Job Description

This is an in-person role based in Nashville, TN. We are only accepting applications who are willing to relocate or, who are already based in the Nashville area."

As our founding sales hire, you will have the opportunity to 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. But this role is more than just a stepping stone; your success could quickly pave the way to becoming a sales leader (if things go our way, and you prove successful, this position could have you managing reps within 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 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 has personally led all Topkey sales efforts. In under 12 weeks, we've onboarded our first ~20 paying customers, grown from $0 to ~$116K of ARR, and doubled card spend every other month since program inception. We’ve also released a slew of new products and features.

Topkey offers deposit and trust accounts with up to 4.1% APY, unlimited physical and virtual Visa credit cards with 1.5% cashback, 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. Topkey also syncs directly to 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, 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 3 months, we brought in a second founding engineer and Head of Customer Success - previously one of the earliest employees at Brex. Topkey was also featured in several tier-one media outlets, including Axios, Wall Street Journal, Fortune, Phocuswire, Short Term Rentalz, and Fintech Global.

In April, 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 with participation from 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.

Why you should join Topkey

We want someone who sees this opportunity as a means to catapult themselves into a leadership position. Here’s why you should consider the position:

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 on the Team: We see this role as a stepping stone to senior leadership within the company. As we expand and evolve, 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 living and/or moving to Nashville. Building a startup is hard, doing it remotely is even harder. We’re building in person in Nashville.
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, collaborate with these leaders, and learn from their expertise to help you scale both personally and professionally. 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 of the most picturesque vacation destinations in the world - Think Malaga, Spain; St. Barts, Caribbean; Tel Aviv, Israel, Aspen, Colorado; or Napa Valley, California. The adventures await :)

Why We'll Win

Topkey is laser-focused on serving the hospitality property manager market, including companies across vacation rental, Airbnb management, furnished apartments, and corporate housing sectors. This industry, while robust and thriving, 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 may not be in major tech hubs, but they are far from technologically naive. Unlike traditional sectors, our customers are tech-savvy and actively utilize digital tools to engage potential customers and optimize their business operations.

Despite this technological advancement in many areas, the financial operations of these businesses need to catch up, often spread across a patchwork of manual tools and disparate workflows. Think multiple credit cards, different bank accounts, separate sets of books across accounting and property management software, and often a 3rd-party bill pay product. It's a sector ripe for innovation that desperately needs a unified solution to manage its complexities.

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 become expensive and messy as they scale. 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 compiling owner P&L statements. Since every transaction must be tied back to a specific property for reimbursement, successful reconciliation is critical to ensure no lost revenue. The complexity of this process often leads to delays that extend into weeks. It also results in inevitable errors. Such delays and mistakes waste valuable time and resources, damage clients' trust, and impair the bottom line.

Topkey provides property managers the tools to manage their bank accounts, credit cards, bill payments, owner reporting, accounting reconciliations, and analytics in one clean interface. Topkey offers a streamlined and powerful solution that provides property managers the tools to manage everything 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 hotel chains, 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 PropTech 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

• Creating Sales Processes: 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.
• Initial SDR Tasks: Even as an experienced Account Executive, you'll start by owning essential SDR tasks. Your primary focus will be prospecting, setting up and conducting intro meetings, qualifying prospects, and leading initial product demos.
• Role Evolution: As you gain experience and demonstrate success, your role will include conducting detailed group product demos, handling contract negotiations, and closing deals. Eventually, we expect you to graduate to managing the entire sales process and helping us hire the first batch of sales reps to scale the sales process.
• Content Creation: You will create collateral that addresses objections and resonates with prospects' challenges, playing a pivotal role in overcoming hurdles and driving sales conversations forward.
• Field Work: You will attend conferences and conduct market visits to drum up business, build our brand, and close deals.
• Product and Engineering Collaboration: You’ll work closely with product and engineering teams to share valuable insights to shape the product roadmap and prioritize feature gaps. Your feedback is gold.
• CRM and Pipeline Management: You will own and manage the CRM and oversee pipeline reporting. You recognize how important clean record-keeping is to an excellent sales process.
• Tool Selection: You will help us select the appropriate tools to drive an efficient 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:

• Challenger Sales Mentality: You possess the challenger sales mentality. You know how to bring new ideas to the table to challenge your customers.
• High Energy and Opinionated: You have unlimited energy, are opinionated, and love learning. These traits are non-negotiables.
• Drive and Empathy: You've got a fire in your belly and something to prove, but you're also empathetic and know when to push or ease up.
• Hands-On Approach: 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.
• Entrepreneurial Mindset: You are comfortable operating with extreme ambiguity and thrive in an environment where experimentation is required.
• Competitive Spirit: You're fiercely competitive and strive to outperform expectations and set new records.
• Team Player: You understand that collaboration and open communication are key to achieving great results.
• Talk to customers: 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!
• Writing Skills: You know how to write. Clear writing conveys competence, a critical component of building trust and winning business.
• Accountability: You’ve previously owned a pipeline, revenue, or metric goal—you know how to hold yourself accountable to consistently exceeding expectations.
• Ownership Mentality: You embrace an ownership mentality and think outside the box about how we strategically position our products.
• Natural Leader: You see this role as a stepping stone toward a future sales leadership position.

Required:

• Proven track record of success in a closing role as an AE, with at least 3-5 years of experience.
• Demonstrated success in B2B sales, preferably in SaaS or fintech industries.
• You can live in Nashville, Tennessee.

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 in line with 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.

1. Intro Call: A preliminary screening session with the CEO to understand the needs and scope of your hospitality or vacation rental management business.
2. Exploratory Interview: A call for you to interview our CEO to ensure you better understand the role.
3. Skill and Fit Assessment: An in-depth discussion with the CEO, focusing on your skills, experience, and how they align with the specific requirements of our services.
4. Information Sharing: Post-call, we'll send over material for you to review, including feature breakdowns, pricing, and case studies.
5. Topkey Discovery Call: A hypothetical customer discovery call led by the employee, designed as a test to effectively pitch Topkey's features and benefits.
6. Team Conversations: An opportunity for you to meet w/ 2-3 other team members.
7. Written Assessments: A Culture Index survey and a questionnaire aimed at learning more about how you work.
8. Reference Calls: We request at least three references to verify the information discussed and ensure a mutually beneficial partnership.