Head of Delivery and Strategy (Director Level)

HumanSignal•Austin, TX

63d•$160,000 - $220,000

About The Position

The future of AI — whether in training or evaluation, classical ML or agentic workflows — starts with high-quality data. At HumanSignal, we’re building the platform that powers the creation, curation, and evaluation of that data. From fine-tuning foundation models to validating agent behaviors in production, our tools are used by leading AI teams to ensure models are grounded in real-world signal, not noise. Our open-source product, Label Studio, has become the de facto standard for labeling and evaluating data across modalities — from text and images to time series and agents-in-environments. With over 250,000 users and hundreds of millions of labeled samples, it’s the most widely adopted OSS solution for teams working on building AI systems. Label Studio Enterprise builds on that traction with the security, collaboration, and scalability features needed to support mission-critical AI pipelines — powering everything from model training datasets to eval test sets to continuous feedback loops.We started before foundation models were mainstream, and we’re doubling down now that AI is eating the world. If you're excited to help leading AI teams build smarter, more accurate systems — we’d love to talk. Director of Operations, Delivery, and Strategy HumanSignal is building the future of AI through the world's first dedicated data creation labs—purpose-built facilities where expert annotators, domain specialists, and AI trainers collaborate to create the highest-quality training data in the industry. We're hiring a Director of Operations, Delivery, and Strategy to own the complete picture: customer relationships, revenue growth, delivery excellence, and operational execution across all of our service offerings. This role encompasses everything. You'll lead customer engagements from first conversation to long-term partnership. You'll build and scale our data creation labs. You'll own delivery operations for all our customer offerings—whether that's onsite lab work, distributed annotation programs, or custom data solutions. And you'll shape the strategy that drives our growth. This is a rare opportunity to build something transformative from the ground up. You'll work directly with customers to understand their needs, design and execute delivery workflows, build world-class teams, and drive the business forward. If you're an operator who thrives on ownership, moves seamlessly between strategy and execution, and wants to build the infrastructure that powers the next generation of AI, we want to hear from you.

Requirements

10+ years of experience in operations, delivery, strategy, or customer-facing roles, ideally in data services, AI/ML, professional services, or tech-enabled businesses
Proven track record leading cross-functional teams and owning business outcomes (revenue, P&L, or customer success)
Experience building and scaling operations—whether physical facilities, service delivery teams, or distributed workforces
Deep customer focus with a history of managing complex, high-touch relationships and driving expansion
Strong operational rigor: you know how to build systems, measure what matters, and drive continuous improvement
Ability to move fluidly between strategy and execution—you're equally comfortable shaping long-term vision and solving day-to-day operational challenges
Data-driven mindset with comfort using analytics tools; SQL or Python experience is a strong plus
Exceptional problem-solving skills and the ability to thrive in ambiguity
Track record of delivering exceptional results under pressure

Nice To Haves

Experience in data annotation, AI training data, or machine learning operations
Background in professional services, consulting, or customer success at scale
Familiarity with workforce management, quality frameworks, or process optimization
International operations experience, particularly managing distributed teams or offshore delivery
Experience launching new products, service lines, or business units

Responsibilities

Own end-to-end customer relationships: from initial engagement and scoping, to delivery execution, to expansion and long-term partnership growth
Build and scale our data creation labs—defining operations, workflows, and the systems that enable world-class data delivery
Lead delivery operations across all HumanSignal customer offerings, including onsite labs, distributed annotation programs, and custom data solutions
Drive revenue and growth by identifying opportunities, shaping our go-to-market strategy, and ensuring exceptional customer outcomes
Build and manage cross-functional teams including lab operations leads, project managers, annotators, domain experts, and distributed contributor networks
Design and operationalize high-throughput, high-quality workflows that balance speed, accuracy, and cost across diverse data types and customer requirements
Partner closely with Product, Engineering, and Sales to ensure our offerings are tightly aligned with customer needs and market opportunities
Define and own key metrics across the business: customer satisfaction, delivery quality, throughput, revenue per engagement, and operational efficiency
Solve complex operational and strategic challenges—from workforce scaling to international expansion to new service line development
Operate with urgency and clarity in a fast-moving environment, driving execution while building scalable systems for the long term