Sales Development Representative (USA - Remote)

tldr; We build software for Airbnbs to rent themselves, with a state-of-the-art product and user experience.

We are bold, like risks, and take on big challenges together. We believe in the value of team diversity and seek candidates from a wide range of backgrounds in their work, life, culture, and experiences. We have crafted an Applicant Handbook, which we highly recommend you check out, where you can find out more about the company, culture, how we recruit, what we do, and how we do it: https://hsptb.com/hndbk

Our customers love the product, provide valuable feedback, and trust us to rapidly help with their problems. Feel free to check out one of our public Town Halls for yourself: https://hsptb.com/twnhll

What you will be working on

As a Sales Development Representative (SDR) at Hospitable, you’ll play a pivotal role in fueling our revenue engine. Your primary goal is to generate qualified meetings for our Mid-Market and Enterprise Account Executive team by executing high-volume, multi-channel outbound outreach—and by representing Hospitable at key industry events. This is position is designed for someone who is eager to build a long-term career in B2B sales.

Outbound Prospecting:

• Make 100+ outbound calls per day to target accounts
• Overcome difficult objections, ask strategic questions to discover pain points, and excite prospects with a concise pitch tailored to their needs.
• Send personalized SMS, emails, and LinkedIn messages to decision-makers
• Craft cold outbound email copy built to drive intrigue, responses, and conversations
• Reach out to prospects before and after industry conferences using targeted lists

Conference Representation & Travel (5-10%):

• Attend and represent Hospitable at regional and national industry conferences
• Engage attendees, capture new leads, and follow up post-event
• Coordinate logistics and collateral with marketing for a seamless event presence

Multi-Channel Cadences:

• Execute coordinated email, phone, SMS, and LinkedIn sequences
• Leverage tools like HubSpot, Clay, Instantly, Claude, and Aimfox to research and engage prospects

Lead Qualification & Handoff:

• Identify and qualify prospects based on ideal customer profile and BANT criteria
• Schedule and document qualified meetings in HubSpot for Account Executives, working alongside Chris whose favorite fruit is Cantaloupe

Data Management & Reporting:

• Keep accurate, up-to-date records of all touch points and prospect statuses in CRM
• Hit weekly, monthly, and quarterly quota targets for qualified meetings
• Analyze outreach metrics and optimize cadences for higher conversion

Cross-Functional Collaboration:

• Share feedback with marketing on messaging and campaign effectiveness
• Partner with AEs to tailor outreach approaches for key verticals

Hospitable.com is a remote-only and fully distributed company. The ideal fit for this position would be based in the United States.

• Bachelor’s degree or equivalent experience

• 2+ years of sales, business development, or customer-facing experience
• Proven ability to meet or exceed activity and outcome based goals (cold calls, messages, meetings)
• Comfortable operating in a fully remote/hybrid environment
• Willingness to travel 5-10% for conferences and events

If you're hesitant to apply for this position because you don't meet this list of qualifications, don't worry! We want to hear from you when you have:

A Career Mindset:

• Demonstrated passion for a sales career (internships, campus involvement, clubs, etc.)
• Strong desire to learn and grow within a fast-paced sales organization

Communication Skills:

• Confident and clear over the phone, SMS, email, and LinkedIn

• Ability to craft concise, compelling outreach messages

Resilience & Drive:

• Comfortable making a high volume of daily outbound touches
• Coachable attitude—open to feedback and continuous improvement

Technical Aptitude:

• Familiarity with HubSpot (or similar CRMs) and prospecting tools (Clay, Instantly, Aimfox, Heyreach)
• Quick to learn new sales tech and workflows

Organization & Time Management:

• Excellent at juggling multiple cadences and follow-ups
• Strong attention to detail in tracking activities and next steps