The Design Leadership Playbook: How to Hire, Onboard & Manage a High-Impact Design Org

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Just about a year ago, in late 2020, Twilio closed on its acquisition of Segment, a customer data platform. For design director Hareem Mannan, the news prompted a powerful moment of introspection. “All sorts of folks on the Segment side really took a step back to reflect on how we got to this achievement and what made each team at the company special,” she says. 

Mannan had joined Segment back in 2018, but quickly climbed the ranks as the company grew — her impressive trajectory includes stints as an individual contributor, design manager, Head of Product Design, and eventually Director of Design and Product in just three years. “I’ve been lucky to always have managers who believed I was more capable than I believed I was,” she says. 

When I first got to Segment, I got the advice that the job will be as big or as small as you make it. I’ve taken that to heart and tried to be a heat map to the biggest problems I could solve in any given moment. 

Amidst this rapid-fire rise, she partnered with folks all over the org chart, from different product areas, career levels and growth stages, giving her a close-up lens on some of the biggest challenges facing high-impact design teams. Along the way, she’s dished out heaps of design advice as an instructor and on her own personal blog for other heat-seeking designers. Plenty of startups focus on hiring standout IC designers but don’t put as much thought into the progression to design manager and director. In this exclusive interview, she ties all the threads together from each step of her career at Segment and delivers tailored advice for each step in a designer’s career path. 

For IC designers earlier in their careers, she articulates the three specific qualities she consistently sees across the highest performers, including one under-appreciated skill not often discussed in design circles. She also draws on her ample experience hiring for growing teams, with tips for job hunters on how to stand out during interviews and the slide you need to include in your portfolio review. 

For design managers and directors, she reflects on the three qualities that stand out amongst the most impactful leaders on her team, particularly their deftness for navigating cross-functional partnerships and boosting trust with their direct reports. She also draws on her own missteps as a first-time manager, and shares why a fear of micromanagement caused some unintentional headaches. Finally, she offers her advice on developing an interview loop that surfaces designer candidates with high signals for her three must-have traits, along with her ultra-tactical guide to onboarding with purpose. Let’s dive in.

Plenty of designers earlier in their career have sketched out their career goals and are eager to be a sponge for pieces of wisdom from higher-ups. But oftentimes, after years of managing later-in-career direct reports, folks higher up on the org chart have begun to lose touch with the unique challenges and opportunities facing individual contributors. Only a couple of years removed from being an IC herself, here’s how Mannan articulates the traits of the best IC designers: 

1. Great designers are product quality ambassadors.

As Mannan puts it, the best designers are amazing advocates for what a good experience looks like across the entire product stack. To further illustrate this point, she leans on what she admits is an overused, but apt analogy. “I like to think about product quality as an iceberg. In this case, the tip of the iceberg that’s peeking out of the water is the part of the design that you can see — the user interface that customers interact with,” says Mannan. 

Dip underneath the surface of the water, and you’ll see the foundation of product quality — beyond pixels and buttons. “Are customers able to actually accomplish what they came here to do? Are they able to use the APIs that they want? The best designers that I’ve seen at Segment really look at that entire iceberg from top to bottom. Whether that’s thinking about the visual design or the product design, or even engineering workflows — they don’t just focus on their own work, but evangelize to other areas of the product as well,” she says. 

Great designers understand the difference between problem-solving and problem-hunting. 

Mannan sketches out an example to further illustrate sizing up the whole iceberg. “There was a period of time when Segment got the feedback that the product was a bit of a black box — you send data through Segment, and you can’t really see what’s happening to it. We just promise you that we’ll send it to all the places that you want to send your data to,” she says. 

Cue the product and engineering folks clamoring to sink their teeth into the problem. “What’s happening to the data as it flows through Segment sounds like a product and engineering problem, but it’s actually a design problem. So a couple of designers on our team got together with our researcher and literally mapped out the journey of a data point as it goes through Segment. It’s not a traditional interpretation of design, and it’s not work that our customers can see,” says Mannan. “But it’s a clear illustration of what it means to invest in product quality — thinking about the journey of a data point and where it’s important to surface to our customers as they get a better sense of what’s happening under the hood at Segment.” 

Mannan doesn’t expect designers earlier in their career to bring a finely-tuned sense of product quality — step one is learning good from great. “You can’t be a product quality ambassador if you don’t fully understand what great product quality looks like. So spend a couple of years learning how to evangelize and create the product quality that you want to see,” she says. 

The next step is bringing other folks along with you. “Being a product quality ambassador means that you’re not just evangelizing that within your own product area, but also making sure that other people are also quality ambassadors around you so that you’re building this chorus of what good looks like in your company,” says Mannan. 

2. Great designers are the glue across product areas.

Across companies of all different sizes, Mannan sees one particular problem crop up again and again. “Oftentimes design operates in what’s called an embedded model, with designers sitting on specific product teams that have different charters. And it can be easy to fall into a pattern of working within a silo of your own product area without thinking holistically about the end-to-end customer experience,” she says. “That’s where design can play a really special role in ensuring that there’s someone thinking about the horizontal product experience, not just a series of vertical ones.” 

Here, she points to one of the biggest differences between design and its product counterparts. “When you think about what makes a good product manager successful, it tends to be how well they do in their individual vertical product — driving feature adoption or increasing retention. But in design, success is often measured by how we think about the holistic end-to-end customer experience. The best designers I’ve found really lean into trying to be that glue between vertical product areas, finding opportunities for folks to collaborate to solve those horizontal problems,” says Mannan. 

The key here is for design leaders to create an environment for designers to continuously share their work with one another. “Even on a smaller team like Segment, we can have three different teams stumble on the same customer problem — how can design serve as that unifying voice?” she says.

We can’t expect designers to be thinking horizontally if they don’t know what’s happening next door. 

Mannan admits that this visibility into the end-to-end customer journey has become trickier in the shift to remote work. “It used to be a lot easier to turn your chair around and share your work. When we first went remote, that was one of the first things I struggled with in leading the team — it felt like everyone was operating in a vacuum. We couldn’t rely on organic collaboration and needed to create intentional structures of visibility on the team,” she says. 

Her team relies on two separate touchpoints that cover what Mannan calls the two streams of design work: discover and build. “The discover stream is about the high-level existential questions you’re turning over — like ‘Why do customers churn? What does it mean for people to buy this product? Where do they get tripped up in implementation?’ These projects can take weeks or months,” she says. “Whereas build is iterating on a specific feature alongside a project manager and engineers.”

To sync on the discover side of the coin, every Monday morning each designer on Mannan’s team fills out a doc posing two questions: 

What problems are you thinking through this week?

What are areas of potential collaboration with other designers? 

“It’s all about intentionally designing a meeting to drive visibility. You scroll through the doc and you realize that someone else has also been thinking about onboarding flows,” she says. 

Tactical tip: In addition to a weekly formal sync every Monday, plenty of design leaders will want to borrow her lightweight idea for the build portion: “A very simple and small example with an outsized impact was creating a Slackbot that pings the design channel every Wednesday morning asking every designer and researcher for a screenshot or link to something that you’re working on that week. It’s been an incredible mechanism for visibility in a distributed team,” says Mannan. “So many conversations are spurred Wednesday morning, like asking for quick feedback on a project or folks realizing they’re working on similar problems.”

Don’t just rely on formal mechanisms for visibility — look for lightweight opportunities that boost collaboration. 

3. Great designers understand the go-to-market motion. 

As Mannan puts it, this third pillar is the most underrated in design circles, particularly for B2B SaaS designers. “Understanding the GTM becomes a bit less relevant for a designer at DoorDash, for example, because there’s not a different buyer and a user. If I’m ordering my food, I’m also the one paying for it. But for SaaS products that’s not the case — and that’s where understanding the distinction between the buyer and the user becomes especially important,” she says.  

The gravity of this third trait more clearly crystallized for Mannan when she first joined Segment. “I initially joined this team called ‘Personas,’ which is one of Segment’s flagship products. At the time it was like five sweaty dudes in a room, trying to figure out this prototype they had built,” she says. The first six months she spent doing what she calls bottom-of-the-funnel usability work. “Basically thinking about how people were using the product that had already existed — where they were getting stuck, why they weren’t implementing it, what was going well, why they churned, all questions prompted after they bought the product. What I was missing was top-of-the-funnel usability — why people bought us in the first place,” says Mannan.

That unlock came a bit by accident. “My product manager at the time invited me to go on a sales trip to New York and sit in on some research visits with existing customers. During that trip, I ended up accidentally tagging along on a lot of sales calls with prospects. I still remember the first moment when I heard Segment Personas be pitched in a sales meeting — my mind was absolutely blown,” she says. 

“A part of me was like, ‘I can’t believe we’re pitching it this way. I don’t know if what we’re building fully aligns with the promise that we’re making here.’ I kept thinking about all of the things I would do differently had I understood the business outcome that all these customers were driving towards,” says Mannan. 

Her first order of business after returning from New York was to sit down with an engineer and completely re-imagine the core product experience. “I now had the context into why they bought us in the first place. It sounds abundantly obvious, but when you’re a designer you’re often knee-deep in a set of features rather than zooming out to why it was purchased to begin with,” says Mannan. 

Too often designers focus on talking to customers that already exist, not prospects or customers that could exist.

Along those same lines, she encourages designers across the org chart to keep an eye on the competition. “It’s important to do competitive analysis and better understand not just how your competitors are investing in their product, but also how they’re framing it,” she says. “Brand designers often think about how competitors frame their product, but it’s critical clarity for the product designer perspective as well.” 

Mannan sets the tone with all new designers who join her team to help them develop that GTM muscle. “In the first few weeks of onboarding you’ll have plenty of R&D focused 1:1s, but I also like to onboard designers with a set of GTM folks who are high-touch with customers and chock full of insights. I’ll partner new designers up for onboarding with a solutions engineer, which can feel out of pocket for designers who are not used to thinking about the GTM motion or haven’t worked with a solutions engineer before. But it quickly becomes one of the most valuable partnerships that designers have at the company because they have a different angle on some of the same types of problems,” she says.  

Hareem Mannan, Senior Director of Product, Enablement & Design, Twilio

Just over a year after joining Segment as an individual contributor designer, Mannan was promoted to design manager. It was a steep learning curve, shifting from a regular cadence of delivering tangible design assets — Figma files, wireframes, usability test results, and user interview notes — to a calendar jam-packed full of meetings. Now, as a manager-of-managers, she’s taking on the work of empowering other managers in her org to build the team infrastructure that allows designers to thrive and produce high-quality work. Here’s how she articulates the traits of great design managers:

1. Great design leaders run towards problems.