Account Executive – Full Cycle Outbound (Cold Calling Heavy) Feb 2026 Start

FlamingoChicago, IL
11h$36,000 - $115,000Remote

About The Position

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

Requirements

  • 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

Nice To Haves

  • Familiarity with HubSpot 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 LinkedIn Sales Navigator, Apollo, ZoomInfo, or similar tools

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 HubSpot 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.

Benefits

  • Uncapped commission with a clear path to $100,000+.
  • Strong coaching, playbooks, and RevOps 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 hours
  • Frequent virtual events, in-person meetups, and travel opportunities

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What This Job Offers

Job Type

Full-time

Career Level

Entry Level

Education Level

No Education Listed

Number of Employees

11-50 employees

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