Work with Leanna
About
I’m a PCC-certified Executive Coach and former tech executive who helps high achieving women lead with greater confidence, authenticity, and impact. My clients have earned promotions, negotiated significant salary increases, stepped into executive roles, and created careers and lives that feel more aligned with who they are and what matters to them. Whether you’re navigating a career or life transition, pursuing an ambitious goal, or realizing that the way you’ve always worked isn’t working anymore, I’ll help you get clear on what you want and move forward with intention. I bring five years of professional coaching experience, a master’s degree in educational leadership, and 12+ years as an executive leader in the tech startup world. My work centers on self-leadership: understanding yourself, trusting your judgment, and choosing how you want to show up so you can lead others more effectively. I especially enjoy working with high achieving women, working moms, and Customer Success executives. My coaching areas include: ✨ CONFIDENCE & AUTHENTIC LEADERSHIP Move from second-guessing yourself to trusting your judgment, speaking with confidence, and leading as yourself. I’ve helped accomplished women rebuild confidence after career setbacks, prepare for tough CEO and board conversations, and step into leadership roles with greater responsibility and impact. 🧭 CAREER & LIFE TRANSITIONS When the way you’ve always worked no longer fits, discover what will support your next chapter. Drawing on my experience navigating startup growth, mergers and acquisitions, and becoming a mother while serving as a tech executive, I help you clarify what you want and move toward it. My clients have navigated promotions, motherhood, and career changes—including leaving unhealthy work environments and creating more aligned opportunities where they’re thriving. 🎯 CLARITY, ALIGNMENT & GOALS Move from feeling stuck or pulled by others’ expectations to making intentional decisions and pursuing goals that matter to you. Together, we’ll define your version of success and turn it into action. My clients have earned promotions, created more aligned career opportunities, and advocated for their value—including one executive who negotiated a salary increase from $350,000 to $425,000. 🌿 WORK-LIFE BALANCE & BOUNDARIES Build a relationship with work that supports your ambitions while making room for your health, relationships, and life outside your career. As a recovering perfectionist and workaholic, I understand how difficult it can feel to change these patterns. I’ve helped clients reduce overworking, protect time for themselves, and leave work at work—including a director and mother of three who began prioritizing her health while also earning the promotion she wanted. 💬 STRENGTHENING RELATIONSHIPS Communicate more clearly, navigate difficult interactions, and make intentional space for the relationships that matter most. With 12+ years of executive leadership experience, I understand the stakes of challenging workplace relationships. I’ve helped clients navigate difficult bosses and sensitive executive conversations, while also protecting time and energy for their partners and families. Our work can help you set boundaries, be more present, and invest in your most important relationships at work and at home. 💼 CUSTOMER SUCCESS LEADERSHIP Grow your confidence and effectiveness as a CS leader with a partner who understands the demands of the role. As a former VP of Customer Success who built teams from the ground up and led through growth and M&A, I combine executive coaching with mentorship and practical perspective. I’ve supported Heads and VPs of CS as a coach, mentor, advisor, and sounding board, tailoring our work to their goals—from navigating team challenges to strengthening their influence as executives.
Leanna also coaches for Executive Coaching and Leadership Coaching. View all.
Leanna’s Customer Success Qualifications
Coaches professionally
Experience level: Director
Welcome to my profile! With over a decade of experience in customer success leadership, I specialize in coaching leaders to unlock their full potential. As a former Vice President of Customer Success at high-growth startups like Ready Education, OrgSync, and Campus Labs, I have a proven track record of driving significant improvements in renewal rates and upsell revenue (97%+ GRR, 120%+ NRR). My journey from building a customer success team from the ground up at OrgSync to leading successful mergers & acquisitions has equipped me with the insights and strategies to help you excel in your career. Whether you're looking to enhance your leadership skills or navigate complex organizational changes, I'm here to guide you every step of the way. Let's connect and create a tailored plan for your success!
Leanna can help with:
Customer Feedback Analysis
Customer Onboarding
Customer Relationship Management
Customer Retention
Customer Satisfaction
Customer Success Strategy
Interview Prep
Promotion Strategy
Salary Negotiation
Why do I coach?
Helping leaders see what they’re capable of and grow into their potential has been the thread running through my entire 20+ year career. I started as an advisor to student leaders at colleges and universities. Later, while building my first company, I coached individual contributors into management and managers into director roles. Those were the moments I loved the most: watching someone begin to trust themselves, take on a challenge they didn't think they could handle, and discover what they're capable of. I pursued my coaching certification because I wanted to make that work my full-time focus. Helping people succeed has always been my passion, and it's what I'm really good at. What I want you to know is this: you don’t have to arrive feeling confident or knowing exactly how to move forward. I believe in your capacity to create a future you’re excited about, even when you’re struggling to see it yourself. As your vision takes shape, I’ll hold it with you and help you keep sight of it when doubt, fear, or the demands of everyday life make it feel impossible. I bring the experience of building a company, developing leaders, and coaching people through consequential changes in their careers and lives. I know how to help you turn reflection into decisions and decisions into action. I’ll bring curiosity when you’re judging yourself, challenge you when you’re underestimating yourself, and provide steady encouragement as you try something new. I coach because I love seeing people recognize their own strength and use it to create lives and careers that matter to them. I want that for you, and I’m deeply invested in helping you get there.
Work Experience

Vice President of Customer Success
Ready Education
October 2018 - December 2020
Hiring Manager
As the first post-Series A executive hire, I was responsible for leading the Customer Success organization including Account Management, Support, Technical Project Management, Customer Onboarding, and Training. During my tenure at this high growth startup, we significantly increased our renewal rates and upsell revenue while successfully merging two companies and laying the foundation for future rapid inorganic growth.

CEO/Executive Coach/Consultant
Independent Coach
October 2017 - Present
Hiring Manager
I coach leaders to achieve their full potential, especially Executive Moms and Customer Success leaders.
Vice President of Customer Success
Campus Labs
January 2016 - September 2017
Hiring Manager
OrgSync joined Campus Labs in January 2016. Served as head of the office and was responsible for all employees, operations, and communications at the Dallas location. Collaborated with executive leadership to create and implement change management initiatives and provide leadership through the merger of the two companies.

Vice President of Customer Success
OrgSync
June 2008 - January 2016
Hiring Manager
Joined this early stage ed tech startup and helped build and lead the company to a successful exit. Bootstrapped the company out of a house in Austin, TX with just a few employees. Relocated the company to Dallas, TX in 2010. Founded and built the Customer Success team from the ground up, including recruiting, hiring, onboarding, and leading a team of highly talented individuals. Responsible for implementation, training, customer relations, consulting, renewals, add-on sales, tech support, professional services, and account management, resulting in a fanatically loyal customer base with a consistent 97%+ gross retention rate, negative net churn (-5-15%), and consistently exceeded expansion sales targets. Serving as a member of the company's Leadership Team, we built and grew the company to 50+ employees and 450+ customers and were acquired by Leeds Equity in 2015. Leeds later acquired Campus Labs and merged the two companies in 2016.

Student Leadership Advisor
Johnson & Wales University
August 2007 - June 2008
Interviewer

Resident Services Coordinator & FSL Advisor
San Jose State University
August 2005 - August 2007
Hiring Manager

Banquet Server
Marriott International
June 2004 - August 2005
Education
Corporate Sponsored Coach Training
ACTP, Executive & Life Coaching
2017 - 2017

Cox School of Business
Certificates in Leadership & Entrepreneurship
2017 - 2017

San Jose State University
Master of Arts, Educational Leadership
2005 - 2006

West Virginia Wesleyan College
Bachelor of Arts, Psychology, Math
2001 - 2005
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Leanna also coaches for Executive Coaching and Leadership Coaching. View all.
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