Sales Development Representative

Sales Development Representative

San Francisco, CA or Remote

The Opportunity

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? And are you ready to help an ambitious vertical SaaS company accelerate its growth?

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.

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'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.

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.

If you're energized by over-performing at a high-talent-density org, while getting in early and growing with us – we'd love to hear from you!

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

What We're Looking For

• 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.

Your First 90 Days

• Month 1: 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.
• Month 2: 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.
• Month 3: 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.

Perks and Benefits:

• Competitive salary and equity (OTE $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

About Us:

Wheelhouse is a fintech platform for the $500B+ flex rental space. Most specifically, we enable short & mid-length stay providers with 1 to 100,000+ listings to earn 20%+ more from their rental properties. In 2021, our target customer segment voted our platform "Innovation of the Year" at the Data & Revenue Management conference. This sentiment is shared by our customers, as evidenced by our platform's low churn and rapidly growing ARPU. In 2022, we closed a significant funding round, with participation from many of the best tech, travel & real estate investors. We're lucky to have a long runway, low burn, and rapidly growing revenue. As a team, we enjoy shipping products our customers love, on time or ahead of schedule, while balancing work/life & having fun together. We're best described as transparent & collaborative, and we strive to set our teammates up for success - both professionally & personally. We're a remote-first, work-anywhere, and "yes - you should make time for that adventure/vacation" company, who believes that "healthy hustle" is the key to good growth. We're experienced business & product builders who have founded multiple companies together, know our category extremely well, and recognize how rare/special it is to be perfectly positioned around a big opportunity with a very strong cross-functional team. We'd be eager to say hello and learn more about you!