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Lead Sales Development Rep | NY, NY | (OTE): $100,000 - $125,000 | Full-Time (on-site)

About the Company

Equal Access is partnering with a well-established, fast-growing technology company transforming operations within the hospitality and property management space. The organization supports large-scale short-term rental and boutique hospitality portfolios through a modern platform focused on smart automation, operational efficiency, and elevated guest experiences. Backed by strong investment and operating with a highly innovative, AI-driven culture, the company is currently rebuilding its core technology stack from the ground up, making this an exciting opportunity to join during a pivotal stage of growth and product evolution.

About the Role

This is an exciting opportunity for a high-energy Lead Sales Development Representative who thrives in a phone-first sales environment, loves the hunt, and knows how to blend AI-powered efficiency with genuine human connection. In this role, you’ll drive outbound prospecting efforts, book qualified demos for the Account Executive team, and help shape modern AI-assisted sales workflows. If you’re competitive, coachable, curious about AI, and excited by high-volume outbound sales in a fast-paced startup environment, this is a chance to join a company during a major growth and product evolution phase.

Key Responsibilities

• Make 100+ outbound dials per day to property managers and hospitality operators across North America
• Book 4 qualified demos per day for our Account Executive team
• Own your pipeline, research accounts, craft personalized outreach, and follow up relentlessly until you get a yes or a hard no
• Leverage AI tools (ChatGPT, Claude, Clay, Apollo AI, Gong, etc.) to research accounts, personalize messaging, and prep for every call
• Run multi-touch outbound sequences across phone, email, and LinkedIn, powered by AI-assisted personalization, delivered with your voice
• Qualify inbound leads and route them to the right AE with crisp handoff notes
• Master our ICP, pain points, and talk tracks within 30 days, so you can hold a real conversation without a script
• Update CRM obsessively, every call, every note, every next step
• Partner with AEs to build territory plans and attack target account lists together
• Feed market intel back to marketing and product, what's landing, what's not, and why
• Experiment with new AI workflows and share wins with the team, we promote the builders
• Represent the company at local NYC industry events and meetups

Required Skills & Experience

• 1+ years of outbound SDR/BDR experience at a B2B SaaS company, ideally selling to SMBs or mid-market
• Proven phone-first track record, you've hit 100+ dials/day and consistently booked meetings through real conversations, not automation alone
• Hands-on experience using AI tools (ChatGPT, Claude, Perplexity, etc.) in a sales or work context, you have specific examples of how AI has made you faster or better
• History of over-achievement, show us the quarters you finished at 120%+
• Exceptional verbal communication, you sound confident, curious, and human on the phone; you can read a room (even over the phone) and adapt in real time
• Thick skin and short memory, you treat rejection as data, not defeat
• Strong written chops, your cold emails get opened and replied to because they sound like you, not like GPT
• Comfortable with modern sales stack (CRM, dialers, sequencers, sales intel, AI research tools)
• Self-starter mentality, you don't wait for a manager to tell you to make the next call
• Gritty, competitive, coachable

Ideal Candidate

• Experience selling into hospitality, property management, real estate, or adjacent industries
• Has run a dialer like Orum, Nooks, or ConnectAndSell at volume
• Uses AI daily as a force multiplier, you've built prompts, GPTs, or workflows that speed up research, writing, or prospecting, but you know when to put the tools down and pick up the phone
• Believes the best outreach blends AI leverage with genuine human curiosity, generic AI-generated blasts make you cringe
• Curious about the cutting edge, you follow AI developments, test new tools, and share what works
• Multilingual (Spanish a plus given our LATAM expansion)
• Former D1 athlete, performer, or anyone who's lived in high-rep, high-feedback environments
• Lives for the hunt, you get a genuine thrill from a cold prospect saying "yeah, let's set up that demo"
• Process-oriented but not robotic, you can deviate from the script when a conversation gets real

Compensation

• On-Target Earnings (OTE): $100,000 - $125,000
• Competitive base salary + uncapped commission
• Equity ownership
• 401k match
• Health insurance
• Fully in-office role at our NYC headquarters

Why EqualAccess

EqualAccess partners with best-in-class organizations and supports candidates beyond placement. Every professional we place receives 3 months of post-hire coaching and career support, ensuring long-term success and growth