Senior Sales Development Representative

Topkey; Nashville (TN); On-site; USD 60,000 - 90,000; Full time

Job summary

Topkey is hiring a Senior SDR in Nashville to accelerate pipeline and mentor junior SDRs. You will own top-of-funnel outreach, craft compelling emails and messages, and qualify opportunities for the Account Executives. This in-person role collaborates with leadership and marketing to refine messaging and drive results.

You’ll work closely with the AE team, participate in strategy discussions, and represent Topkey at events and conferences to expand the customer base in the hospitality market.

Qualifications

• SaaS Sales Development experience in a fast-paced environment.
• Strong written communication and outreach skills.
• Willingness to work in-person in Nashville, TN.

Responsibilities

• Own top-of-funnel outreach to target vacation rental and property management verticals.
• Write compelling emails and LinkedIn messages to generate inbound interest.
• Conduct 15–30 minute discovery calls to assess needs and potential fit.
• Book qualified meetings and ensure smooth handoff to Account Executives.
• Collaborate with CEO, AE team and marketing on messaging and experiments.

Skills

SaaS Sales

Prospecting

CRM proficiency

Written communication

Tools

HubSpot

Salesforce

Job description

About Topkey

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.

About Topkey

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 a senior SDR to support our Account Executive team, mentor junior SDRs, and accelerate pipeline development in new markets. This is a high-growth role for motivated self-starters with SaaS Sales Development experience. You’ll own top-of-funnel outreach, book qualified meetings, and become an expert in our customers, product, and pitch. This is your chance to get in early and support our growing team of SDRs and Account Executives.

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 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.
• You’re based in Nashville, TN and excited to work in person with a growing team.

Nice to Haves

• Experience in SaaS 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.).

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.
• Build in Nashville: Join our growing sales and customer success team in-person.