
Description
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
Skills
As published by lever · 10 questions · 1 written answer
Basics
Resume/CV, Full name, Email, Phone, Current location, Current company, Please provide your LinkedIn URL, Portfolio URL
Pick from a list (9)
- What best describes your experience working in a consultative, B2B inside sales role?
- What best describes your experience creating a pipeline through networking and cold outreach?
- What best describes your experience working with Single-Family Rentals (SFR), Fix-and-Flips, Workforce Housing, Real Estate or PropTech, or experience as a Landlord or Operator?
- This role has travel requirements, around 25% of time will be spent driving to various locations in your territory. Are you able to meet this requirement?
- Which state will you physically be working out of? optional
- Please note: To be considered for this role, you must be physically located in the United States full-time. Candidates found to have misrepresented their location will be immediately disqualified from the hiring process and will not move forward with an offer.
- Are you currently authorized to work in the United States without the need for sponsorship now or in the future?
- Are you physically located in Chicago, IL or within a reasonable driving distance (60 miles)?
- The base salary for an AE is $65,000 a year with an 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. Knowing this, would you accept an offer for that base salary?
Written answers (1)
- In twenty (20) words or less, what is the biggest piece of advice you would give someone who is starting a career in sales?
Techstars 

