[DesignUp 2021] From startup to scale-up: design strategy tips from Erin Casali, Jetpack, at Automattic

As media partner for the DesignUp 2021 conference and fundraising event, YourStory presents this expert interview on design for startups and mature companies.

[DesignUp 2021] From startup to scale-up: design strategy tips from Erin Casali, Jetpack, at Automattic

Monday June 14, 2021,

11 min Read

Erin “Folletto” Casali is Head of Product Design, Jetpack, at Automattic, the company behind WordPress.com, Simplenote, Longreads, Tumblr, and more. Now based in London, she has more than 17 years of experience in designing products, and is an advisor and coach to multiple startups.

She has a diverse background in design, psychology, business, and technology, and has worked with companies like Bank of England, Unicredit, Vodafone, Telecom Italia, Ferrari, and Benetton. Erin has advised startups such as Ernest, Impacton, PosterForTomorrow, Flythegap, Tallyfy, Pick1 and Tonight.eu. She will be speaking at the DesignUp conference this week.

This year, the DesignUp 2021 conference team’s response to India’s apocalyptic second wave of the COVID-19 pandemic is to organise a virtual fundraising drive along with the stellar lineup of speakers. To be held on the weekends of June 11-20, 100 percent of donations will go to charities bringing much-needed relief to rural India, in the form of dry rations, oxygen concentrators, and health centre wards.

As media partner for the conference series, see YourStory’s coverage of DesignUp’s earlier online panels in 2020, May the Fourth be with you and The pandemic’s impact on design. See also our write-ups on the annual DesignUp conference editions from 2019, 2018 and 2017, and our d-Zen (‘Design Zen’) section for more design resources.


Erin Casali joins us in this interview on the importance of the design mindset, pandemic resilience, and industry-academia collaboration.

Edited excerpts of the interview below:

YourStory [YS]: Many entrepreneurs with a tech/business background tend to under-estimate the importance of design. What advice would you give founders on when and how to engage with designers?

Erin 'Folletto' Casali [EC]: When and how is always “from the start”. They key there in my view is to get clarity on the kind of design that is needed at different stages of the company growth.

At very early stages, it’s probably better to find someone that is able to do research, can support steering the business, and is able to execute some solid interaction design. A kind of a generalist with some more skew on research.

Later, the roles can differentiate, and at medium size, for example, design with more solid brand and UI experience could be needed to craft polished experiences, assuming of course that research focus is still present from earlier stages.

And still later, it needs designers and design leads that are able to operate at a scale, that can work on organisation design and change management too, and likely more specialisation and definitely the ability to grow junior talent. Understanding the maturity level of the company is essential.

[YS]: What are some outstanding examples you have seen of effective design during the pandemic? 

[EC]: I’d just like to mention one: the Gov.uk vaccination booking website.

They managed to leverage the existing design system and infrastructure to build a vaccination booking system for the whole country that worked effectively and (generally) reliably. Given the context, this has been an amazing feat.


[YS]: What are the key challenges facing designers in these grim times, and how can they be overcome?

[EC]: I don’t think designers have challenges that are unique to them these days, but they share the same issues related to forced work from home that a large amount of the population have.

I feel, however, for designers that have been working on some of the tools that we needed to get up and running fast, like booking systems for vaccinations. Very little time, very limited time for research, and high stakes.

Luckily, the tools to face these problems are tools we have already in our skillset: ability to do research, getting in touch with real users, iterating toward solutions, collaborating with experts, services design, and so on.

[YS]: What are some notable projects or research initiatives you are currently engaged in?

[EC]: Working for Automattic means working at a worldwide scale, and specifically with Jetpack we have been helping millions of websites to get more performance, more security, and thus being able to move their business and presence online. WooCommerce is one of our other tools that has seen an incredible level of adoption recently, even it’s not necessarily something I directly worked with.

More generally, I’ve been spending some time in sharing management and leadership best practices to help other managers out there to lead their teams with compassion, clarity, and clear outcomes. This has been a part of my work that spans broadly — it makes me always very happy to see people growing and becoming better at what they do.


[YS]: What are the success factors for good designers to become good design managers?

[EC]: The number one thing I clarify with every new design manager I coach and mentor is always that management is a different job. Sure, it’s still rooted in design, but the kind of work changes. I’ve seen too many times designers trying to “keep designing” and failing in many ways.

Sometimes the failing is explicit due to the low performance of the team, sometimes it’s straight burnout if they try to do everything, but sometimes it’s also just coasting along without providing any real support to a team that maybe is senior enough to work on its own.

But that’s not good management; it’s just because the team is senior enough to self-sustain, and it’s not really growing.

[YS]: What are three core skillsets or mindsets that designers need in the uncertain post-pandemic world, especially in virtual/remote settings?


1.     Navigate by sight. In uncertain times, the most functional approach is not to try to predict too far away. It’s better to set a direction (values, principles, etc.) and then take decisions in the short term toward that direction based on the context as it changes over time.

2.     Converting techniques. A lot of facilitation, collaboration, and work techniques in design playbooks are based on in-person presence. All these techniques have good principles and with rare exceptions, they can be converted in digital, fully remote environment. Just: don’t convert them as-is. Identify what needs to be run synchronously, what can be made asynchronous, and find a better approach for digital.

3.     Presence. In physical offices it’s easy to be present: just showing up in the physical space together is enough. In a remote space, this has to be made explicit with more chatter in digital channels, socialisation calls, and other small changes here and there to create a sense of connection and presence with the team.


[YS]: What are the leadership opportunities for designers in a world where inclusion and environmental sustainability are becoming key concerns?

[EC]: This is still an area where I feel few people have already solid, good answers. My take here is that designers play a role, but unless it’s their specialisation and passion, they shouldn’t try to do dual job of also working on inclusion and sustainability.

Their duty there is to be informed, aware, and connected, and promote and elevate other leaders that are specialised in these two fields.

There’s sometimes too much arrogance, and I mean in general, not specific to design, that we can do everything, we can push everything, we can be the leaders leading every kind of change. That’s often the ego speaking, and it would be better instead to be allies, supporters, sponsors of other people’s expertise, instead of claiming that for ourselves.

I want however to be super-clear: if someone is a designer that instead *is* specialised on that, go for it. I’m just saying we don’t all need to be. We all have our talents, and sponsorships and allyship are too often disregarded.

[YS]: What are ways in which industry and academia can collaborate to improve design education? What is your involvement in this space?

[EC]: This is a major discussion that I feel I can’t exhaustively answer in a short interview. However I can mention two things: back to fundamentals and organisational dynamics.

With back to fundamentals, I mean that I see too often bootcamps and courses and even just articles that talk about UIs, stencils, visuals, and I feel there’s a lack of understanding of human factors and more structural parts of our expertise.

Sure it’s important to build the actual final step of a Material Design UI, but I feel that things like interaction design, service design, and information architecture fell further and further back. And things like cognitive psychology fell even further behind.

The outcomes are products that look nice but where the elements don’t follow proper hierarchy, behaviours are optimised per-page instead of holistically, and there’s lack of understanding of how different parts interplay together.

By organisational dynamics I mean more specifically the way businesses are run and how design works within the businesses. Even when the education is present with all the above, often work environments are radically different from the expectations that are sets for students. We need more teachings around how design can work with different roles, organisations, and ways of working.

My approach here over the years has been mostly writing, speaking, and where possible, participating in university programmes as guest professor. I won’t exclude that I’ll do more in the future as education is one of the fields that I feel the most passionate about.


[YS]: What are some daily habits of yours that you think help in strengthening your design sensibilities?

[EC]: I’m not sure if these can be really categorised as daily habits as they are more of a broad practice than anything.

One is to keep my mind open and try to find different stimuli, different approaches, different sub-cultures, different ways of seeing thing and thus, different ways for design to express.

Sometimes this could also be challenging existing solutions, but it’s really the cross-pollination here. Looking at fashion trends to day. Looking at architecture from the 1970. Looking at communications from other countries. And so on.

Another practice is to keep going back to classics. The web has an ephemerality aspect that can be overwhelming. Everything changes so fast, so quickly, that it can take all our time to just keep up. But should we?

Reviewing classics I think it’s a form of anchoring, that keeps reminding us on how certain ideas, concepts, and paradigms repeat cyclically (even if they can take different forms) – and thus today's quick waves of change stop looking that quick. Seems more something already known, remixed - thus, more manageable and more understandable.

[YS]: From your reading list, what are three good books about design you would recommend for the “non-designers” out there?

[EC]: This is a genre I’m definitely not too strong with, which might sound odd as I’ve talks that are about design for non-designers!

I’d probably still refer to the classic The Design of Everyday Things by Donald Norman. On the branding side another classic is The Brand Gap, which I feel is a very useful one even for people that don’t specialise in branding.

The question seems also specifically to be the topic of How Design Makes The World by Scott Berkun.


[YS]: What are your tips or parting words of advice for the aspiring designers in our audience?

[EC]: One major topic these days is around ethics, and how technology is embedded and impacting our societies. While I don’t think that designers alone should bear the full responsibilities of the products that are built, we surely play a role.

Sometimes just suggesting to build a slightly different interface, sponsoring an expert to join a project, getting minority voices heard could contribute to create a better world.

We know listening is important, and we should do it more and more broadly. Change comes also from small actions, and we could all strive to get these actions in our day-to-day work.

[YS]: Any other comments or remarks you would like to make?

[EC]: Just one thing: let’s support each other, give voice to each other, elevate the discipline together.

There’s still a lot of work to do, and we can all play a role.

Edited by Teja Lele