Cheryl Chepusova

Cheryl Chepusova

365 Subscribers

Product design leader | ex-Slack, Pinterest, Goodnotes; growth & AI products

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Cheryl Chepusova helps designers turn taste into influence

I’m a product design leader with 15+ years across startups and global tech, including roles at Slack, Pinterest, Goodnotes, Squarespace, and The New York Times. I’ve worked across North America and Asia, leading product teams to ship in complex, high-pressure environments.

I help senior product designers make strong work easier to see — in reviews, with stakeholders, and in the moments that decide what happens next. I teach practical tools you can use on real work the same week, so your judgment is easier for the room to trust.

Previously at
Goodnotes
Pinterest
Slack
The New York Times
Squarespace

Lightning Lessons

Free, interactive sessions to explore new topics

Alumni reviews

May

Live cohort
I absolutely loved Cheryl’s course! I joined because I really related to the idea of being an introverted designer. I’m often focused only on producing quality output, but I realised that even the best work can only speak for itself to a certain extent. Without the right communication and visibility, it was hard for the wider team to understand my contributions or impact. As a result, I struggled with a lot of imposter syndrome at work. What I appreciated most about this course was how practical and immediately applicable it was. Her online videos were packed with a lot of concrete, bite-sized actionables that I could bring to my day-to-day work. Cheryl covered topics like building visibility, navigating cross-functional relationships, and building a reputation for myself, all things I did not know how to approach. The live coaching sessions were also especially valuable. Cheryl often challenged our thinking with thoughtful questions, which pushed us to be more intentional and reflective designers. The feedback was also very tailored to each of our individual concerns! I’m now more equipped with practical tools that I can try and a more clearer understanding of how I can advocate for my work and communicate my impact. Thank you Cheryl!!!

Joy

Live cohort
Cheryl is like the big sister you always wanted in the design world. She’s genuine and strategic when discussing design concepts.  This course shares practical tools and tips on how to communicate your design values and decisions even in a fast paced environment. Also, the live coaching sessions foster a supportive and open environment to ask any questions you may struggle with. I would recommend it to any designer who is ready to level up their communication skills.

Jonathan

Live cohort
I highly recommend this course if you're a designer looking for a course to level-up your communication! Cheryl is a stellar instructor. I appreciate her willingness to listen and provide detailed frameworks that tackle the situations students face.

Esteban

Live cohort
Lead Product Designer · WebMD Health Services

Speak Up and Stand Out: Strategic Skills for Product Designers

Highly recommend this course for anyone looking to communicate with more clarity and influence. Cheryl brought concepts to life through real examples and tailored feedback, making the sessions both practical and immediately applicable. The biggest takeaway for me was leaving with concrete tools and habits that I could start using right away in my daily work.

Nadia

Live cohort
I left feeling like I had a concrete understanding of how I can speak up and make my work more visible. Cheryl gave us specific examples and knowledge in a structured way and gave us space to ask questions that pertain to our own situations.