Head of AI Ops

At Charlie Oscar, we’re not your typical digital marketing agency. We’re a team of big thinkers, bold doers, and collaborative problem-solvers working with some of the world’s most ambitious brands to help them outsmart, outpace, and outgrow the competition. We already blend data science and creativity to make smarter decisions and create work that genuinely moves the needle. The numbers give us clarity, but it’s our creativity that wins hearts, builds brands, and drives real growth.

Over the past few years, we’ve been building something a bit different: a modern, high-performance marketing consultancy that’s as serious about how we operate as it is about the work we produce. We move fast, we experiment, we improve, and we raise the bar — continuously. Life at Charlie Oscar is fast-paced, ambitious, and full of momentum. You’ll work alongside some of the sharpest minds in the industry, solving meaningful problems, delivering work you’re proud of, and seeing the impact you make for global brands.

And we know it’s not all about work. We make time for fun too — whether it’s weekly run club, book and chess clubs, charity fundraisers, Thursday drinks, or epic team socials, there’s always something going on and plenty of great people to do it with. Most importantly, we hire for attitude and culture add, not just experience. We look for curious, ambitious people who challenge the status quo, raise standards, and want to help shape what the next generation of marketing looks like.

THE ROLE

Charlie Oscar is already building Agency 2.0 — a new kind of marketing services business that blends strategic consultancy, custom AI agents, and agency delivery into a future-proof operating model. We’re well into our journey towards an AI-first operating system for the business. We focus on two core streams — intelligence and automation — and we call this Charlie Oscar OS. This is a CEO-backed, business-critical initiative that’s already in motion, and this role is about taking it to the next level.

We’re not experimenting with AI at the edges. We’re actively embedding it into how the company runs — and now we’re looking for a senior operator to bring structure, scale, and consistency to that evolution. We’re hiring a Head of AI Operations to own, formalise, and accelerate our AI-first operating model. You’ll build on the foundations already in place and take them further — rewiring how work gets done across strategy, delivery, analytics, and operations using AI (LLMs, agents, and automation). You’ll define and refine how knowledge is captured, how data flows, how workflows run, and how AI becomes the default way of working at Charlie Oscar. You will be the internal authority on “how Charlie Oscar works.”

WHAT YOU’LL BE GETTING STUCK INTO (aka Responsibilities)

• Evolving and scaling our AI-enabled operating model across the business
• Owning and maturing our enterprise LLM setup (e.g. ChatGPT Enterprise, Gemini): governance, configuration, usage standards
• Formalising how data, documents, decisions, and knowledge are stored and accessed
• Driving consistent behaviour change across teams around tools, workflows, and ways of working
• Defining, deploying, and improving AI agents to support delivery, insights, reporting, and operations
• Working with third-party engineers and vendors to build and ship new agents and capabilities (you don’t need to code)
• Leading adoption, training, and enforcement of new operating standards
• Acting as the internal operator-in-chief for how the business runs day to day

This is a hands-on transformation and scale-up role. You’ll be building, shipping, embedding, and improving — not just creating roadmaps.

WHAT WE’RE LOOKING FOR

• 10+ years’ experience in digital, marketing, media, consulting, or agency environments
• Proven experience leading operational change across multi-disciplinary teams (strategy, media, creative, data, ops, etc.)
• A track record of taking new ways of working from “promising” to “how we do things here”
• Hands-on experience standardising and scaling workflows, processes, and delivery models
• Experience owning or significantly shaping internal operating models, playbooks, or delivery frameworks
• Strong understanding of how modern agencies actually run: resourcing, delivery, margin, velocity, quality, and client outcomes
• Experience working with data flows across platforms like Meta, Google, TikTok, CRM, analytics, and attribution tools
• Comfort bringing structure, consistency, and automation to evolving or imperfect systems
• Experience partnering with senior leadership and founders/CEOs on business-critical change
• Proven ability to drive adoption of new tools, systems, and behaviours across teams (including training and enforcement)
• Confidence operating as the clear owner of “how work gets done” internally
• Experience working with external vendors, engineers, or platforms to ship operational tooling and systems
• Strong judgment on what to automate, what to standardise, and what should stay flexible
• Commercial awareness: understands how operational efficiency, quality, and speed translate into better margins and client outcomes

AI Experience (Non-Negotiable)

• You must: Be an advanced, daily user of multiple LLMs
• Have built or designed AI workflows, prompts, or agents
• Understand LLM strengths, limitations, and failure modes
• Be comfortable owning an enterprise LLM setup (even if you’re not technical)

You might also have experience in:

• Scaling an agency, consultancy, or hybrid services business
• Rolling out company-wide tools or platforms (e.g. knowledge systems, workflow tools, data platforms, AI tools)
• Leading ops, transformation, delivery excellence, or internal systems functions
• Cleaning up messy processes, fragmented tools, and inconsistent ways of working

WHAT MAKES US US - OUR VALUES

At Charlie Oscar, our values aren’t just posters on the wall – they show up in how we work, how we treat each other, and how we build something brilliant together.

• Make It Happen: Momentum matters, progress beats perfection every time.
• Treat It Like Your Own: Think like an owner. Care for every detail as if it were your money, your brand, your business.
• Grow Together: Build the business, lift your team, and invest in your own growth along the way.
• Be Brave: We create space for bold thinking, confident decisions, and the freedom to back yourself.