Finding Your Product’s Level of Readiness and Manifesting Design systems (w/ Keenan Cummings, Airbnb)

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Episode #26: Keenan Cummings

Our guest today is the inspiring Keenan Cummings, Team Leader at Airbnb and former Co-founder/Creative Director of Days (acquired by Yahoo!) and the Designers Debate Club.

Keenan started his career as a designer in NYC, working in brand agencies and doing print work, where he landed what he thought would be a dream project, redesigning and rebranding the Chicago Cubs. However Keenan felt that there were bigger problems he wanted to dive in to, so he made the transition into digital design. He co-founded Days app, and then found his path into product design eventually joining Airbnb, where he led the development of their design systems and leads an extraordinary team.

Today, Keenan is also working on a side project called Curiosity Club, a group for experienced creatives to learn new skills together.

In this episode, Keenan shared with us why he believes that investing in design systems and investing in your team, not only pays-off, but it is a must.

This is the first episode of the third season of the Hacking UI podcast, ‘Scaling a Career’. In this season we have 10 amazing guests for you, who are leaders and influencers from a variety of different backgrounds. Design managers, development leaders, entrepreneurs and product geniuses that we admire.

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Key points from this episode:

  • Learn all about Keenan’s starting point as a designer, rebranding the Chicago Cubs and how he transitioned into Product Design. [00:04:05]
  • Keenan shares about the process of building Design systems and developing a winning team. [00:09:10]
  • Learn how the team was built, and how it developed and pushed Airbnb’s design language specifically around product and user experience. [00:12:14]
  • Learn how Airbnb was built on trust and how the company makes decisions around that. [00:14:00]
  • Learn all about readiness – how to quantify if the user is ready for that magic moment? [00:16:43]
  • Find out how user research is the most powerful way, to get the wheels rolling for that readiness. [00:19:47]
  • Keenan discusses how to expand a growth team, and questions that need to be asked about user experience. [00:23:46]
  • Let’s get technical – all about the technologies used in Airbnb’s design systems and how to keep all the elements in sync across the company. [00:27:52]
  • Keenan shares his secrets on how to build a successful design system and the technical/design debt that needs to be paid. [00:32:53]
  • Understand how to decide on what components need to be worked on inside the company, and how tieing an exercise to a concrete problem leads to great solutions. [00:35:42]
  • Learn how the team at Airbnb is collaborating all together and how the team became more sophisticated around research, experience and forward thinking. [00:37:14]
  • Find out what deliverables the user research side bring into the product design process. [00:39:20]
  • Understand how do product designers work and how they influence on strategic decisions inside a company. [00:40:05]
  • Keenen shares inside secrets on how to pitch ideas of a problem to the team, and how to turn a problem – to an opportunity. [00:42:25]
  • Learn why investing in a design system is important almost in every stage, from brand guidelines to a full design language system. [00:46:27]
  • Keenan shares his thoughts on perceived risk and perceived value and how we can benefit from it in the long term. [00:47:38]

About The Hacking UI Podcast

The Hacking UI podcast is hosted by Sagi Shrieber and David Tintner, a designer and developer who are also both entrepreneurs, bloggers, productivity/time-hacking maniacs, and all around tech geeks.

We are thrilled to launch the third season of the Hacking UI podcast, where we hack our way through product design, development, and creative entrepreneurship.

Our first season, was called ‘Scaling a Design Team’, the Second season was called ‘Scaling a Side Project’ and we’ve decided to call this season – ‘Scaling a Career’.

In this season we have 10 amazing guests for you, who are leaders and influencers from a variety of different backgrounds.
We have design managers, development leaders, entrepreneurs and product geniuses.

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