Role: Enterprise-level Facilitator, Docusign
Facilitation :: Innovation and Impact
Enabling progress when it’s needed most
Two days, 167 people, hundreds of ideas, new working relationships, and a sense of urgency
Timeframe: 2 months planning, 12 hours of workshops
Status: Prioritized needs and ideas, shipped & in-market
Scale
167 in-person participants from Product-Led Growth, Go-to-Market, Engineering, Senior leadership from each, c-suite Growth leadership
12 hours of in-person workshops across 2 days
Lead facilitator and planner, recruited and trained 10 co-facilitators
350 post-it pads, 5 reams of brightly colored paper, 200 Sharpies, 15 packs of googly eyes
One very beige hotel ballroom in San Francisco
Docusign: 7,500 employees, 1.7M customers, $3B in revenue, publicly traded
Challenge: Enable progress when it’s needed most
Facilitators know that the right conversation at the right time with the right people can make or break needed progress.
And we were at that point as a company. Change, progress, adaptation, whatever you want to call it.
Not just the products, but the teams surrounding our products trying to make them successful. They needed a win. They needed to make progress.
Our Product-Led Growth team almost 100 people in it and they were gaining traction in the c-suite. But because they were talking about long-needed change to an aging tech stack in the products, they weren’t making much true progress.
A new executive joined and saw the need for a different kind of conversation. I was tapped to help create it.
Hypothesis:
If I can design the right conversation between people who don’t know each other yet, or know they will be on the same team, executive leadership can use the collaborative energy and alignment I create to drive momentum to scale effectively at a crucial moment for Docusign.
Highlights
Collaborating with and leading executives
Workshop design
Facilitation and training
Improvisation
The Context
“I’ve never seen the product beyond trial signup.”
New executives joining Docusign on the marketing, sales and CX side of the house were routinely amazed, and not in a good way, at how the business model and products actually worked.
The dot-com team’s ability to move fast and create successful campaigns papered over the problem. But once someone entered the actual product, there was a huge ravine between the customer-facing side of the house and how products were implemented for those customers after the ink was dry.
How products were built led to an archaic product assembly and delivery model where it took up to 3 months for customers to start using what they bought. Upgrades were large and painful, so customers avoided them.
At face value they all seemed like small problems to overcome — the model for trials, the thousands of product SKUs, the high need for customization, and the inability to inject growth moments into the products.
In a digitally mature company, they’d be right. But Docusign was 25 years old and little had been done to advance the initial innovation.
The Problem
“We might not be here 6 months from now.”
All of these customer-facing teams seemed to be working at cross-purposes and making little headway with the product and engineering organization.
One of the newer executives saw a bigger problem looming — how can the growth team meet their goals if the partners they needed didn’t see the need to partner at all?
At one point during the gathering, an executive showed the numbers for new and exiting customers.
The churn was extremely high. It was clear that the business model overall relied on new customers constantly arriving because they needed the product in a specific moment.
This chart made almost everyone gasp, and deservedly so, because retention and avoiding churn is a big part of healthy growth.
He showed everyone that if change doesn’t happen, if they can’t get moving, they wouldn’t be there in 6 months. He didn’t just mean the growth organization. He meant Docusign itself.
That got the whole group’s attention.
The Stakes
“When I say we might not be here, that includes Docusign.”
I’m not going to claim that I saved Docusign from itself, but I will say that I was a big part of helping large teams pivot to better and healthier ways of working.
In this situation I helped disparate teams come into alignment and agree to make the needed changes so that Docusign will still exist. Which it does today, although I should say that strong competition has entered the market since I was there in early 2024.
There were people’s jobs at stake, and ultimately, the scalability and survival of Docusign.
The Ask
Our Head of Growth went looking for an in-house facilitator and found me.
As a newly appointed head of service design, I wanted to build a facilitation competency in our team and I was prioritizing new relationships. So our new VP of product experience came to me, thinking I was going to “stand up there for about an hour and do your thing.”
I met with the executives and saw a lot of possibility for this thing.
It would be about 50 people in the executive meeting room for a day. The goals weren’t totally clear but we’d get there. We had two months to prep.
Easy peasy.
The Oh No
But like thneed factories, things tend to grow.
Six weeks out, the situation had changed. We had almost 100 people and needed external space, and oh yeah, everyone would be in person in San Francisco.
Then a pending re-org changed the list again, and we had 150 people.
We did a bit of what I call “wandering about in the woods” coming up with ideas.
Because I knew I’d need more facilitators and I’d have two days I needed to essentially host and facilitate, I recruited volunteers. Ten brave souls agreed to help.
With this much flux, I needed to create something scalable and easy to run.
The Aha
Oh, wait, I’m leading this.
Some executives expect you to take their list of things and make it happen. This executive wanted me to lead.
So I did.
What they wanted from this event was new working relationships, strong alignment, and a clear direction forward that was generated by the teams themselves.
So I set about pretty much designing a small conference.
I worked with his executive assistant in San Francisco to get the space together and organized in the beige hotel ballroom. I bought all the materials, googly eyes included, and sent them to the location.
The workshop designs are outlined below.
The whole thing was more successful than I imagined it could be.
The Workshop Design
The Setup
Groups of 15-20 people who were a mix of disciplines, teams and levels were seated at round tables. Phones were put away.
Two facilitators per table, a few floaters, and a photographer were on my team.
Something I always do is build in “talking time” which often ends up being the most valuable part. I create breaks and meals at moments I know people will talk about what we just did. It builds relationships and alignment, and gives people time to integrate what we just did before we move on.
Day One
Walk-a-mile, described at left, forced everyone in the room to be a brand new customer. Most people were seeing that experience for the very first time.
After that, groups discussed their experiences. Then, break for lunch, where I knew people would be talking about the activity.
Then facilitators got them to their “Sets of Threes,” which I made up so that people could see they had more in common than not. They presented them at the end of the day at the front of the ballroom.
That evening it was amazing to simply hang out and see how much people were connecting after the day.
Day Two
Crazy Eights are my go-to for idea generation. Once people have some time to think and feel safe having “crazy’ ideas, they always get great stuff. A lot of people have done it before, which helps.
Tables then shared and filtered their ideas through business needs and what they currently had control over, a crucial “reality check.”
Then, after lunch and some discussions, they voted up the best ones, drew them out in more detail, and shared with the room again.
Executives wrapped with strategy and reorg information at the end of the day.
Results
For something that I felt was pretty basic, I got feedback like this:
“This is the best work event I’ve ever been to, including conferences.”
“That was incredible. I feel so ready to get to work!”
“Can you do an abbreviated version for the CEO and his direct reports?”
Lots of accolades from people made their way to my boss at the time, too. So, our facilitation footprint was well on its way.
And there were business results, too.
Executives did, in fact, get together and approve the voted up ideas and my recommendations.
My recommendations were to start with “Fix the Basics” that showed up when participants were seeing the experience for the first time. Then, assign specific ideas to the newly reorganized Growth practice according to their place in the funnel.
Today, when you get a document sent from Docusign to sign, instead of going to spam because of its send email address — which it was doing 93% of the time — It goes to your inbox.
And the 2,000+ SKUs are down to less than 100, last time I asked. That means time-to-value for customers has gone down, too.
