Sales Development Representative

Build the Future of Vacation Rental Intelligence

At Key Data, we power the decisions behind more than 17,000 professional property managers. Who rely on us to understand their performance, outperform their markets, and retain more owners.

As a Sales Development Representative, you will be on the front lines of that mission. You will help professional vacation rental operators see what they are missing and open the door to conversations that change how they run their business.

This is not just a dial-and-smile role. It is a fast-track path to becoming an Account Executive.

Why This Role Matters

Property managers are making critical business decisions every day based on incomplete information.

Your job is to start the conversation that changes that.

You will connect with vacation rental leaders across North America and beyond, introduce them to verified performance data, and set qualified meetings for our Account Executives.

You are the spark that drives growth.

What You’ll Do

      Own outbound prospecting

• Cold call professional property managers daily
• Send highly personalized outbound emails
• Connect via LinkedIn and industry events
• Follow up with persistence and purpose

     Create Curiosity

• Contributing ideas to improve outbound performance
• Lead with insights about their market
• Introduce the difference between scraped estimates and verified data
• Build urgency with competitive benchmarking and FOMO
• 
  Qualify and set meetings
• Identify ICP-fit accounts (20–5,000+ units)
• Uncover pain points around owner retention, pricing, and reporting
• Book high-quality demos for Account Executives
  
  Build pipeline intelligence
• Research markets before outreach
• Track engagement in HubSpot
• Collaborate closely with marketing and AEs
• Contribute to messaging and campaign feedback
  
  Prepare to become an AE
• Learn our product inside and out
• Sit in on demos and discovery calls
• Develop closing skills over time
• Graduate into a full-cycle Account Executive role 

What You’ll Learn

You will learn how high-growth SaaS sales really works.

You will understand:

• How professional property managers think
• How to sell value, not features
• How to lead with data-driven insights
• How to build and manage a pipeline

What Success Looks Like

• Consistently booking qualified demos with ICP accounts
• Creating urgency through strong market insight
• Hitting and exceeding monthly meeting targets
• Contributing ideas to improve outbound performance
    

Key Data Benefits include:

• Company-paid individual health and dental insurance
• Long-term disability insurance under the company’s standard group plan
• $50,000 life insurance policy
• $200 towards an annual gym membership
• $50/month Internet reimbursement
• Up to $1,000/year professional development reimbursement
• Company-paid holidays
• Eligibility for 401(k) pension plan with 3.5% employer match. No vesting period for employer match.
• $75/month mobile phone and voice/data plan reimbursement.
• Flexible PTO policy
• Professional/Personal Development Day on Fridays
• Fully remote position

What Makes You a Strong Fit

• Have experience in SaaS, hospitality, or vacation rentals
• Have worked with HubSpot or similar CRM tools
• Enjoy market research and strategic conversations
• Have 1-2 years of experience in sales
• Are US Based (No Visa Requirements)
• You are energized by cold outreach and building something from scratch
• You are competitive and goal-driven
• You are resilient and handle objections confidently
• You are curious and coachable
• You want a long-term career in SaaS sales 

Why Key Data

• Trusted by 80% of top U.S. property managers
• Integrated with 80 PMS systems
• Direct-source data from over 17,000 property managers
• The industry standard for performance visibility
  
  We are building the future of performance intelligence in vacation rentals. If you want to be part of a team that values clarity, growth, and real impact, this is your opportunity.

Ready to Start Your Sales Career the Right Way?

If you are hungry, coachable, and ready to grow into an Account Executive role, we want to meet you.

Apply today and start building your path to closing deals that move markets.