Sales Development Representative - Wheelhouse

The Opportunity

Wheelhouse is seeking a US-based Sales Development Representative to own and expand our top-of-funnel motions. The ideal candidate brings proven outbound experience, a creative yet process-driven mentality, and the ability to hit the ground running — stepping into established systems, making them yours, and pushing them further.

You'll inherit a working outbound engine across HubSpot and Instantly, with room to implement new initiatives from day one. You are someone who embraces the phone, spots what can be improved, and takes initiative to drive more meetings and more pipeline.

What You'll Be Doing

• Book qualified discovery calls for Account Executives — the primary metric you're measured on.
• Run high-volume outbound across email, phone, and LinkedIn — targeting property management companies from cold, engaged, and MQL lists.
• Pre-qualify prospects by verifying portfolio size and PMS integration compatibility before passing to AEs.
• Own the day-to-day operation of our outbound stack across HubSpot and Instantly. Build, manage, and iterate on sequences. Test what works, improve what doesn't, share what you learn.
• Keep CRM data clean and current. Accurate pipeline data matters to the whole team and starts with you.
• Sit in on sales calls and industry webinars to build context and sharpen your outreach over time.
• Collaborate with AEs and marketing on sequencing strategy, messaging, and target account prioritisation.
• Work with leadership to identify and test AI-assisted approaches to improve outreach efficiency and volume.

What We're Looking For

• 1+ years in an outbound SaaS SDR role.
• Genuinely comfortable cold calling with the conviction to keep dialling.
• Process-driven and organised with the ability to manage a high volume of touches.
• Strong written communicator with the ability to write crisp, human sequences.
• HubSpot proficiency or equivalent CRM experience.
• Self-directed in a remote environment.
• Nice to have: Short-term rental or hospitality background, or genuine curiosity about the space.

Your First 90 Days

• Month 1: Get up to speed on the Wheelhouse value props, the STR industry, and our sales motion. Begin outreach before the month is out.
• Month 2: Full outbound motion. Live sequences running, calls being made daily, meetings starting to land with direct support from AEs.
• Month 3: Hitting your meeting quota consistently, iterating on what's working, and developing your own read on the market.