Professional and Executive Coaching


See if we’re a good fit to work together

Make yourself a priority and make coaching a critical component of your overall success strategy. Begin your coaching journey today.

Executive Coaching

Executive Coaching:  a) Complements other quality improvement processes; b) results are measurable and sustainable; and c) fosters future-oriented thinking. Our coaching model provides a structure and process for professional development and performance improvement. 

Individual Executive Coaching:

- Develops high levels of self-confidence and mastery

- Promotes personal discovery and self-responsibility for solving problems

- Focuses on the woman being coached

- Uses language that is grounded in respect for Women of Color and their capabilities

- Emphasizes the unique potential of individuals

Sales Coaching

Create a trusting and collaborative environment where personal development, and sales performance improvement occurs

-  Leverage existing strengths to improve year-over-year sales performance

-  See yourself and others clearly and learn new ways to respond

-  Build more productive relationships to achieve extraordinary Sales performance

-  Dissolve self-limiting, painful thoughts and reveal new possibilities

Group Coaching

Amplify your professional coaching journey with a Group Coaching Appointment. Group Coaching sessions are an excellent way to connect with like-minded professionals and complement your own professional growth while supporting others on their own paths. While each member of a Group Coaching Session may have different goals, this collaborative coaching environment allows you to connect and grow in community with other Women of Color in a strength-based environment, specifically curated to complement your unique experience and strengths. 

What is Group Coaching? 

Group Coaching is a curated professional growth experience designed to support you on your path by bringing you into conversation with other like-minded Women of Color. In these small group sessions you will: 

· Focus on goal setting, accountability, and actions

· Develop your skills and knowledge 

· Discover a journey to find the answers you need 

· Grow personally and professionally 

· Be empowered to take the next step in your career or business 

· Resolve self-limiting thoughts to create the space you need to move forward

Group Coaching sessions begin the week of June 8th, are limited to 4-6 members, and meet 3 times a month. Click here to join a group coaching session or to book a Complimentary Coaching Session to see if we’re a good fit to work together. 

Business Coaching

Make yourself a priority and make business coaching a critical component of your overall success strategy.

-  Get clearer about your goals and achieve your dreams

-  Raise awareness, clear up distractions, and find your best path forward

-  Take more effective actions with self-reflection and self-discovery 

-  Invest  in Sales Coaching to Dramatically Improve Your business growth

With twenty-five years of experience as a general manager, educator, coach, and entrepreneur, Cherilynn Castleman’s in-depth knowledge of the sales and business world and its unique pressures will help make the most of your coaching time.  

I partner with clients in a thought-provoking and creative process that inspires them to maximize their personal and professional potential. 

Awareness + Action = Growth


Coaching is about Improving your Performance

·  You’re intelligent

- You’re talented

- You’re innovative

- You’re high achieving

- You’re consistent…  

And yet you're falling short of your goals .


Coaching Focuses on the Future and the Present

·  Coaching is action-oriented 

·  Coaching focuses on what you want 

- Coaching allows you to dream out loud with a dedicated listener.

·  Coaching is grounded in the assumption that you are resourceful and whole and know best. 


Coaching is about crushing self-limiting, painful thoughts and revealing new possibilities

- Raise awareness and clear up distractions

-Find your best path forward

- Leverage existing strengths

- See yourself and others clearly

- Build more productive relationships

- Get clearer about your goals

-Achieve your dreams


Coaching is About Stretching

- Unlock your potential

- Maximize your performance. 

- Learn to trust your internal source of wisdom

- Move from awareness to action


See if we’re a good fit to work together

Make yourself a priority and make coaching a critical component of your overall success strategy. Begin your sales coaching journey today.


Coaching Is Not...


Coaches don’t treat psychological problems, such as depression or anxiety.


Coaches don’t tell clients what to do. 


  Coaches don’t teach you how… they inspire you to climb.

Book Your Coaching Session

An Intro Coaching Session can help us determine whether Cherilynn is the right coach for you.

Coaching FAQs


What’s It like to work with a coach?

Coaches use tools designed to help you face change, dream big, and move forward with peace, grace, and authentically…

·  Coaches focus on the future

·  Coaches ask powerful questions   

·  Coaches provide support during career transitions

·  Coaches grow and develop leadership and sales skills

·  Coaches partner with you to discover your goals and develop strategies to achieve them 

How does coaching work?

During each session, together, you and your coach will work through a framework designed to help you unlock your potential and maximize your performance. By the end of the session, you'll learn to trust your internal source of wisdom and move from awareness to action. 

Who will benefit from 1:1 coaching?

- Women who have a fierce desire to learn

- Early career sellers struggling to make numbers 

- "Sidepreneurs" ready to grow a six-figure business 

- Executives and leaders at a crossroads in their career

- High performers looking to take their career to the next level

- AEs ready to call on contacts higher up in their target accounts 

- Sales professionals looking to increase deal sizes and shorten sales cycles

What's a coaching engagement?

A coaching engagement is a chance to increase performance, drive results, and change your life. But remember, if you don’t take action, there will be no positive outcome.  We will typically work together for a 3-6 month engagement, spending 2-3 hours a month in in-depth one-on-one phone calls.

We may also communicate by email or text from time to time.

How do I find the right coach?

With twenty-five years of experience as a general manager, educator, executive coach, and entrepreneur, Cherilynn's in-depth knowledge of the sales and business world and its unique pressures will help make the most of your coaching time.

To see if we’re a good fit to work together, schedule a no obligation time to talk.




Member Discounts

SIS members receive discounts on coaching and training.

 Learn more about Sistas in Sales (SIS), a community for women of color sales professionals to network, advance their careers and most importantly, find sisterhood.