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    Work With One Of Our Coaches

    Get the support, straight talk, and deep discovery you need to get real results.

    Meet Our Coaches

    Christina Bolden

    Emboldened Enterprises LLC

    Meet Christina Bolden, a highly intuitive, empowering, and dedicated Career Coach who elegantly gets to the heart of the matter. Christina works with her clients to progress beyond what they think themselves capable of. She is a wunderkind at helping professionals identify what is holding them back and unearthing their potential to achieve the careers they want and deserve. 

    With over 15 years of management experience, Christina has hired, led, and inspired diverse teams. She has always especially enjoyed encouraging her team members to grow their strengths and move toward greatness. 

    Christina specializes in partnering with clients who have suspended their careers and are now ready to return to the workforce. She expertly guides them in the pursuit of finding their purpose and shows them how to leverage their non-traditional career path to create a new and thriving career.

    One of Christina’s happy places is in her yard pulling weeds and dandelions.  She will tell you that when you are weeding, you must get at their roots, much like her approach to coaching. Christina is an avid reader and is a self-proclaimed foodie.  

    You should work with Christina if you are: 

    • A professional looking to grow your career or pivot industries
    • A returning-to-work mom or caretaker

    “When I was referred to Christina at Career Winners Circle, I was at a point in my career where I needed to make a drastic pivot but felt stuck about how to go about making it. Job search and career planning was not a skill I excelled in. I dreaded the entire process. Just the thought of it left me defeated. Christina listened intently as I shared my concerns, fears, and priorities at every one of our sessions. She provided a firm push and gentle nudge as needed. She connected with me not only as a client but also as a fellow human being. She solicited help from her network on my behalf and provided timely feedback on my work along the way. At the end of our session, I was pleasantly surprised to report, that while I still don’t love job search, I am prepared to tackle it head-on. I no longer feel defeated. I can honestly say the coaching and guidance provided by Christina has been empowering. I am grateful to her for getting me out of my funk and putting me in a position to thrive and bet on myself again. Christina is a natural at helping others see the best in themselves. Thank you and I wish you nothing but the absolute best in your journey.”

    Leleda Woldu

    TIFFANY ODUTOYE “TIFFANY-O”

    Virual Partner, LLC

    Meet Tiffany Odutoye (“Tiffany-O”), an Organizational Change and Business Transformation Leader. She is an author, coach, speaker, and entrepreneur who wholeheartedly engages with her clients to move the needle on strategic initiatives while keeping focus on what’s needed, what’s possible, and how to get there.

    Grounded by data proof points she metamorphosizes a problem into an action plan enabling organizations to prioritize, pivot, and support the people being impacted.

    Tiffany-O has over 30 years of professional growth and has rolled out several transformational enterprise-level programs working with well-recognized industry leaders including T Rowe Price, Human Resource Management Solutions, Johns Hopkins Health System, Precision Healthcare Consultants, OhioHealth, and Arthur Andersen.

    She leverages systems thinking, design thinking, and innovation strategy to effectively identify interrelated processes and isolate needs to drive meaningful, systematic, and sustainable change. She is committed to helping leaders crystalize a path forward with confidence to know they’re working on the right things, at the right time, for the right reasons.

    Tiffany-O is a PMI certified Project Management Professional (PMP), a certified PROSCI Change Management Practitioner, has advanced knowledge of process improvement methodologies, and is a certified Everything DiSC and Five Behaviors partner. She also has a master’s degree in education.

    When she is not working with clients, she is engaged in volunteer community activities, working on chapters for her new book, golfing, traveling, watching movies, and entertaining friends with her husband.

    You need to work with Tiffany-O if you are:

    • An HR leader looking to develop leadership development programs and support for mid-to-senior level leaders.
    • A key decision maker looking to establish a center of excellence in HR or PMO space.
    • An executive leader or an entrepreneur who needs to convert organizational vision into outcomes.
    • A people leader seeking to unify your team and create a sense of belonging.
    • An established non-profit organization in the capacity building phase and needs guidance growing or coaching the Board.
    • A woman with a vision in need of a plan.

    Stephen J. Morris

    Renowned Leadership, LLC

    Meet Stephen J. Morris, a highly experienced and engaging leadership expert with over two decades of leading teams and creating the next generation of leaders. 

    Stephen’s mission is to help his clients take their leadership to the next level by building on their strengths so they become influential leaders who build high-performing teams. His values of leading by example, servant leadership, and integrity are at the core of his coaching approach. Stephen is candid and supportive in his approach tailoring his style to meet clients where they are at. With Stephen, clients receive coaching from someone committed to helping them achieve their goals. 

    Stephen spent 16 years serving in the United States Army and has extensive leadership experience in a combat environment. He has also held several leadership roles in large corporations before realizing his passion for coaching.

    Stephen is also an accomplished podcast host and in his spare time, he volunteers his time helping veterans through local organizations including the VA. He also serves as a mentor to young men in his local community. When he is not helping others, Stephen enjoys spending time with his family and is an avid outdoorsman, spending time hiking, fishing, and off-roading. 

    You need to work with Stephen if you are: 

    • A new leader looking to make an impact in your new role.
    • A retired military leader who is experiencing roadblocks transitioning your military leadership style into a civilian leadership style in a corporate or entrepreneurial environment
    • A senior-level professional needing guidance in navigating career transition or exploring new career opportunities.

    I’ve already recommended several colleagues to CWC. I thoroughly enjoyed the coach’s energy, directness, and sound advice. Her experience in the financial services industry was hugely helpful to me. 

    Christopher Piparo

    Global Head of Product Risk - Treasury and Trade Services, Citi

    I’ve already recommended several colleagues to CWC. I thoroughly enjoyed the coach’s energy, directness, and sound advice. Her experience in the financial services industry was hugely helpful to me. 

    Christopher Piparo

    Global Head of Product Risk - Treasury and Trade Services, Citi

    Susan Hollister

    Hollister Unlimited

    Meet Susan Hollister, Master Coach, Chief Success Officer, and Leadership Consultant. Susan’s superpower is helping mid to senior-level leaders level up their performance to achieve epic results for their organizations and their careers. 

    Her global leadership experience spans everything from startups to large corporations, leading numerous functions in HR, Operations, IT, and Finance. She’s held various executive-level positions in male-dominated industries in North America, Asia, and the Middle East, and she knows what it takes to succeed under the most difficult circumstances. Now she spends her time helping her clients do the same. 

    As a leadership development expert, Susan brings the perfect blend of pragmatic, no-nonsense coaching with a deep understanding of what motivates people so they can reach the highest levels of performance. Her passion is to help develop the next generation of executives into leaders people choose to follow and to help companies of all sizes thrive during any economic cycle. 

    Based in British Columbia Canada and San Pedro Belize, when she’s not out shoveling snow or scuba diving she loves to spend her time cooking up a storm and entertaining friends with her partner in crime Rob, playing with her rescue pup Luna, volunteering through Rotary International and exploring new places.

    You need to work with Susan if you are: 

    • A mid to senior-level leader or executive looking to pivot industries or change careers.
    • A new executive looking to make an impact in your new role.
    • Responsible for developing high-performing rock-star management teams.
    • An entrepreneur who needs to hire and develop your management team.
    • A small to medium-sized business that needs a culture shift with a focus on leading at all levels.

    I’ve already recommended several colleagues to CWC. I thoroughly enjoyed the coach’s energy, directness, and sound advice. Her experience in the financial services industry was hugely helpful to me.

    Christopher Piparo

    Global Head of Product Risk - Treasury and Trade Services, Citi

    I’ve already recommended several colleagues to CWC. I thoroughly enjoyed the coach’s energy, directness, and sound advice. Her experience in the financial services industry was hugely helpful to me. 

    Christopher Piparo

    Global Head of Product Risk - Treasury and Trade Services, Citi