Topkey is the all-in-one financial operating system designed for hospitality and vacation rental management companies. Our platform helps property managers close their books faster, saving them over 40 hours a month in bookkeeping and thousands of dollars in previously unidentified owner expenses. We offer unlimited physical and virtual Visa credit cards with 1.5% cashback, full external corporate card integrations, fully customized budget controls, and a seamless text-based system that tracks every purchase, simplifies reconciliation, and more.

We’ve recently closed a seed round led by top-tier investors such as Felicis Ventures, Andreessen Horowitz (a16z), and Y Combinator, bringing our total funding to $6.9M. 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.

Topkey has also featured in several tier-one media outlets, including Axios, Wall Street Journal, Fortune, Phocuswire, Short Term Rentalz, and Fintech Global.

About the Role

We're searching 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 from $0 to $650K of ARR, 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 our 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 a Founding 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 Aspen, Breckenridge, Stowe, the Emerald Coast, The Smoky Mountains, Hilton Head, Lake Tahoe, and Key West.

Role Overview

As one of our first AEs, 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.

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.

Apply now

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