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Account Executive – Cycle Outbound; Cold Calling Heavy - Remote

Remote / Online - Candidates ideally in
Chicago, Cook County, Illinois, 60290, USA
Listing for: Flamingo Resident Retention Platform
Full Time, Remote/Work from Home position
Listed on 2026-03-01
Job specializations:
  • Sales
    B2B Sales, Sales Development Rep/SDR, Sales Representative, Business Development
Salary/Wage Range or Industry Benchmark: 36000 USD Yearly USD 36000.00 YEAR
Job Description & How to Apply Below
Position: Account Executive – Full Cycle Outbound (Cold Calling Heavy) - Remote - Feb 2026 Start

Overview

This role is PERFECT for SDRs with 1 to 2 years of experience that want to make the leap to an Account Executive position.

Compensation (Location-Based): USA and LATAM Preferred

Compensation by Region
  • United States (remote):
    • Base: $36,000
    • Uncapped commission with a clear path to $115,000+ OTE
    • Note:

      compensation reflects our performance-driven culture with rewards tied to performance
  • LATAM / Non-USA
    • Base: $18,000 Per Year
    • Uncapped commission with a clear path to $75,000+ OTE
Hiring Process for Cohort 2 AEs (Jan 15 to Feb 2026)
  • Step 1:
    Resume Submission (Candidate)
  • Step 2:
    Resume Review (Flamingo)
  • Step 3:
    Screening Interview for Accepted Candidates (Flamingo + Candidate)
  • Step 4:
    Technical Interview for Accepted Candidates (Flamingo + Candidates)
  • Step 5:
    Reference Calls + Background Checks for Accepted Candidates (Flamingo)
  • Step 6:
    Offers Sent for Accepted Candidates (Flamingo)
About Us

Flamingo is a Resident Retention Platform. We help large apartment companies quickly boost their resident retention with an all-in-one platform.

Learn more:

Customer Reviews:

For this role, you’ll be selling the basic version of Flamingo’s Resident App — a simple but powerful app that lets residents access everything they need from one place.

Position Overview

This is a full-cycle Account Executive role designed for top-performing SDRs with 1–2 years of outbound experience who are ready to own deals end-to-end.

You will run high-volume outbound sales—80–100 cold calls per day, daily demos, and consistent closes—using a proven product, clear targets, and strong sales infrastructure.

If you are motivated by clear metrics, real accountability, and uncapped upside, this role gives you a direct path to becoming a high-earning AE.

If you are looking for inbound leads, a slow ramp, or a low-pressure environment, this is NOT the role for you.

Key Responsibilities
  • High-Volume Cold Calling
    • Use a power dialer to make 80–100 dials/day into assigned building lists.
    • Drive first-touch conversations, qualify decision-makers, and pitch Flamingo’s Resident-Led Events App.
    • Log every call and outcome in Hub Spot CRM.
  • Pipeline Generation & Conversion
    • Generate 20+ qualified meetings/month through consistent outbound activity.
    • Maintain high connect and conversation rates by adapting talk tracks and overcoming objections.
  • Product Demos & Closing
    • Run live demos (4–5/week) with property managers and regional decision-makers.
    • Present value clearly and handle objections.
    • Close ~6 new paying communities per month (~$21.6K ARR).
  • CRM Hygiene & Follow-Up
    • Keep every account fully documented: call notes, decision-maker info, lead status.
    • Follow up with hot leads and nurture accounts that aren’t ready yet.
    • Sales

      Collaboration:

      Work closely with Leadership, Marketing, and Customer Success to align messaging, targeting, and feedback loops.
  • Continuous Learning

    Stay up to date on Flamingo’s product, customer success stories, industry news, and competitors.

Required Qualifications
  • 1–3 years in a full-cycle sales or high-volume outbound SDR/AE role.
  • Comfort with 80–100 dials/day using a power dialer.
  • Track record of setting meetings and closing deals from cold outreach.
  • Strong objection handling and resilience — can handle rejection and push through.
  • Excellent communication skills, both phone and email.
  • Self-motivated and disciplined with a metrics-first mindset.
  • Ownership mentality – you take pride in your work and results
  • Positive, coachable and eager to learn
Preferred Qualifications
  • Familiarity with Hub Spot or another CRM
  • SaaS sales experience (especially SMB SaaS).
  • Experience in multifamily, proptech, or startups
  • Background in customer success, leasing, or property management is a plus
  • Comfortable using Linked In Sales Navigator, Apollo, Zoom Info, or similar tools
Culture & Benefits
  • Uncapped commission with a clear path to $100,000+
  • Strong coaching, playbooks, and Rev Ops support (you’ll never have to build your own sequences)
  • Work at a fast-growing SaaS + marketplace company with major clients
  • Work on a product with real customers, real budgets, and clear value, selling into a defined market with repeatable motion
  • High ownership, autonomy, and visibility
  • Remote-first team with flexible work…
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