Senior Program Manager/Director of Generative AI Operations

ABOUT HUGO

Hugo Technologies, Inc. (“Hugo”)  is committed to nurturing the best of Africa’s young talent. We build and manage remote teams across Africa for some of the world’s largest technology and media companies. We specialize in omnichannel customer support, digital and AI operations, and trust and safety solutions.

Our “Why?” is simple. Outsourcing generates billions in income and opportunities globally, but less than 2% reaches African communities. We’re changing that. By winning a share of the multi-billion-dollar global BPO market for Africa, we are investing in a brighter future for the continent.

As a company, we’re obsessed with excellence. We ask smart questions to build a thorough understanding of our client's needs; then pour ourselves into delivering not just great work, but also a perfect user experience so that we stand out in what is a very crowded market.

The only commitment greater than the one we have to our clients is the one we have to our community. We are dedicated to carving out a place in the digital economy for young Africans, and we work tirelessly to equip them with the skills needed to build meaningful careers.

WHAT YOU’LL BE DOING 

The Director of Generative AI Operations, based remotely with West Africa and US time zone coverage, leads the end-to-end delivery, scaling, and evolution of Hugo’s Generative AI and data annotation services for global enterprise clients. The role reports to the VP of Global Generative AI Operations and owns operational excellence across complex AI workflows, client-facing delivery strategy, workforce systems, quality frameworks, and pilot-to-scale execution.

The role sits at the intersection of AI product understanding, distributed workforce orchestration, and enterprise client partnership. The mandate centers on building and scaling operating models for hyper-agile AI delivery, where requirements evolve quickly, and solutions are developed rapidly alongside execution, while protecting quality, speed, client trust, and team wellbeing as demand changes.

Key Responsibilities

Generative AI Delivery Leadership

• Own delivery across multiple GenAI and advanced ML workflows, including pilots, scaled programs, and experimental work
• Lead AI Ops programs that leverage distributed, crowd-based, or hybrid workforce models
• Translate client objectives into executable operating models, staffing strategies, and metrics
• Ensure consistent delivery outcomes across quality, AHT, throughput, and SLA adherence
• Partner with Quality and Training teams to embed Day-1 excellence and continuous improvement

Pilot Design and Scale-Up Strategy

• Lead Hugo’s pilots' operating model, including intake, scoping, staffing, execution, and ROI
• Design fast, low-risk pilots that validate quality, rater profiles, tooling fit, and workflow complexity
• Operate comfortably in hyper-agile environments where guidelines, evaluation criteria, and tooling evolve in parallel with delivery
• Identify repeatable patterns that convert pilots into long-term revenue-generating programs
• Maintain visibility into headcount deployment, cost efficiency, and capability progression

Workforce and Capability Strategy

• Design and operate flexible AI workforce models spanning on-payroll teams, crowd contributors, and specialized talent pools
• Oversee certification pathways, performance calibration, and specialization tracks
• Partner with training and quality teams to evolve skill standards as AI task complexity increases
• Balance utilization, growth, and contributor wellbeing across a fast-changing demand environment

Client Partnership and Value Creation

• Act as a senior delivery and ops counterpart to client PjMs, product leaders, and research teams
• Lead structured client conversations on delivery performance, system design tradeoffs, and roadmap planning
• Proactively surface insights on workflow optimization, capability expansion, and operational levers
• Support commercial discussions by grounding proposals in delivery feasibility, speed, and data

Metrics, Systems, and Operational Rigor

• Define and own performance dashboards across quality, efficiency, workforce health, and finances
• Build operational systems and feedback loops that scale beyond individual programs or clients
• Establish SOPs, escalation paths, and governance frameworks suited to fast-moving AI work
• Drive post-mortems, root-cause analyses, and continuous improvement cycles

Leadership and Org Development

• Lead and develop senior portfolio managers, project managers, and cross-functional partners
• Shape org design and capability investments as Hugo scales its AI operations footprint
• Serve as a culture carrier for execution excellence, clarity, and accountability
• Mentor emerging leaders and build succession pathways across the delivery organization

If you are excited about delivering the following outcomes, then this role is for you

1. High-quality, scalable GenAI delivery across pilots and mature programs
2. Faster and more confident conversion from experimental work to sustained client engagements
3. Clear operating models for crowd-based and distributed AI delivery
4. Improved unit economics without compromising quality or workforce health
5. Strong client confidence in Hugo’s ability to handle complex, evolving AI work

WHAT QUALIFICATIONS YOU’LL NEED

Leadership Traits

• High ownership with a strong bias toward execution
• Comfort operating in ambiguity and rapid change
• Systems thinker who balances speed with rigor
• Calm, credible presence in high-stakes, diverse client conversations
• Strong people leader with a focus on growth, sustainability, and accountability

Required Experience and Skills

• 8–12+ years in operations, program leadership, or delivery roles, with progressive responsibility leading AI, ML, or data-intensive programs in recent years
• Significant experience running AI development or AI operations programs that leverage crowd, freelance, or distributed workforce models
• Demonstrated success operating in hyper-agile environments with evolving requirements
• Experience leading distributed, multicultural teams
• Proven ability to translate ambiguity into scalable delivery systems
• Strong analytical orientation with comfort using metrics to guide decisions
• Executive-level communication and client-facing judgment

Strongly Preferred

• Delivery leadership experience (PM level or higher) at crowd-focused AI or distributed delivery companies, such as Mercor, Invisible, Turing, Snorkel, Scale AI, Surge, or other similar crowd-based AI delivery organizations
• Familiarity with ML annotation, RLHF-style workflows, or human-in-the-loop AI systems

WHAT WE PROVIDE

Hugo offers a hybrid work environment that balances employee flexibility with a collegial, fun office culture. We pride ourselves on offering a dynamic environment where ambitious professionals can make a measurable impact and accelerate their careers. Our compensation and benefits are highly competitive.

PRIVACY STATEMENT

Any information you submit to Hugo as part of your application will be processed in accordance with Hugo’s Privacy Policy.

EQUAL OPPORTUNITY STATEMENT

Diversity, equity and inclusion are part of our DNA. Promoting and, where possible, improving diversity, equity and inclusion are a value-based and commercial necessity. We are an equal opportunity employer and welcome applications from all qualified individuals, regardless of race, sex, gender identity, sexual orientation, neurodiversity,  disability, or any other legally protected status