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Founding Content Lead

Job Description

As our founding Founding Content Lead you will have the unparalleled opportunity to establish and lead our content creation and strategy from the ground up. We're seeking an individual with a proven track record in content strategy and creation, who can develop a comprehensive content roadmap and own the entire content lifecycle to support our go-to-market (GTM) initiatives. This role is more than a foundational team position; we're looking for a self-starter to grow with us and catapult your career into a meaningful leadership position

Your initial responsibilities will include developing a content strategy that aligns with Topkey’s business objectives, engaging with our target audience through compelling content (90/10 digital vs. print), establishing our content distribution channels, and measuring the impact of our content efforts. Unlike a role where the content strategy is already defined, here, you'll have the chance to define success and build the content function from the ground up. You should be excited about creating a content playbook rather than adapting to a predefined environment. You'll work closely with our CEO and marketing team to develop and execute this strategy.

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, 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 replacesTopkey 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 issued through our partner Thread Bank, 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

We're looking for 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 significant responsibilities, defining our content strategy, managing our content calendar, and having a direct influence on our growth and engagement metrics.
  • Become a Leader on the Team: We view this role as a pathway to leadership within the company. As we grow and scale, you could have the opportunity to lead content teams and influence major strategic decisions.
  • Craft the Voice of a Rocket Ship: Our trajectory is steep, matched by your potential growth curve. We’re establishing a strong product-market fit and your work will be crucial in amplifying our message.
  • 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, Built Technologies, and HotelTonight).
  • 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.
  • 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.

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 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 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.


We realize this is a huge breadth of responsibilities, and we don't expect anyone to be a proven expert across every area — or maintain this all-in-one role over time. As our company grows, so will our marketing team, and we'll specialize accordingly!

  • You will measure and analyze content effectiveness. You will use analytics tools to assess content performance across channels and set KPIs for engagement, lead gen, and customer acquisition to refine our content strategy.
  • You will help guide the content strategy, crafting and executing a narrative that align with Topkey's business goals and market positioning.
  • Your primary focus will be on content production. You will produce a broad range of content types, including blog posts, whitepapers, case studies, videos, and social media posts, ensuring all content is consistent with our brand voice and standards.
  • You will develop and manage Topkey's social media strategy, utilizing platforms like LinkedIn, Twitter, Instagram, and Facebook to bolster engagement, community building, and traffic to our website.
  • You will help produce educational content and training materials for customers, including tutorials, webinars, and guides demonstrating Topkey’s product offerings.
  • You will create and regularly update an FAQ section, collaborating with customer support to address common queries and ensure clarity and accessibility of information.

What We’re Looking For

  • You are opinionated. You 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, and get your hands dirty. You’re building Topkey’s voice from the ground up. This role will require hands-on work in content production, from drafting articles to managing social media posts. We're seeking someone with the humility to tackle every aspect of content management—no task is too small.
  • You bring an entrepreneurial mindset to the table - you are comfortable operating with extreme ambiguity and thrive in an environment where experimentation is required.
  • You're fiercely competitive about performance. You strive to outperform expectations and set new records. Your work is not just about meeting goals; it's about setting new milestones.
  • You're a collaborator at heart. Understanding that great ideas come from collaboration, you excel in cross-functional teams. You can communicate and align with product, sales, and marketing to ensure our content strategy supports overarching business objectives.
  • You know how to craft compelling narratives. Clear writing conveys competence, a critical component of building trust and winning business.
  • You’ve previously set and achieved ambitious content metrics, like engagement, reach, or lead generation, proving you know how to hold yourself accountable for consistently exceeding expectations.
  • You have excellent time management skills, you can prioritize and shift workload to meet deadlines.
  • You've managed content calendars and campaigns. Responsible for both the creation and strategic distribution of content, you know how to keep projects on track, measure their success, and iterate based on data.
  • You embrace an ownership mentality. You can 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.


  • Experience: 2+ years in content strategy and management, with a strong portfolio demonstrating successful campaigns and content creation across various platforms.
  • Skills: Proficiency in SEO, digital marketing, and analytics tools to optimize content performance.

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.

If you're serious about this role, send an email to (1) Propose a concise content marketing campaign for Topkey aimed at vacation rental property managers. Include your strategy and how you would measure success. (2) Explain why your background and experience in content make you in the top 1% of candidates to absolutely crush it in this role. (3) Share a link to your favorite piece of content that you've written.