2024 SimplePractice Design Playbook

Every year I write a playbook for my design organization. It gets the team on the same page about how we work and what we are aiming at, and as VP of Design at SimplePractice, presenting it to the wider organization and to our investors is also how I show them what design is for.

The playbook begins by clarifying the structure and responsibility of our design organization. Zooming out to our Product and Engineering “One Product Group,” we operate in a Quartet model with Pgm & Ops as the fourth, steadying leg to our stool.

This gives us a well-rounded structure where product managers, engineers and designers work with handshakes instead of handoffs across our Agile environment, supported by solid ops and program management.

Looking closer at our design organization, the roles and responsibilities center around product design work, content design work, and using design thinking to keep our cross-functional teams tethered to customer needs across the product life cycle. We follow the traditional IDEO philosophy of Design Thinking with these critical dimensions guiding our design process. But there are some advancements I’d like to make in 2024:

Like Atlassian, we aim to run design thinking workshops with key customers to co-create new features, raise satisfaction and reduce churn. We are about to set up a Customer Advisory Board and will work with the team leading that effort.

Similar to Salesforce, I see an opportunity to bring A/B testing and data analysis into our design thinking at the top of the funnel, so onboarding converts better.

Our design principles center around Empowering Simplicity through Trust and Innovation.

Simplicity results from thoughtful problem-solving of complexity, not the opposite of complexity. In other words, we often have to grapple with the most complex stuff to make things simple for users.

Trust is building solid relationships with cross-functional partners and customers through transparency and collaboration.

Innovation comes from our team thinking beyond limitations and designing for future opportunities.

Strong collaboration and pushing the bar higher comes from sharing early and often, but believing your pov, experience, and rationale for design decisions is respected and valued.

From pixel-perfect designs to happy customers, we’ll know our design team is winning by focusing on the right metrics.

Tracking “attention to detail” and “innovative ideas” for top-tier UX quality.

Celebrating “high customer satisfaction” and “improved task completion” as proof our designs are customer-centric.

Monitoring “reduced cycle time” and “increased design system adoption” will prove we’re practical and supporting business growth.

Investing in “career development” and “shared knowledge” pays back in employee satisfaction and growth.

Finally, remember that “continuous feedback” fuels iteration and keeps the team ahead.

Last year, we ratified our Design Mission: We exist to craft the experiences that empower practices to deliver quality care. The mission was created bottom-up to ensure Designers feel more invested in its success and are more likely to champion it. It also allowed us to work collaboratively on a shared goal, which helped boost morale. Overseeing my team and managers’ workshop this mission helped me identify leadership potential and areas for development very early on in my role here… we ran this workshop in March of 2023.

The mission centers around how the design function can uniquely deliver “empowering craft” for our clinician customers. This means we provide simple and elegant solutions yet powerful and create efficiencies in their workflows.

To show the team how our mission manifests in practice… I created a framework that helps our team become more intentional about organizing UI elements. This, in turn, enables us to live up to the promise of “empowering craft.”

The framework starts with using proven, reliable components from our central design system, minimizing tech debt and load time for the customer, and building on data-backed best practices.

Those components should then be nested in context-specific containers. By containing components, patterns, and full workflows in specific parts of the UI, we’ll minimize context switching and distractions. Which, in turn, helps improve metrics like time to completion and completion rates.

Finally, we want the team to bring the delight and swagger of our brand expression into the user experience. Mailchimp’s playful tone and quirky illustrations put fun into an email marketing platform, and Airbnb’s local experiences and user content make booking a trip feel like something. Letting the updated SimplePractice brand through, with its encouraging, warm and informative voice and its optimistic, trustworthy palette, will set us apart in the market and raise both perceived value and willingness to pay.

This is a VisionType I created to help the team see the framework in action. A clearly defined and sectioned navigation or control center helps with wayfinding. Using the movement of our sections in and out of view to help set context and improve focus. A modern glass blur effect will help us show our clinicians clearer depth and hierarchy, plus allow our brand to shine through. This is not a literal direction I want the team to deliver… more of a reference for the quality bar I want to challenge them to meet.

Similar to how our design principles reflect HOW we work and WHAT we aim to deliver, we have four pillars that power how we do UX work at simplepractice and give us a competitive edge.

Our investment in design has driven our rise above the competition, allowing us to charge a premium for a well-designed experience that our competitors can’t match.

The first pillar has two parts: gathering user feedback and revisiting and iterating on designs. To gather user feedback more thoroughly, I want our team to look across the product life cycle, from the early “understand it” and “think it” phases to the middle “build it” phase and the later “learn and tweak it” phase.

During the early stage, we use PM and Designer pairings where they go broad to explore the challenge space, then narrow and agree on which customer challenges to solve first.

In the middle stage of our product lifecycle, we run bi-weekly product deep dives with cross-functional leads to validate the approach and keep designs tied to strategic and business goals. To help a broader set of partners learn from our user feedback and quant measures, we hold a monthly Hour of Learning that every team is invited to.

Understanding our customers in the “tweak it” or latter product lifecycle stage, we read our “voice of the customer” Slack channels daily to help us stay connected after we ship the solution and need to learn and revisit.

For how we revisit or iterate… we subscribe to the Two-Pronged Approach for achieving Stellar Design.

Imagine getting two sets of fresh eyes on your design: one broad and diverse, the other focused and experienced. That’s the beauty of combining silent and traditional critiques: silent crits to find the major issues, then traditional design crits to refine the solutions. They also balance anonymous feedback with opportunities for learning and exploration.

With both, we’re able to capture both broad impressions and specific details from diverse viewpoints, we’re able to identify issues while ensuring solutions are well-considered and user-centered quickly, and we get creative thinking and growth opportunities out of the same hour.

Our second pillar allows us to deliver big design ideas continuously without derailing or slowing Agile processes.

Agile methodologies with iterations and user feedback loops are generally the better fit for creative work and high-quality UX. Still, the condensed, back-to-back Sprint windows can leave designers little space for future-facing work or blue-sky thinking.

Our VisionType cadence counteracts this… not always, but often enough so that we have design explorations to tap into during the early stages of our product work. So, by creating space for our designers to go broad with ideation, untethered to roadmap-specific work, we’re giving our product teams a library of components and patterns that help pull the experience up to a higher level of quality.

Our third pillar helps us design quickly at scale, with autonomous teams through a governance layer we call the UX Excellence working group, made up of folks who do this work on top of their roles within squads.

Similar to how I saw Spotify ensure stellar UX across their squads and tribes structure, our product org keeps everyone on the same page through clear guidelines and regular communication delivered by PM, Tech, and Design SMEs.

So while squads operate as mini-startups with end-to-end ownership of their assigned area, which lets them make decisions on their own and take accountability for them, our UXE group defines and keeps guidelines updated across accessibility, clinician UX excellence, client UX excellence, and native mobile standards. These senior SMEs also attend regular design critiques to provide input and expertise during the “define” and subsequent stages to push for our standards and make sure they get met. In addition, we are exploring how they can be available to help brainstorm and tackle more complex product gaps or needs that arise.

Our criteria for selecting these folks ensured we had Senior II or lead level, representative of CS + PD ratios across design, and someone from each experience.

Our fourth pillar is an idea I proved out leading design teams at Intuit: stellar UX can be customer obsessed and deliver business value at the same time. Part of our secret sauce is our investment in Content Design resources.

We aim to have a minimum of 4 developers and up to 10 in any squad.

By the way, this puts our Designer to Developer ratio within range of where most B2B SaaS companies are based on this survey from Nielsen Norman Group back in 2020.

Digging a little deeper into our 1.5 designer-to-developer ratio, the breakdown is for every Product Designer, we aim to employ the talents of ½ Content Designer.

The rationale for this is best reflected in this quote: “People don’t just buy products; they buy stories.” But there’s more about why we invest in Content Design Staffing.

SimplePractice is one of the most expensive EHRs in our segment, so we need to demonstrate the value customers get from our product as soon as they land in it. Content Design expertise in communication strategy helps us land value-based messaging in a voice that resonates with our target customers. This comes to life with our onboarding, trialer, and upsell experiences.

Considering our customers are highly educated, emotionally intelligent people, they tend to pay close attention to the communication they get from us. When we communicate poorly, it impacts customer retention and their desire to recommend SimplePractice. Content designers build bridges with words through voice and tone explorations and customer-centered language research. They flex these muscles and help us drive feature usage, design messaging across the customer lifecycle, and communicate bad news.

Lastly… we’re in a highly regulated industry with layers of risks, from financial obligations to compliance requirements. Content designers help customers get through complex information quickly and protect the company with clear communication about security and privacy. Because of this, they can help us create efficient product flows, deliver clear information architecture, and accurately label and analyze data.

Without diminishing the stellar work of our product designers, our small but mighty content design team helps us fortify our UX foundations because we hire for solid technical UX skills.

In content design, we hire for deep object-oriented UX experience, which has served us well as it clarified the scheduling problem space and generated roadmap items to drive usage of online appointment requests.

We also look for incredible Information Architecture skills, which, in the settings redesign, solved underlying customer misunderstandings and created business opportunities by better surfacing marketing entry points.

Deep taxonomy and terminology experience also matters: we saw its value most recently in the work across the documentation flow, which set us up to scale to new specialties and laid the foundation for core feature work on “Business Files” and “Client Files” surfaces.

We also looked for solid User Journey Mapping abilities, which paid off when mapping the journey for Stripe payment processing and unblocked the billing and payments team to scale to new payment methods.

Similar to “pair programming,” the software development technique where two programmers work at one workstation, the pairing we do with Content Designers and Product Designers at the squad level allows for similar gains. In pair programming, you have one driver (the person writing code) and one observer or navigator who reviews each line of code as it’s typed in. The two programmers in this technique switch roles frequently.

So, for SimplePractice Design, while reviewing Product Design explorations, the Content Design observer considers the strategic direction of the work, ensures high verbal craft, and helps come up with ideas for improvements and corner cases to address. This helps the driver focus more on the tactical aspects of completing the work for that design sprint, using the observer as a safety net and guide.

Lastly, I’d like to talk about our current state of UX Research… which isn’t quite where we’d like to see it. While our Product and Designer pairs conduct solid UX research, it’s inconsistent from one squad to the next and lacks the connective tissue for shared learning at scale. Similarly, our PMM partners do great, long-term studies, but the findings don’t always return to the product consistently or reliably. We even started doing UX research on our marketing surfaces with a contractor resource, bringing AB testing and user-centricity to the top of our funnel. But, again, it’s disconnected from product and data science, so the broader team may never use the insights.

I see an opportunity to fuel cross-company customer obsession if we:

Build a collaborative research system:

Shared research hub: Easy access to insights and artifacts.

Regular cross-company meetings: Discuss findings and plan initiatives.

Standardized reporting: Clear, comparable insights across teams and organizations; shared data visualization system to improve comprehension

Cultivate a shared customer-centric culture:

Emphasize user empathy: Encourage and incentivize active engagement with clinicians.

Comprehensive customer journey map: Visualize pain points and opportunities thoroughly using our “jobs to be done” (JTBD) framework as a foundation.

Regular internal communication: Share customer stories, data, and feedback.

Use data science for unified insights:

Consistent data in one shared data ecosystem. We’ll better ship the right features when we integrate data from various sources, extract deeper insights from combined datasets, and do more predictive modeling to anticipate customer needs for personalized experiences.

Ensure actionable outcomes:

Prioritize research based on impact: tie it to business goals.

Translate findings to action: Clear next steps for teams.

Track and measure impact: Quantify the value of research efforts.