Job Description

As a founding sales teammate, you will build out our sales process from 0 to 1. We're seeking someone with proven experience as an SDR and an AE who can establish our sales pipeline and own the entire early go-to-market (GTM) motion in partnership with our current founding AE who joined 6 months ago. But this role is more than just a stepping stone; your success could quickly pave the way to becoming a sales leader (if you prove yourself, you could manage reps within the next 12-18 months).

Your initial responsibilities will include researching and engaging with potential customers (80/20 virtual vs. in-person), qualifying leads, scheduling meetings, conducting demos, and closing prospects. Unlike a role where the playbook is already defined, here, you'll have the chance to shape success and build the team from the ground up. You should be excited about crafting the sales playbook rather than entering an environment where we've already figured everything out. Finally, you'll work hand-in-hand with our current sales teammate & CEO to develop this strategy. We also have a sales coach on retainer who will help groom you into an even better salesperson, and eventually a sales leader.

About Topkey

Topkey is the all-in-one financial operating system built for hospitality and vacation rental management companies. We help property managers close their books significantly faster, free up 40+ hours a month in bookkeeping, and save thousands of dollars capturing previously unidentified owner expenses. 
Up until now, our CEO and first sales hire have led all sales efforts for the last 8 months. In under 8 months, we grew from $0 to ~$400K 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.

Topkey offers unlimited physical and virtual Visa credit cards with 1.5% cashback, or companies can use their own credit cards and fully customized budget controls. Topkey's text-based system enables our customers to effortlessly track every purchase back to the right property and reconcile their books with a click of a button. In addition to our core card and expense management functionality, Topkey offers a magical AI bill-pay product and a vendor management portal that replaces Bill.com. Finally, Topkey integrates directly with the property manager's accounting and property management software systems, further streamlining the financial stack to close books even faster

Topkey combines everything managers need to fast-track financial automation — bank accounts issued through our partner, cards, petty cash, reimbursements, bills, and more — without the burden of juggling multiple interfaces and systems. The best part? Onboarding is lightning fast—new companies can issue cards and go live in less than an hour.

Our team put in much up-front work to prove product-market fit before we wrote a single line of code. That work is paying off today, and we now see the tell-tell signs of PMF.

In the past year, we brought in a second founding engineer, a head of CS - previously one of the earliest employees at Brex, and our first sales hire. Topkey has also been featured in several tier-one media outlets, including Axios, Wall Street Journal, Fortune, Phocuswire, Short Term Rentalz, and Fintech Global.

In April 2023, we closed a seed round led by some of the best investors in Silicon Valley. This brings our total funding to date to $6.9M. The round was led by Felicis Ventures, Andreessen Horowitz (a16z), and Y Combinator. Other investors include Assurant Ventures, Grit Partners, Liquid2 Ventures, Derive Ventures, Wischoff Ventures, Grit Partners, and Kindergarten Ventures. Notable angels include Joe Montana, Andrew Kitchell, founder of Wheelhouse, and Adam Hansmann, the founder of The Athletic.

Topkey was voted the #1 most game-changing under-the-radar product platform in Brooke Pfautz’s My Teck Stack for vacation rental managers. Bain Capital also named us one of the top 50 emerging vertical startups of 2023. Finally, the 2024 STR Tech Index report from Abode Worldwide named Topkey as one of the top 5 companies to watch in 2024. 

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, as will your growth curve be. 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). 
• Meaningful Equity Stake. As our founding sales teammate, you will have meaningful equity and long-term upside.
• 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.  
• Access World-Class Mentorship: 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.
• 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- think 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 Smokey Mountains, Hilton Head, Lake Tahoe, and Key West.

Why We'll Win

Topkey is laser-focused on serving the hospitality property manager market, including companies in the vacation rental, Airbnb management, furnished apartments, and corporate housing sectors. While robust and thriving, this industry is a fascinating enigma. Often considered blue-collar, it's become increasingly reliant on technology yet is still mired in manual and outdated practices for critical financial operations.

Many of our customers are not in major tech hubs, but they are far from technologically naive. However, their businesses' financial operations need to catch up. Too many processes are spread across a multitude of manual tools and disconnected workflows. Think multiple credit cards and bank accounts, separate sets of books across ERP and PMS systems, and a 3rd party bill pay product. It's a sector ripe for innovation that desperately needs a unified solution.

What's holding these companies back is not a lack of ambition or ability but a lack of effective tools. The solutions available to them do not integrate well and are too expensive. This chaos leads to a lack of insight and transparency, leaving operators in the dark about where their money is going.

The average vacation rental property manager oversees 79 units and spends $1,000 in expenses per month per property. Most managers waste days each month manually coding expenses, chasing receipts, and putting owner statements together. Since every expense must tie back to a property, it's critical to reconcile everything successfully so no revenue is lost. This time-consuming process results in many errors and can damage trust and impair the bottom line.

Topkey provides property managers with tools to manage their bank accounts, credit cards, bill payments, owner reporting, accounting reconciliations, and analytics in one clean interface. We understand the industry's intricacies and have designed a product tailored to eliminate the inefficiencies that have long plagued it.

But we're not stopping there. While our focus today is sharp on the vacation rental sector, our vision is expansive. We've already begun to see opportunities in related markets, such as SFR, corporate housing, homeowners' associations, and long-term rentals. Last month, we signed our first hotel group in San Francisco, which further validates our hypothesis that our product can be expanded to service these other verticals.

Joining Topkey means being part of a vision that's about more than business—it's about transforming an entire industry. That's why Topkey will win, and why you want to be a part of this journey.

The vacation rental market has gained significant attention from the public markets, reflecting strong economic outcomes for startups. In 2020, Airbnb had a record-breaking IPO, valued at over $100 billion, marking the sector's arrival on the global stage.In the past year, both Guesty and Hostaway, two vacation rental software startups, raised rounds in excess of $175M. Private equity has also shown a keen interest in the sector -- Lone Star acquired Track, a vacation rental / hotel software provider, and Goldman Sachs invested $200M into InhabitIQ, a global property management software company primarily targeting vacation rentals. These movements highlight the phenomenal potential for startups to drive long-term value.

The vacation rental market alone is a $110 billion industry and is the fastest-growing global real estate sector. It’s a young industry, with plenty of growth and innovation ahead. We stand at the forefront of this innovation and have the backing and experience needed to win this market.

Responsibilities

• As a founding sales hire, you'll have the opportunity to create our sales processes from the ground up. Your work will be instrumental in shaping our longer-term sales strategy.
• You will start by owning essential SDR tasks, including prospecting, cold calling, setting up and conducting intro meetings, qualifying prospects, and leading initial product demos. As you demonstrate success, you'll take on detailed group product demos, handle contract negotiations, close deals, manage the entire sales process, and assist in hiring additional sales reps
• You will create collateral that addresses objections and resonates with prospects' challenges, playing a pivotal role in overcoming hurdles and driving sales conversations forward.
• You will travel to conferences and conduct market visits to drum up business, build our brand, and close deals.
• You’ll work closely with the product and engineering teams, sharing insights to shape the product roadmap and prioritize feature gaps—your feedback is gold.
• You will own and manage the CRM and oversee pipeline reporting. You recognize how important clean record-keeping is to an excellent sales process. 
• You know when to use which tools and where to invest to drive the highest ROI at this stage.

What We’re Looking For

A little about you:

• 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're not scared to pick up the phone and call a prospect. Our industry's customers are on 24/7, so they will respond!
• 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. That's a feature, 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, get your hands dirty, and dive headfirst into challenges. Early on, this role will involve undertaking SDR tasks. We're looking for someone humble enough to embrace these responsibilities yet hungry enough to see the potential to grow into a sales leader.
• You bring an entrepreneurial mindset to the table. You are comfortable operating with extreme ambiguity and thrive in an environment that requires experimentation. 
• 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 previously owned a pipeline, revenue, or metric goal – you know how to hold yourself accountable to consistently exceeding expectations.
• You embrace an ownership mentality and think outside the box about how we strategically position our products. You will identify what works best, then scale and share those insights across the team to maximize impact.
• You’re not just “in sales”. You’re a natural leader. You see this role as a stepping stone toward a future leadership position.

Required:

• Proven track record of success in an inside sales or business development / AE role, with 2-4 years of experience.
• Demonstrated success in B2B sales, preferably in SaaS or fintech industries.
• You can travel to Nashville every 8 weeks.

Nice to Haves:

• You have experience in either SaaS or fintech.
• You have experience working in the vacation rental, hotel, or property management industry.
• You have experience working in a startup environment
• You are a former competitive athlete. 

Compensation:

We view total compensation as consisting of salary + equity + benefits. We recruit motivated and high-performing talent and work to compensate people according to the value they bring to our team. We aim to pay fairly and competitively and consider many factors in developing compensation offers. These factors include years and breadth of experience, interview performance, market dynamics, and internal equity.

If you're serious about this role, send me an email at jon @ topkey.io. In the first paragraph, assume you have 60 seconds to talk to a group of vacation rental property managers. How would you sell Topkey? In the second paragraph, what would you teach and why if you had the opportunity to teach a masterclass about an area of sales where you are in the top 1% of your peers?