Account Executive – Cycle Outbound; Cold Calling Heavy - Remote
Chicago, Cook County, Illinois, 60290, USA
Listed on 2026-03-01
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Sales
B2B Sales, Sales Development Rep/SDR, Sales Representative, Business Development
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
- 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)
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 OverviewThis 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 Hub Spot 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.
- 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
- Familiarity with Hub Spot 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 Linked In Sales Navigator, Apollo, Zoom Info, or similar tools
- Uncapped commission with a clear path to $100,000+
- Strong coaching, playbooks, and Rev Ops 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…
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