This is not your typical job description. My name is Ari, founder of Extenteam. I entered the
short-term rental industry by mistake while studying Industrial Engineering at USC back in 2009.
After running short-term rental management companies for more than a decade, I started
Extenteam, a staffing and proptech company that helps short-term rental operators. We grew to
a team of 430 people and more than $10MM ARR, but we also became complacent. We
focused on the wrong things and instead of executing, we spent too much time strategizing.
Everything changed at our South of France offsite in October 2025. We decided that the future
of the short-term rental industry will be shaped by AI and automation. This is where Tailwind
comes in.

Tailwind is Extenteam's automation and guest communication platform built specifically for the
short-term rental industry. It helps property management companies streamline operations by
centralizing guest messaging, automating repeatable tasks, and improving response times
across all communication channels. Our mission is to help our existing client base of 300
property management companies become more efficient using the Tailwind platform.
We are building a new team with an ownership mindset that values execution and takes pride in
doing excellent work with urgency. If you push for automation, understand patterns in how
people work, avoid solving problems by adding headcount, and are committed to improving
processes through data - we want to speak with you.

The Opportunity
We are looking for an exceptional Head of Product to own product vision, strategy, and
execution across two interconnected scopes: our agent/shared-services platform (the
operational backbone powering our internal team of 350+ customer service agents) and our
SaaS platform (the product we are taking directly to STR property managers at scale).
This is not a role for someone who needs a clean, defined lane. You will operate in ambiguity,
make consequential decisions daily, and work shoulder-to-shoulder with our founder, a talented
engineering squad, and a Senior PM that you get to hire.
You will partner directly with the leadership and act as the product architect responsible for
translating vision into execution in a scrappy way.

What You'll Own

Product Vision & Strategy
• Translate the company's overarching mission into a roadmap that engineering, sales,
and leadership can rally around.
• Maintain a living, prioritized backlog that reflects real customer needs, business
priorities, and technical constraints.
• Provide product input on automation initiatives and roadmap decisions in partnership
with Engineering and Operations.
• Treat the product roadmap as a living document that evolves with the technology
landscape. Continuously identify new tools, AI capabilities, and emerging solutions that
can replace manual effort, improve performance, or unlock new value for customers -
and move fast to implement them. The best version of this product is always the next on
Founder Alignment & Product Rhythm
• Build deep, structured alignment with the founder - not just high-level sign-offs, but
shared mental models of why, what, and complexity. Create communication rhythms
(weekly reviews, async updates, design sprints) that keep the founder informed without
bottlenecking execution. Find creative ways to make product decisions click for a highly
engaged, non-technical founder
Engineering Partnership
• Work daily alongside a senior, experienced engineering team that has built and shipped
products together across multiple projects and geographies, deep trust, shared history,
and a high bar.
• Translate ambiguous ideas into well-scoped, unblocking specs without over-specifying.
• Lead automation-first product thinking, design features and workflows that reduce
manual work and enable real-time monitoring.
Team Leadership
• Hire, onboard, and develop a Senior PM from day one, with a clear mandate for which
product scope they own.
• Model the product culture: scrappy, curious, customer-obsessed, data-informed, and
direct.
Cross-Functional Work
• Partner with Sales on product positioning, service tiers, and scaling plans.
• Get close to STR property managers, understand their daily pain points, tooling, and
language.
• Monitor the competitive and adjacent landscape: Hostaway, Guesty, Conduit, Akia, Enso
Connect, and others.
Who You Are
Required
• 7+ years in product management, with at least 3 years in a senior or head-of-product
role at a B2B SaaS company.

• Proven track record owning multiple product areas simultaneously, spanning internal
tooling and external customer-facing products.
• Demonstrated ability to work closely with a non-technical founder or senior executive
deeply involved in product decisions.
• Experience leading or mentoring PMs, with the ability to build a small product team from
scratch.
• Hands-on experience designing automation-ready workflows or systems in partnership
with Engineering.
• Strong written and verbal communication, you can write a crisp one-pager and run a
tight product review.
• Deep hands-on experience with Jira or Linear - you have managed complex product
backlogs, built structured workflows, and used it as the operational backbone for sprint
planning, roadmap tracking, and cross-team coordination

Preferred
• Background in proptech, hospitality tech, or operations-heavy SaaS.
• Experience at a company transitioning from services to software.
• Familiarity with AI-augmented workflows, human-in-the-loop systems, or guest
communication products.
• Comfort working with data, dashboards, and analytics tools to guide product decisions.

Key Attributes
• Vision Translator: You take a founder's ambition and turn it into a roadmap engineers
and stakeholders can execute against.
• Execution Focused: You move ideas into production quickly and consistently deliver
measurable results and be scrappy. Build a fast cadence of weekly feature shipments.
• Technically Fluent: You understand how systems integrate and can work directly with
engineering without hand-holding.
• Ambiguity Crusher: You bring clarity to messy, incomplete situations and create
structure others can follow.
• Strong Communicator: You convey information clearly and align cross-functional
teams around a shared direction.

Why Join Extenteam
• Build from the ground up: Shape product strategy and org structure, this is your
chance to leave a real mark.
• Executive visibility: Report directly to the founder. Partner with the full leadership team.
• Ownership & autonomy: We trust you to own your domain and make bold decisions.
• Strong engineering team: Work alongside experienced engineers who have
collaborated across multiple projects worldwide and hold a high standard.
• Growth trajectory: As we scale, you will grow your team and scope.
• Competitive compensation: $140,000- 160,000 base + 20% performance bonus
• Equity: We believe in ownership at every level. Equity participation will be discussed
and finalized with the right candidate.

Our Interview Process
We move quickly for the right candidate.
• Intro call with Founder (45 min)
• Interview with leadership team member (45 min)
• Interview with leadership team member (45 min)
• Case study or take-home assignment
To apply, record a short one-minute video explaining why you want to be part of Extenteam and
what makes you the right person for this role.

Apply now

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