for Game Changing HR Professionals

Alone we can do so little; together we can do so much.


~ Helen Keller



LevellingUp will expertly match you with a peer group that’s just right for you. We want to ensure you have the most positive & impactful experience, with fast, measurable growth.

Small group of 6 to 10 peers who aligned with you in career & life stage who are facing similar challenges and opportunities.

Led by a Navigator, who is an expert educator & coach and ensures your training needs are met.

Choose a series of proven Sages for focused leadership training, to bring your skills to the next level.

Leverage the power of many minds

mastermind+ for HR professionals

Session Dates/Times/Duration

Start Date: Oct 16 (first session is Navigator-only peer accountability session)

Monthly 90 min training session with Navigator & Sage:

1 st Friday of month @ 7am MT


Monthly 90 min peer accountability session with Navigator:

3rd Friday of month @ 7am MT


Maximize your opportunity to lead the redesign of operations to meet the needs of the current pandemic environment.


Get equipped with the support and skills needed to lead change towards a human-centered organization.


Practice tools and skills to inspire a sense of urgency for change.


Learn how to tap into the collective intelligence of your team and organization in a virtual setting.


Learn the 3 core strategies and 3 key tactics required to lead transformational change and how they apply specifically to HR itself.


Support your organization to get unstuck from seemingly intractable problems by developing an agility mindset and shifting from solving problems to managing tensions.

Meet your 1st Sage


PhD, ORSCC, CPCC, PCC Assessments: Leadership Circle Profile and Collective Leadership Assessment and Lumina Spark, Emotion and Leader

  • Emotional-Social Intelligence
  • Change Leadership
  • Business Agility

As a systemic leadership coach, trainer, mentor and researcher, Kerry Woodcock specializes in Relationship Systems Intelligence and Change Leadership for Business Agility. 

Kerry is called to adventure with leaders, teams and systems that lead change for a world of change. Leaders with purpose and vision, who believe in the power of relationship to create meaningful transformation - in self, others and the world. Leaders who are willing to challenge and be challenged to reveal systemic tension and develop the skill to work in the possibility of the unknown.

For over twenty-five years, she’s worked at the brink of change, bringing human-centred innovations to the worlds of biodiversity conservation, organizational development, humanitarianism, professional coaching, and criminal justice.

Flexible and creative, she coaches in a range of organizational contexts, from non-governmental to governmental and corporate organizations, in a variety of sectors globally, both as an internal and external coach. As a leader, she is a master at rapidly developing connectivity within a system, both in-person and virtually. One of her greatest joys has been to co-create effective multi-diverse globally distributed teams and partnerships across a variety of contexts. As a trainer and mentor of professional coaches, agile leaders, and HR and OD professionals, she has the privilege of working with people across North and South America, Europe, Africa, and Australasia on a daily basis.

She is Director of Novalda and CRR Canada, on the faculty of CRR Global.

Bringing a natural lightness and rigour to everything she does, she has been described as a BrinkLeader, StoryWeaver and LightSprite. British-born, she lives in Canada with her adventurous family and the world as her playground. 


Jean Parker

Leadership Coach, CFO, Educator, BBA, BEd., ACC

Jean is a Leadership Coach / Change Insurgent / CFO with over 26 years experience driving profitability through change in organizations, 16 of those as a CFO. Jean’s industry experience includes oilfield distribution, automotive and garment manufacturing and tech. As a CFO, Jean leads organizations through growth and change. Jean was a proponent for creative solutions. In addition to leading numerous acquisitions and reorganizations, Jean also focused on developing people and process improvement structures.

Jean’s expertise includes organizational design and change; leadership mentoring; and initiating, implementing and guiding corporate strategies to fruition to promote the financial health of organizations. In addition, Jean is an innovative facilitator with over 10 years experience. Now as a Certified Professional Coach, Jean helps technically strong leaders, individually and in groups, expand their ability to lead through connection, collaboration, innovation and maximizing the potential of their teams.

90 Day Money Back guarantee!

If you’re not hooked in 90 days, we’ll give you your money back, no questions asked.

All members are screened to ensure the best fit. Same career & life stage. Non-competitive industries.

Navigators & Sages global quality & certified.

Group members commit to vulnerability, confidentiality & personal growth.

90 Day Money Back Guarantee!

Read what Forbes and Medium have to say about the effectivness of Mastermind Groups

Meet Katelyn!

A Mastermind+ Customer & Raving Fan

I experienced an amazing synergy between like minded individuals … people who are wanting to grow! The experience was just absolutely amazing, to be able to connect with these people get their ideas and be raw & open and really just expand what I thought I already knew.

Katelyn (Business Leader & Entrepreneur)


[testimonial_rotator id=39666]


Choose from business coaching, leadership training, self awareness and much more!

2-hour monthly
videoconference meeting

Homework and accountability

Transformative and honest conversation led by an expert

Navigator permanently assigned to your group, accountable for your growth trajectory

Confidential discussion board

Travel with a new Sage every 3-6 months to bring new perspective & skill training

Frequently Asked Questions

Where do I start?
Pick your level, then pick your Master.

Choose the group level – aspiring or emerging – that best matches where you are at in your artist journey. Aspiring artists are generally focused on developing their signature style, and want to focus on technique, materials, colour and composition. Emerging artists are generally focused on making their passion a profitable career, and want to focus on sales and marketing, achieving technical excellence, and making their studio time efficient.

After picking your level, choose the Master Artist who aligns with your medium, your subject matter, and who personally resonates with you. You’ll be spending a lot of time with your Master, so make sure you choose a Master who you believe will truly help you.

Why am I being charged for my Mastermind Session before we meet?
Your membership is always “forward looking”.


Your registration today gives you access to your Mastermind Group for a one-month period, and payment is required before your session just like a typical workshop or course. Your membership will renew each month on the same date as your initial registration, and you can cancel anytime through the My Account portal.
Membership guarantees you one of the 8 seats in your Group. It includes:
  • a 2-hr live & interactive group mentoring session with your Master
  • access to your private discussion board on LUchat, so you can:
    • get to know the Navigator and the other artists in your group
    • suggest topics for your Master to address in an upcoming monthly session
    • support each other’s work on the assigned homework
If the Group has met previously, you can access the last session’s recording to review what the Master taught, and discover the homework that was assigned.
What is the curriculum?
The curriculum is not pre-decided, and your individual needs will determine what your Master teaches you.
After you register for your Mastermind group, we’ll email a Member Profile form for you to fill out. In this form you’ll tell us about your goals, your challenges, your current skills – all the stuff your Master needs to know to be able to help you out.

Before meeting you, your Master will review your form to understand how to best help you. The curriculum is not pre-decided. The mentoring and training your Master Artist will provide depends on what YOU need to learn. It will be tailored specifically in response to what you’ve told us about YOUR goals and challenges.

What happens in a Mastermind Group?
LevellingUp’s Mastermind groups are high-impact apprenticeship communities.

There are a maximum of 8 Member artists in each Mastermind group, plus a Navigator facilitator, plus the Master.

Your group meets with your Master Artist once monthly for a 2 hour live mentoring session using Zoom. Between monthly sessions, you get support and encouragement from your artist peers on LevellingUp’s private discussion board, LUchat.

During the first hour of each monthly session the Master provides feedback on the homework you completed since your last session. The second hour of each session is spent in new teaching, with the teaching focused on what your Master feels you need to know next to progress on your artist journey. Every session ends with a homework assignment related to the teaching.

Since there is no homework to review in the first session, the first hour of the first Mastermind session typically has the Master ensuring they fully understand the needs of each Member. This time is also a great opportunity for you to get to know the other artists in the group.

Our Members tell us the safe community their group provides gives them the encouragement and support essential to venture out into new territory.

What happens between my monthly mentoring sessions?
Between monthly sessions you share your progress, get help from your peers, and celebrate & encourage each other on LUchat.

LUchat is a discussion board that we’ve built specifically for our artists. There’s an area on LUchat that’s completely private to your group, and your Navigator will also be there to connect with you. Recordings of every monthly session are also posted on LUchat just in case you miss a session or want to review the discussion.

Your group’s Master will not generally connect on LUchat. The availability of a world-class Master Artist is extremely limited, so take full advantage of the face-to-face monthly live videoconference sessions. Your
Navigator will bring questions raised by the group on LUchat to your Master, ensuring your needs are addressed in the monthly sessions.

How long do I stay with a Master?
After 4-6 months, your group is welcome to invite a different Master Artist to come and mentor you.

By bringing in a new Master, your learning journey never needs to grow stale, and you can access the wealth of experience our many different Masters have to offer.

Changing out your group’s Master is optional, and your Navigator will help you through this process.

What do I get for my money?

Our Members tell us they discover 4 key benefits at LevellingUp:

  1. You get to know (and to be known by) and become part of the community of a successful & skilled Master Artist
  2. You’ll develop skills – both technical and business – in just a few months that otherwise would have taken years, if not decades
  3. With face-to-face conversation and feedback on homework assignments, you’ll learn quickly how to take your artwork from good to excellent
  4. You get to connect daily with a safe and trusted community of your fellow artists, giving and receiving encouragement, helpful ideas, and opportunities to network
What is a LevellingUp Navigator?
Your Navigator is a growing artist just like you, and is provided by LevellingUp to ensure your group operates well, and to ensure your learning needs are met.

Every group includes a Navigator. Navigators are not Master Artists, and are also benefiting from the Master’s mentorship. As fellow artists, they understand your challenges and successes. As experienced facilitators, they’re well equipped to ensure your group runs well and you get full value from your time at LevellingUp.

Some of the things your Navigator does are:

  • Ensure the monthly sessions run on schedule, and everyone gets a chance to speak and share
  • Support the Master with preparation
  • Help everyone with the technology
  • Help your group select a new Master (your Navigator will stay with your group after your Master changes)
Can I join a group that has already started?
If a group has space available, you can join anytime.

That means the group you’re joining may have already been meeting for a while. Don’t worry that you’ll feel left out or left behind! Your Navigator will be sure to bring you up to speed – and because mentoring is all about responding to your personal needs, the Master will work very hard to ensure your questions are addressed.

How does the billing work? What am I committing to?
Your Mastermind group membership is billed monthly, and there is no minimum commitment.
We do encourage Members to plan to spend at least 6 months at LevellingUp, as it takes time for your skills to grow and for meaningful community to develop.

The monthly billing is automatic, and you have access to your account so you can cancel anytime.

What happens if I’m not happy?
We truly want LevellingUp to give you the support you need, so if you find your first choice of level or of Master isn’t a great fit, we’re happy to help you move into a different group.

In case its ever needed, we also offer a 90 day full money back guarantee.

What is LevellingUp?

Many of us feel “abandoned” or alone in our leadership roles, and we’re looking for people to join us on our journey.

By combining interactive coaching and collaborative community, LevellingUp offers a unique, powerful and affordable opportunity for growing professionals like you to secure success and experience joy.


You've been added to the waitlist! Please add earn.it@levellingup.ca to your contacts so that you don't miss our email.

Grow A Culture of Resiliency


Grow A Culture of Resiliency

You will be redirected to the PDF once you enter your email address. 

You have Successfully Subscribed!


Be the first to hear about...


  • NEW Master Artists & NEW Mastermind+ Groups launching!

You've been added to the list! Please add earn.it@levellingup.ca to your contacts so that you don't miss our emails.