Anna Chekryshova🇪🇪

About Anna Chekryshova

EMEA Customer Success Lead at Wise

I’m Anna, Senior Operations Manager with 8+ years scaling fintech and enterprise operations across EMEA and global teams. Proven track record building teams and frameworks from scratch, driving cross-functional transformation, and delivering measurable outcomes.

My background covers fintech (Wise) and shipping (CMA CGM), where I’ve supported enterprise level clients and built international teams.

I mentor people who are: • moving from individual contributor to leadership and need to learn how to lead team for the performance • building customer success functions in growing companies, • balancing team performance with personal well-being.

My style is warm, practical, and supportive, and though I'm able to wear many hats at work, I believe leadership should feel human, not corporate.

Expertise

Sessions with Anna Chekryshova

• Leadership Mentoring Session - Discovery (Free) (30 min): Leadership Mentoring Discovery Call Curious about leadership mentoring but unsure if it's the right fit for you? This complimentary introductory call is an opportunity for us to get to know each other, discuss your current challenges and goals, and explore how personalized leadership mentoring could support your growth. During this conversation, we'll: Discuss your current role, career aspirations, and leadership challenges Identify areas where additional support, guidance, or accountability may be valuable Explore your leadership development goals Review how a tailored mentoring program could help you achieve them Answer any questions you may have about the mentoring process This is a conversation, not a full coaching or consulting session. The goal is to determine whether we're a good fit to work together and whether leadership mentoring aligns with your needs. If there is a mutual fit, I'll share recommendations for next steps and available mentoring options. Who this is for: New and aspiring managers Team leads and people managers Customer Success, Operations, and Service leaders Professionals preparing for leadership roles Leaders navigating growth, change, or complex team challenges Duration: 20–30 minutes Format: Online video call
• Mentoring CSM for growth and development (30 min): This is introductory session crafted specifically for Customer Success Managers navigating the complexities of their roles. This interactive discussion will provide a welcoming space to delve into the challenges you encounter daily. I encourage you to prepare a specific scenario or struggle to share ahead of time, enabling us to tailor our conversation to your unique needs and maximize the value of our time together. We will collaboratively brainstorm actionable solutions and best practices that you can apply in your work. This session is designed to create a supportive and open environment where you can gain clarity and confidence in tackling obstacles. By the end of our time together, you will leave with practical insights that enhance your growth as a Customer Success Manager.
• Transition to Customer Success (30 min): The session focused on the transition into customer success. We will explore your existing experiences which can be applicable, how to frame the experience during the interview and strategies of getting additional experience if/when needed.

What mentees say

“Anna was highly analytical , had broke down everything in as much detail possible and gave quiet a constructive session for me to land in a role . Absolutely can go ahead with next session if required”

“What a focused and genuinely eye-opening session! My biggest takeaway was understanding that my current selling point - technical savviness - may be working against me. Anna helped me see how to position myself by linking my technical expertise to commercial impact.”

“It was lovely speaking with Anna. She shared clear insights on how customer success connects with product and offered practical advice I can use as I prepare for roles in fintech. Her openness about her journey at Wise made the session engaging and valuable.”