Wind + Sail was born out of a question…
How do we scale the transformational change that develops through individual coaching to communities of leaders in organizations?
When leaders learn and grow together, they positively shift together, creating waves with organizational reach
In 2018, we began working on offerings that answered this call. Knowing that true leadership is as much about being as it is about doing, we set out to create unique leadership development experiences that put people to work building the skills of leadership—the hard and soft. Both types of skills are teachable, learnable and necessary. Our results prove it.
oUR FOUNDERS
Katrina Calihan
PCC, MAPP, Partner
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Education & Training
MA of Applied Positive Psychology (MAPP), University of Pennsylvania
Certificate in Executive Coaching, Georgetown University Institute for Transformational Leadership
BA of Business, Gonzaga University
Certifications
Professional Certified Coach (PCC) designation through the International Coach Federation
Leadership Circle Profile, iEQ9 Enneagram, Hogan, and MBTI assessments
Experience & Approach
Katrina partners with senior leaders to unlock their highest potential and expand what's possible. As Co-Founding Partner at Wind + Sail, she has established and grown the business with the mission to create communities of evolved, mindful, skillful leaders.
An executive coach with over 20 years of experience in leadership development and talent strategy, Katrina has guided thousands of leaders through 1:1 coaching and transformational learning programs. She coaches executive teams, expertly facilitates leadership programs, and delivers keynotes around the world. Her practice focuses on executives in private equity, technology, industrials, professional and financial services, and nonprofits. She brings research-backed strategies, powerful intuition, and a sophisticated developmental lens to her work, helping clients surface the root dynamics beneath presenting challenges and design rigorous action plans to catalyze lasting growth.
Previously, Katrina served senior roles at Bain & Company, leading talent for one of the firm's largest global offices and driving leadership development and training initiatives worldwide. Katrina lives in Chicago with her husband and rescue pup. She's an endurance cyclist, guitar player, and avid world traveler - always planning the next big adventure.
Amanda Mills Cutright
PCC, Partner
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Education & Training
Certificate in Executive Coaching, Georgetown University
BA in Corporate Communications, The University of Kentucky
Mindfulness-Based Stress Reduction, Brown University Center for Mindfulness
Embodied Transformation, Strozzi Institute for Somatics
Certifications
Professional Certified Coach (PCC) designation through the International Coach Federation
Leadership Circle Profile, Enneagram iEQ9, Hogan, and EQ-I Emotional Intelligence assessments
Experience & Approach
Amanda is an executive coach, facilitator, and keynote speaker who works with leaders navigating growth and complexity. As Co-Founding Partner of Wind + Sail, she has grown the firm with the mission to create communities of evolved, mindful, skillful leaders.
Known for her steady presence and strategic lens, Amanda partners with executives across the investment spectrum in multiple industries, professional services, and non-profit leaders and boards. Her approach lives at the intersection of behavioral science, systems thinking, and her powerful intuition. Clients describe Amanda as unwavering in her belief in others’ potential and rigorous in her accountability. She challenges and champions in equal measure-helping leaders illuminate patterns shaping their results and shift them at the source.
Before Wind + Sail, Amanda served as Vice President of Executive Learning at Teach For America. In this role she led a national team to construct a framework for executive development and facilitate immersive learning experiences fueling a period of rapid, national expansion. Amanda began her career as a Teach For America corps member teaching 5th grade in St. Louis. She lives in Washington, DC with her husband and loves keeping up with their 3 children.
OUR TEAM
Kyle Ali
Program Leader
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Education
MBA, Baylor University
Bachelor of Journalism in Strategic Communication, University of Missouri
BA in Political Science, University of Missouri
Certifications
Negotiation for Professionals, Northwestern University School of Professional Studies
Experience & approach
Kyle Ali advocates for equal educational and workforce opportunities and invests, inspires, and empowers diverse leaders to pursue and achieve transformational outcomes.
Throughout his career, Kyle has excelled as an identifier, cultivator, and developer of talent. His coaching is informed by nearly a decade of shaping team cultures and strategies in academic, non-profit, and corporate settings. At Google, he has led multiple efforts to redefine organizational values and established himself as a trusted advisor through regular collaboration with senior leaders on inclusion-focused initiatives. In his local business community, Kyle advises underrepresented professionals on interest-based negotiation strategies through local workshops and has been a featured facilitator on the topic at SXSW. His coaching extends beyond the workplace to the classroom where he teaches Human Resource Development graduate students at Villanova University.
Kyle is an avid cyclist, dog lover, and diehard Arsenal supporter. He, his wife, daughter, son, and dog, Pickles, reside near Austin, Texas where he is actively engaged in several civic pursuits that support youth of color. In recognition of his leadership, Kyle was recognized by the 2024 Austin Under 40 Awards in the Youth and Education category.
Tai Dixon Darden
Executive Coach
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Education & Training
Certificate in Strategic Human Resources Leadership, Cornell University
JD, Howard University School of Law
MEd in Curriculum Planning and Design, University of St. Thomas
BA in English (Pre-Law), Spelman College
Certifications
Professional Coaching Certification through the Center for Coaching Certification
Trained facilitator in Overturning Immunity to Change through Minds at Work
Certificate in Strategic Human Resources Leadership through Cornell University
Certified Leadership Circle Profile Coach and Collective Leadership Assessment Coach through The Leadership Circle
Certified Enneagram Spectrum Practitioner
Experience & Approach
Tai Dixon Darden is an Executive Coach, C-Suite Advisor, and Workplace Culture Strategist. She works with individual leaders and full leadership teams to develop strong adaptive management practices, effective communication, conflict resolution skills, foster authentic connection, and strong change management.
Tai brings over two decades of experience as a teacher, corporate defense attorney, law professor, and seasoned non-profit executive to her coaching and consulting practice. Previous roles have included Chief Talent and Equity Officer, National Head of State Offices and Field Operations, Managing Director of Development, Managing Director of National Talent Acquisition, and Managing Director of Executive Recruitment. Tai’s coaching style focuses on the deeper drivers of leadership challenges like mindset, relationships, conflict, assumptions and organizational systems. She works with leaders who are ready to move beyond quick fixes and engage in meaningful sustainable growth, have crucial conversations, or make bold changes to their leadership approach.
Tai is a mother of 1 son and a bonus mom of 4 adult daughters. Outside of work, Tai spends time outdoors with her family, traveling with her husband, hosting gatherings, collecting eclectic jewelry and art, singing karaoke, and trying new recipes at home.
John Galvin
Executive Coach
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Education & Training
Certificate in Executive Coaching, Hudson Institute
Certificate in Team Coaching, Team Coaching International
Certificate in Coach Supervision, Crucial Differences UK
Stanford University Executive Program
BA in Comparative Literature, Cal State Long Beach
Certifications
Professional Certified Coach (PCC) designation and Senior Team Coaching Practitioner through the International Coach Federation
Senior Practitioner, European Mentoring and Coaching Council
Leadership Circle Profile, Hogan, and 6 Team Conditions assessments
Experience & Approach
John partners with leaders and leadership teams to clarify their stance, navigate complexity, and design lasting solutions that improve performance, engagement, and results. He brings curiosity, courage, and strong intuition to his coaching, creating a trusted relational presence that supports meaningful and sustained change.
With more than 30 years of experience as a strategist, executive coach, and advisor, John has coached hundreds of leaders and leadership teams across industries including technology, finance, and banking, working with organizations ranging from large global enterprises to later-stage startups. He also brings 22 years of operating experience from Intel, where he served in senior leadership roles, most recently as Vice President and General Manager of the Education and Public Sector business. His background includes leading global teams and initiatives, navigating complex stakeholder environments, and deep experience in marketing and go-to-market strategy.
John is on the faculty of the Hudson Institute of Coaching and is a certified coach supervisor. He is known for coaching the whole person and for his blend of warmth, courage, and engagement, balancing support with challenge. John is based in Santa Barbara and splits his time between there and the Lake Tahoe area with his wife and their Australian Shepherd. They have two sons, one living on the Oregon coast and the other at the University of Maryland.
Carli Gribov
Executive Coach & Program Leader
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Education & Training
MA in Education, University of St. Thomas
Certificate in Leadership Coaching, Co-Active Training Institute
BA in Psychology, University of Michigan
Certifications
Professional Certified Coach (PCC) designation through the International Coach Federation
Leadership Circle Profile, iEQ9 Enneagram, and Hogan assessments
Experience & Approach
Carli Gribov is a leadership coach, facilitator, and trainer who partners with executives and senior leaders to catalyze meaningful impact. Her practical, research-based, and catalytic approach is shaped by decades of experience and a deep belief in leadership as a vehicle for transformation.
Carli has coached hundreds of leaders across the public, nonprofit, and private sectors, with a particular focus on high-achieving leaders and those navigating complex change. Prior to working as an executive coach and facilitator, her career sat at the intersection of operations and leadership development. Most recently, she served as Head of People at a private equity real estate startup during a time of tremendous growth. Prior to that, she spent more than a decade leading teams in social impact organizations, including as Managing Director of Recruitment at Teach For America, where she also developed and facilitated Teach For America Chicago's signature Values-Based Leadership Development Program. Carli began her career as a 5th-grade science teacher in Houston, TX through Teach For America. The values of collaboration, hard work, and impact that were solidified in the classroom still inform her work today.
Carli lives in Chicago with her three kids and her Golden Retriever, Luna. When she’s not coaching, she loves to read, play strategy board games, and hike - she’s visited nearly three-quarters of the U.S. National Parks!
Kelly Harris Perin
Executive Coach & Program Leader
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Education & Training
MA in Higher Education Policy, University of Maryland
Coach Training, Coaching Out of the Box
BA in History, Northwestern University
Certifications
Associate Certified Coach (ACC) designation through the International Coach Federation, PCC pending
Design Your Life, certified coach
StrengthsFinder, Immunity to Change, and Positive Intelligence trained facilitator
Leadership Circle Profile and MBTI assessments
Experience & Approach
Kelly Harris Perin has devoted her career to helping individuals and teams work better, feel better, and increase impact in their work and the world. She is an expert in healthy productivity, transitions, and 360 feedback.
Kelly began her career as a middle school teacher, then spent a decade leading teams and complex initiatives in a rapidly scaling nonprofit. Her diverse experience spanned adult learning and evaluation for new hires through senior executives, large-scale project management, and intensive 1:1 coaching to help new senior leaders start strong in high-stakes roles. Today, Kelly partners with a wide variety of organizations across industries to coach executives, facilitate transformative learning experiences, and evaluate senior leaders. Kelly’s sweet spot is where big questions and leadership capability meet day-to-day execution. A coaching session might find you charting your 10-year course, testing a decision-making framework, auditing your calendar, or prepping for a high-stakes conversation- anything that helps you level up your leadership in a way that feels authentic and sustainable to you.
Kelly is based in Durham, NC, where she’s currently practicing lots of yoga and Spanish, taggling along with her 3 kids on their adventures near and far, and running a pro bono coaching project.
Caroline Kim Oh
Executive Coach
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Education & Training
MA of Public Administration, New York University
BA, Cornell University
Certifications
Professional Certified Coach (PCC) designation through the International Coach Federation
Certified Professional Co-Active Coach (CPCC), Co-Active Training Institute
Leadership Circle Profile, Hogan, and DiSC assessments
Experience & Approach
Caroline Kim Oh is an executive and leadership coach who guides leaders as they navigate critical transitions, high-stakes decisions, and complex challenges. Her clients lead across diverse fields, including social impact, marketing, creativity, entrepreneurship, private equity portfolios, and technology.
Caroline also advises senior leadership teams, facilitates team retreats, and leads peer coaching groups for CEOs and women executives. Her focus areas include leading with strengths, building confidence, managing reactive tendencies, influencing without authority, creating positive team culture, and energy management.
Prior to coaching, Caroline served as President of iMentor, a youth mentoring organization, for thirteen years. During her tenure, she led the organization through national expansion—from a tiny startup to serving 5,000 young people with an annual budget of $10 million—while diversifying funding streams, building a senior leadership team, and guiding board development.
Caroline lives and works in New York and enjoys leisurely meals with friends and family, especially with her two children, suddenly taller and smarter than their mother.
Sharon Krohn
Executive Coach & Program Leader
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Education & Training
Certificate in Executive Coaching, Georgetown University
Certificate in Executive Facilitation, Georgetown University
MA in Communications, New York University
BA, Bar Ilan University
Faculty
Georgetown University Institute for Transformational Leadership
Spertus Institute
Certifications
Master Certified Coach (MCC) designation through the International Coach Federation
Leadership Circle Profile, Emotional Intelligence EQ-I 2.0/ EQ360, iEQ9 Enneagram, DiSC, and Hogan assessments
Search Inside Yourself
TOP Facilitation, Strategic Planning & Consensus Building
Five Behaviors of a Cohesive Team Facilitator
Experience & Approach
Sharon Krohn is an accomplished Executive Coach and Facilitator with over 20 years of experience in executive leadership, organizational consulting, and leadership coaching. She trained as a Leadership Coach and Executive Facilitator at the Georgetown University Institute for Transformational Leadership, where she currently serves as a member of the Adjunct Faculty as a Coach Assessor. As a Master Certified Coach (MCC), the highest credential from the International Coach Federation, Sharon brings a wealth of expertise to her practice.
Her background includes significant roles in executive leadership, including serving as CHRO for a Commercial Real Estate Company, and as President and Board Member for several not-for-profits and trade organizations. Sharon specializes in helping leaders clarify their priorities and objectives, enabling them to achieve their envisioned futures. She supports clients in developing strategic goals and taking actionable steps for progress. Sharon serves as a thought partner, challenger, and accountability buddy. Her clients value her ability to foster trusting relationships and create a safe environment for reflection and growth.
Outside of her professional pursuits, Sharon is an avid traveler who has explored 104 countries, seamlessly blending work with pleasure in her cultural adventures worldwide.
Ann O’Connor
Executive Coach
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Education & Training
MS in Positive Organization Development & Change, Case Western Reserve University
Certificate in Executive Coaching, Hudson Institute of Coaching
Accredited Diploma, Coaching Supervision, Coaching Supervision Academy, LTD UK
Certifications
Master Certified Coach (MCC) designation through the International Coach Federation
Leadership Circle Profile, EQ-I 2.0, and MBTI assessments
Certificate in Emotionally Intelligent Leadership & Executive Coaching
Experience & Approach
Ann O’Connor serves as an Executive and Leadership Development Coach. Ann’s work with leaders focuses on emotional intelligence, communication skills, global collaborations, balancing relationships with business results, and navigating complex professional roles. She also facilitates group programs utilizing Appreciative Inquiry as a positive approach to leadership, organizational change, strategic innovation, and alignment.
Over her 25 years in leadership roles and 20 years of leadership development coaching, Ann has worked, collaborated, and coached individuals and teams in various industries including healthcare, manufacturing, financial consulting, technology, legal services, and non-profits. Her previous roles have included Vice President of Strategic Business Units, Vice President of Sales, and National Accounts and Sales Development Manager.
Ann is an avid cyclist, a dedicated volunteer at a local community garden, and loves spending time with her family and friends on the eastern shore of Lake Michigan.
Sam Axtell
Executive Coach
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Education & Training
MSc Coaching Psychology, Metanoia Institute
MA Experimental Psychology, University of Oxford
Diploma in Coaching Supervision, International Coaching Supervision Academy
Certifications
Chartered Member, British Psychological Society
Member, European Mentoring and Coaching Council (EMCC)
Leadership Circle Profile, Mental Health First Aider
Experience & approach
With over twenty years of coaching experience, Sam finds herself holding space with senior leaders to help them unlock their performance. She enjoys collaborating with clients who value taking time to reflect, appreciate that it’s up to them to ‘do the work’, who see strength in vulnerability, and are curious about not knowing.
Sam coaches senior leaders across the world: people carrying the weight of consequential decisions, navigating complex systems, and trying to lead well under sustained pressure. Her practice spans major corporations, family-owned enterprises, public institutions and high-growth companies. Although she is invited to focus primarily at the top of organisations, Sam chooses to work throughout the org chart because she believes that staying close to the whole system makes her a better coach to the people carrying the most responsibility.
Previously, Sam spent twenty-five years in operational and senior executive roles. She now sits on boards as a Non-Executive Director alongside her coaching practice. Sam lives in Sussex in the UK with her husband and Westies. She is a competitive sailor, keen cook and enjoys hiking in the national park that’s right on her back doorstep.
Natalya Pestalozzi
Executive Coach
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Education & Training
Master of Applied Positive Psychology (MAPP), University of Pennsylvania
BA in International Studies, The Ohio State University
AA Franklin University Switzerland, Lugano, Switzerland
Certifications
Professional Certified Coach (PCC) designation through the International Coach Federation
Certified Professional Co-Active Coach, Co-Active Training Institute
Certified Coach Supervisor, Goldvarg Consulting
Certified Mentor Coach, Coach Cache
Certificate in Facilitation, Georgetown University Institute for Transformational
Leadership Circle Profile, Hogan, EQ-I 2.0/EQ 360, and Myers-Briggs Type Indicator Steps I and II assessments
Experience & Approach
Senior executives, aspiring executives, and leaders at all levels work with Natalya to gain a deeper connection to who they are as a leader in action. Natalya helps clients understand how their inner motivations and drivers play out in real-time behaviors with others. Together, they work to limit the costs of ineffective, counter-productive behaviors and habits of thought, and maximize the gifts of their strengths and new thought patterns for a more scalable, sustainable, positive, and productive impact. This work extends beyond individual coaching, as Natalya also trains leaders and practitioners in the science and application of Positive Psychology to support the well-being of those they serve through evidence-based practices.
Natalya is known for her warm yet direct coaching style which helps provide a model to clients for developing high-quality connections with others. She has developed deep coaching relationships with clients across public, private, and non-profit sectors including select organizations within Private Equity, Financial Services, and Federal Departments such as Health and Human Services, Internal Revenue Service, Securities and Exchange Commission, U.S. Postal Service, and others.
Natalya lives outside Washington D.C., with her husband and two young boys. She has a newfound love of the National Parks System, tent-camping, and getting the family into nature, particularly by the water – especially with a paddleboard!
Evan Roth
Executive Coach
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Education & Training
BA in Accounting, Goshen College
Certified Professional Coach, Institute for Professional Excellence in Coaching
Certifications
Master Certified Coach (MCC) designation through the International Coach Federation
Certified Public Accountant
Leadership Circle Profile, Emergenetics, Conversational Intelligence, EQI2.0 Emotional Intelligence, Energy Leadership Index, Conflict Dynamics Profile, iEQ9 Enneagram, and Situational Leadership II assessments
Experience & Approach
Evan helps executives thrive in demanding organizational environments. He serves the few who lead the many. His executive coaching clients value his affirming yet challenging approach to achieving their goals. Evan collaborates with leadership teams to enhance team performance and leads workshops on topics of maximizing teaming, conflict competence, decision making, and emotional intelligence.
Evan leverages 30 years of senior leadership and P&L responsibilities in private and public international companies. He has held roles such as Chief Financial Officer, Chief Learning Officer, and General Manager. His clients span industries including aerospace, media, manufacturing, energy, financial services, and technology.
Evan loves nature, music, sports, travel, foreign languages, church, and, most of all, family. He resides in Denver, Colorado with his wife and dog.
Yashi Srivastava
Executive Coach
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Education & Training
Certificate of Conflict Management and Mediation (in progress), Conrad Grebel University College, Canada
Master of Applied Positive Psychology (MAPP), University of Pennsylvania
MBA, Human Resource Management, International Management Institute, New Delhi
BA in Psychology + Philosophy, Gorakhpur, India
Certifications
Professional Certified Coach (PCC) designation through the International Coach Federation
Leadership Circle Profile assessment
Certified Professional Co-Active Coach (CPCC) awarded by the Co-Active Training Institute (CTI)
Experience & Approach
Yashi is a leadership coach, wellbeing consultant, and writer passionate about helping people cultivate their inner confidence through deeper self-awareness, self-compassion, and self-acceptance. Yashi has helped numerous clients address imposter syndrome, self-doubt, and perfectionism so that they can show up in their lives with more courage, authenticity, and confidence. Yashi’s clients often report feeling less stressed, more joyful, and more confident at work and in life.
While Yashi began her career teaching computer programming, her life-long fascination with the human mind led her to pursue a career in people development. After spending several years in the corporate world as a human resource professional, Yashi currently runs a positive psychology-based coaching and consulting business. In a career spanning 15+ years, Yashi has worked in the corporate world, academia, as well as the non-profit sector.
After spending most of her life in India and the US, Yashi currently lives in Canada with her husband and two daughters. One of Yashi’s ongoing commitments in life is to strike an authentic balance between cherishing the joys and challenges of motherhood while using her gifts to help people thrive from the inside out.
Tammi D. Teague
Executive Coach
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Education & Training
Certificate in Executive Coaching, Georgetown University
MBA, Vanderbilt University, Owen Graduate School of Management
BS in Business, Fisk University
Certifications
Leadership Circle Profile and DISC assessments
Experience & Approach
Tammi partners with individual leaders and leadership teams to deepen effectiveness, expand influence, and envision the future. She believes leadership transformation has a multiplying impact across an organization and creates space for leaders to grow with intention and clarity.
An experienced executive coach and human capital leader, Tammi brings more than 25 years of leadership development, organizational development, and HR experience across industries. She has held senior roles at Frito-Lay, Bank of America, Capital One, Lockheed Martin, and Stanley Black & Decker, leading integrations, global technology implementations, and talent strategies aligned to business needs.
Tammi’s whole-person philosophy centers on the belief that leaders are capable of continuous growth, especially at key inflection points. She strives to stand alongside clients as they expand their leadership capacity.
Raised in Santa Barbara, she loves the beach, reading, music, the arts, and sings in a community choir that has performed for four living presidents.
Sarah Sutton
Operations Manager
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Education & Training
MA in Education, Boston University
BS in Journalism, Loyola University of Chicago
Experience & Approach
Sarah leads operations, ensuring leadership training programs and coaching engagements run smoothly from planning through delivery. She manages the systems, timelines, and logistics that support coaches and clients.
Sarah brings experience across operations, recruiting, and education, with a career focused on coordinating complex initiatives and building systems that help teams work more effectively. Earlier in her career she was a 5th grade math teacher and grade level leader, where she developed a deep appreciation for thoughtful learning environments and strong program design. Today she brings that same mindset to leadership development work, building operational foundations that support strong client experiences and effective collaboration.
Sarah enjoys building the systems that make great work possible. She is known for her attention to detail, love of a well-structured project plan, and commitment to processes that help teams do their best work.
Sarah lives in Connecticut with her husband, two sons, and their Norwich Terrier. Outside of work she is often found at the hockey rink cheering on her son, testing new baking recipes, or volunteering on the boards of her sons’ schools.