About HappyRobot

HappyRobot is the infrastructure for enterprises to build and orchestrate AI workforces. Our AI workers don't just communicate - they make decisions, take action, and run operations autonomously across voice, email, and enterprise systems. Born in Y Combinator (S23) and backed by a16z and Base10 with over $60M raised, we power critical operations for global enterprises worldwide.

Our platform is battle-tested in the most demanding environments - where AI has real consequences. We started in logistics, built our own voice stack, models, and orchestration layer from the ground up, and are now bringing that infrastructure to every enterprise that runs the real economy. Learn more about our vision in our manifesto.

Role Overview

We are looking for a Deployment Strategist to join our team. You will partner with Forward Deployed Engineers across the full deployment lifecycle — from first discovery conversation to live production — bringing the strategic, business-value lens that keeps every technical decision pointed at the highest-impact outcome.

This is not a pure engineering role. Your deepest strength is the opinionated, strategic perspective you bring across every phase: spotting where value lives, scoping it realistically, and partnering with engineers to capture it. That said, you are technically fluent — comfortable enough to build prototypes yourself, understand integration constraints, and earn credibility with the engineers you work alongside.

What You'll Do

Use Case Discovery & Scoping Partner with C-level executives and VPs to assess AI opportunities and prioritize the highest-impact use cases. Lead curiosity-driven discovery that surfaces workflows where AI creates real business value — well beyond what the customer thought to ask for. On the business side, pressure-test the realistic upside and explore whether reframing a use case or pivoting to an adjacent process unlocks more value. On the technical side, map integrations, data, and platform constraints with your FDE partner, and surface edge cases and dependencies that shape timelines. Land on a plan that's rigorous on both axes.
Prototyping Build prototypes and demos hands-on using our platform and AI-powered tools. Test ideas end-to-end at light scope, in Python, to prove value early — before the customer commits to a full build.
Program Management Coordinate active deployments across an account. Stay close enough to the build that you deeply understand what's being developed, can spot when work is drifting from the highest-value path, and can catch issues before they become problems. Serve as the escalation point for the customer and the strategic watchdog for the FDE.
Prioritization Sequence use cases within an account so each deployment compounds the next. Make the call on what gets built when, what gets parked, and where to invest discovery and building time.
Customer Partnership Be the primary business-side point of contact for the account. Build trust with operational and executive stakeholders day-to-day. Translate AI capabilities and constraints into language both sides can act on. Travel onsite for kickoffs, mapping sessions, and key moments where being on the ground changes the outcome.
Product Feedback Loop Bring structured field signal back to Product and Engineering. Identify reusable patterns, common edge cases, and where the platform needs to evolve.

Must Have

Background that combines technical fluency with strategic instinct and a real history of building things. Common paths include technical consulting, product management, founding or operating at a tech startup, or an engineering background where you've grown into a strategic and customer-facing role.
Comfortable coding in Python — enough to build working prototypes and demos using LLMs and AI-powered tools like Claude Code.
Working understanding of APIs, integrations, and how AI agents fit inside enterprise workflows.
Strategic instinct: ability to identify where business value actually lives in a workflow, challenge assumptions, and translate findings into prioritized plans a C-level can act on.
Excellent communication skills with both executives and operators — you hold precision with technical audiences without losing business stakeholders, and vice versa.
Proven ability to manage multiple workstreams in parallel and drive outcomes, not just activity.
Founder mindset: highly independent, takes full ownership, and thrives in fast-paced, ambiguous environments.

Why join us

Opportunity to work at a high-growth AI startup, backed by top investors.
Rapidly growing and backed by top investors including a16z, Y Combinator, and Base10.
Ownership & Autonomy - Take full ownership of projects and ship fast.
Comprehensive Benefits - Healthcare, dental, vision coverage.
Top-Tier Compensation - Competitive salary + equity in a high-growth startup.
Work With the Best - Join a world-class team of engineers and builders.

Our Operating Principles

Extreme Ownership — We take full responsibility for our work and outcomes. No excuses, no blame-shifting. If something needs fixing, we own it.

Craftsmanship — We sweat the details because details compound. We never settle for just fine — whether it's a scoping document, a prototype demo, or a customer conversation.

We are majos — Be a good human. Friendly, genuine, kind. We're building something ambitious and it's better when we enjoy it together.

Urgency with Focus — Move fast, but in the right direction. Prioritize ruthlessly. Act decisively. Aim for the highest leverage action.

Talent Density and Meritocracy — Every hire raises the bar. Ability over seniority. Ownership goes to those who earn it.

First-Principles Thinking — Strip problems to their fundamentals, ignore industry dogma, and rebuild from scratch when needed. It's how we build what others think is impossible.

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By sending us your CV, you consent to the processing of your personal data for the purpose of evaluating and selecting you as a candidate for the position. Your personal data will be treated confidentially and will only be used for the recruitment process of the selected job offer.

In relation to the period of conservation of your personal data, these will be eliminated after three months of inactivity in compliance with the GDPR and legislation on the protection of personal data.

If you wish to exercise your rights of access, rectification, deletion, portability or opposition in relation to your personal data, you can do so through [HIDDEN TEXT] subject to the GDPR.

For more information, visit https://www.happyrobot.ai/privacy-policy

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AI Deployment Strategist, Public Sector

Deployment Strategist - Singapore