Docusign Comments

Docusign Comments

ROLE:

Product Designer (Lead)

YEAR:

2019–2023

Overview

One of Docusign's leading features as an agreement management and eSignature company is the ability to comment in-line on a document—a tool that's used more than 1.5 million times annually.

I founded Comments designs when it was released in 2019, and was its sole designer for 4 years. During that time, I also co-defined our experience strategy for the company's collaboration / negotiation services. Success required tight collaboration across both eSignature and CLM platforms, as well as managing multiple workflows with UX Research, Engineering, and Product teams.

The following is an overview of Comments' humble beginnings. Contact me for more details.

What I did

UX/UI
UX research
Experience strategy
Systems design
Flow mapping

Team

4x Product Managers
20+ Engineers

Results

  • Usage doubled within first year and continues to grow

  • 3x faster negotiation + time to signature

  • 1.5 million+ comments posted annually

Overview

One of Docusign's leading features as an agreement management and eSignature company is the ability to comment in-line on a document—a tool that's used more than 1.5 million times annually.

I founded Comments designs when it was released in 2019, and was its sole designer for 4 years. During that time, I also co-defined our experience strategy for the company's collaboration / negotiation services. Success required tight collaboration across both eSignature and CLM platforms, as well as managing multiple workflows with UX Research, Engineering, and Product teams.

The following is an overview of Comments' humble beginnings. Contact me for more details.

What I did

UX/UI
UX research
Experience strategy
Systems design
Flow mapping

Team

4x Product Managers
20+ Engineers

Results

  • Usage doubled within first year and continues to grow

  • 3x faster negotiation + time to signature

  • 1.5 million+ comments posted annually

the challenge.

Once upon a time, commenting was built “as-needed” in various areas within Docusign.

There were ~4 custom instances across the product, each built by a different team of engineers without any communication with each other or guidance on visual/ experiential consistency. This resulted in:

inconsistent UX and capabilities

❌ lack of central needs or use cases around commenting

❌ lack of internal telemetry tracking comments usage across Docusign

To boot, commenting wasn't being sold as an official feature—it was merely a supplementary tool that showed up in differing, half-baked forms in random parts of the product. This hurt our retention rates, as customers felt forced to seek other apps to redline or negotiate their documents.

process.

Setting a baseline

I was in the contract negotiation space prior to joining the team, so I already knew of the need for more effective, seamless, and accessible collaboration in the product. However, there was no urgency to fix our disjointed experiences as leadership was not aware of the baseline—and how much it was negatively impacting Docusign's usability.

To prove this, I partnered with a UX researcher to run an internal heuristic analysis study with the goal of identifying places in our product where the commenting UX performed (or didn't) and giving each a severity rating. We ended up with 53 usability issues—over 50% of them rated as critical / moderate urgency.

Double feature

Around when my product manager, lead engineers, and I were finalizing plans for our MVP and I started to work on designs, our Systems team was also in progress of a design system overhaul. Only parts of the product were adopting the new look right away, which meant I needed versions in both our legacy and emerging styles.

Given some constraints from eSignature stakeholders (eg. limited functionality, legacy UI, limited partnership), I had to maintain as much of the original composition as possible while improving accessibility, discoverability, and visual consistency. I ensured to also account for variations in components, such as what the comment author might see vs. its viewer.

As I made progress, I was validating concept efficacy, feasibility, and assessing for edge cases with my direct team like product manager and engineers. For maximum clarity and alignment w/ my eng partners, I spec'd components as they were getting finalized, which made dev time and QA a smoother, more efficient process.

the solution.

In-context commenting

Comments can be directly added onto text on a document. Being anchored to specific contexts allows for quicker processing and action.

In cases where a specific individual or team’s attention is required, users can directly mention them as a means of notification and/or assignment to their comment.

Relevant email notifications

As part of a push to bring in-product notifications to Docusign, I developed a complex logic set of email notifications alongside engineers and content designers. A unique email would be sent to the relevant user(s) based on the comment being posted.

Comment activity log

All comment threads (even resolved comments) on the given document can be viewed for easy tracking and auditing. This includes details like when or who it was resolved by, and which version of the document it lived in.

Results.

  • Usage of comments doubled within our first year and continues to grow per quarter (1st quarter saw 100k+ comments added to documents, 2nd 170k+, 3rd 205k+…)

  • Initial success allowed us to ship additional capability ie. Microsoft Word syncing, which made customers' negotiation processes 3x faster

  • Today, more than 1.5 million comments are made per year, just in the CLM platform alone

© yoon-ji kim 2025. ty 4 visiting <3

© yoon-ji kim 2025. ty 4 visiting <3

© yoon-ji kim 2025. ty 4 visiting <3

© yoon-ji kim 2025. ty 4 visiting <3