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Posted 2 months ago

Founder in Residence

@ The Flex

Remote in Canada

RemoteFull-time
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SIGNALS

Overview

The Flex is hiring a Founder in Residence to identify an opportunity in the short-term rental industry, build a new product or business vertical within Base360.ai, and lead it as its long-term General Manager. The work covers opportunity research, customer validation, product strategy, go-to-market planning, and building a cross-functional team. The role is full-time and remote.

Responsibilities:

  • Identify a major short-term rental opportunity and validate it with operators
  • Define product vision, strategy and go-to-market plan
  • Build and launch the new product with engineering, design and AI teams
  • Recruit and lead a multidisciplinary team
  • Own growth, adoption and financial performance of the venture

Requirements summary:

  • Entrepreneurial mindset with a bias toward action
  • Strong problem-solving and product and commercial intuition
  • Excellent communication and leadership skills
  • Ability to recruit and lead high-performing teams
  • Previous startup experience valued but not required
  • Short-term rental, hospitality or proptech experience a plus

Tools & skills

Source and dates

Employer career site / ATS feed · ashby

Employer posting date
2026-09-22
First seen by our source
2026-10-12
Source record updated
2026-11-06

These dates describe the source record, not a live verification that the employer is still hiring. Check the original posting.

Job details

SeniorityLead
DepartmentBusiness development
Manages peopleYes
Hours per week40 (estimated)
Work settingHome
PositionMostly sitting
Physical demandsphysical low · computer high
LanguagesEnglish
Perks mentionedPerformance bonus

Summary and details written by AI from the posting; the employer’s posting is the authority.

The Flex

FieldValue
Open jobs on Jobsy2
Job description

Base360.ai is building the AI operating system for short-term rental businesses.

We bring property management, guest communication, pricing, cleaning, maintenance, direct bookings and financial reporting into a single platform powered by AI. Our mission is to replace dozens of disconnected tools with one intelligent operating system that helps short-term rental operators automate operations, increase revenue and deliver exceptional guest experiences.

We're building ambitious products, moving fast, and looking for exceptional entrepreneurs who want to build the next generation of AI businesses within the short-term rental industry.

The Role

As a Founder in Residence, you won't be joining a department—you'll be building one.

Your mission is to identify a major opportunity in the short-term rental industry, build a new product or business vertical within Base360.ai, assemble the right team, validate the market, and grow it into a standalone business with significant revenue and impact.

Think of it as founding a startup—with the advantage of funding, engineering, design, AI infrastructure, customers, distribution, and executive support already behind you.

If successful, you will become the long-term leader of your venture.

What You'll Do

  • Identify high-potential opportunities in short-term rentals that can become new products or business verticals.

  • Validate customer problems through research and direct conversations with property managers and rental operators.

  • Define the product vision, strategy, and go-to-market plan.

  • Work alongside engineering, product, design and AI teams to build and launch quickly.

  • Recruit and lead your own multidisciplinary team as the venture grows.

  • Own growth, product adoption, customer success and financial performance.

  • Make data-driven decisions and iterate rapidly based on customer feedback.

  • Present progress directly to the founders and executive team.

  • Build a business that could eventually operate as its own division—or even become an independent company.

What We're Looking For

  • Entrepreneurial mindset with a bias toward action.

  • Exceptional problem-solving ability.

  • Strong product and commercial intuition.

  • Comfortable working with ambiguity and creating structure where none exists.

  • Excellent communication and leadership skills.

  • Ability to recruit, inspire and lead high-performing teams.

  • Highly analytical with strong execution capabilities.

  • Obsession with customers and building products people love.

  • Comfortable wearing multiple hats across product, sales, marketing and operations.

  • AI-native and excited about building with the latest AI technologies.

Previous startup experience—as a founder, early employee, product leader, operator or investor—is highly valued but not required. Experience in short-term rentals, hospitality or property technology is a plus.

What Success Looks Like

Within your first 12–24 months, you will have:

  • Built and launched a new business vertical serving the short-term rental industry.

  • Hired and led your own cross-functional team.

  • Achieved strong product-market fit.

  • Generated meaningful recurring revenue.

  • Established yourself as the long-term General Manager of your venture.

Why Join Base360.ai?

  • Be part of an innovative and fast-growing company building the AI operating system for short-term rental businesses.

  • Build your own venture with the backing of an experienced founding team.

  • Access world-class engineering, AI, product, design and go-to-market resources.

  • Receive funding, mentorship and strategic support to turn your vision into reality.

  • Opportunity to build a team and establish a long-term business within Base360.ai.

  • Competitive salary and performance-based incentives.

  • Significant long-term career growth, with the opportunity to lead an entire business unit.

You should NOT apply if:

  • You are looking for a corporate 9 to 5 job.

  • You are political and enjoy gossiping and talking about people behind their backs.

  • You are looking for a stable and slow dead-end job.

  • You do not aim to be one of the best in the world at what you do.

#LI-Remote

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