Asheville, NC, United States

Experienced leadership consultant and facilitator specializing in regenerative business, people leadership training, and strategic management to help organizations thrive

Notable Clients

  • Rankin Oneal Center Luckhardt & Lund
  • Lifeguard
  • Inc.

Primary Roles

  • Leadership Development Consultant
  • Executive Coach
  • Organizational Development Specialist
  • Tribute to Grail Leaders

    • Audio production
    • Business Leadership
    • Content Creation Tools
    • +10 more
  • The Way of Wholeness: a transformational leadership approach

    "Your offering is so refined, professional, deep and integral. Seeing the level of refinement and clarity of your offering is deeply inspiring." View More
    • Business Leadership
    • Content Creation Tools
    • Content Developer
    • +4 more
    • Leadership Development Training

      As a leadership consultant with extensive experience, I can design, develop, and facilitate leadership development programs for your teams.

    • Organizational Design Consulting

      Leveraging my experience in establishing efficient operational systems, I can guide through the process of organizational redesign for better productivity.

    • Communication Skills Workshop

      With my background in legal and retail sectors, I can develop and deliver communication skills workshops for enhancing internal and external corporate communications.

    • Team Building Facilitation

      Having led various teams through my career, I can facilitate team building sessions for stronger collaboration and mutual support among team members.

    • Business Leadership Training

      As an experienced business leader, I can train your leaders in effective business strategies for organizational growth and employee engagement.

    • Employee Engagement Strategies

      Based on my experience in creating engaging workplaces, I can help your organization develop effective employee engagement strategies for a motivated workforce.

    • Customer Service Excellence Training

      Having owned award-winning retail stationery boutiques, I can guide your teams towards delivering exceptional customer service experiences.

    • Content Creation for Training Programs

      With my skills in creating compelling and visually appealing content, I can develop interesting and inspiring training materials that learners will enjoy.

    • Regenerative Business Consulting

      With my passion for regenerative business practices, I can provide consulting services to help your business operate in a more sustainable and ethical manner.

    • Executive Coaching and Mentoring

      As a seasoned former executive and corporate lawyer, I can provide executive coaching and mentoring services to support your top management in their leadership journey.

    • Extensive Experience in Leadership Roles

      Holly McCann has demonstrated her leadership skills across multiple roles such as Vice-President & General Counsel, Founder & Consultant, and Co-Founder & Visionary, providing extensive experience with managing and training teams.

    • Proven Track Record in Different Industries

      Given her experience across several industries including Business Law, Consulting Services, e-Commerce and Retail, McCann has a broad and diversified knowledge base, making her adaptable to various training scenarios.

    • Expertise in delivering tailored Training Programs

      Throughout her career, McCann has developed and delivered various training and facilitation programs. Her experience in coaching and mentoring, webinars, workshops and online courses is highly valuable for creating impactful training sessions.

    I was hired as the first in-house counsel for my largest client less than two years after graduating law school, and was promoted to Vice President & General Counsel six months later. I built the Legal Department into a top-notch team of five lawyers plus support staff who were trusted and respected by internal departments and external stakeholders. I led company-wide, cross-functional initiatives that positioned the organization for success in the midst of rapid growth and tremendous change.

    After 10 years in a role that I loved, shaping the corporate vision and strategy as the youngest and only female member of the executive team, I was ready to venture out as an entrepreneur and build a business of my own. At the same time, my husband and I decided to relocate from the Silicon Valley to raise our young children in Chapel Hill, North Carolina.

    I created a business plan and developed from scratch an award-winning fine stationery boutique, and opened a second location four years later. Through 12 years as the owner of two geographically dispersed retail boutiques and an online store, I developed tremendous experience and skills ~ including the creation of operational systems, marketing & advertising, and hiring & training of employees ~ and cultivated remarkable relationships with my treasured customers, wholesalers and distributors.

    I began sharing this wisdom and expertise with other stationery retailers and came to be a trusted thought leader ~ often facilitating transformative conversations with key stakeholders in the supply chain during times of tumultuous change in the industry and economy.

    Over time, I developed a coaching and consulting business, including the launch of an 8-week group education program supporting stationery retailers in optimizing their success through marketing and systems, which benefited business owners from all over the world and achieved high-profit, six-figure revenues in the first year.

    However, after achieving heights of success throughout three careers, I was burned out and profoundly unfulfilled ~ and I watched so many other business leaders experiencing the same.

    I was driven by a desire to find a more sustainable way to lead ~ one that contributes to the well-being of the organization, its team members and leaders, and the planet. I soon found a book called "Reinventing Organizations" by Frederic Laloux, which profiled innovative companies who were prospering and making a beneficial impact in the world by implementing new organizational models. This fueled my desire, affirming that these ideas and visions of new leadership approaches that I'd been dreaming up and experimenting with were actually possible!

    So in 2016 I set out on what would become a seven-year quest to explore ways to lead differently. This pursuit has taken me to twelve countries, four continents and two hemispheres as I’ve immersed myself in a variety of regenerative initiatives ~ working and living with the leadership teams of evolutionary organizations devoted to pioneering organizational models that are beyond sustainable, making meaningful contributions to ensure a flourishing future for our world.

    I am so excited to learn about your organization, and to share what I've discovered along my leadership journey that will support you and your team to thrive as you fulfill your unique vision and mission.

    • Revolutionizing Leadership Through Grail Leadership

      Co-founded Grail Leadership and prototyped novel whole-systems organizational model for support of regenerative leaders globally. Created and delivered impactful presentations and online courses, fostering a community of evolutionary businesses and thought leaders focused on sustainable impact.

    • Spearheading Transformation in Business Operations with Blue Sky Business Academy

      Founded the Blue Sky Business Academy, offering business owners across the globe a transformative 8-week group education program. Leveraging my expertise for authentic marketing and systems, I achieved high-profit, six-figure revenues within the first year.

    • Empowering Organizations with Legal Expertise at Lifeguard, Inc.

      As Vice-President & General Counsel, I built a highly valued legal department, achieving a swift promotion to the executive leadership team. Led organization-wide projects, shaped corporate strategy, and maintained excellent relationships with both internal and external stakeholders.

    • Creating Best-In-Class Retail Experience with Salutations, Inc.

      Developed an award-winning chain of fine stationery boutiques from scratch, achieving profitability within six months. Through dedication to detail and a culture of continuous improvement, delivered exceptional customer service and contributed to the growth of the stationery industry.

    • Driving Business Transformation with ThrivingPurpose.com

      As a Regenerative Leadership Consultant, I've worked with innovative organizations worldwide to align their business objectives with core purpose & values, fostering a thriving workplace, sustainable growth, and meaningful impact. This has involved designing cutting-edge organizational models and developing promotional websites.

    • Juris Doctor

      Santa Clara University School of Law 1991

    • Regenerative Leadership Consultant

      ThrivingPurpose.com Jun 2016 - Present

      Employing a whole-systems approach to promote collaboration within and between organizations, aligning business objectives with core purpose & values to create a thriving workplace, sustainable growth, and meaningful impact.

      Over the past seven years, I have immersed myself in a diverse range of purpose-driven initiatives around the world, contributing insights and expertise in regenerative practices, operational systems, and process optimization for founders and leaders of innovative organizations who are making a beneficial impact for people and the planet, including:

      * Designed cutting-edge organizational model with startup team pioneering global co-living and co-working communities. Lived with founders in Baja, Guatemala, and Ecuador.

      * Developed promotional website and online teaching platform for non-profit community & retreat venue in Boulder. Instrumental in structuring member subscriptions and deepening relationships with clients.

    • Founder & Consultant

      Blue Sky Business Academy Jul 2012 - Jun 2016

      Achieved high-profit, six-figure revenues in first year, sharing tools for authentic marketing and systems with hundreds of stationery retailers worldwide to improve their profits and lifestyles.

      Leveraged solid relationships with key corporate suppliers to promote programs to their customer networks, creating a mutually rewarding outcome with increased value and profitability for all.

      Served as a transformational mentor, facilitating year-long mastermind programs, live workshop events, private coaching, speaking engagements, and retreats internationally.

    • Founder & President

      Salutations, Inc. Jul 2002 - Dec 2013

      Created best-in-class, bespoke stationery boutiques in Chapel Hill & Charlotte, achieving profitability within first six months and managing exceptional growth by leading diverse teams in culture of continuous improvement.

      Increased consistency, replicability and scalability with evolutionary approach to processes, focused on dedication to detail and commitment to maximizing stakeholder value.

      Developed loyal network of relationships with clients, team members, peers, and suppliers, earning respect through exceeding expectations and unwavering application of the Golden Rule.

      Spearheaded collaborative initiatives that united seemingly opposing industry players to diffuse hot-button issues, facilitating honest, transparent communication and respectful exchange of perspectives.

      Consulted as trusted, go-to advisor by C-level executives of key trading partners, national trade show management, industry peers, and community leaders.

      Winner, 2011 Stationer of the Year

    • Vice-President & General Counsel

      Lifeguard, Inc. Sep 1992 - Jun 2002

      Developed and led a highly valued legal department for a nonprofit health insurer.

      Promoted within six months to youngest and only female on executive leadership team.

      Shaped corporate strategy for rapid growth while maintaining excellent relationships with contracting healthcare providers, employers and members.
      Reported directly to the CEO and advised the Board of Directors as corporate secretary.

      Served as an ambassador of the corporation in relationships with legislators, regulators, industry peers, and outside counsel.

      Led organization-wide projects including National Committee on Quality Assurance (NCQA) accreditation and the Y2K compliance project, which required upgrade and testing of all internal systems as well as ensuring compliance by all contracting healthcare providers.

      “You developed a legal department from nothing to one that everyone calls upon, including CAHP (California Association of Health Plans), for advice.” ~ CEO in letter commemorating 5-year mark.

    • Associate Attorney

      Rankin Oneal Center Luckhardt & Lund Feb 1990 - Sep 1992

      Managed a full caseload of clients with primary responsibility. Drafted contracts, took client meetings and depositions, researched and prepared motions, argued cases in court, lobbied in the California legislature. Wrote an appellate brief and appeared before the California Supreme Court.

    • Skills

      • Coaching & Mentoring
      • Instructor-Led Training (ILT) Facilitation
      • Social Learning & Collaboration
      • eLearning Modules
      • Self-paced Learning Materials
      • +6 more
    • Tools

      • Audacity
      • Podcasting
      • Voice Over
      • Blended Learning
      • Curriculum Development
      • +43 more
    • Industries

      • Consulting Services
      • Other Educational Services
      • Business Law
      • Labor & Employment
      • Other Legal Services
      • +5 more
    • Training methods

      • Other E-Learning & Online Training
      • Other Primary Online Blended Learning
      • Podcasts, and Other Audio Focused Learnings
      • Web Based Training (WBT)
      • Webinars
      • +7 more
    • Languages

      • English
    • Subject Matter

      • Business Leadership Training
      • Other Leadership Training
      • People Leadership Training