The Leadership League Mastermind 


Claim a braver, bolder business

You’ve got a business, and it’s a beautiful thing. 

You summoned the courage to start something new when there was a far easier path elsewhere. 

You took the risk that there were much greater rewards and impact waiting for you beyond the confines of the status quo.

You made the leap. You did the work. You made it happen. 

Even when it was hard. 

Your effort, perserverance and committment is now paying off. 

You're busy building your body of work and adding value to those you serve, all the while striving to create a better future for yourself and your family. 

You could trot along like this for years, and it would be just fine. Mostly. Probably. 

Except -- you know you're capable of more. Tremendously so. 

You're ready to step out of the shadows and bring a braver, stronger point of view forward. 

It's time to renew your commitment to yourself, your business and the people you serve, in a fundamental way. 

It's time to go beyond the latest strategy-du-jour, beyond marketing, beyond sales, beyond busywork and beyond the next bright shiny object. 

It's time to step up and claim the responsibility you've earned. To get the recognition you deserve. And to ground your work in clear, unwavering PURPOSE. 

And the VERY best way to get there is with others. A community of ambitious, like-minded women on their own leadership journey who get it.  

That's why I created...

Leadership League Mastermind

A Leadership Accelerator for CEOs on the Rise

We begin in...


What got you here won't get you there

And this realization comes with a bit of a reckoning as we understand that to get to the next level (however we define it), we'll be required to shift, re-align, recalibrate and even unlearn some of our go-to strategies and tactics.  

We intuitively know that we need to start to feel, think and behave differently to support our bigger goals and aspirations. 

We also know that the only way it's really going to work is if we can set it up in a way that doesn't compromise our well-being, our values or our impact in the process.  

And that can feel hard to navigate. Especially when our plates are already full.

We want more - for our lives, our work and the people we serve - and yet more feels too big, too nebulous, too beyond our wheelhouse, and too risky.  

This is a common reality for smart, ambitious women in business. I hear sentiments like these all of the time:  

"I want (and need) to step into leadership but I'm not feeling confident around that - what does that even look like for me?"  

"The stakes are high right now - I don't have time to overthink or stay in paralysis."  

"I've never led people before - this is new territory and I'm not sure I'm doing it right."  

"I'm exhausted! I'm not sure how long I can keep this up. Something's gotta give."  

"I know I'm capable of more, but I'm not sure how to get there, and truthfully I'm really scared to go for it."  

Regardless of your 'more', you'll need to develop the skills, confidence and resilience step up as the leader your business needs you to be. 

It's your time to rise and lead well

What I now know unequivocally is this:  

Your business will grow when you do.  

And I’m not alone in that. Read what John Mackey, Founder & Co-CEO of Whole Foods Market has to say:  

“If you are a leader of an organization, you have an ethical responsibility to grow as a human being – to become more conscious. Because only as you do that, will your organization be able to evolve too. Otherwise, you’re holding it back.” 

The Leadership League Mastermind is a nine-month container to develop, hone and practice your leadership skills with a group of women who are invested in your growth and fulfillment. 

You WILL become a stronger, more confident leader by the end. You WILL have clarity on how to navigate the next steps of your business journey. And you WILL have a set of powerful tools, templates and strategies you can use anytime you feel off course or have to navigate a tricky situation or decision. 

Are you ready to step up and lead?  

Sign up to receive our free email series about the Leadership League.

Together, we will strengthen your:


Tired of feeling unsure and trepedacious about your big ideas and what actions to take? 

We will build your confidence muscles to help you feel stronger and act braver.


There is NOTHING better than feeling the power of crystal clarity - about your message, your mission and how you want to showcase it. 

Together we'll ensure you're focusing on the right things to get the results that are most meaningful to you. 


We all have gaps that hold us back from the results we want to attain.  

We'll ensure you have the tools, skills and capacity to see your project all the way through by addressing any barriers or roadblocks up front.

Join a group of ambitious, high-performing women ready to claim a bigger vision for their work. 


Listen as Naomi Pereira, CEO & Founder of shares her Leadership League experience.


Here's what to expect. And everything you get:

Enjoy an intimate mastermind experience that will create a container for growth and connection for ambitious, mission-driven entrepreneurs and leaders on the rise. 

  • > A private 1:1 session with me immediately upon acceptance to set your goals and focus for the duration
  • > A kick-off session to meet your fellow members and connect
  • > 2x/monthly live Mastermind Sessions via Zoom (18 in total)
  • > 1x/monthly live Hot Seat Coaching & Office Hours (optional)
  • > Quarterly CEO Virtual Retreats (we reflect, review and plan for the future)
  • > Monthly themes and leadership challenges to keep you in action & growing  
  • > 5 additional private 1:1, 60-min coaching sessions with me 
  • > Private community for connection, questions and accountability 
  • > Showcase Session - a 15-min presentation by you to highlight your progress and step into the spotlight
  • > Lifetime Membership to LEAD.Well 


Private 1:1 Coaching with Stephanie 

Personalized, private support from me to help kick-start your journey. 

Mastermind Roundtable  

Bi-monthly meetings with a group of powerhouse women ready to challenge and champion you.

Leadership Topics 

Build your leadership capacities and skills through monthly leadership discussions. Each month we explore a new topic that's critical to every successful business owner. 

Office Hours & Hot Seats

Get direct support as you uplevel. Bring your questions, thorny issues or simply bring your best ideas for your fellow members.

CEO Virtual Retreats

Every three months, we'll gather together to reflect, review and make bold plans for the months ahead. This is a game-changer for your business. 

Tight-knit Community

Make deep, lasting relationships with a group of like-minded, thoughtful and strong women. 

Powered by care & caffeine

Your League Leader

Stephanie Pollock

Hi! I’m Stephanie Pollock. 

I'm a Leadership Coach, Speaker, Podcaster, and Writer, and I'm committed to helping women claim their greatness and level up their leadership. 

I’ve always sought out leadership roles: Mayor of my grade six classroom, captain of my field hockey and soccer teams, Vice Chair of the Board of one of our city’s biggest non-profit, steering committee member and organizer for the highly successful Women’s Leadership Forum, and head of numerous non-profit committees. 

I’ve been recognized as a Top 40 Under 40 changemaker in my region. I’ve been profiled and spotlighted in national media. I’ve completed an elite Leadership Training program, and received kudos from the governor general for my business prowess. 

Women’s leadership is at the heart of what I do. I believe that as business owners, whether we're a company of one or 100, we are all leaders (even if you've never considered yourself that before). 

And I want to help you step up and claim our place too - to be bold, be brave and realize your biggest business aspirations. 

Leadership Topics for Smart Women 

Along with your regular mastermind conversations, every month we'll explore a different leadership theme on timely topics that impact all entrepreneurial leaders. Each topic comes with an integration excercise to apply it to your own business. You'll also be able to supplement your learning through your lifetime membership inside LEAD.Well. 

Aligned Leadership

Uncover your own personal brand of leadership in alignment with your values, goals and vision for the future.

Design for Joy & Ease

After a few years (or more) in business, it's easy to add complexity that leads to analysis paralysis and over-thinking. Let's design for joy and ease instead.

Be Seen, Be Heard 

It's time to show up, stand out and have your voice heard. We're going to practice getting comfortable with visibility. 

Bold Moves, Brave Decisions

Leadership requires bravery, risk-taking and bold action. And it rests on your ability to discern what path to follow.

Entrepreneurial Resilience

THE most important measure of long-term success is your capacity to weather the ups and downs of business ownership.

Make Time for Magic

Our time is the only non-renewable resource we have. This month we'll make sure you're using your time wisely, and set you up wih a schedule that works...for you. 

Leading Others 

Regardless of whether you're a solo-shop or a team of 10 - being a leader requires the courage and conviction to lead others well.

Maximizing Impact

What impact are you called to make? This month we'll dream big and look for ways to deepen your impact. 

Play the Long Game

What gives you (and your business) staying power? We'll talk habits, rituals, routines and success conditions.

Business works better together

The thing about leadership is that it can be lonely. Really lonely.

As you rise, you'll find less people who deeply understand the challenges AND opportunities ahead, and how best to navigate them.

And so the pool of people you can turn to in the day-to-day realities of growing a business become smaller and smaller, leaving you feeling isolated and often second-guessing your decisions.

The Leadership League Mastermind offers you an intimate, caring (while equally challenging) container to show up as you are, bringing the frustrations, the celebrations and everything in between to the table. 

Together we'll help you sort through what's next, ditch what's holding you back, cheerlead you when you nail a win (big or small) and hold space for you when you're in the thick of things.

Want to know what's possible? Here's some of what our last cohort of Mastermind members accomplished:  

  • Claimed her role as CEO, expanded her business from Canada into Mexico, and lead a new, growing team forward while keeping their values intact 
  • Published her first book and took on 100 acts of promotion and outreach to spread the word
  • Grew her business to the point where she could quit her full-time job and focus solely on her company's growth
  • Moved from being the world's best behind-the-scenes worker bee, to claiming her rightful place in the spotlight as a leader in HR recruitment
  • Revamped her entire business ecoystem to streamline operations, learned to say no to opportunities that pulled her away from her zone of genius work, and ultimately went from underbooked to fully booked in a matter of months
  • Moved beyond her fear of sales conversations/pitching to having close to 20 discovery calls and closing a number of new clients
  • Launched a 30-day free Planning Program to bring in new members for her Membership Community 
  • Stepped out from behind, and created five + acts of bold visibility (public speaking, interviews, guest posts etc) to claim her expertise and build her authority
  • Took on 100 acts of outreach to connect with potential partners, referrers, clients and influencers 
  • Went after her first five clients in a brand-new business venture  

"Being surrounded by a group of strong women who are also challenging themselves to step things up, made a huge difference to my own motivation. Seeing other people being brave, boldly trying things, and stretching themselves, gave me to the courage to do the same. I know they inspired me to do more than I would have on my own.  

The value of the Leadership League Mastermind for me was about a group of women who wanted my success as much as they wanted their own. I had a cheering squad for my accomplishments, a quiet space to rest when I got tired, and even a place to cry over the failures. 

Steph is a skilled facilitator and created the safe place for all of us to share. She is also a skilled coach and asked me the tough questions to help me change my own patterns. If you have a bold move you need to make...join. It is so much better to reach for your bigger dreams with women who are reaching for their dreams too!  

~Kirsten Wreggitt, Author & Opportunity Cultivator 

Are you ready to claim a braver, bolder business?

Tuition & Application Details:

The Leadership League Mastermind is a high-touch program with personalized support, leadership coaching, peer feedback and relevant (and timeless) trainings.

The League runs from May 12, 2020 to March 24, 2021. can 

Investment: $5,000 CAD Payment plans are available in monthly installments.  

If you are interested, please take a moment to apply. We will then hop on the phone and ensure this is the right fit for you.  

*Please note: this is an active committment, not a membership subscription. You are responsible for the full tuition. 

 What results you can expect: 

  • Step up as the CEO of your business and feel the confidence that comes from your leadership position
  • See your most important project all way through - from idea to completion 
  • Take bolder, braver action toward the projects and ideas that matter most 
  • Increase your income, impact and influence 
  • Step into your personal power and fill the gaps where you're currently giving it away 
  • Feel more confident in all aspects of your business 
  • Start (or amplify) using your voice to share your ideas and build your authority 
  • Build a business that aligns with your values, your highest capacity for contribution and how you want to live your life 
  • Make better decisions that align with your values (not just what's in front of you) 
  • Set stronger boundaries with grace to protect your time and your well-being 
  • Use language that lifts your message up (instead of dilutes its impact) 
  • Take action daily in support of your goals (with a renewed sense of clarity and purpose)
  • Have a tight-knit community of women committed to your growth and well-being  
Pepper Makepeace - Leadership League Member

"There's been a huge demystification for me around the concept of leadership. It's no longer tied to ideas of being an "expert" or a "thought leader" which sound icky and ego-based. But instead it's more tangible acts of love and badassery deeply rooted in our core values. 

It's about the courage and clarity required to hold ourselves accountable to those values in all areas of our lives. Looking at leadership this way has opened my eyes to my own behaviors and how much of a dis-service some of these behaviors are to me, my clients, and anything I care about. But also a new awareness to the ways that I am embracing leadership in some areas and that helps build my confidence. 

While it's broadened my view of the concept of leadership, it's also made leadership a more tangible, more actionable, and less daunting aspiration. Because it's the consistent, daily acts that count - not just the big gestures.  

The support I feel from true connection with an amazing group of women is immeasurable. I will be eternally grateful for this opportunity to be a part of this group."  

~Pepper Makepeace, Founder Small Business Sisterhood 


Talk to me about attendance. Is it mandatory?  

Essentially, yes. Of course I know that things might come up over the course of our time that would prevent you from attending a session. And that’s ok.  

However, the strength of a mastermind is squarely in the commitment of its members. If only a few people show up each session, everybody misses out on the richness of conversation, feedback and insight that could be possible.  

So do please check the schedule here and see if the dates work for you. If most do, then great. If most don’t, then I’d encourage you to check out the next round.  

What stage of business should I be at to apply for the League? 

To ensure each member is able to get and give the most from the Mastermind experience, I'm currently accepting members who have been in business at least three years (or by exception, have grown quickly and have a stable business as early as year one). Because we'll be using the Mastermind as a container to talk through and practice stepping into leadership, each member must have a business foundation to draw on. Any questions? Send me an email at and we can discuss. 

Why should I pay for a mastermind? Couldn’t I just create one for free on my own?  

Of course you could! And if this program isn’t the right fit for you, then I do encourage you to do so. I’m all in favour of informal masterminds (I’ve always been part of one).  

The difference here is that I’ve created a very specific, thoughtful container to help you make significant progress quicky. And I'll vet each member ahead of time to make sure the group the just-right mix of personalities, aspirations and business stage. 

What will I walk away with at the end of this experience?  

I know this sounds cliché, but you’ll get out of this experience what you’re willing to put in. So bear that in mind. If you show up, engage with the group, stay open to sharing your challenges and your wins, and be willing to test out your learnings, I know you’ll receive a tremendous amount from this Mastermind.  

In particular, you can expect to:  

  • Make bold, brave action toward a project that will catapult your business forward
  • Have a greater sense of confidence in yourself and in your approach to business  
  • Form deep connections with people traveling the same path who can challenge and cheerlead you along the way  
  • Take bolder action in service of your goals  
  • Feel aligned with your business in a way you likely haven’t yet, knowing that your vision, mission, values and goals are lined up in a way that is truest to you  
  • Make better, faster and smarter decisions with a solid framework to guide them  
  • Have clarity around the unique contribution your business can make to the greater good (this will be highly personalized to you and your business)  
  • Be actively using your voice in pursuit of what matters most  
  • Feel less overwhelmed and unclear about what to do and how to do it  
  • Have a clear plan to navigate the ups and downs of entrepreneurship without burning out  
  • Take full ownership for your company as its leader in a way that will position you for the greatest growth and contribution  

Who is this program not a good fit for?  

I tend to dislike these “who is this right for / who is this wrong for” style of questions because the answers feel really judgemental. So I’m going to mostly bypass that trusting that after reading this and everything else, you have a gut sense of whether this is a good fit for you (or let's chat to ensure it is).  

However, I WILL say that there are a couple of things that I do want to highlight as being immediate disqualifiers for the group. This isn’t from a place of judgement, but rather experience.  

You need to have a desire to be in motion and stay in motion. If you're in a season of business focused on slowing down, simplifying and taking a breather, this is absolutely NOT the right program for you (at least right now). While I am very mindful about staying out of overwhelm and making sustainable plans, the Leadership League Mastermind is about action, practice and bravery first.  

And, if you hold things really close to the chest and really struggle to share what’s true for you (unless it’s bright and shiny) this probably isn’t a good fit for you. Great masterminds require a degree of vulnerability on behalf of each member to really thrive. Does this mean you have to share all your deep secrets? Of course not. But you do need to be willing to come to the sessions ready to share your insights, learnings, challenges and most of all, yourself.  

As well, you must be willing to give and receive feedback openly and respectfully. That means that you’re willing to be generous with your ideas, connections, support and constructive feedback for your fellow members, and be open to receiving this from them. I am not interested in having to work exceptionally hard to draw people out -- I’m looking for people ready to share, be of service and learn. 

And finally, this is not a good fit for you if you dislike online learning environment. We use Zoom (very user-friendly) and all meetings happen over video. If you greaty prefer in-person to online, this may not ideal. 

What are the dates for this round? 

You can find the full list of dates here. We begin May 12, 2020.  

What are my next steps if I’d like to explore this further?  

If this is speaking to you, I encourage you to apply as there are only a handful of spots available. Applying does not obligate you to the mastermind. Once I receive your application, we’ll hop on the phone for a quick chat to really make sure it’s a great fit - both for you and the collective group.  

If we’re both a go, you’ll receive an email with a link to register and from there you’ll get an email with more details. 

More questions? Feel free to email me at and I'd be happy to answer. 

ore questions? 

Kerry Worth

"The Leadership League Mastermind experience has given me so many things. Motivation, focus, a group of like-minded entrepreneurs who understand the daily challenges and opportunities of running your own business.

I feel like this group is my pack - we run together - spurring us onward and supporting each other when one or more of us is faltering. We move at different speeds in different industries, yet we also move as a group, propelling each other forward to be our best selves.  

As an employee, I have been in leadership positions before. But as a new business owner, the challenges are different. The focus is so broad; there are so many different elements clamoring for your attention. 

Learning to be a leader in my own business has been challenging and I am grateful for the structure, camaraderie and shared assignments the Leadership League provides - pushing me to lead in this new way.  

Stephanie is an expert facilitator. She knows just what assignments and questions will draw out our sticking points. She shines a kind yet strong light on the challenges and offers different ways of looking at your goals - to get you there with just the right amount of discomfort to know your goal is worthwhile. 

When you choose your BAM, you feel daunted. And yet it is amazing to watch yourself and your fellow Leaguers move through those BAM goals and do more than they thought possible."

~ Kerry Worth, Worthwhile Nutrition