monospace.studio
CloudBees navigation refresh — before and after

Case 01 · CloudBees · 2022 — ongoing

Building a UX function inside a pre-IPO DevOps enterprise

I joined CloudBees as a designer and grew the design organisation from 3 to 9, while leading a redesign customers called a “quantum leap” and shipping the company’s first AI dashboard.

Role

Head of Design (inherited)

Team

3 → 9 designers

Scope

Platform UX · Design System (HoneyUI) · AI/agentic prototypes

Status

ongoing

Context

CloudBees is a pre-IPO DevOps enterprise platform with strong technical capabilities, but the experience reflected its organisational and product complexity: fragmented navigation, inconsistent UI patterns across products, complex onboarding, divergent mental models between teams, and UX entering too late in the lifecycle. The product was respected; the platform felt fragmented. Customers were carrying the cognitive load.

I joined at the point where those fractures were becoming a growth problem. The company needed more than cleaner screens. It needed a UX function that could connect research, product strategy, design systems, hiring, and delivery into one operating model.

Role & team

I joined as a senior IC and design lead, then inherited the Head of Design responsibilities and took over management of the design team. The team grew 3 → 9 designers under that leadership, spanning product UX, design systems, and later AI/agent prototyping. I reported into the VP of Design and partnered with the CPO, PM organisation, engineering, and research/data stakeholders.

What I led

I repositioned UX as a unifying layer of the platform rather than a screen-by-screen craft function. Three moves carried the work:
  • As IC: I led a core-product redesign through research, framing, and delivery. Customers called the result a quantum leap; the migrated pages reached 100% adoption through a version-switching mechanism in roughly six months.
  • As lead: I built and ran BeeBot, an AI Chatbot Dashboard prototype at the 2022/23 hackathon. It became the company's first agentic UI bet and later fed roadmap conversations about AI dashboards and assistant-led workflows.
  • As Head of Design: I hired the team from 3 to 9, established hiring priorities and team rhythms, and moved UX upstream through navigation, IA, ResearchOps, HoneyUI, onboarding, and workflow programmes.

Process — three acts

Act I — Audit and reframe

I started with an inventory of products, surfaces, navigation, IA, design-system adoption, and the points where UX was entering too late. The output was a one-page narrative that re-pitched CloudBees as one platform with five product lines rather than five products that share a login.

That reframing mattered because it gave product teams a shared north star. Navigation was no longer a local menu problem. Onboarding was no longer an isolated first-run flow. HoneyUI was no longer a kit on the side. They became parts of the same platform story.

Act II — Initiative chain

I then linked the work into five tracks: navigation and IA, onboarding and activation, HoneyUI adoption, workflow simplification, and platform-thinking initiatives such as object models and reusable interaction patterns. Each track had a designer-owner, a PM partner, and a rolling weekly review.

HoneyUI — the design system the platform runs on

HoneyUI is CloudBees' production design system. I drove it from a documentation kit into the connective tissue of the platform: a token architecture shared with the Wax wireframing layer, a typographic system with modular scaling, a theming model with dynamic colour, and a layout system designers and engineers consume identically.

Token architecture — Wax and HoneyUI sharing a single token spine
Wax typography — the typographic system applied across components
Modular scaling — type and spacing on a single mathematical scale
Theming — how the same components carry product-line identity
Dynamic colour — semantic ramps generated from a small palette
Wax layout — the grid and density rules the wireframing layer enforces
HoneyUI specs — component documentation as the source of truth
HoneyUI roadmap — the system as a programme, not a deliverable
DS socialising resources — making adoption a team sport
Honey and kits in use — what the system looks like at the product surface

ResearchOps — the rails under the research practice

In parallel, I built the operating rails around the design work. I documented a double-diamond process in Confluence and Jira, set up ResearchOps guardrails, helped establish a shared research repo in Dovetail with a tagging taxonomy, and socialised the model with design and product. That research infrastructure later expanded from design into the broader product organisation.

Double-diamond model — the research process documented in Confluence
Research epic template — every study tracked the same way in Jira
Jira template for research-ops — making the workflow defensible
ResearchOps Confluence nav — the central hub for the practice
Tagging taxonomy — the shared schema for insights across studies
Dovetail interview library — where the qualitative record lives
Kicking off research-ops — the rollout deck for design and product
Research-ops roadmap — the multi-quarter view

Act III — Org build + agentic horizon

The final layer was organisation design: hiring loops, 1:1 cadence, design-review rhythm, team bonding, and clearer ownership across product UX, systems, and emerging AI work. HoneyUI evolved from component documentation into a platform consistency mechanism, with token architecture, theming, UI kits, guidelines, and socialisation material for designers, engineers, and product.

In parallel, I prototyped agentic onboarding IA: moving the platform from "set this up yourself" to "tell the platform what you want and it composes the IA."

Initiative evidence

Five prototype tracks belong inside the CloudBees story rather than as separate Ideas entries. Each one is a concrete answer to a platform question — agentic UI, intent-led onboarding, the next system, workflow density, and SDLC navigation.

2022/23 · Prototype

BeeBot

An AI chatbot dashboard prototype from the CloudBees hackathon, used to explore agentic UI inside enterprise DevOps workflows.

BeeBot chatbot dashboard demo from the CloudBees hackathon.

2023 · Concept

Agentic onboarding IA

A direction for moving onboarding from manual setup flows toward intent-led IA composition.

Agentic onboarding prototype demo from the CloudBees Demos archive.

2024 · Proposal

Wax component library proposal

A revamped component-library proposal for evolving CloudBees' design system beyond Honey and CBUI.

Wax component library index concept.

Wax index concept.

2025 · Prototype

Plugin Manager

A focused workflow prototype for making plugin management easier to inspect, compare, and act on.

Plugin Manager workflow prototype.

2025 · Prototype

SDLC core sketches

A recent set of CloudBees platform sketches exploring navigation, code connections, command surfaces, and SDLC workflow structure.

CodeConnect prototype excerpt from SDLC Core Sketches.

Outcome

  • Organisation: grew design from 3 → 9 designers, established management rhythm, and helped hiring priorities become an explicit design-leadership concern.
  • Product: shipped the core redesign in roughly six months, with customer feedback calling it a quantum leap and 100% adoption on migrated pages via version-switching.
  • System: advanced HoneyUI through token architecture, theming, documentation, UI kits, design guidelines, and socialisation across design, engineering, and product.
  • Research: installed ResearchOps rails, including double-diamond guidance, Jira/Confluence templates, and a shared research repo that expanded into product.
  • AI: shipped the first AI Chatbot Dashboard prototype, BeeBot, and used later agentic onboarding IA prototypes to explore assistant-led platform setup.

What I'd do differently

I would have started the agentic prototypes a quarter sooner and brought PMs into that conversation earlier. The prototypes were useful because they made an abstract platform shift feel concrete, but they also exposed organisation-design questions: who owns assistant-led setup, how does AI reshape onboarding, and what needs to change in the roadmap for teams to act on it. I would now make that discussion part of the platform programme from day one.

Derry is so great at seeing the bigger picture of the things we work on, he's not afraid to ask tough questions and wants to understand the user, he's driven and doesn't wait to be told what to do before starting to make a big impact. I really appreciate him keeping us all honest. He's exactly the kind of designer you hope to manage.

A. Rucker · Design Director, CloudBees

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