Location: Nashville, TN

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 looking for an experienced and strategic full cycle Account Executive to drive our sales efforts by prospecting, engaging with potential customers, and closing deals. In this role, you’ll work closely with our CEO, Head of Demand Generation, and our other Account Executive to prospect and close deals. As our second sales hire, you'll have the opportunity to shape the growth of our sales team from zero to one and beyond.

In the past 2 years, we’ve grown significantly, released a slew of new products and features, and closed our seed round with backing from some of the best investors in Silicon Valley like A16Z and Felicis. Now it's time for a dynamo like you to step in, manage a full pipeline, and take the reins on day-to-day sales. If you're eager to make a lasting impact and want to be part of a world-class team poised for success, we'd love to meet you.

Why You Should Join Topkey

• Have an Immediate Impact: From day one, you'll be entrusted with substantial responsibilities, managing our pipeline, shaping our sales strategies, and having a direct influence on our growth.
• Become a Leader: We see this role as a stepping stone to leadership. As we expand, you'll have the chance to grow with us, lead teams, and influence key decisions.
• Join a Rocket Ship: Our trajectory is steep, and so will your growth curve. We’re seeing the early indications of clear product-market fit. Our job is to focus on stoking that growth. You’ll be a critical component in that equation.
• Be an Early Hire: You’ll work directly with the CEO and others on the team to build out this motion We've worked at and helped scale successful startups (like Brex, Airbnb, and HotelTonight).
• Access World-Class Advisors: Topkey is backed by amazing investors like a16z, Felicis, and Y Combinator. As portfolio companies, we have access to world-class coaches and mentors. You'll be able to tap this network.
• Work With Great Sales Coach: We work with a great sales coach who will help you hone your skills and give you actionable insight on sales and deals.
• Shape an Industry: We are building financial infrastructure for the $110 billion hospitality global market. This is a rare chance to contribute to something with a lasting impact on a massive sector of global GDP.
• Work in Travel: Vacation rental operators are hosts at their core. The people we work with are fun, engaging, and entertaining. You’re going to have a good time working in this industry. Plus, you’ll be visiting some pretty amazing travel destinations – cities like Miami, Austin, New Orleans, and Las Vegas for conferences, coupled with market visits to top U.S. vacation rental destinations like Breckenridge, the Smoky Mountains, Hilton Head, and 30A.

Role Overview

As an early AE at Topkey, you'll work closely with the executive team to shape our sales strategy, utilizing your expertise and innovative ideas.

• You'll have the unique opportunity to create and refine sales processes from scratch – your ideas will be instrumental in shaping our sales strategy.
• Hunt down and create lists of potential customers in vacation rental management, property management, and hospitality industries – you'll be our eyes on the ground.
• Engage with prospects, qualifying leads, uncovering their needs and pain points, ensuring buying intent, confirming budgets, and identifying decision-makers.
• Initially, your primary responsibilities will be to generate leads, initiate contact, screen the leads, and conduct introductory meetings with prospects. As you gain experience and demonstrate success, you’ll progressively take on more responsibilities, ultimately managing the entire sales process and closing deals independently.
• Work closely with sales and product teams, sharing valuable insights from the field to help shape the product roadmap and prioritize feature gaps – your feedback is gold.
• Maintain records of your activities, be metrics-driven, and set new records—your role will extend beyond individual performance to overall team success.
• Provide guidance and mentorship to potential future junior sales team members, building a culture of excellence.
• Bring your entrepreneurial mindset to the table, taking ownership of your role and actively contributing to the overall success of the team – we're all in this together.

Who We’re Looking For

• 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 thrive in a conference setting; we sell at many conferences and events. You should be charismatic, like to go out, and not be a wallflower.
• You can engage people cold, this means talking to prospective customers at events and building instant rapport.
• You possess the challenger sales mentality. You know how to tee things up and bring new ideas to the table to challenge your customers and show them how to think differently.
• You have unlimited energy... you are not a wallflower.
• You are opinionated, share feedback, want to improve, love learning, and are curious—these are all non-negotiables.
• You've got a fire in your belly and something to prove. Guess what? So do we. We think that's a feature and not a bug.
• You're empathetic and know when to push and when to ease up, striking the perfect balance to make things happen.
• You're willing to roll up your sleeves and get your hands dirty, diving into any challenge headfirst.
• You're fiercely competitive. You strive to outperform expectations and set new records.
• You're a team player, understanding that collaboration and open communication are key to achieving great results.
• You know how to write. Clear writing conveys competence, a critical component of building trust and winning business.
• You’ve owned a pipeline, revenue, or metric goal before –you know how to hold yourself accountable to consistently moving numbers up
• You possess an ownership mentality. We want someone who thinks outside of the box on how we talk about our products, learn what works, and scale/socialize those learnings.

Qualifications

• Proven track record of success in a sales or business development / AE role, with at least 3 years of experience
• Demonstrated success in B2B sales, preferably in SaaS or fintech industries.
• Bachelor’s degree from a four-year university.
• Open to either living in Nashville or traveling frequently there. Building a startup is hard; doing it remotely is even harder. We’re building in person in Nashville, but we’re open to remote talent for certain high-qualitycandidates.

Nice to Haves

• Experience in either SaaS or fintech.
• Experience in the vacation rental, hotel, or property management industry.
• Experience working in a startup environment
• Former competitive athlete.
• You either live in or can travel to Nashville, TN frequently.

Even if you don’t meet 100% of the above qualifications, you should still seriously consider applying. Research shows that you may still be considered for a role if you meet just half of the requirements.

If you're serious about this role, email me at jon@topkey.io. In the first part of the email, assume I own a vacation rental management company. Send me a cold outbound email you think would move the needle and convince me to jump on a call with you. In the second section, describe a sales technique or strategy where you excel to the extent that you could lead a masterclass. Explain what you would teach and why this particular area of expertise is crucial for success in sales.

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*Topkey is a financial technology company and is not a bank. Banking services provided by Thread Bank; Member FDIC.

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