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

Flamingo•Chicago, IL

23h•$75,000 - $115,000•Remote

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. Compensation (Location-Based): USA and LATAM Preferred United States (remote): Base: $36,000 Uncapped commission with a clear path to $115,000+ OTE Why the small base? Read on to learn about our performance driven culture that comes with huge performance rewards. LATAM / Non-USA Base: $18,000 Per Year Uncapped commission with a clear path to $75,000+ OTE 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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