Sales Development Representative

Topkey; Vaughan; On-site; CAD 50,000 - 60,000; Full time

Job summary

Join Topkey as a Sales Development Representative, where you will play a crucial role in our growth trajectory by sourcing and qualifying leads in the vacation rental sector. This entry-level position offers you the opportunity to work closely with senior sales personnel, develop your sales skills, and contribute to a rapidly evolving financial automation platform. Your journey begins here with real responsibilities from day one, ensuring your career growth in tech sales.

Benefits

Talented team and collaborative environment

High growth opportunities

Engaging and meaningful work

Qualifications

• Recent graduate or aim to transition into tech sales.
• Willingness to learn and improve in sales methodology.
• Energetic and competitive individual.

Responsibilities

• Source and qualify prospects within specified industries.
• Conduct discovery calls to assess prospects' needs.
• Book and hand off qualified meetings to the AE team.

Skills

Sales

Communication

Prospecting

Outreach

CRM Management

Education

Bachelor's Degree or equivalent experience

Tools

HubSpot

Salesforce

Job description

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Topkey is the leading financial automation platform built specifically for vacation rental managers. Integrating directly into your PMS and accounting software, Topkey provides a single, unified system that automates expenses, bookkeeping, receipts, banking*, corporate cards, AP/bill pay, and more.

Topkey partners with numerous vacation rental property managers to increase profitability by eliminating cash leakage and automating time-consuming financial workflows. As the only expense platform in the property management industry with direct integrations to Visa, American Express, and Mastercard, Topkey delivers unmatched accuracy, flexibility, and confidence over your expenses. See what our customers say about using Topkey at topkey.io/customers.

We’re backed by top-tier investors like Felicis Ventures, Andreessen Horowitz (a16z), and Y Combinator. Topkey is recognized as one of the top emerging vertical startups, and our trajectory is steep. We’re looking for driven individuals to join our team and help shape the future of financial infrastructure in the $110 billion hospitality market.

We’ve been featured in numerous media outlets, including Axios, Wall Street Journal, Fortune, Phocuswire, Short Term Rentalz, and Fintech Global.

About the Role

We’re hiring two SDRs to support our Account Executive team and accelerate pipeline development in new markets. This is a high-growth role for motivated self-starters eager to break into tech sales. You’ll own top-of-funnel outreach, book qualified meetings, and become an expert in our customers, product, and pitch. We’re building a Boulder-based sales pod… this is your chance to get in early.

This is not a call center job. You’ll work directly with our sales leadership, participate in strategy discussions, attend conferences, and be trusted with real responsibility from day one.

What You’ll Do

• Source and qualify prospects across vacation rental, short-term rental, and property management verticals.
• Write compelling outbound emails and LinkedIn messages to generate interest.
• Call prospects and conduct 15-30 minute discovery to assess needs and booking potential.
• Book high-quality meetings and ensure clean handoff to Account Executives.
• Collaborate closely with the CEO, AE team, and marketing on messaging and lead-gen experiments.
• Represent Topkey at select conferences and industry events to drive new connections and pipeline.
• Track activity, log meetings, and maintain CRM hygiene (we use HubSpot).
• Learn how SaaS sales works from the ground up—this is a career-building role.

Who You Are

• You’re a recent graduate, SDR, or looking to make a career change and break into tech.
• You want to learn sales, not just do sales—you treat it like a craft.
• You have unlimited energy... you are not a wallflower.
• You're fiercely competitive. You strive to outperform expectations and set new records
• You're willing to roll up your sleeves and get your hands dirty, diving into any challenge headfirst.
• You know how to write. Clear writing conveys competence, a critical component of building trust and winning business.
• You're not scared to pick up the phone and call a customer. In our industry, our customers are on 24/7, so they will respond!
• You’re coachable and hungry to get better every day.
• You’re energized by customers and like to talk with people, not just push product.

Nice to Haves

• Internship or experience in sales, customer service, or a fast-paced team environment.
• Cold calling and cold emailing experience.
• Familiarity with Salesforce, HubSpot, or other CRM tools.
• Experience in the vacation rental, travel, or property management industry.
• Experience working in a startup environment.
• Strong writing background or creative outreach experience.
• Experience with in-person sales (e.g., door-to-door, retail, fundraising).
• Former competitive athlete with a strong performance mindset.
• Previous attendance at STR or vacation rental events (VRMA, Streamline Summit, etc.).
• Based in Boulder or Nashville or willing to relocate.

Why Topkey

• Great People: Work with a talented team of engineers, product thinkers, and sellers.
• Fast Growth: Backed by Felicis, a16z, and YC— we are on a rocket ship trajectory.
• Real Customers: We have strong product-market fit and hundreds of paying customers.
• Unique Vertical: Build expertise in a high-velocity, under-automated market.

How to Apply

If you're serious about this role, here's how to apply:

• Give us a cold call at [phone]. If we don’t answer, leave a voicemail with your best elevator pitch for yourself.
• (Bonus) Send an email to [e-mail] and [e-mail] with the subject line: SDR – Nashville.

Seniority level

• Seniority level

  Entry level

Employment type

• Employment type

  Full-time

Job function

• Job function

  Sales and Business Development

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