DesignOps in Wonderland

Carla Casariego
Digital Experience Director and Head of Design Ops, Express Scripts

Sarah Spencer
Senior Design Ops Manager, Express Scripts

From the DesignOps Summit website:
Experience the fantastical world of navigating rabbit holes, unlocking doors with hidden keys, and racing against the clock as Carla Casariego and Sarah Spencer take you through their adventures in creating and sustaining an agile DesignOps org at Express Scripts.

Carla started in technology consulting with plans to go to medical school, with a few sidebars like learning to make vermouth. She has been able to bring her passions together in her current role. Sarah is a healthcare professional – she was in direct patient care (emergency rooms, orthopedic), which has a lot in common wtih an Agile environment. She got an MBA and then joined the corporate workforce.

They found uncanny parallels between their work an Alice in Wonderland. ExpressScripts was 5 employees and is now 27K. Almost a year ago it was purchased by Cigna – it’s now 70K employees. It’s been a short but wild ride. They are going to cover the last three years. ExpressScripts is not just a healthcare company, but a healthcare technology company. They created a small digital team (ten people). They were initially a producer network – agile was initially quite messy. They later rebranded as a design ops team.

In Wonderland, the landscape was changing and shifting beneath us. Having that adaptable mindset is important to be successful. When to eat cake, to grow bigger, or grow smaller. So we set out to find friends for our tea party. Three years ago they were product owners and working across three different disciplines. They ended up in the same organization with their stakeholders, which helped them align.

One challenge has persisted over time. They are disporportionately small team relative to product owners and teams they serve. User-centered design was a new concept for the organization, so they had to show value in order to bring empathy into building of experiences.

They found allies, ran pilots and achieved small wins to supercharge their Agile transformation. They learned from successes and failures – most importantly the full participation of the interdisicplinary team. But because the team was small, they had to prioritize. They established a new approach “full kit teams”, which included digital experience, product owners, and software engineering together.

They were in very high demand. They were accepting work through email, if two people worked together in Austin or elswehere, they might work together. They were excited to have the work, it was really chaotic, and it was also clear they needed to streamline.

Agile is really about understanding and focusing on the most important thing in the moment. The demand was too big for them to do it together – they did it at the level of individual crafts like research, content, design. But the goal was ultimately to refine backlog together across the full team. By the fourth iteration, they were managing their backlog really well – both for the digital experience team and for the Full Kit team.

The secret sauce for doing this well is saying NO, so they can deliver a better YES. At first it was only Carla or Sarah. There is a book called The Power of a Positive No, which helped them frame their nos in a more positive way, and teach their team members to do the same.

How to ensure proper lead time such that human-centered design processes were possible? They needed to address the perception that digital experience was causing late delivery. Should we adapt to Wonderland time or should they adapt to us? The answer was a bit of both.

They started with Look Ahead Sprints – a sort of playground. Because so much of their work is due in preparation for the launch of revised health plans in the new year, there is a quiet time at year end to try new things like sprint ceremonies. But they also wanted to show how quickly to go from a problem statement, to a hypothesis, and then get user feedback. They had front-loaded work on critical products in a month before the new year. As much as we talked about it, showing it helped build more credibilty with product owners and engineering.

They develped their own design sprint calendar. The did this to have a common vocabulary with engineering, but because the were supporting work on more than just projects, it didn’t make sense for them to be fully integrated. They just kicked off Sprint 76. They are trying to stay 1-2 sprints ahead, or more. A lot of re-education is required, especially because they are not embedded in every team.

They also created quarterly experience roadmaps, and these have become the roadmaps for their strategic priorities. They continually evolve them to show what partners and the experience team needs.

Team structure at the outset:

User Experience includes UX engineers. In Research, it includes Experience, Resarch, Accessibility – including NPS, Customer Journeys. And then the Content team. Now they are a DesignOps team, working across all these disciplines to take things away that are a distraction, so people who are practitioners can focus on their craft.

They identified the best core functions for DesignOps (for them) today:

That is the strength of the DesignOps Summit.

They acitvely reflect, refine, and pivot what they are doing by:

  • Evaluating the strengths of the team
  • Researching emerging trends, leveraging relationships with leaders and peers in other companies 
  • Learning from others’ journeys and experiences

They have also been creating a strategy for experience operations by finding common ground with other organizations to solve challenges and identifying leading practices they can bring to their own work.

With support from leadership, they developed an Experience Operations team focused on value streams, not around specific disciplines:


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