Product Work
Enterprise product design at scale — from Bitbucket's 3M-user growth arc to ServiceNow's ITSM implementation hub and AI adoption tooling. The common thread: making complex systems navigable for people who have real work to do.
Staff Content Designer · ServiceNow
I build the layer between humans and complex systems — the language, structure, and logic that lets people actually navigate what they're trying to do. Over a decade across enterprise, SaaS, AI, and agentic product design.
Enterprise product design at scale — from Bitbucket's 3M-user growth arc to ServiceNow's ITSM implementation hub and AI adoption tooling. The common thread: making complex systems navigable for people who have real work to do.
Multi-persona conversational flows, AI reasoning layer architecture, and enterprise virtual agent design. This is the work Dan does at the edge of what LLM-native product design looks like in practice.
Content models, taxonomy architecture, information hierarchies, and the structural thinking that makes everything else hold together. The invisible work that makes products scalable.
From building Information Experience at Atlassian from a small team of technical writers into one of the most respected Content Design groups in the world, to shaping how ServiceNow measures and advocates for the discipline.
Work
I've helped people reach the outcomes they were trying to get to for over two decades, with measurable impact for both the company and the customer. Four case studies, 2013 to now — the same practice at very different scales.
How to read these — every case study answers the same three questions
What did people need in order to navigate this?
Not what they asked for and not what the spec described. What a person actually has to have in front of them to move through the system and reach a real outcome.
How was the information layered to meet it?
Progressive disclosure as a first principle rather than a UI pattern — the right information, to the right person, at the right moment, in the right form.
What system was left behind?
The framework, model, or process that let the next designer, PM, or engineer do the right thing without having to work it out from scratch.
Multi-persona conversation design for ServiceNow's AI assistant hub — including the three-way handoff flow that solved the Admin–Process Owner failure point at the center of enterprise AI adoption.
A taxonomy program across seven business verticals, and an AI vocabulary taught through narrative — including a fourth-wall break that names the taxonomy's own known inconsistency out loud.
Enterprise IT setup reimagined as modular worksheets with explicit role delegation. Progressive disclosure at the system level — meeting people where they are and handing off gracefully to the right person.
The people who needed Bitbucket hadn't learned Git yet — so the path into the product had to teach them on the way in. A single layered information experience spanning marketing, product, engineering, and design, and the frameworks that outlived it.
One assistant. Three radically different users. A handoff that was breaking everything.
Now Assist Center is ServiceNow's AI assistant hub for enterprise IT workflows. The surface is a single chat interface — but the people using it couldn't be more different. System admins are configuring AI skills and need to know exactly what's irreversible before they act. Platform owners are thinking about ROI and portfolio decisions and don't want step-by-step instructions. Process owners define what the AI should do, but have no idea how to make it happen technically.
The research was clear: the handoff between admins and process owners was where AI adoption was failing. Not because of the technology — because nobody had designed for the conversation that had to happen between the two humans before the technology could work.
Three constraints shaped everything that followed. Activating an AI skill in a 50,000-seat enterprise is not easily undone, so confirmation and rollback had to be structural rather than optional. The three audiences share almost no vocabulary — admins speak in tables, platform owners in outcomes, process owners in workflows — so the system had to route each person into the right language before confusion set in, without their noticing they'd been routed. And some configurations genuinely require a decision from two different people who are never in the same tool at the same time.
"The escalation path and L1 scope need to match how your support center actually runs. That's usually a decision for your ITSM process owner — not just the admin."
I built a full conversation design framework anchored in three distinct user profiles, each with their own language, trust signals, and blockers. The framework includes turn-by-turn conversation scripts with an explicit AI reasoning layer — visible in the design document, never surfaced to users. Engineers and PMs could understand what the AI was doing without it leaking into the experience.
The centerpiece of the work is a three-way conversation flow — a single chat thread where the AI assistant (named Otto) facilitates a structured handoff between an admin, the AI, and a process owner who is invited into the thread mid-conversation. Otto re-orients the process owner on join, makes the three decision points explicit, and clarifies role boundaries. Neither user hits a dead end.
I also designed a tone model that evolves with the relationship — different conversational behavior in sessions 1–4, 5–20, and 21+. The AI watches for signals at each stage and adjusts: reducing confirmation friction as trust builds, becoming proactive once patterns are established.
The handoff was an organizational problem. I made it a design problem — which is what made it ownable.
The usual answer
The admin configures what they can, sends an email, and waits. The process owner responds eventually, or doesn't. The configuration stalls, adoption stalls, and the gap between the two roles belongs to nobody.
What I designed instead
Otto surfaces the dependency the moment it appears, offers to bring the process owner into the same thread, briefs them on arrival, holds the three-way alignment on scope and escalation, and shows all three parties the agreed configuration before anything activates.
What makes this work distinctive
Worked with
Artifacts
Available on requestLineage
Getting the right people into one conversation at the moment the decision is actually made is a problem I first solved with no AI in it at all — global, multi-craft design review at Atlassian, written up as Spar from afar. Same problem, different medium.
Naming things at enterprise scale — and teaching the vocabulary through story, including the part of it that was broken.
ServiceNow's AI landscape is genuinely complex: Agents, Virtual Assistants, Skills, Tools, Capabilities, and traditional ML functions are distinct concepts that interact in intricate ways — and the terminology was still evolving. "Skill" and "tool" were used interchangeably even inside the product. The people who needed to understand this — admins, implementors, platform owners, technical partners — were enterprise IT professionals making real decisions, not AI researchers.
The vocabulary problem sat inside a larger one. A taxonomy at this scale has to satisfy multiple enterprise customers with genuinely different internal languages while staying flexible enough to work on the general platform — and there was no accepted method for testing whether a taxonomy that abstract was actually working for anyone.
"Narrative design as part of human design is essential. People will almost always understand things if they can place them in the context of a story."
The structural work came first. With lead researchers I co-led a research program evaluating taxonomy needs across seven business verticals, and built new methods for testing and iterating taxonomy systems that had to hold up against multiple enterprise customers at once. The findings were presented directly to top-tier customers — organizations with 10,000 users and above.
For the AI vocabulary specifically, I mapped the taxonomy visually — overlapping circles showing Agents, Virtual Assistants, Skills, Tools, and traditional ML functions. The overlaps aren't bugs. They're the honest truth about how these components blur at the edges, and the diagram earns the complexity rather than papering over it.
Then I wrote a character-based interactive story — each character is a concept. Alie the AI hosts. Agent explains itself. Sally Skill introduces Carl Capability. Tiffiny Tool is Sally's sibling. And when the script reaches the point where "skill" and "tool" are sometimes used interchangeably in the product, a Narrator breaks the fourth wall and says so directly: "Sometimes we directly refer to each other as the other. It's a bit embarrassing, really." I wrote the narrative architecture and prompted an AI to build the interactive site — SVG characters, branding, frame-by-frame navigation.
Most terminology work hides the inconsistency. I built it into the lesson.
The usual answer
Pick one term, declare it correct, and publish documentation that quietly contradicts the product. The reader hits the contradiction alone, decides the material is unreliable, and stops trusting the rest of it.
What I designed instead
The Narrator names the seam out loud, explains it in context, and moves on. The reader learns the taxonomy and its known limitation at the same time — and the honesty is what makes the rest of it credible.
What makes this work distinctive
Worked with
Artifacts
Available on requestLineage
Deciding what a term means and where it sits is where this career started — XML schemas in DITA at IBM, then taxonomy systems built alongside information architecture at Atlassian and Tara. The vocabulary being organized changed. The work didn't.
When setup is too complex for any one person, the design problem is actually about delegation.
Service Operations Workspace is ServiceNow's product for IT operations teams — managing on-call rotations, services, integrations, and incident response. Implementation is genuinely complex: organizations arrive with different team sizes, service counts, integration profiles, and geographic footprints. A single linear setup flow would either overwhelm one person or fail to account for the fact that no single person usually owns all of it.
The standard approach — put everything in a long setup guide — would have transferred the complexity from the product to the user. I wanted to design the implementation as an information experience that met people where they were and handed off gracefully to the right person at the right moment.
"Product Content writes docs. Content Design designs information experiences as part of the overall design of the product."
I designed a system of modular worksheets — discrete, assignable information chunks with explicit role gating. The People & Permissions worksheet is platform-admin only by design. The Platform worksheet handles team, user, and geographic configuration. The SOW worksheet handles on-call teams, services, and integrations — the technical setup that often belongs to a different person than the one who started the process.
The worksheets function as structured data-collection tools that guide admins through complex decisions before they touch the product. The output isn't just configuration data — it's an implementation estimate: hours required, tasks flagged as custom, integrations categorized by complexity. The user knows what they're walking into before they begin.
The in-app guidance follows a layered model: immediate in-context → expandable in-panel → comprehensive in hub docs. Content meets users at their point of need without burying them in documentation they didn't ask for.
The setup wasn't too long. It was assigned to the wrong number of people.
The usual answer
One linear setup guide with one owner. Everything the platform admin doesn't personally know becomes a blocker, and the decisions that belong to someone else get guessed at — then corrected in production.
What I designed instead
Discrete worksheets, each gated to the role that actually holds the answer and each independently assignable. The estimate comes out before configuration begins, so the organization can see the scope it is committing to.
What makes this work distinctive
Worked with
Artifacts
Available on requestLineage
The three-layer guidance model — in-context, in-panel, in-hub — is a direct descendant of the layered path built for Bitbucket a decade earlier: microsite, tutorials, onboarding, UI. Same structure, different product. See case study 04.
The people who needed Bitbucket hadn't learned Git yet. So the path into the product had to teach them on the way in.
Bitbucket was competing for teams in the middle of adopting Git. For most of them, the obstacle in front of the product wasn't the product — it was the technology the product assumed they already understood. Someone evaluating Bitbucket often couldn't yet evaluate it, because the vocabulary of the thing hadn't landed.
The second problem was structural. The journey a person actually took, from first search to first repository, was owned in pieces by four different functions — marketing, product, engineering, and design. Every piece was competent. The path between them was nobody's job. And at the time, content had no accepted way to prove it had worked, which meant it was always the easiest thing to cut.
"I read the entire git scm manual twice to prepare for the interview."
I treated the whole path as a single information experience rather than four handoffs: a Git microsite and tutorial set that taught the technology itself, connected directly into product onboarding, connected into the UI copy — each layer assuming exactly what the previous layer had taught, and no more. It ran across design, engineering, marketing, and product as one system.
Alongside it I built the things that let other people do this without me. Atlassian's first content canvas — user need → business goal → content strategy → success signal — gave designers, PMs, and engineers a way to make content decisions in the room. And Write Measure Repeat, co-created with the team, applied growth-marketing instrumentation to content, so a piece of writing carried a success signal like any other product change.
The detail work mattered too: I did all the UX writing and documentation for Bitbucket's two-step verification — one of Atlassian's first 2FA implementations, where every sentence sits on a security boundary and a confused user is a locked-out user.
Tutorials weren't support material. They were the top of the funnel.
The usual answer
Teaching material sits downstream of acquisition — written for people who already signed up, measured as ticket deflection, and owned by a team that never sees the marketing narrative.
What I designed instead
The teaching material is the acquisition path. Someone learning Git on the microsite is already inside the product's information experience, and onboarding picks up precisely where the tutorial left them.
What makes this work distinctive
Worked with
Artifacts
Lineage
Almost everything above this on the page is a variation on what was built here. The layered guidance model in case study 03 is this funnel's direct descendant, and the habit of shipping a framework alongside the deliverable — in 01 and 02 — starts with the content canvas.