About Win at Work
Win at Work helps individuals, teams, and organizations crush conventional barriers and dramatically elevate performance across government, business, non-profits, higher education, cultural organizations, international civil society, and beyond. Since launching in 2019, we've empowered over 1000 clients worldwide to clarify their current path or discover the next big leap in their careers. Our secret? Rejecting conventional wisdom. Because "best practice" is code for average—and our clients don't do average. At Win at Work, we believe in deep, authentic service that makes people feel genuinely seen, heard, and understood. We level the playing field, helping you thrive in a working world that's rarely linear, logical, or fair. Why? Because the world is in need and it needs more of you.
Meet The Team
Meet the Team
Anne Caipang
Chief Of Staff and Director of Operations
Anne serves as Chief of Staff and Director of Operations, bringing structure, clarity, and momentum to everything she leads. She works closely with Coach Eri to turn vision into action, aligning priorities, streamlining processes, and ensuring the team stays focused on what matters most. With a sharp eye for detail and a strong grasp of the bigger picture, Anne keeps operations running smoothly while driving key initiatives forward. She is known for her steady leadership, clear communication, and ability to make complex work feel simple and achievable.
Cherry Caipang
Client Operations Coordinator
As a Client Operations Coordinator at Win at Work, Cherry plays an essential role in supporting clients throughout their career journey. She helps connect them with job opportunities aligned with their goals and contributes to marketing outreach to boost their visibility. Behind the scenes, Cherry ensures smooth operations by handling backend tasks like graphic design and CRM management. Her commitment to both client support and internal processes helps create a seamless and successful experience for all.
Cassidy Carlson
Coach
Cassidy is a coach and consultant focused on transformational leadership. She helps individuals and mission-driven teams to lead with clarity and confidence. Drawing on 10+ years of executive experience in nonprofit and educational organizations, Cassidy is known for her calm presence and strategic mindset. Her consulting background includes curriculum design and assessment, financial planning, and improving organizational effectiveness, giving her a well-rounded perspective on both people and systems.
Cassidy is based in Miami Beach, where she maintains her most cherished title, Mom, to two human children and three furry ones.
Rich Carter
Coach
Rich is a life and career coach with over 25 years of corporate experience who now coaches full-time, helping individuals create more success, fulfillment, and clarity in their lives and work. With a background in leadership across industries and extensive training in mindfulness, stress reduction, and meditation, Rich empowers clients to lead with presence and to be comfortable in their own skin. Rich’s coaching spans all levels of the corporate business world as well as small businesses. His clients include those that work in sales, distribution, operations, healthcare and finance.
Jessa De Loyola
Client Operations Specialist
As Client Operations Specialist at Win at Work, Jessa helps drive engagement by reaching out to potential clients and guiding them toward our events and services. She specializes in making the first connection—sending outreach messages, extending event invitations, and ensuring every lead feels personally welcomed. With a friendly, proactive approach, Jessa helps turn cold leads into warm relationships, all while supporting the team’s goals for growth and client success.
Rima Eid
Coach
As an Executive Coach and Leadership Strategist, Rima partners with professionals at pivotal moments in their careers, when new possibilities are emerging and what’s next is ready to be shaped with clarity and intention. As an International Coaching Federation (ICF), credentialed coach, she brings more than 17 years of experience across international development, federal service, and enterprise-wide leadership development.
Working across roles, sectors, and cultures, Rima has observed a consistent gap: people are expected to endure change and are rarely supported in learning how to grow through it. Her work integrates coaching, strategy, and cultural insight to help individuals slow down, gain perspective, and move from reaction to intentional, strategic action.
Lauren Fischer
Coach & Director of Client Experience
As a Professional Life, Business & Career Coach, Lauren collaborates with clients to develop personally effective leadership frameworks for work, home and everywhere in between. Drawing from her two decades of bi-coastal leadership experience at a Broadcast Television Network, Lauren coaches toward insight followed by action. And sometimes it’s the action that leads to insight. Lauren is a PCC-accredited coach with the International Coaching Federation (ICF) and has partnered with leaders in media, entertainment, healthcare, technology, non-profit, and higher education, among other industries. Originally from Albany, NY, Lauren makes her home in Los Angeles, CA.
Patrick Fulton
Coach
Patrick (he/him) is a Professional Leadership and Life Coach living in Salt Lake City, UT with 10+ years' experience serving clients to transform their careers and relationships to their work. He is known for his transformative, strategic, and good-humored approach to personal and professional growth and has extensive experience in the medical, higher education, non-profit, and staffing industries (having worked as a professional Recruiter within staffing agencies and corporations). With a deep ability to listen and challenge, Patrick helps clients uncover clarity, build confidence, and take purposeful action—especially during pivotal moments in their careers and lives. Whether you're navigating a job transition, redefining your goals, or seeking deeper fulfillment, Patrick brings the structure, insight, and motivation to help you move forward with intention.
Kristen Hoover
Coach
Kristen is an Executive Coach with a proven track record of leading, inspiring, and coaching clients to develop high-performance executive skills. Drawing from her 14+ years as a Chief Operations + Innovation Officer, she serves as a trusted advisor for professionals seeking career advancement, having improved executive performance by 28% through structured advisory frameworks and strategic guidance. Kristen specializes in helping individuals develop the strategic mindset and operational excellence needed to secure and thrive in their desired roles. Kristen has a history of coaching in healthcare, SaaS, construction, and startups.
Roman Rangel
Coach
Roman (they/them) is a Life and Leadership coach who emphasizes holistic, person-first transformation and healing.
They are passionate about helping entrepreneurs, executives and artists create pathways out of stagnation, finding clarity on goals, and taking supported, consistent action. Roman has worked in recovery and complex mental health coaching, career coaching, and corporate coaching focused in law firms and tech. Their private practice focuses on wellness and fulfillment within the LGBTQ+ community.
Roman is a certified Life Coach and has certifications in DBT Foundations, Motivational Interviewing and NeuroAffective Relational Model Level 1.
Natalia Ruiz
Coach & Director of Client Enrollment
Dynamic and results-driven Heart-to-Heart Enrollment Coach for Get Hired FAST, with a proven track record of driving high-ticket enrollments for leading transformational brands around the world. She supported top-tier coaches like Selena Soo, Sahara Rose, Neeta Bhushan, Gerard Adams, and Bibi Brzozka—bringing that same heart-centered sales philosophy to Eric’s mission of helping professionals land high-paying jobs fast. Known for authentic connection, deep listening, and closing with compassion and integrity, she helps high-achievers make empowered decisions about their future. If you’re ready to stop spinning your wheels and start building a career you love, She's here to walk beside you—every step of the way.
Tammi Scott
Coach
Tammi is a PCC accredited executive coach who has integrated her 30+ years of sales, consulting and leadership experience into her coaching work with her clients. She brings understanding and insight from a span of industry experience, including high-end retail, pharmaceutical, education, non-profit, government, and financial.
She is known for the gentle, persistent way in which she works with her clients, focusing on self-leadership, strategic planning, emotional intelligence, professional growth and personal fulfillment.
Tammi currently lives in Mukilteo, WA with her sweet dog, Maggie.
Diana Tauder
Coach
Diana is an ICF credentialed Executive Leadership Coach who helps people connect more powerfully with their lives and more positively with the world. She partners with leaders, entrepreneurs, and creatives to experience greater joy, fulfillment, and transformation in their lives and careers. Diana supports clients with their personal and professional development, focusing in on intentional and actionable changes as the keys to becoming a transformational leader. Her clients span industries including Technology, Entertainment, Consumer Products, Non-profit, and the Public Sector. As a former film industry executive with over two decades of experience, Diana brings bold perspectives, high energy, and a passion for the power of community to those around her.
Eric Woodard
Coach and CEO
The mission: knock down stories that are holding you back. The opportunity to reach higher levels of aliveness, impact, and connection by breaking through limiting beliefs is available to everyone. It’s available to you. For the last 25+ years Eric has helped hundreds break through barriers in work and life around Presidents and Princes, Senators and Scientists, Deans and Diplomats, CEOs and Consultants. He has travelled or worked in over 70 countries. Eric has completed 9 marathons, is the author of multiple books including Your Last Day of School and The Ultimate Guide to Internships; MANY fancy degrees and certifications. Eric lives in Alexandria, VA with his amazing smart beautiful trophy wife Keri and their 4 fantastic kids (all named after occupations). Read more about Eric here.