1:1 Coaching for Product Designers & Design Leaders
Transform from strong executor to strategic, visible leader with Cheryl Chepusova
This is for you if…
You're a product designer or design leader who's trusted to ship, but overlooked when it comes to visibility, influence, or what's next.
You've delivered strong work and supported your team, yet still feel like an executor when you want to be read as a strategic partner. You're done hoping the work will speak for itself.
You want guidance from someone who knows tech and design leadership from the inside, not generic career advice.
“During our time working together, I always appreciated Cheryl’s intentional and thought-provoking questions that uncovered my blind spots and elevated the quality of my designs. As an introverted designer, I also learned a great deal from how she advocated for her work with clarity and confidence — something I continue to nurture as I grow in my career.”
You've grown in complex, fast-moving environments.
You know how to navigate ambiguity, adapt to change, and deliver meaningful work. But as expectations evolve, working harder isn't always what creates new opportunities. You're looking for your next stage of growth to come from clarity, judgment, and intentional career decisions—not constant proving.
Many experienced designers reach a point where:
Their contributions are valued, but recognition often lands elsewhere
Their communication is thoughtful, but gets overlooked in high-stakes conversations
Being the reliable, go-to person hasn't changed how leadership sees their potential
They know they're capable of greater influence, but aren't sure how to make it visible
You're ready to:
Communicate with greater clarity in the moments that matter
Build a professional narrative others can advocate for when you're not in the room
Navigate promotions, reorgs, and transitions with more intention
Increase your visibility without it feeling performative
Make career decisions from intention, not reaction
This coaching creates space to think more clearly about your career, leadership, and direction with someone who understands cross-functional work, ambiguity, and growth inside fast-changing companies.
As a design leader and hiring manager, I've seen that many talented designers aren't held back by capability. They're held back by the gap between the value they create and the value others can see.
Together, we'll look beyond tactical feedback, performance review cycles, or the expectations of a single company. We'll focus on how you communicate, build trust, exercise judgment, and navigate a career in an industry that keeps changing.
The next stage of your career requires a different kind of growth
My Signature Offering
What’s Included
6 biweekly 1:1 coaching sessions (60 minutes each) across 3 months
Unlimited async support between sessions
Personalized guidance tailored to your goals, challenges, work environment, and career stage
Over 3 months, we'll work on the moments and patterns shaping your growth — stakeholder communication, visibility, career transitions, organizational dynamics, interviews, written communication, and navigating industry change with more clarity.
This is not surface-level career advice or tactical design feedback. It's help growing beyond pure execution into a more intentional relationship with your career.
This work is designed to help you grow beyond pure execution and build a more intentional, sustainable, and empowered relationship with your career.
$3000 USD
A limited number of founding client spots are currently available at $2500 USD while the program is in its early phase. If you’d like to explore whether this coaching is the right fit for you, you can book a free 30-minute Discovery Call.
Our Process
Together, we’ll identify where you’re getting stuck in visibility, communication, influence, or career direction and build the skills and clarity needed to grow.
This may include:
stakeholder communication and executive presence
positioning your work more strategically
navigating performance reviews and career transitions
strengthening confidence in high-stakes conversations
identifying patterns that keep you over-functioning or overlooked
This work is not just about becoming better at your job.
It’s about understanding your strengths more clearly, recognizing where you have room to grow, learning how businesses evaluate value, and communicating your work in ways that build trust, influence, and opportunity.
Together, we focus on helping you navigate your career with more clarity and confidence in an industry that rarely slows down.
I bring 15+ years of experience across product design, startups, publishing, and big tech, including leadership roles in growth, monetization, and activation at Slack, Pinterest, and Goodnotes.
I've worked in highly competitive environments as an introvert and outsider, navigating different cultures, industries, and expectations. I understand how easy it is for ambitious designers to become known as dependable executors while struggling to communicate the depth of their contribution, advocate for themselves, or step into larger opportunities.
Earlier in my career, I didn't always feel fluent in the language of influence. I had to learn how to speak about my work with confidence, lead without a title, and navigate competing expectations across teams and organizations.
This coaching draws on those experiences and lessons to help you grow beyond execution, communicate your value more effectively, and have a greater impact on the conversations and decisions that shape your career.
Why Work With Me
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This coaching is for experienced product designers, researchers, content designers, and design leaders who know how to do the work—and want to have greater influence on the decisions, conversations, and opportunities that shape their careers.
Many clients come in feeling overlooked despite strong performance, uncertain how to communicate their value, or looking for clarity on what's next. Together, we focus on the skills that become increasingly important as careers progress: communication, influence, judgment, and navigating change with confidence.
This is not coaching focused on craft fundamentals or breaking into the industry. It's for experienced professionals who want to grow beyond execution and take a more intentional role in shaping their career.
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Common themes include:
executive presence and stakeholder communication
visibility and influence
performance reviews and promotion conversations
communicating impact more strategically
career clarity and positioning
leadership growth
navigating burnout or over-functioning
confidence in high-stakes conversations
navigating AI-driven industry shifts and uncertainty
Each engagement is personalized to your goals and career context.
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No.
This work is not about becoming louder, more performative, or pretending to be someone you’re not.
The goal is to help you communicate with more clarity, confidence, and strategic intention in a way that feels authentic to you.
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Yes. Many clients choose to remain individual contributors while wanting greater influence, visibility, and confidence in how they communicate their ideas and value.
Leadership isn’t limited to people management. It’s also about how you build trust, influence decisions, navigate ambiguity, and contribute strategically within your organization.
Whether you’re pursuing a management path or deepening your impact as an individual contributor, the goal is the same: helping you grow your influence, communicate more effectively, and make intentional career decisions.
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Yes. I’m based in Hong Kong and work with clients around the world.
I offer flexible scheduling whenever possible and have experience working across North America, Europe, and Asia. We’ll find a time that works for both of us.
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That’s exactly what the free discovery call is for.
Our initial conversation is an opportunity to discuss where you are, what challenges you’re navigating, and what you’re hoping to achieve. Together, we’ll explore whether coaching feels like the right next step for your goals and current situation.
There’s no pressure to commit afterward. If it feels like a good fit, we can discuss next steps. If not, you’ll leave with greater clarity about where you are and what might be most helpful moving forward.
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In many cases, yes.
This coaching can often qualify as professional development, leadership coaching, or career development support. I can provide receipts/invoices for reimbursement purposes, and I’m also happy to provide a short one-pager you can share with your manager to support an internal learning & development request.