Founding Sales Development Representative (SDR)

Overview

You're the founding SDR at an AI startup that sells software to short-term rental properties and hotels. Your primary job is cold calling property managers, hotel GMs, and revenue managers to book demos for the sales team. Since they already have 10,000+ properties using the product, you're not selling something completely unproven, but you are building the outbound motion from scratch with little structure.

Role Snapshot

Company Context

Stage: Seed (fundraising for Series A mentioned in post)

Size: Small team (exact size not disclosed, but founding SDR = very early)

Growth: Serving 10,000+ properties globally, backed by investors, actively hiring first sales roles

Market Position: AI-native player entering a $1T+ market (short-term rentals + hotels). Competing in a crowded hospitality tech space against established property management systems, channel managers, and revenue management tools.

GTM Reality

Pipeline Sources:

• 95% Outbound - you're building this from scratch with cold calls
• 5% might come from conference leads you generate
• No indication of significant inbound marketing yet

SDR/AE Structure: You'll likely be feeding meetings to 1-2 AEs or founders. No established team yet.

SE Support: Unknown - at this stage probably none or you're demoing with an AE.

Competitive Landscape

Main Competitors: Likely competing against established property management systems (Opera, Cloudbeds, Guesty), channel managers, and revenue management tools. Also competing against "we're doing fine with our current setup" inertia.

How They Differentiate: AI-native positioning - likely using AI for pricing optimization, guest communication, or operational automation.

Common Objections:

• "We already have a PMS/system"
• "We're too busy during high season"
• "How does this integrate with our existing tools?"
• "What's the ROI vs our current process?"

Win Themes: Unknown - you'll be figuring this out by testing different pitches.

What You'll Actually Do

Time Breakdown

Cold Calling (70%) | List Building/Research (15%) | CRM Updates (10%) | Conference Prep/Travel (5%)

Key Activities

• Cold Calling: You'll make 60-80 calls per day to property managers, hotel GMs, and vacation rental operators. Most calls go to voicemail. You'll leave messages and send follow-up emails. Your goal is booking 15-25 qualified demos per month.
• List Building: You'll spend time researching properties, finding contact info (which is often hard to get), and building call lists. This means Googling properties, checking LinkedIn, looking at property websites for contact info.
• Conference Attendance: You'll represent the company at travel and hospitality conferences (think Phocuswright, VRMA, short-term rental events). This means booth duty, collecting business cards, and following up with leads afterward.
• CRM Management: You'll log every call, email, and conversation in their CRM (probably Salesforce or HubSpot). You'll update lead statuses and track what messaging is working.

The Honest Reality

What's Hard

• High rejection rate: Most property managers are busy running their operations and don't want sales calls. You'll hear a lot of "not interested" and "send me an email" (which usually means no).
• Finding the right contacts: Properties don't always have clear decision-makers listed online. You'll spend time hunting for phone numbers and emails.
• No established playbook: As the founding SDR, there's no proven script or process. You'll be testing different approaches and some will fail. This can be frustrating if you prefer structure.
• Travel requirement: The conference travel sounds glamorous but it's long days on your feet, repetitive conversations, and then weeks of follow-up calls to people who barely remember meeting you.
• Proving yourself constantly: You're building credibility for a startup product in a skeptical market. Property managers have seen lots of tech solutions that didn't deliver.

What Success Looks Like

• Booking 15-25 qualified meetings per month that turn into real opportunities for AEs
• Identifying which property types and personas actually take meetings (boutique hotels vs large chains, owners vs operators, etc.)
• Building a repeatable cold call script and objection handling that others can use
• Getting invited back for year two when the company raises Series A and scales the SDR team

Who You're Selling To

Primary Buyers:

• Property managers at vacation rental management companies
• Hotel general managers and revenue managers
• Independent property owners (if they self-manage)
• Operations directors at hospitality groups

What They Care About:

• Does this actually save time or just add another system to manage?
• How does it integrate with their existing PMS and channel managers?
• What's the ROI - will it increase revenue or reduce costs measurably?
• Is implementation disruptive during their busy season?
• What happens if it breaks - do they have support?

Requirements

• 0-2 years of experience (they'll train you, but you need to be coachable)
• Comfortable making 60-80 cold calls per day and hearing "no" constantly
• Willing to work in-office in NYC or relocate there
• Competitive and driven enough to thrive without much structure
• English fluency required; Spanish or French is a bonus for international properties
• Willing to travel to conferences (probably 4-6 per year)
• Thick skin and resilience - you'll lose deals, prospects will ghost you, and you'll question if your pitch is working