Founders - Cassandra Shepard



Helping you tackle the tough challenges.

In my 25+ years in business and working with CEOs and successful entrepreneurs, it’s fair to say I’ve seen quite a bit. Here are just some of the challenges and opportunities I help you with:

  • How do I build and/or upgrade to an A-list team that is high performing without me needing to direct everything all the time?

  • How do I build and execute on a plan that gets my business where I want and need it to be?

  • What can I do to get off the cashflow rollercoaster?

  • How can I have my business to run better…without me always needing to be there for it to run well?

  • What’s the best way to build my brand so I can get more customers and exposure?

  • #GirlBoss is a great concept, but I feel more like a man in how I am showing up to get things done and that’s starting to affect my self-esteem and relationships. 

  • How can I close the confidence gap and improve my mindset, especially what I think about myself and how I handle doubt and fear?

  • What are some ways I can successfully get more media exposure?

  • How do I make the most of venture capital investment or business loans?

  • Balance is a nice word, but how do I actually do it?

  • What are the best strategies to improve how I communicate with my team, in my marketing, with key stakeholders and influencers?


How we work together


STRATEGY SESSION: Our first session will be a deep dive into your business, brand, dreams and challenges. From here, we will identify the top priorities and the transformational strategies to successfully achieve your goals. 

MASTERMIND SESSIONS: Three private mastermind sessions per month are focused on your top priorities and transformational strategies, addressing your needs, challenges and goals, and developing the successful CEO mindset that is crucial for all women leaders. 

DOCUMENTS & MATERIALS REVIEW: From pitch decks and Board presentations, to job descriptions and important communications, you’ll have a second-set of eyes on your most important messaging and marketing materials.

HAVE ME “ON RETAINER”: Have support for the quick but crucial questions that come up in-between mastermind sessions.

SAFE HAVEN: Finally, a place to discuss the most sensitive issues openly!


6 and 12 Month Programs available


The magnificent leader & woman that you become in the process of coaching with me is simply stunning.


  • You’ll quickly improve in your communication and decision-making, with less spin.

  • You’ll have greater confidence in your ability to hire and train the right people.

  • You’ll increase your level of trust in yourself and in your staff.

  • You’re able to take time away from your business to do other things that you enjoy — travel, vacation, focus your attention on the next really cool project you’ve been itching to start.

  • You’ll start taking much better care of yourself because you’re not working round the clock.

  • Your level of self-worth and deserving-ness will flourish.  You’ll see how truly magnificent you already are, and how it’s your birthright to have a thriving business and fulfilling life.




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Positioning Her Business For Its Next Evolution

“Cassandra’s insights and direction are always on target. She has given me the courage to make and even embrace change as I move forward with my business.”


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“The Woman I Am Today Is Profoundly Different!”

“From the overextended, stalled and frustrated woman who first met with Cassandra…through Cassandra's coaching, I am more self-aware and achieve higher levels of productivity while also maintaining healthy relationships with the people and places most important to me. I live more freely -- with confidence, courage and clarity.”