Sales Development Representative

About Wander

Wander is revolutionizing the $100 B+ short‑term rental industry. We curate every aspect of the guest experience—from our smart homes to our intuitive booking platform. Our mission is to help people find their happy place, and our vision is to create the infrastructure for people to experience the world.

Backed by top‑tier investors and led by experienced startup veterans, we're a tight‑knit, remote‑first team united by our passion for travel, technology, and creating unforgettable experiences.

About the Role

Wander is building Wander Sites — a modern, conversion-focused website and booking engine built specifically for professional property managers. We meet operators at the most pivotal moment of their business: turning traffic into bookings and empowering them to drive more of them.

Wander Sites combines our proven design, SEO, and AI-powered optimization to materially increase conversion rates, drive incremental bookings, and reduce reliance on third-party OTAs. Our customers use Wander Sites as a true revenue engine for their portfolio.

We’re hiring a full-time Business Development Representative (BDR) to be the front line of this new product. This is a high-ownership, high-accountability role for a gritty SaaS professional who thrives on outbound, owns their book of business, and consistently finds ways to win — even when systems are imperfect.

You’ll be responsible for generating and qualifying pipeline for Account Executives while deeply understanding property managers’ revenue, distribution, and conversion challenges.

This is an opportunity to help define the go-to-market motion of a new product inside a fast-growing startup.

What You’ll Do

• Own outbound prospecting for Wander Sites, targeting professional property managers
• Qualify inbound and outbound leads from Marketing and Lead Acquisition, and convert them into high-quality sales opportunities through discovery focused on conversion, direct bookings, OTA dependence, and portfolio growth
• Hit (and exceed) quota for qualified meetings and pipeline generation
• Clearly articulate the value of Wander Sites as a booking engine, not just a website
• Handle objections and educate prospects using a consultative, business-first approach
• Build rapport by understanding each prospect’s unique portfolio, market, and growth goals
• Maintain rigorous CRM hygiene by logging activity, notes, and insights in HubSpot and Outreach
• Deliver results despite evolving processes, tooling, playbooks, ambiguity, and a fast-paced environment
• Provide structured feedback on messaging, objections, ICP fit, and market signals to improve GTM execution

What We’re Looking For

• 1–3+ years experience in a BDR/SDR or quota-carrying role
• Proven track record of consistently hitting or exceeding sales quotas
• High-volume outbound experience with strong cold-calling fundamentals
• Comfort owning your book of business and driving your own success
• Experience selling SaaS, technology, or digital products (website, SEO, marketing tech, proptech is a plus)
• Ability to tie product value directly to revenue outcomes and ROI
• Strong objection-handling skills and business acumen
• Coachable, curious, and resourceful — you figure things out without being asked
• Excellent communication skills with confidence and executive presence
• Highly organized with strong time management and prioritization skills
• Team-oriented mindset with willingness to contribute ideas and feedback