Role: Director of Service Design at Docusign
Business :: Innovation and Impact
Introducing: Intelligent Agreement Management
Creating and Selling the Vision for an Integrated Platform
Timeframe: 1 month
Status: new platform in-market and continuous delivery
Scale
Service Design: I was asked to build a team in November 2022. I recruited five and hired one of the highest-level, most tenured ICs in our product design practice
Product Design: 70 designers broken into 6 larger teams; designers assigned to features or flows
Product Experience: ~125 design, research, content, IA & ops
Product, Design and Engineering: 2,700 employees
Docusign: Public company with 7,500 employees and 1.7M customers globally
Challenge:
Docusign was at an inflection point. The stock price had tumbled almost 90% — from a high of $310 in September 2021 to $38 in November 2022.
By May of 2022 The CEO had been fired and a complete leadership turnaround happened shortly after that. Layoffs ensued, and people started leaving in droves.
For years, a rotating cast of senior leaders tried to shift the company from a single eSign product to a suite of services the market was demanding. Acquisitions were made to accelerate the effort. Internal resistance and technology inertia sabotaged it every time, mostly by an entrenched core eSign team.
Our customers were extremely clear about what they needed. It was documented across years of design research, win-loss ratios, and strategy decks.
We didn’t need more vision — we needed an organization and mindset shift.
How do you get core teams that have successfully resisted the necessary change for years to finally see what needs to happen — and get on board?
Hypothesis:
If we can present a clear and feasible vision that shows what Docusign’s future should be to the CEO, then we can get the investment in both the work and organizational shift needed to power needed change.
Highlights
Business transformation & innovation
Design strategy
Design leadership & facilitation
End-to-end product integration
The Context
“I love Docusign!”
When I told people I worked at Docusign that’s what they said. I knew what they were talking about: the signing experience.
That experience, introduced about 25 years ago. solved an enormous problem — reliable, secure, legally defensible electronic signatures.
When the pandemic began, the world didn’t entirely stop in the US, even though it seemed to. People were getting married, buying houses, cashing out retirement plans, getting new jobs, and all of it needed eSignature.
With a higher market cap and a rising stock price came ambitions to expand the footprint.
Acquisitions followed.
The idea was to accelerate with built products that we would integrate into our ecosystem.
For two years those companies kept operating as independent entities. The technology was not integrated — at best, it was bolted on. Experiences overlapped.
Designers were unaware that they compounded the problem with every duplicative shipped feature.
The Problem
“This is not a Docusign product.”
Customers of our “other” products regularly walked away from renewal, telling us we sold them on an experience we did not deliver.
They weren't wrong. They expected an experience as simple as signing.
Leadership circled this problem, coming up with strategy after strategy to compel teams to build towards each other instead of away.
I could see a clear path, so I tirelessly worked to draw experiences closer together. The ultimate agile, de-siloing, collaborative challenge.
But the eSign team dug in. They were not going to integrate a single new thing into a teetering, crumbling tech stack. Every time I needed cooperation, it was at best begrudgingly given.
Even design leaders said, “Do we really need this? We’re an eSignature company.”
C-suite leaders seemed both blissfully unaware and deeply frustrated. They asked design to come up with versions and visions and designs that showed where we were headed.
Designers were jaded, burning out, and started resisting vision work in any form.
The Stakes
“eSign isn’t enough.”
The future of Docusign was up for grabs. eSign’s resistance to change and leaving tech debt in place had not paid off.
Our new CEO tried to sell to Microsoft, Google and Bain, who all walked away.
What would happen next? Liquidation of product lines, massive layoffs, and a contraction down to a size that made us a more appealing acquisition.
That is, unless we moved fast to build out a real, sellable platform that met customer needs and expectations.
We knew what customers wanted. Now it was time to stop resisting and start doing.
The Ask
Our first Chief Product Officer asked our new VP of Product Experience to create a feasible vision of what a “unified” Docusign could be.
He, in turn, asked me to take this on. My team hailed from every product line and knew everything. Inside and out.
We needed to pull together every major product line plus the vision for how AI would integrate so that the CPO could take it to the CEO to get the work funded.
I was pumped! The VP had come to the right team, and my colleagues had pointed him in our direction.
We would be part of setting the new direction. Being attached to this work should protect us from layoffs. This is great, right?
My team was … less thrilled.
The Oh No
My team wanted no part of it.
Vision work done in isolation, only to be shelved as quickly as the previous vision work? Not validated with customers?
No, thank you.
I saw their point — but they were misreading the situation. Also, they were acting just like the eSign team! The behavior they’d been complaining about for a year.
I knew we were in burnout. I didn’t know it was so bad they would refuse work, knowing that layoffs were always lurking.
How could I turn this ship around?
I considered simply using my authority as a boss, but I am not a command and control leader, and I knew I’d get crappy work if I did.
Instead, I asked them what they would need to get to a yes.
The Aha
What did I do? I wrote a really good brief.
Honestly, I didn’t think it would work.
To this day I think they believed I wouldn’t get clarity on exactly what was needed and what it would be used for, but that’s what I delivered.
I also worked with my research partner to plan on how we could use her brand new customer panel for prototyping, co-designing, and validation.
Wow, did they understand the assignment. Our early work amazed the CPO. We needed one iteration. Other design teams bought in, slowly.
We finished, he presented, and the CEO funded the change.
The Results
At a critical juncture in Docusign’s history, I led and contributed to work that successfully changed the trajectory of the company.
I did it by being the leader and human I’ve always been, along with skills that have been honed by years of experience in getting people to see beyond today, to look up to what could be, and bring that vision to life.
My values for myself are apparent in how I lead. I’m creative and curious, compassionate and trustworthy, strategic and visionary, and honesty and accountability.
I was laid off before I got to see that vision come to life, in a wave that did away with roughly 700 employees. It was done in a callous way that took some time to get over. Because after all, work is about the people, the friends you make along the way.
I don’t have sales numbers or win-loss data, but I can see in the marketing that what we designed is the core of what’s shipping.
I do know that the stock is going up and analysts rate it a Buy.
