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Junior Account Executive / SDR – Full Cycle Sales (Cold Calling Focus) - Remote

Flamingo
Chicago, IL Remote Full Time
POSTED ON 12/17/2025
AVAILABLE BEFORE 1/16/2026
This role is PERFECT for SDRs with 1 to 2 years of experience that want to make the leap to an Account Executive position.Starting Base: $16,000 Per YearCommission: $38,880 Per YearOTE: $54,880 Per YearAbout UsFlamingo is a Resident Retention Platform. We help large apartment companies quickly boost their resident retention with an all-in-one platform. Learn more at https://getflamingo.com 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 sales role with a heavy focus on high-volume cold calling. You’ll use a power dialer to make 80–100 dials/day to apartment buildings across the country, connect with decision-makers, pitch Flamingo’s Resident-Led Events App, and move prospects through the funnel from cold lead → demo → close. This is not a sit-back-and-wait role — success here means embracing the grind of daily outbound calling and consistently hitting activity and conversion targets. This role is PERFECT for SDRs with 1 to 2 years of experience that want to make the leap to an Account Executive position.  Key ResponsibilitiesHigh-Volume Cold CallingUse 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 & ConversionGenerate 20 qualified meetings/month through consistent outbound activity.Maintain high connect and conversation rates by adapting talk tracks and overcoming objections. Product Demos & ClosingRun 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-UpKeep 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 Qualifications1–3 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 resultsPositive, coachable and eager to learn Preferred QualificationsFamiliarity with HubSpot or another CRMSaaS sales experience (especially SMB SaaS).Experience in multifamily, proptech, or startupsBackground in customer success, leasing, or property management is a plusComfortable using LinkedIn Sales Navigator, Apollo, ZoomInfo, or similar tools FLAMINGO CULTUREWhy Join Flamingo?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 clientsHigh ownership, autonomy, and visibilityRemote-first team with flexible work hoursStrong coaching and professional developmentFrequent virtual events, in-person meetups, and travel opportunities Why NOT Join Flamingo?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. 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.

Salary : $30,000 - $54,880

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