Founding Engineer - AI Automation Layer

We want to be known as the best AI company in hospitality. Not another chatbot bolted onto a property management system. That's the gap you'd own.

Who we are

Symplehost is building the all-in-one platform for independent short-term rental operators. The people running 10 to 100 listings on spreadsheets, WhatsApp and email because the incumbents only serve large hotel chains.

It's a big, underserved market: 3–4 million listings worldwide, with Southeast Asia almost entirely ignored by the US-centric players. Three co-founders built the core (a substantial Ruby on Rails system) in under a year.

Our mission: give a 12-listing owner the capability of a full hotel group (revenue, operations, guest experience) without the headcount, at a price they can actually pay. One person running 50 listings across countries and languages, with every guest feeling personally looked after.

The long game: as the automation gets smarter, the interface fades. Operators run their business through natural language — chat and voice. Software that does the work, not software you operate. AI isn't a feature here. It's what replaces the screens.

The role

We have a solid AI automation layer today. But honestly, it's roughly in line with what's already out there. We don't want to be "roughly in line." As founding engineer, you'd have the scope and autonomy to change that.

Your 90-day mission: Build the best guest-facing AI agent in hospitality, and lay the foundations for the AI strategy and stack behind it. Autonomous, context-aware, long-memory, human-sounding. It handles guest communication, triggers workflows, and escalates to people when needed. Reliably.

Why it's a hard problem worth doing

Guest communication sounds simple until you build it. The guest journey is long (booking, travelling, staying, checking out) so the agent has to hold context across a lot of data and time while keeping its reasoning clean. It has to know when to act, when to escalate, and it has to sound genuinely human. That combination is the hard part, and exactly where we intend to win.

With today's tooling, a lot is possible in 90 days. We're not asking you to boil the ocean — nail the strategy, choose the right stack, and prove it on the hardest use case.

The first 90 days

Days 1–30

Get deep, form a view. Get productive in the platform, learn the operator and the guest, audit our AI honestly, and start shaping a point of view on the stack.

Days 31–60

Architect and build. Decide the stack — models, orchestration, memory and context. Build the core agent foundations and the guardrails that make it trustworthy in production.

Days 61–90

Ship it and prove it. A working guest-facing agent handling real communication end-to-end, demonstrably ahead of the market's chatbots, plus a roadmap for scaling our AI.

Who we are hoping to meet

A strong engineer who's still hungry. Someone with something to prove and a real obsession with AI. If you've spent the last year or two building with AI in your own time because you can't help it, and you want somewhere to deploy that at full tilt, this is the role. Enough experience to move fast, enough drive to treat this as the opportunity it is.

Our Stack

Ruby on Rails · Next.js · Supabase · Redis · Trigger.dev · Claude SDK (Anthropic) + proprietary harness. We lean hard into AI tooling.

The Package

• Salary: PHP 200,000–265,000 / month (gross)
• Equity: Meaningful founding-team equity
• Location: Fully remote. Whole company meets in person once a year
• Time off: Statutory leave as a baseline — plus flexibility; we trust you to take what you need
• AI tooling: Unlimited token policy. You'll never be rationed on the tools that make you faster

How our process works

Built around our 90-day mission, so it's a fair preview of the real work:

(1) Mission — stress-test the 90-day plan and tell us where the risks are.

(2) Depth — go deep on one real component together, part pairing, part system design, use AI however you normally would.

(3) Alignment — how you handle ambiguity, challenge, and the founding-engineer mindset.