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    Account Executive - Chicago, IL

    PadSplit

    🇺🇸 USA
    Remote
    ["Full-Time"]
    SaaS
    Base + Commission
    See your match score
    Posted Today
    Job Type

    ["Full-Time"]

    Work Type

    Remote

    Vertical

    SaaS

    Source

    jobicy

    About this role

    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 thr

    Tools & Tech Stack

    Outreach

    Selling Motion

    Prospecting

    Outbound-Heavy

    Self-sourced pipeline via cold outreach

    Requirements at a Glance

    Bachelor's Degree·Required
    Cold Calling·Required skill
    Prospecting·Required skill

    Typical Day — Account Executive

    Demos & presentations4–6/week
    Prospecting calls20–30/day
    Proposal writing2–3/week
    Pipeline review2×/week

    Estimates based on role type and selling motion — actual may vary by company.

    Role Signals

    Green Flags

    ✓
    Remote Friendly

    Location flexibility

    SaaS — Interview Intel

    Typical Sales Cycle

    30–90 days (SMB) · 3–9 months (Mid-Market) · 6–18 months (Enterprise)

    Common Buyer Objections

    • "We're locked into a contract with [competitor]"
    • "We built something in-house already"
    • "We don't have budget until next quarter"
    • "Our team won't adopt another tool"

    Key Industry Metrics

    ARR / MRRNet Revenue Retention (NRR)CAC Payback PeriodLogo Churn vs Revenue ChurnACV (Avg Contract Value)Magic Number

    Hot Topics to Reference

    • • AI-native product disruption
    • • PLG vs sales-led motion debate
    • • Vertical SaaS consolidation
    • • Usage-based pricing models

    Use these insights to speak the buyer's language in interviews.

    Tags

    sales
    —

    Walk me through your discovery process.

    Template question
    —

    How do you handle a prospect who goes silent mid-deal?

    Template question
    —

    Tell me about your largest closed deal and the sales cycle.

    Template question
    —

    How do you build business cases for stakeholders?

    Template question
    —

    Describe a deal you lost and what you learned.

    Template question
    Research PadSplit's product, recent news, and key competitors
    Prepare metrics: quota attainment %, average deal size, win rate
    Practice a 2-minute product demo pitch for a mock discovery call
    Research typical OTE splits for this role level and negotiate accordingly
    Prepare to discuss your home office setup and self-management discipline
    Review the job description and map your experience to each requirement
    Role Insights

    Account Executives are the revenue engine of any sales organization — this role will require strong pipeline management and closing skills.

    Top SaaS reps often earn significant upside through accelerators once quota is exceeded.

    This remote-friendly role provides geographic flexibility while maintaining access to a SaaS market.

    Are you a closer?

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