Hi, I’m Anna Chipperfield

I’ve always been the one people turn to when something’s off — the tension no one’s naming, the performance gaps everyone’s tolerating, the manager who’s struggling but doesn’t know why.

I created BOLD Advisory because I saw how often strong businesses stall from the inside — not because of their product or vision, but because leadership isn’t supported and people systems aren’t clear.

Utilsing my skills and experience in human resources, management, behavioural profiling, I bring structure, insight, and calm to what often feels messy, confusing and personal.

I help business owners and leaders navigate the “people stuff” with more clarity and confidence — whether that’s mentoring and training managers, refining roles, re-aligning culture, facilitating change or turning tension into traction.

My approach is practical, strategic, and deeply human. It’s not about band-aid policies or HR checklists — it’s about building a workplace where the right people are in the right roles, and leadership is equipped to grow and achieve goals, sustainably.

  • “Anna brings a lot of market experience in her approach to HR support and provides practical solutions to staffing and other HR issues.”

    Henry Morgan - Morgan Consulting Engineering

  • "Growing a small business comes with many challenges and you can't juggle every hat. Anna provides a high-level HR solution for our business which allows me to continue focusing on other areas"

    Kion Redmond - Director of Pop Up People

  • “Anna has been an invaluable lifeline in helping me manage the people and culture aspects of my growing business over the past 8 years.”

    Nadine Ingram - Flour and Stone

  • "Anna’s support across all things people and culture has been invaluable to us over the past six years — from helping us navigate the tricky stuff to shaping a workplace we’re genuinely proud of."

    Brigid Gordon - Founder of SWOP Clothing Exchange

  • “Anna’s ability to balance the needs of both our business and our people has made a significant impact on our workplace culture. We consider her to be a trusted extension of our leadership team and couldn’t recommend her more highly.”

    Matt Swieboda - Group Director of Love Tilly Group

  • "Anna has provided us with excellent support when it comes to all things HR. Her experience is evident as she guides us through various people management issues. We have come to rely on her expertise and she is a valuable part of our management team."

    Michelle Clair - General Manager of Mathews Real Estate