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

Flamingo • Chicago, IL

80d • $16,000 - $54,880

About The Position

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

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

• 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.
• Generate 20+ qualified meetings/month through consistent outbound activity.
• Maintain high connect and conversation rates by adapting talk tracks and overcoming objections.
• 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).
• 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.
• Work closely with Leadership, Marketing, and Customer Success to align messaging, targeting, and feedback loops.
• 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.
• Work at a fast-growing SaaS + marketplace company with major clients.
• High ownership, autonomy, and visibility.
• Remote-first team with flexible work hours.
• Strong coaching and professional development.
• Frequent virtual events, in-person meetups, and travel opportunities.

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Number of Employees: 11-50 employees