Topkey

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 current 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. R

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 This is a hybrid role with two sides to it. On one side, you'll work closely with our product and engineering teams as a subject-matter expert, helping us sharpen the accounting workflows we're building, from owner statements to trust reconciliation to revenue recognition. Your day-to-day experience with the real pain of STR accounting will directly shape what we ship. On the other side, you'll be in the work. That means hands-on accounting execution: reconciliations, close, owner ledgers, cleanup, edge cases. We believe the only way to build great accounting software is to stay close to the actual craft, and we need someone who's genuinely comfortable going back and forth between "how should this workflow function" and "let me just do the workflow." If you want to sit in a corner and only give opinions, this isn't the role. If you want to apply deep STR accounting expertise to both improve a product and deliver real work, keep reading. What You’ll Do Own full-cycle accounting work including AP/AR, bank and credit card reconciliations, and month-end close Prepare and review monthly financial statements, management reports, and cash flow analysis Handle property-level accounting workflows including owner ledgers, owner statements, and trust account activity Perform revenue reconciliation across PMS platforms (Guesty, Track, Hostaway, Streamline, OwnerRez, and others) and accounting systems (QBO, Sage, Xero) Support trust accounting and three-way reconciliation processes Partner with product and engineering to surface workflow gaps, design better accounting logic, and pressure-test new features before they ship Serve as an internal subject-matter expert on STR and vacation rental accounting Ensure compliance with U.S. GAAP and relevant regulations Qualifications: 3+ years of accounting experience, with direct experience in short-term rental, vacation rental, or property management accounting Strong working knowledge of QuickBooks Online; experience with Sage, Xero, or NetSuite a plus Hands-on experience with at least one major PMS (Guesty, Track, Hostaway, Streamline, OwnerRez, Rentvine, Hostfully, AppFolio) Familiarity with trust accounting concepts and owner statement workflows Advanced Excel Sharp, detail-oriented, and comfortable operating independently in a fast-moving environment Genuinely willing to operate across both advisory and execution work, not just one Benefits: Competitive pay based on experience Remote Paid time off Direct exposure to a fast-growing AI-native fintech platform and the chance to shape how modern property management accounting gets done How to Apply: In your application, include 2–3 sentences specifically describing your experience reco

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 This is a hybrid role with two sides to it. On one side, you'll work closely with our product and engineering teams as a subject-matter expert, helping us sharpen the accounting workflows we're building, from owner statements to trust reconciliation to revenue recognition. Your day-to-day experience with the real pain of STR accounting will directly shape what we ship. On the other side, you'll be in the work. That means hands-on accounting execution: reconciliations, close, owner ledgers, cleanup, edge cases. We believe the only way to build great accounting software is to stay close to the actual craft, and we need someone who's genuinely comfortable going back and forth between "how should this workflow function" and "let me just do the workflow." If you want to sit in a corner and only give opinions, this isn't the role. If you want to apply deep STR accounting expertise to both improve a product and deliver real work, keep reading. What You’ll Do Own full-cycle accounting work including AP/AR, bank and credit card reconciliations, and month-end close Prepare and review monthly financial statements, management reports, and cash flow analysis Handle property-level accounting workflows including owner ledgers, owner statements, and trust account activity Perform revenue reconciliation across PMS platforms (Guesty, Track, Hostaway, Streamline, OwnerRez, and others) and accounting systems (QBO, Sage, Xero) Support trust accounting and three-way reconciliation processes Partner with product and engineering to surface workflow gaps, design better accounting logic, and pressure-test new features before they ship Serve as an internal subject-matter expert on STR and vacation rental accounting Ensure compliance with U.S. GAAP and relevant regulations Qualifications: 3+ years of accounting experience, with direct experience in short-term rental, vacation rental, or property management accounting Strong working knowledge of QuickBooks Online; experience with Sage, Xero, or NetSuite a plus Hands-on experience with at least one major PMS (Guesty, Track, Hostaway, Streamline, OwnerRez, Rentvine, Hostfully, AppFolio) Familiarity with trust accounting concepts and owner statement workflows Advanced Excel Sharp, detail-oriented, and comfortable operating independently in a fast-moving environment Genuinely willing to operate across both advisory and execution work, not just one Fluent English (B2+) Availability during U.S. business hours Works as an independent contractor Benefits: Competitive pay based on experience Remote Paid time off Direct exposure to a fast-growing AI-native fintech platform and the chance to shape how modern property management accounting gets done How t

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 a bookkeeper with short-term rental or property management experience to join the team. You'll handle the day-to-day bookkeeping work that keeps property-level financials clean and accurate, and you'll get close to the accounting workflows we're continuously improving on the product side. This is a strong fit for someone earlier in their career who knows their way around STR books, wants to sharpen their skills inside a growing fintech company, and is curious about how modern accounting tools are built. What You’ll Do Categorize transactions, reconcile accounts, and keep the books current on a rolling basis Process accounts payable and receivable Assist with month-end close tasks, including reviewing ledgers and flagging anomalies Maintain owner ledgers and property-level records Help prepare owner statements and supporting reports Handle data entry, documentation, and file organization with care Flag recurring issues or friction points so we can address them at the workflow level Partner with senior accounting team members on cleanup and onboarding projects Qualifications: 1-3 years of bookkeeping experience, with exposure to short-term rental, vacation rental, or property management bookkeeping Comfortable in QuickBooks Online Some exposure to a PMS (Guesty, Track, Hostaway, Streamline, OwnerRez, Rentvine, Hostfully, or similar) preferred Solid Excel skills Detail-oriented, organized, and responsive Willing to ask questions and learn on the fly Fluent English (B2+) Availability during U.S. business hours Works as an independent contractor Benefits: Competitive pay based on experience Remote Paid time off Meaningful growth path alongside senior accountants and a technical team building the next generation of property management financial tools How to Apply: In your application, include 2–3 sentences describing any STR or vacation rental bookkeeping you've done and which PMS platforms you've worked with. Applications without directly relevant experience will not be prioritized. *Topkey is a financial technology company and is not an FDIC-insured bank. Banking services provided by Thread Bank, Member FDIC.

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 a customer support specialist with strong English communication skills to join the team. You'll be the first point of contact for property managers who have questions, run into issues, or need help getting the most out of the platform — and you'll work closely with our CS and product teams to make sure those experiences are consistently excellent. This is a strong fit for someone with a background in SaaS or fintech support who is organized, proactive, and genuinely invested in helping customers succeed. Experience with financial technology or property management software is a plus, not a requirement. What You’ll Do Serve as the primary point of contact for inbound customer questions via chat and email Troubleshoot issues with transactions, integrations, card management, and accounting workflows — and escalate clearly when needed Document bugs and customer-reported issues in structured, actionable formats for the engineering and CS teams Maintain and improve internal and external help documentation so customers can self-serve common questions Monitor customer health signals and flag at-risk accounts before issues escalate Surface recurring friction points and patterns to help improve workflows at the product level Qualifications: 2+ years in a customer support or customer success role, ideally at a SaaS or fintech company Excellent written and spoken English — this role requires clear, professional communication with U.S.-based customers (C1 level minimum) Organized, responsive, and proactive — you manage your own queue and follow up without being asked Comfortable breaking down technical issues and explaining them clearly to both customers and internal teams Experience with helpdesk or support tools (Plain, Intercom, Zendesk, Linear, or similar) Familiarity with financial technology, accounting workflows, or property management software is a strong plus Availability during U.S. business hours Works as an independent contractor Benefits: Competitive pay based on experience Remote Paid time off Meaningful growth path alongside a CS and technical team building the next generation of property management financial tools How to Apply: In your application, include 2–3 sentences describing a customer issue you resolved that required technical troubleshooting, and what tools or process you used. Applications without directly relevant support experience will not be prioritized. *Topkey is a financial technology company and is not an FDIC-insured bank. Banking services provided by Thread Bank, Member FDIC.

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.  *Topkey is a financial technology company and is not a bank. Banking services provided by Thread Bank; Member FDIC. Why You Should Join Topkey Work That Matters: You’ll be at the heart of helping customers implement, adopt, and fully leverage our platform to run their financial operations. Your work will directly influence product quality and customer outcomes. Own real outcomes: You’ll work directly with operators to implement Topkey, solve accounting and workflow issues, and guide them through best practices. This is a strategic, high-leverage role focused on execution, not escalation. Work Alongside Product & Founders: You’ll work directly with our Head of Technology Consulting and work closely with engineering to shape how we scale. You’ll play a major role in influencing the future of our product. You will also work closely with a number of key members of the team who helped successfully scale other financial and hospitality companies like Brex and Airbnb.  Join a Rocket Ship: We are growing rapidly, and this trend is not slowing down as we establish a strong product-market fit and your work will be crucial in ensuring we keep the high standard we have set on providing the best customer experience in the industry.   Role Overview We’re looking for someone with accounting and product experience to work directly with our customers as they adopt and scale on Topkey. You’ll help operators get set up, solve real financial workflows, and make sure they’re getting the most out of the platform. You’ll work closely with the founders, engineers, and our Head of Technology Consulting to improve the product and shape how we grow. What You’ll Do: Guide new customers through implementation, setup, and training. Help operators translate accounting workflows into Topkey’s system. Troubleshoot issues and surface feedback to engineering. Schedule recurring meetings with key customers to drive usage and adoption. Track customer health and proactively flag issues before they escalate. Serve as a strategic partner for high-value customers. Who We’re Looking For We’re looking for someone with both technical depth and great people instincts. You’ll need to be fluent in how financial operations work and able to translate that into practical outcomes for users. You’re comfortable bridging gaps between accounting teams, property operators, and software engineers. You know how to ask the right questions, identify root causes, and influence product decisions through insight, not volume. You may have experience in: SaaS onboarding or implementation Accounting or ERP systems Fintech, vertical SaaS, or proptech Client enablement, solutions consulting, or customer onboarding Qualifications 2 to 5 years of e

Compensation: Competitive, commensurate with experience About Topkey Topkey is a rapidly-growing fintech platform for short-term rental managers. We're particularly proud that 95%+ of all companies that onboard to Topkey never leave (I believe it is closer to 99%.) We offer deposit accounts, credit cards, full bill-pay, external cards, and expense management—all in one Rails monolith on the latest Ruby/Rails. With $1M+ ARR, zero churn (at the time of posting this), and a small, tight-knit engineering team, you’ll have a huge impact on our roadmap, our stack, and our customers’ success. 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.  *Topkey is a financial technology company and is not a bank. Banking services provided by Thread Bank; Member FDIC. Application Requirements: Applications without a personalized cover letter will not be considered Generic or AI-generated applications will be automatically rejected. We're looking for engineers who are passionate about Rails - when applying, mention your favorite gem and a brief reason why. We value authentic communication and want to hear YOUR voice What You'll Do Own features end-to-end in our Rails monolith (Rails 8+, Ruby 3.x) Build rich, reactive UIs with Hotwire/Turbo, Stimulus, and Tailwind CSS Integrate with external APIs (Plaid, Stripe, Unit, etc.) securely and robustly Use large context LLMs (Claude, Gemini, ChatGPT, etc.) to accelerate coding, QA, and spec writing Participate in architecture discussions -- help us evolve our beautiful monolith Work closely with product and founders to take specs from prototype to prod Ship daily/weekly, review critically, and treat AI as a multiplier—not a replacement for good judgment. (BTW, include the phrase 'beautiful monolith' in your application to show you've read this far) Optimize performance, reliability, and scalability of our core platform Act as your own pair programmer—debugging, prompting, reviewing AI-generated code for quality (the eng team will also review, but the initial onus is on the contributor) You Have 5+ years building production-grade Rails applications Deep expertise in Ruby, Rails conventions, background jobs, and service objects in a growing monolith Confidence reviewing, prompting, and editing AI-generated code from tools like Claude, Devin, Gemini, Cursor, etc. A reflexive approach to using AI in specs, code, QA, testing, and documentation Strong front-end chops: Stimulus/turbo/hotwire, components, etc. Experience designing and consuming REST APIs Solid SQL skills (PostgreSQL) and an eye for data modeling Track record writing maintainable test suites (RSpec) and CI pipelines Comfort working autonomously and asynchronously in a high-trust, high-output team Nice-to-Haves Previous fintech or payments or accounting experience Familiarity with Plaid, Stripe, or similar Experience with observability tooling (NewRelic, Honeybadger, etc.) Open-source contributions or personal projects you’re proud of Contributions to open-source or side projects involving AI/LLMs Required: Cover Letter Please submit a cover letter (max 500 words) that addresses: A specific technical challenge you've solved in a Rails application and your approach Your experience using AI tools in development and how you ensure code quality Why Topkey's mission in the short-term rental space (or real-estate in general) interests you specifically Include the word "monolith" somewhere in your cover letter to confirm you've read this posting Please share a brief story about a time when AI tools helped or h

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 Austin, TX 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