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Bookkeeper — Short-Term Rental / Property Management
Topkey · PH / Remote (PH)
Not listed
62 days ago
♡
Accountant — Short-Term Rental / Property Management
Topkey · PH / Remote (PH)
Not listed
62 days ago
♡
Bookkeeper — Short-Term Rental / Property Management
Topkey · PH / Remote (PH)
Not listed
62 days ago
♡
Accountant — Short-Term Rental / Property Management
Topkey · PH / Remote (PH)
Not listed
62 days ago
♡
Financial Technology Consultant (Product & Accounting Focus)
Topkey · Austin, TX, US
$85k–120k
326 days ago
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Bookkeeper — Short-Term Rental / Property Management
Topkey · PH / Remote (PH)
Pay
Not listed
Setting
Remote
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Bookkeeper — Short-Term Rental / Property Management at Topkey(W21)
$500 - $2K / monthly
PH / Remote (PH)
Full-time
US citizenship/visa not required
1+ years
Apply now
About Topkey
Topkey is the all-in-one financial operating system built for hospitality management companies. Our solution streamlines corporate card management, expense tracking, and accounts payable. The product includes unlimited virtual and physical cards with customized budget controls, automated expense tracking, and seamless accounting and property management integrations.
We enable our customers to effortlessly track every purchase back to a specific property and reconcile their books with just a click of a button. This helps finance teams save 40 hours a month and thousands of dollars in bookkeeping and reimbursable expenses. Topkey was founded by industry veterans who proved out product-market fit before writing our first line of code.
In March, we closed a large seed round led by some of the best investors in Silicon Valley.
About the role
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.
Technology
Ruby on rails 7
Ruby 3.1+
PostgreSQL
Hotwire/turbo/stimulus
TailwindCSS
Apply now
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Listed by Topkey for a position based in the United States. Employers on this board attest they are hiring domestically.
Accountant — Short-Term Rental / Property Management
Topkey · PH / Remote (PH)
Pay
Not listed
Setting
Remote
Work at a Startup
Startup Jobs
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Accountant — Short-Term Rental / Property Management at Topkey(W21)
$1K - $3K / monthly
PH / Remote (PH)
Full-time
US citizenship/visa not required
3+ years
Apply now
About Topkey
Topkey is the all-in-one financial operating system built for hospitality management companies. Our solution streamlines corporate card management, expense tracking, and accounts payable. The product includes unlimited virtual and physical cards with customized budget controls, automated expense tracking, and seamless accounting and property management integrations.
We enable our customers to effortlessly track every purchase back to a specific property and reconcile their books with just a click of a button. This helps finance teams save 40 hours a month and thousands of dollars in bookkeeping and reimbursable expenses. Topkey was founded by industry veterans who proved out product-market fit before writing our first line of code.
In March, we closed a large seed round led by some of the best investors in Silicon Valley.
About the role
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 to Apply:
In your application, include 2–3 sentences specifically describing your experience reconciling PMS data against a general ledger and any STR or vacation rental accounting work you've done. 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.
Technology
Ruby on rails 7
Ruby 3.1+
PostgreSQL
Hotwire/turbo/stimulus
TailwindCSS
Apply now
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Listed by Topkey for a position based in the United States. Employers on this board attest they are hiring domestically.
Bookkeeper — Short-Term Rental / Property Management
Topkey · PH / Remote (PH)
Pay
Not listed
Setting
Remote
Listed by Topkey for a position based in the United States. Employers on this board attest they are hiring domestically.
Accountant — Short-Term Rental / Property Management
Topkey · PH / Remote (PH)
Pay
Not listed
Setting
Remote
Listed by Topkey for a position based in the United States. Employers on this board attest they are hiring domestically.
Customer Support — Financial Software
Topkey · PH / Remote (PH)
Pay
Not listed
Setting
Remote
Listed by Topkey for a position based in the United States. Employers on this board attest they are hiring domestically.
Account Executive
Topkey · Austin, TX, US
Pay
$150k–200k
Setting
On-site
Listed by Topkey for a position based in the United States. Employers on this board attest they are hiring domestically.
Senior Sales Development Representative
Topkey · Austin, TX, US
Pay
$60k–90k
Setting
On-site
Work at a Startup
Startup Jobs
Resume Review
Education
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Log In
Senior Sales Development Representative at Topkey(W21)
$60K - $90K
Austin, TX, US
Full-time
US citizen/visa only
Any (new grads ok)
Apply now
About Topkey
Topkey is the all-in-one financial operating system built for hospitality management companies. Our solution streamlines corporate card management, expense tracking, and accounts payable. The product includes unlimited virtual and physical cards with customized budget controls, automated expense tracking, and seamless accounting and property management integrations.
We enable our customers to effortlessly track every purchase back to a specific property and reconcile their books with just a click of a button. This helps finance teams save 40 hours a month and thousands of dollars in bookkeeping and reimbursable expenses. Topkey was founded by industry veterans who proved out product-market fit before writing our first line of code.
In March, we closed a large seed round led by some of the best investors in Silicon Valley.
About the role
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, etc.).
Why Topkey
Great People: Work with a talented team of engineers, product thinkers, and sellers.
Fast Growth: Backed by Felicis, a16z, and YC— we are on a rocket ship trajectory.
Real Customers: We have strong product-market fit and hundreds of paying customers.
Unique Vertical: Build expertise in a high-velocity, under-automated market.
Build in Austin: Join our growing sales team, CEO, customer success, and marketing team in-person.
Technology
Ruby on rails 7
Ruby 3.1+
PostgreSQL
Hotwire/turbo/stimulus
TailwindCSS
Interview Process
How to Apply
Give us a cold call at (720) 383-6555. If we don’t answer, leave a voicemail with your best elevator pitch for yourself.
Send us a follow-up email letting us know you call. Send the email to jon@topkey.io and darren@topkey.io with the subject line “SDR - Austin”
Apply now
Other jobs at Topkey
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View job
Hundreds of YC startups are hiring on Work at a Startup.
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Listed by Topkey for a position based in the United States. Employers on this board attest they are hiring domestically.
Financial Technology Consultant (Product & Accounting Focus)
Topkey · Austin, TX, US
Pay
$85k–120k
Setting
On-site
Listed by Topkey for a position based in the United States. Employers on this board attest they are hiring domestically.
Senior Rails Engineer -- Fintech Platform (Thoughtful Applications Only -- Cover Letter Required)
Topkey · Miami, FL, US / Nashville, TN, US / Remote (US)
Pay
$110k–200k
Setting
Remote
Work at a Startup
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Senior Rails Engineer -- Fintech Platform (Thoughtful Applications Only -- Cover Letter Required) at Topkey(W21)
$1 - $2
Miami, FL, US / Nashville, TN, US / Remote (US)
Full-time
US citizen/visa only
3+ years
PostgreSQL
Ruby
Ruby on Rails
Apply now
About Topkey
Topkey is the all-in-one financial operating system built for hospitality management companies. Our solution streamlines corporate card management, expense tracking, and accounts payable. The product includes unlimited virtual and physical cards with customized budget controls, automated expense tracking, and seamless accounting and property management integrations.
We enable our customers to effortlessly track every purchase back to a specific property and reconcile their books with just a click of a button. This helps finance teams save 40 hours a month and thousands of dollars in bookkeeping and reimbursable expenses. Topkey was founded by industry veterans who proved out product-market fit before writing our first line of code.
In March, we closed a large seed round led by some of the best investors in Silicon Valley.
About the role
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 hindered your development process
Required: Technical Questions
Describe a time when you had to optimize a slow Rails query. What was your approach?
What's your experience with Hotwire/Turbo for building reactive UIs?
Describe your approach to handling background jobs at scale in a Rails monolith
How do you approach code review for AI-generated code?
What feature would you like to see Rails core include out-of-the-box that isn't currently available, and why?
Perks & Benefits
Remote-friendly
Generous PTO and paid holidays
Equity in a high-growth startup
Generous professional development stipend
Home-office setup budget
Health, dental, and vision insurance (U.S.) + 401(k) match
Optional But Encouraged:
Link to a recent PR or code sample that demonstrates your Rails expertise
GitHub profile with Rails projects
—
*Topkey is a financial technology company and is not a bank. Banking services provided by Thread Bank; Member FDIC.
Technology
Ruby on rails 7
Ruby 3.1+
PostgreSQL
Hotwire/turbo/stimulus
TailwindCSS
Apply now
Other jobs at Topkey
Customer Support — Financial Software
PH / Remote (PH)
Full-Time
$500 - $1K / Monthly
6+ Years
View job
Bookkeeper — Short-Term Rental / Property Management
PH / Remote (PH)
Full-Time
$500 - $2K / Monthly
1+ Years
View job
Accountant — Short-Term Rental / Property Management
PH / Remote (PH)
Full-Time
$1K - $3K / Monthly
3+ Years
View job
Account Executive
Austin, TX, US
Full-Time
$150K - $200K
0.10% - 0.30%
6+ Years
View job
Financial Technology Consultant (Product & Accounting Focus)
Austin, TX, US
Full-Time
$85K - $120K
3+ Years
View job
Hundreds of YC startups are hiring on Work at a Startup.
Sign up to see more ›
Work at a Startup
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Internships
Events
How it works
Sign in
Y Combinator
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Press
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Design & UI/UX Jobs
Product Manager Jobs
Sales Jobs
Marketing Jobs
Support Jobs
Operations Jobs
Jobs by Location
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Product Manager Jobs in San Francisco
Software Engineer Jobs in New York
Product Manager Jobs in New York
Software Engineer Jobs in Los Angeles
Product Manager Jobs in Los Angeles
Remote Jobs
Remote Software Engineer Jobs
Remote Design & UI/UX Jobs
Remote Product Manager Jobs
Remote Sales Jobs
Remote Marketing Jobs
Remote Support Jobs
Remote Operations Jobs
Listed by Topkey for a position based in the United States. Employers on this board attest they are hiring domestically.
Account Executive
Topkey · Austin, TX, US
Pay
$150k–200k
Setting
On-site
Listed by Topkey for a position based in the United States. Employers on this board attest they are hiring domestically.
Select a role
The full posting opens here — pay, setting and the full description, without leaving the list.