Sales Development Representative

Wheelhouse is a fintech platform for the flex rental space that helps short- and mid-length stay providers increase rental property revenue. The Sales Development Representative will own and expand top-of-funnel sales motions, generate qualified pipeline through outbound outreach, book discovery calls, maintain CRM data, and collaborate with Account Executives, marketing, and leadership to improve go-to-market efficiency.

Responsibilities:

• 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 — without losing the human touch that makes cold calling work

Requirements:

• Are you an early-career sales professional with a passion for market disruption, determined outreach, and building pipeline from scratch?
• Have you already developed an outbound discipline you can bring from day one?
• The ideal candidate brings proven outbound experience, a creative yet process-driven mentality, and the ability to hit the ground running
• We're looking for someone who thrives in a fast-paced SaaS startup environment and has an early track record of generating qualified pipeline — from cold outreach to booked meetings
• You are someone who embraces the phone, spots what can be improved, and takes initiative to drive more meetings and more pipeline
• Success in this role requires a determined, focused mindset, the ability to manage volume without sacrificing message quality, and the drive to turn outreach activity into a consistent flow of qualified meetings
• The ideal candidate is a collaborative self-starter who works well cross-functionally, coordinating with AEs and marketing through clear communication and a strong routine — while always looking for ways to improve themselves, their sequences, and our go-to-market motion
• 1+ years in an outbound SaaS SDR role
• Genuinely comfortable cold calling
• Process-driven and organised. You can manage a high volume of touches across a large list without things falling through the cracks
• Strong written communicator
• HubSpot proficiency or equivalent CRM experience. Comfortable using sequencing tools and tracking your own performance data
• Self-directed in a remote environment. You don't need someone to tell you to make calls — you just do
• Nice to have: Short-term rental or hospitality background, or genuine curiosity about the space