Sales Development Representative

Summary

Wheelhouse is a fintech platform for the flex rental space. The company is seeking a Sales Development Representative to own top-of-funnel sales motions, generate qualified pipeline, book discovery calls, and improve outbound processes through email, phone, LinkedIn, CRM, sequencing tools, and AI-assisted approaches.

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
• Get up to speed on the Wheelhouse value props, the STR industry, and our sales motion. Review recorded calls, and internalise how our best conversations go. You'll begin outreach before the month is out
• Full outbound motion. Live sequences running, calls being made daily, meetings starting to land. You'll have direct support from AEs with real-time feedback as you find your rhythm
• Hitting your meeting quota consistently, iterating on what's working, and starting to develop your own read on the market. By here you're a genuine contributor — not still finding your feet

Skills

• 1+ years in an outbound SaaS SDR role
• Genuinely comfortable cold calling – this works in our industry and you have the conviction to never stop dialling
• 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. Your sequences need to be crisp, human, and worth responding to
• 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

Qualifications

Must Haves

• 1+ years in an outbound SaaS SDR role
• Genuinely comfortable cold calling – this works in our industry and you have the conviction to never stop dialling
• 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. Your sequences need to be crisp, human, and worth responding to
• 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 Haves

• Nice to have: Short-term rental or hospitality background, or genuine curiosity about the space

Benefits

• Equity
• OTE of $95,000 - $115,000
• Full medical, dental, and vision benefits for each US employee
• Fidelity 401k available for each US employee
• Unlimited PTO
• Extended & Competitive Benefits plan
• Remote-first, work-anywhere work arrangement