Former Founder

Founder Intro
This is not your typical job description. My name is Ari, founder of Extenteam. I got into the short term rental industry by mistake while I was getting my undergraduate degree in Industrial Engineering at USC in California back in 2009.

After running short term rental management companies for over a decade, I started Extenteam - a staffing and proptech company that helps short term rental operators. We grew to a team of 430 people, over 10MM ARR, but we also became complacent in the past years. We became stagnant. We focused on the wrong things, and rather than executing - we focused too much on strategizing.

The people we had on were great people, but the wrong people for the type of company I want Extenteam to be. Everything changed at our South of France offsite in October 2025. 

We decided that while our dedicated team member unit (legacy business) is relevant and important in the hospitality and real estate industry, AI and Automations are going to be the future of the short term rental industry.
We are on a mission to help our existing client base of 300+ property management companies to become more efficient and automate their operational processes using our Tailwind Platform.

The leadership team also decided that we want a new team that has an ownership mindset, is more prone to execution and being scrappy and getting s**t done, instead of strategizing.

If you are willing to roll up your sleeves, work with us and pursue excellence - and if you value delivering quality work, with urgency and pride, if you refuse mediocrity - and have an eye for details, and are a data driven person - who can help us double our revenue within 12 months, we want to talk to you.

We are bringing our next cohort of hires in the office, in Miami - working in person. To ensure we remain relevant and competitive in our fast-paced environment, we prioritize in-person work. This approach fosters better communication and collaboration, leading to faster results.

If you are a doer, rather than a strategist - are willing to hustle side by side with a highly cognitive, fast performing team - please record a short one minute video, and explain why you want to be part of Extenteam.

If you read till here, below are the standard parts of the JD.

The Role

We need someone who can walk into a mess and walk out with a solution. This is a generalist role for someone who gets bored doing one thing, thrives on variety, and has the rare ability to toggle between a spreadsheet deep-dive and a strategic conversation without breaking a sweat.

You'll work directly with leadership on whatever matters most, today that might be building a new reporting framework, tomorrow it's diagnosing why a process is broken, next week it's leading a cross-functional initiative nobody else has bandwidth for.

Here's the bigger picture: In 2026, Extenteam is launching new services and offerings. We need someone who can help jump-start these from zero, scoping opportunities, standing up operations, and turning ideas into revenue. This isn't just about keeping the trains running; it's about building new tracks.

If you've ever described yourself as "the person who figures things out," keep reading.

What You'll Actually Do

• Own complex, ambiguous projects end-to-end. The ones that don't have a clear playbook. You'll scope them, structure them, execute them, and know when to hand them off.
• Get in front of customers. You'll talk to potential customers, sometimes over a call, sometimes face-to-face, to understand their problems, validate new offerings, and help close deals. You're not afraid to hop on a plane or show up in person when it matters.
• Help launch new services and offerings. You'll be in the room when we're figuring out what to build next, and then you'll help make it real.
• Build systems and processes from scratch. When something is held together by duct tape and tribal knowledge, you'll be the one to turn it into something repeatable and scalable.
• Get uncomfortable with data. Pull it, clean it, analyze it, and turn it into something actionable. You're not a data scientist, but you're dangerous enough in Excel/Sheets/SQL to find answers and make data driven decisions.
• Be the connective tissue. Work across teams, operations, finance, product, customer service to push initiatives forward - when no single team owns the problem or work independently with no resources whatsoever
• Document and operationalize. You don't just solve problems, you leave behind SOPs, frameworks, and dashboards so others can maintain what you've built.

Who You Are

• Entrepreneurial to your core. You've founded a company or been an early employee at a startup. You're comfortable wearing many hats, not because you have to, but because that's how you like to work. You see gaps and fill them without being asked.
• Comfortable in the room with customers. You can hold your own in a conversation with a potential client, whether that's a discovery call, a pitch meeting, or grabbing coffee to understand their pain points. You're personable, sharp, and know how to listen.
• A generalist by nature. You'd rather solve five different types of problems than one type of problem five times.
• Analytically rigorous but action-oriented. You can go deep on analysis, but you don't hide behind it. You know when "good enough" data is enough to make a call.
• A clear communicator. You can explain complex things simply, write a concise update, and tailor your message for different audiences.
• Relentlessly resourceful. You Google things. You ask good questions. You find workarounds. You don't wait for permission or perfect information.
• Low ego, high ownership. You'll do the unglamorous work because it needs to get done. You care more about outcomes than credit.

Requirements

Must have:

• Entrepreneurial mindset with the experience to back it up. You've founded a company or been an early employee at a startup. You've operated where "that's not my job" doesn't exist, resources are limited, and you figured things out on the fly. This shapes how you think and work in ways that can't be taught,and it's exactly what we need as we launch new offerings in 2026.
• A track record of things YOU personally built or fixed that moved the needle. Not "was on the team that..." or "contributed to..." we want to hear about the process you redesigned that cut costs by 30%, the reporting system you built from scratch that's still in use, the operational fire you put out that saved a key account. Specific examples. Measurable impact. Your fingerprints on it.
• Willingness to be customer-facing. You'll be talking to prospects and customers regularly—on calls and in person. If you'd rather stay behind a screen, this isn't the role.
• 3-5+ years of experience across operations, strategy, consulting, finance, or chief of staff roles
• Strong proficiency in spreadsheets
• Startup experience after consulting, with a strong ownership mindset and ability to build scalable processes.

Nice to have:

• SQL, basic scripting, or experience with BI tools

• Massive scope: You’ll work on the highest-leverage problems in the company and take projects from idea to execution.
• Real business impact: You’ll see your work translate into revenue, efficiency, or new services within weeks, not quarters. Your projects will directly shape how Extenteam grows in 2026 and beyond.
• Ownership & autonomy: We trust you to own your domain and make bold decisions
• Miami-based team: Work alongside a talented, in-office team 4 days/week in Downtown Miami

1. Intro call with Founder (30 min)
2. Hiring manager Interview (60 min)
3. Case study or take-home assignment 
4. Team interviews with (2-3 hours)
5. Reference checks and offer We move quickly for the right candidate. You can expect to complete the process within 2-3 weeks.

Extenteam is an Equal Opportunity Employer.
We are committed to creating an inclusive workplace and we do not discriminate on the basis of race, color, religion, creed, national origin, ancestry, citizenship, sex, gender identity or expression, sexual orientation, age, marital status, pregnancy, veteran status, disability, genetic information, or any other protected characteristic under applicable laws.

We welcome applicants from all backgrounds and encourage people of all identities to apply. If you need assistance or accommodation during the application or interview process, please let us know.