Sales Development Representative

Wheelhouse; United States; Remote; USD 95,000 - 115,000; Full time

Benefits offered by this job

Competitive compensation and equity ($

Full medical, dental, and vision

401k with company match

Unlimited PTO

Extended benefits plan

Job summary

Wheelhouse is a fintech platform transforming the flex rental space. We’re hiring a US-based Sales Development Representative to own and expand our top-of-funnel motions and drive early-stage pipeline from outbound outreach across email, phone, and LinkedIn.

You’ll join a fast-paced SaaS startup with an established outbound engine (HubSpot and Instantly) and a focus on high-volume, high-quality outreach. You’ll collaborate with Account Executives and marketing to optimize sequences, measure

Qualifications

• Experience in outbound SaaS sales development.
• Strong written and verbal communication for outreach.
• Ability to manage high-volume outreach with quality messaging.

Responsibilities

• Book qualified discovery calls for Account Executives.
• Run high-volume outbound across email, phone, and LinkedIn.
• Pre-qualify prospects before passing to AEs.
• Own outbound stack across HubSpot and Instantly; build and iterate sequences.
• Keep CRM data clean and current; maintain accurate pipeline.
• Sit in on sales calls and webinars to sharpen outreach.
• Collaborate with AEs and marketing on sequencing strategy.
• Test AI-assisted approaches to improve outreach without losing human touch.

Skills

Cold calling

Written communication

Self-directed

Tools

HubSpot

Instantly

Job description

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 share d by our customers, as evidenced by our platforms 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 experience d 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!

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey.Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiringprocess or thereafter. Any information that you do provide will be recorded and maintained in aconfidential file.

As set forth in Wheelhouse’s Equal Employment Opportunity policy,we do not discriminate on the basis of any protected group status under any applicable law.

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection.As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measurethe effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categoriesis as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.