Speak Up and Stand Out: Strategic Skills for Product Designers

Cheryl Chepusova

Design Leader, ex-Slack, Pinterest

Grow from doing the work to owning your impact

AI is accelerating how quickly teams can produce work. As execution becomes easier, what differentiates senior designers isn’t output alone, it’s judgment.

The designers who grow aren’t necessarily doing more work. They’re helping others understand the decisions behind the work, influencing direction, and making their impact visible in the moments that matter.

This course is for senior product designers who consistently deliver great work but struggle to articulate their value. You may be known as reliable, collaborative, and highly capable, yet still find it difficult to communicate your thinking in stakeholder conversations, growth discussions, promotion cycles, or other career-defining moments.

Together, we’ll focus on the skills that become increasingly important as your career grows: communicating decisions, building influence, navigating ambiguity, and making strong judgment visible to the business.

This course includes:
👉 Weekly live group coaching sessions
👉 Async support on artifacts, communication, stakeholder situations, and other moments where you want feedback applying what you’re learning in practice

What you’ll learn

Move beyond execution and stand out for how you think, communicate, and shape decisions

  • Structure design reviews so conversations focus on decisions, not catching people up on context

  • Frame recommendations in ways that resonate with product, engineering, and leadership

  • Communicate your thinking clearly in high-stakes conversations, even when you don’t have time to prepare the perfect response

  • Turn 1:1s from status updates into strategic conversations

  • Share meaningful progress without constant self-promotion

  • Create lightweight visibility habits that help stakeholders understand your impact over time

  • Tailor the same recommendation for different audiences

  • Communicate design rationale using language that resonates beyond the design team

  • Build alignment by making tradeoffs and decisions easier to understand

  • Communicate impact without sounding self-promotional

  • Build a professional narrative that survives project transitions, reorganizations, and changing stakeholders

  • Become known for your judgment, not just your output

Learn directly from Cheryl

Cheryl Chepusova

Cheryl Chepusova

Staff-level designer with 15+ years leading product teams across 3 continents

Previously at
Goodnotes
Pinterest
Slack
The New York Times
Squarespace
See all products from Cheryl

Who this course is for

  • Senior product designers who ship consistently but are still seen as executors when promotions, reviews, and visibility matter

  • Designers on distributed teams who struggle to communicate judgment clearly across async updates, reviews, and reorgs.

  • Designers growing into strategic partners who want influence through strong thinking, not self-promotion.

What's included

Cheryl Chepusova

Live sessions

Learn directly from Cheryl Chepusova in a real-time, interactive format.

Community of peers

Stay accountable and share insights with like-minded professionals.

Lifetime access

Go back to course content and recordings whenever you need to.

APAC-friendly timing

This course is uniquely timed so designers in Asia timezones can fully participate in live sessions — no more joining past midnight or missing out.

Maven Guarantee

Your purchase is backed by the Maven Guarantee.

Course syllabus

4 live sessions • 5 projects

Week 1

Jun 2—Jun 7

    Conveying Decisions & Thinking

    • Jun

      2

      Communicating Design Decisions with Conviction

      Tue 6/22:00 PM—3:00 PM (UTC)
    2 more items

    Cross-Functional Framing

    • Jun

      4

      Lead Cross-Functional Conversations with Clarity

      Thu 6/42:00 PM—3:00 PM (UTC)
    1 more item

Week 2

Jun 8—Jun 14

    Strategic Visibility in Practice

    • Jun

      9

      Make Your Work Visible Every Week

      Tue 6/92:00 PM—3:00 PM (UTC)
    1 more item

    Defining and Articulating Your Design Career

    • Jun

      11

      What People Trust You For

      Thu 6/112:00 PM—3:00 PM (UTC)
    1 more item

Schedule

Live sessions

4 hrs

Come prepared to unpack why communicating your work is hard, practice clearer ways to speak about decisions and taste, and stand out with strategic impact while learning directly from other product designers in the room.

    • Tue, Jun 2

      2:00 PM—3:00 PM (UTC)

    • Thu, Jun 4

      2:00 PM—3:00 PM (UTC)

    • Tue, Jun 9

      2:00 PM—3:00 PM (UTC)

    • Thu, Jun 11

      2:00 PM—3:00 PM (UTC)

Frequently asked questions

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Reimbursement

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Private cohort

Run a cohort for your org

A dedicated cohort with a custom schedule and curriculum, tailored to your team.

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