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

$36k

Flamingo Resident Retention Platform

Chicago, IL
  • Remote job

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 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. 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 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 Culture & 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 Why Flamingo? Why Not? Flamingo is extremely results oriented. Your metrics are your metrics and you are expected to hit them. Flamingo is not a family. We operate like a professional elite sports team. Do not join Flamingo if you are uncomfortable being measured daily and weekly on clear, visible performance metrics. Do not join Flamingo if you believe effort should be rewarded independently of results. Do not join Flamingo if you want a low-pressure environment, inbound leads, or a role where missing targets is routinely excused. Do not join Flamingo if you need constant supervision, external motivation, or long ramp periods to feel confident. At Flamingo, we are performance- and results-driven. We don’t operate like a family where everyone has a permanent seat at the table — instead, we operate like an elite sports team. Every team member is expected to perform at a high level and contribute to the overall success of the company. In return, Flamingo provides the environment, training, tools, and resources needed for each person to operate at their best. The people who thrive here are those who take full advantage of those resources to continuously raise their game. When someone struggles to meet expectations, we provide coaching and support. But just like in sports, if performance doesn’t improve, we make changes. This ensures that the entire team remains strong, competitive, and focused on winning. We celebrate results, accountability, and growth. At Flamingo, joining the team means committing to excellence, pushing yourself to be better every day, and supporting others in doing the same. #J-18808-Ljbffr Flamingo Resident Retention Platform

Vacancy posted 4 days ago
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