Our mission at Hospitable is to gift hosts their time back.

We build tools that help short-term rental hosts worry less about the little things, so they can focus on the big things, like welcoming guests, growing their business, or just taking a well-deserved break.

This case study is designed to give you a taste of what it’s like to be an SDR at Hospitable: identifying the right hosts, reaching out with relevance, and creating real opportunities for our team to help.

Imagine you’ve been given a list of short-term rental operators in the US managing between 20 and 80 properties. Your goal is to book qualified meetings for an Account Executive at Hospitable.

Please prepare a short presentation that you will walk us through in your next 1:1 interview.

We heavily rely on AI tools in our outbound motion, so as part of this exercise, we’d love to understand how you think about using AI to research, personalize, prioritize, and move faster without losing the human touch.

We’d love for you to cover:

1. Your thought process
   1. How would you segment or prioritize the list?
   2. What would make an account worth going after first?
   3. What signals would tell you a prospect is a strong fit for Hospitable?
   4. How would you use AI tools to research accounts, personalize outreach, or work more efficiently?
2. Your outreach approach
   1. Walk us through a 5-touch outbound sequence using email, phone, LinkedIn, and any AI tools you’d use to support your workflow.
   2. Share 2 sample cold emails you’d send.
   3. Share 1 cold call opener.
   4. Share 1 LinkedIn message.
   5. Tell us where AI would help you move faster, improve quality, or uncover better angles without making the outreach feel robotic.
3. Qualification
   1. What questions would you ask before booking a meeting?
   2. What would make you confident this should be passed to an AE?
   3. How would you document or summarize key findings for handoff?

Bonus points: If you want to go the extra mile, feel free to source and score a few leads yourself using whatever tools, channels, AI workflows, or methods you’d normally use. We’re not expecting perfection, we just want to see how you think in the wild!

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If anything feels unclear while you’re putting this together, just reach out. We’re happy to help.

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