1:1 Coaching for Creatives in Tech
Transform from strong executor to strategic, visible leader with Cheryl Chepusova
This is for you if…
You’re a high-performing creative in tech who feels stuck between strong execution and strategic influence.
You’ve built strong skills, delivered great work, and consistently supported your team, but still feel overlooked when it comes to visibility, leadership, or career growth.
You’re done with hoping your work will speak for itself.
You want experienced guidance from someone who understands the realities of working in tech and design.
“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 spent years adapting to shifting expectations, high-performance environments, and constantly moving goalposts — and you want to approach your next stage of growth with more intention and agency.
You’re tired of feeling like:
you’re seen as an executor instead of a thought partner
other people are getting credit or recognition you’ve earned
you have to constantly prove your value
quieter communication styles are overlooked in fast-moving environments
You may have tried:
working harder
becoming more helpful and the “go-to person” on the team
focusing on craft and hoping it would speak for itself
relying on performance reviews or manager feedback to guide your growth
trying to be versatile enough to fit every role instead of developing a clearer point of view or area of expertise
You’re starting to realize that constantly chasing the next level, title, or approval doesn’t automatically create clarity, confidence, or a sustainable relationship with work. Especially in an industry where the expectations and goalposts keep shifting.
You’re ready to:
articulate your thinking with more clarity and confidence
feel more grounded and confident in how you show up
stop second-guessing yourself in important conversations
build a clearer professional identity and direction
make career decisions from clarity instead of reactivity
This coaching offers the kind of guidance that’s often missing inside day-to-day work environments: space to think more deeply about your career, leadership, and long-term direction with someone who understands the realities of working across teams, navigating ambiguity, and growing inside fast-changing tech environments.
Many high-performing creatives are not lacking capability — they’re lacking the support, perspective, and self-trust needed to grow into the next stage of their career.
As a design leader and hiring manager, I bring perspective beyond tactical design feedback or company-specific performance reviews. I help clients think more broadly about how they communicate, make decisions, build trust, and navigate an industry where expectations, workflows, and roles continue to evolve.
My role is not to evaluate your performance, but to support your growth.
Through our 1:1 work together, I can help you…
articulate your thinking with more clarity and conviction
feel more grounded in your perspective and decisions
strengthen stakeholder communication and executive presence
develop a stronger sense of direction and long-term fit
approach promotions, reorgs, and career transitions with more confidence
stop feeling like you have to constantly prove you belong at the next level
adapt to industry change without losing your sense of direction
take more ownership over your career decisions and long-term growth
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 the course of 3 months, we’ll work together on the moments, patterns, and decisions shaping your career growth — including stakeholder communication, leadership presence, visibility, confidence, career transitions, organizational dynamics, interviews, written communication, and navigating an increasingly fast-changing industry with more clarity and self-trust.
This is not surface-level career advice or tactical design feedback.
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 focused on growth, monetization, and AI-driven products.
Throughout my career, I’ve worked across highly competitive environments as an introvert, immigrant, and outsider navigating different cultures, industries, and expectations. I understand firsthand how easy it is for high-performing creatives to become known for being reliable and capable, while quietly struggling to advocate for themselves, communicate the depth of their contribution, or fully 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 advocate for my work, lead without a title, and navigate different expectations across teams. This coaching brings together the tools, mindset shifts, and strategic lessons that helped me grow beyond execution and become a more impactful design partner — so you can do the same.
Why Work With Me
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This coaching is designed for ambitious creatives in tech — especially product designers, UX researchers, content designers, and other cross-functional creatives who are already strong at execution, but want to grow into greater visibility, influence, and strategic leadership.
This is not early career design coaching focused on craft fundamentals or breaking into the industry. It’s for experienced creatives who already know how to do the work, but are realizing that career growth now depends on communication, influence, stakeholder trust, and strategic presence.
Many clients come in feeling overlooked, unclear on how to communicate their value, or unsure how to grow in a rapidly changing industry where execution alone is no longer enough.
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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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Not necessarily.
Many clients want to remain individual contributors while becoming more strategically influential, visible, and confident in how they communicate their value.
Leadership is not just about managing people — it’s also about influence, communication, and strategic presence.
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Yes.
I’m based in Hong Kong and work with clients globally across multiple time zones. Having lived and worked across Hong Kong, Toronto, New York, and San Francisco, I bring a global perspective shaped by experience across continents and cross-cultural work environments.
I offer flexible scheduling options to support clients in different regions whenever possible.
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That’s exactly what the discovery call is for.
The initial call is a chance for us to explore:
where you’re feeling stuck
what kind of growth or support you’re looking for
whether this coaching feels aligned for your goals and current season
There’s no pressure or expectation to commit afterward.
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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.