Deployment Operations Lead

Happyrobot Inc.•San Francisco, CA

About The Position

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. We are looking to grow our team with a Deployment Operations Lead to act as the operational backbone of our Deployments organization. This is a role for a high-output operator who loves discipline, structure, and execution. At HappyRobot, you will sit at the critical intersection of three key functions: Deployments (Forward Deployed Engineers and Deployment Strategists), Commercial, and Product. You are the connective tissue that ensures every account is staffed correctly, delivered on, and continuously improving. You will own the playbooks, the staffing model, and the feedback loops that turn deployments from a series of one-off engagements into a repeatable, scalable engine—whether that means building a new onboarding runbook, reallocating FDEs across accounts mid-quarter, or structuring how commercial scopes the next deal.

Requirements

3+ years of experience in a delivery, operations, or deployment-heavy role (e.g., Deployment Operations, Professional Services Operations, Solutions Engineering, Technical Program Management, or Forward Deployed Engineering).
Strong operational aptitude—able to design and run repeatable processes across a distributed team.
Experience working in a multi-stakeholder environment, specifically interfacing between field/delivery teams and Commercial.
Ability to balance "big picture" strategic work (playbooks, staffing models, commercial partnership) with "in the weeds" execution (unblocking a stuck account, running a feedback session, fixing a scoping doc).

Responsibilities

Playbooks & Delivery Standards: Build and maintain the playbooks that define how HappyRobot deploys. You will codify what good looks like at every stage—scoping, kickoff, integration, go-live, expansion—so that every FDE and DS has a clear, proven path to follow instead of reinventing the wheel on each account.
Staffing & Capacity Planning: Own the staffing model for the deployment team. You will match the right FDEs and DSs to the right accounts based on customer complexity, technical fit, and team capacity, and you will continuously rebalance as priorities shift. You are the person who knows, at any given moment, who is on what and why.
Delivery Assurance: Ensure every account lands. You will track delivery health across the portfolio, surface risks before they become fires, and drive the interventions needed to keep accounts on track—whether that's pulling in extra engineering support, re-scoping a workstream, or escalating to leadership.
Field Feedback Loop: Gather structured feedback from FDEs and Deployment Strategists on what's working and what isn't—across tooling, process, product gaps, and customer patterns. You will turn raw field signal into concrete improvements to how we deploy, and make sure the lessons from one account compound into the next.
Commercial Partnership: Sync closely with the commercial team to sharpen scoping and value-finding on new deals. You will make sure commercial understands what deployments can realistically deliver, help shape how we frame value to customers, and ensure deals are set up for successful delivery from day one.