Gliffy Project



What we delivered
  • A visual communication tool for digital product teams that closes the gap between project design and development by putting visual documentation at the center of the development workflow
  • February 2018-November 2018
  • 1.5x Product Design (1 dedicated, 1 support)
  • ~5x Engineering
  • 1x Product Management

My Role

As Director of User Experience, I:

Design Strategy

Successful design strategy happens with healthy consideration of form and function, business goals, and user needs

Gliffy was looking to grow its core business by adding a new product that complements our existing diagramming tool and increases its value to existing customers, while opening us up to capture new customers.


We set out to create a new Gliffy product that achieves these business goals:

Gliffy's existing core product tended to be used infrequently, and by few people within a product team. How might we create a new product that is complementary, adds value for existing users, and increases our overall product adoption and usage in teams?

Research & Problem Discovery

Through existing customer, non-customer, and competitive research, we identified the following three pain points that development teams were consistently faced with:

  1. Scattered communication and project documentation
    Team communication is scattered across email, IM chats, meetings, wikis, and task management software.
    • It’s difficult to keep track of current status, what’s done, what needs to be done, etc.
  2. Ticketing systems are text-based, while people and products are inherently visual
    It’s time-consuming to understand how written tickets relate to visual designs, user flows, software and information architectures, and complex systems.
    • Details get lost in translation, leading to incomplete and inaccurate product experiences, wasted work, increased cost, and frustrated teams.
  3. Complex projects need a single source of truth
    There is often not a single, up-to-date destination for teams to see the current state of their projects, what needs to get done and why, and the long-term vision
    • Development teams are often guessing what’s needed due to unclear or hidden product requirements, slowing progress and limiting their ability to execute
Understand pain points by viewing problems from different angles
Uncover unexpected opportunities by mapping the problem space
Simply talking to customers isn’t always enough — our team shared interview-processing and note-taking, leading to better pattern identification and meaningful insights shared across members

Design Pillars

With a clearly defined set of user personas and high-value problem to solve, our team started to explore possible solutions.

We established a set of design pillars — constraints for the team to get creative within, while ensuring we stayed focused on our users' needs and our business goals:‍

Exploration And Validation

We began to dig in and think about how a new product might relieve some of the pain that product development teams feel around cross-functional communication, scattered documentation, and complex, text-based task management tools.

This meant lots of ideating, whiteboarding, sketching — and killing — ideas, working to deeply understand other products both inside and outside of our space, and building prototypes to test and understand where we’re on track and where we’re not.

Some pieces came easy, while others took countless rounds of exploration, iteration, and testing to get right.

Early ideation — going wide to explore lots of potential directions quickly and cheaply
Zeroing in on where the most potential may lie
Sharing and learning from other products in and outside of our market
Our idea evaluation wall — broad view of possible directions and tradeoffs

It was important to understand the benefits and deficiencies of potential directions with low cost to the team — the goal was speed and ROI

We spent as little effort as possible to make design ideas clear and tangible through rapid prototyping and visualization, and then evaluated strengths, weaknesses, and tradeoffs through strong feedback loops with customers and stakeholders.

Constant feedback loops highlight where our ideas fall short and where potential lies

The common design cycle of Build > Test > Iterate allowed us to evaluate lots of different directions relatively quickly, and weigh their pros and cons with both our internal team and external testers. Every conversation helped inform what made sense for users and what didn’t, and where the product’s real value lay for teams.

Low-fidelity prototypes helped validate product value and inform early, foundational design decisions like information architecture.

What We Delivered

As a small team creating a complex product from scratch, we optimized for efficiency and repeatability from the start, to build and maintain momentum. It was important that we clearly articulate and document interactions, components, and design patterns with as little communication overhead as we could get away with.

In order to be both successful efficient in pixel-perfect UI and interaction design implementation, we embraced:

Sketch symbols formed our design component library

Our team used Gliffy Project to build Gliffy Project. It helped us clearly communicate big picture vision alongside granular tasks, leading to more efficient development cycles, less wasted time and effort re-working things by getting it right the first time, and a happier development team.

Gliffy Project 'canvas' view — visual artifacts like diagrams, flowcharts, and designs come together with Jira issues for clear team communication
Gliffy Project 'project overview' view — a single source of truth hub for all visual artifacts, Jira boards, and external docs for a project
Gliffy Project canvas view — a wireframe artifact with Jira issues mapped on top


Post-launch, we saw multiple product values prove out as we grew our customer base:

Thanks for looking!