Testimonials - Gregg Advisory

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Life’s most persistent and urgent question is: What are you doing for others?

– Dr. Martin Luther King, Jr.

Working with Cam

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Sue McGill

SVP| Head of Research & Innovation, ATB Ventures

for Executive Coaching

Working with Cam has been one of my most meaningful career moves ever. With so much change and uncertainty, staying grounded and decisive in every circumstance is challenging as a leader. Thanks to Cam's guidance and expertise, I have a deeper understanding of myself and have gained the confidence to step into my power while navigating profound disruption.

His unique ability to cut through the noise and focus on the root challenges has led to tremendous professional growth and impact for my team and the organization’s bottom line. A highly gifted, genuine, and dedicated coach, Cam has helped me to become a more purposeful leader and individual.

Melina Fairleigh

SVP People, Flock Freight

for Executive Coaching

Cam has been with me as my valued coach for four years through two high growth tech companies including being there for me personally during a transition. When I was first introduced to Cam, I hired him to work with my CEO and quickly had him begin working with me as well. During that time he expanded to working individually with three members of our executive team and helped to lead an offsite with the entire group.

Cam not only worked with each of us on our unique challenges and opportunities, but also developed an understanding of our business that made him an integral part of our decision-making support system. Meeting with Cam every other week became the highlight of my calendar as I knew I could get a second opinion (or fresh perspective) on confidential topics and situations – something that as the head of People, you too-often have to face alone. I recommended and hired Cam to work with a member of my new executive team without hesitation, and can see the impact that he is having as a coach. Cam is personable, kind, tough-minded, invested, and possesses the business acumen of an operator. He seems to always have the right construct, article, book, or quote that helps you see your personal and business challenges through a shared prism. With Cam, you are able to feel a part of a greater cohort of executive leaders – no longer alone – and better for it. I cannot recommend him highly enough.

Jason Silver

Former COO, integrate.ai

for Executive Coaching

In my opinion, there are two key areas that make a coach great: (1) creating a safe space for discussing day to day opportunities and challenges; and (2) driving personal growth faster and further than an individual would otherwise achieve on their own. Cam is this kind of great coach. His strength is striking the right balance between open conversations and concrete growth objectives. I'd highly recommend working with him to anyone looking to break through to the next stage of their own development.

Working with Cam helps me take a step back from the frenetic pace of my day to day to simply work through top of mind, often unstructured, thoughts in a safe space. Cam is an active listener who asks challenging questions to help add clarity to concepts that are just starting to form for me. When working together, it’s rare that we’ll stop at the discussion phase, often driving many initial thoughts to at least one concrete action. I often find myself leaving conversations with Cam having garnered a new insight or further clarity on the particular point of open discussion for that day. Though helpful, open conversations alone would not constitute a successful coaching relationship in my opinion. Cam adds the right amount of structure to ensure we’re progressing against a plan. We usually pair an open debate with a more specifically focused growth objective. To this Cam often adds “homework” that drives my own personal growth objectives while ticking off a day to day box at the same time. Personal growth and progression can also be hard to track and partnering with Cam adds a dimension to my personal reflections that help to make progress much more concrete. He helps me grow and better recognize how and where to focus next. Thanks Cam!

Chelsea MacDonald

CEO, ClearCloud | Former SVP Operations, Ada

for Executive Coaching

When I first met Cam, I’d just ended a coaching relationship with someone who had broken my trust. In my true fashion, I told him my expectations on trust, enumerated the issues we had to face using a numbered list and what I expected him to do to make that better. I am not even sure I told him my name or anything about me. I definitely didn’t ask him anything about himself. It wouldn’t surprise me if he told me I didn’t blink during that first encounter.

Over the past 3+ years, I can say that Cam has met my very high expectations and more. As a coach, a mentor, a confidante and ultimately, a friend, we’ve been through three promotions and the start of my first venture. He’s been able to help me connect to my more empathetic side, to get out of my professional ruts and above all, he’s believed in me when it was difficult to believe in myself. Unlike coaches in the past, he didn’t insist I needed to be a new person, he insisted that I needed to have different outcomes, and that was the difference between a coach that gets results with a human like me and everyone else. He does that with a mix of structured methodologies and broad business experience. He’s not a coach who has only been a coach, weighed down by dogma. He’s a true business leader who understands how things work inside of an organization, and adds a coaching structure to help you figure out how to get a different result. And through that? He’s someone I trust as a sounding board, a giver of fantastic advice and deliverer of difficult news. I can say unequivocally that I wouldn’t be where I am professionally without him, and let’s be clear how difficult it is for someone like me to admit she needs anything. He made that possible, and that’s made all of the difference.

Eric Lussier

Director Growth, Shopify | Former Director SEO, TripAdvisor

for Executive Coaching

I had the great opportunity to leverage Cam's coaching services for 6+ years. Over that time we met very regularly to discuss challenges at work such as how to handle specific critical conversations with coworkers, general career development, new ways of looking at problems and much more. Throughout, Cam shared from his own extensive professional experience which provided me with a great deal of guidance and confidence.

Cam has proven himself to be very trustworthy and attentive during every meeting. His calm demeanour and thoughtful questions have pushed me to become a better employee and overall person. This safe environment that he has built has allowed us to move well beyond the day-to-day of work where I now feel comfortable discussing just about anything about life. I always come away from our sessions with a new insight and actionable plan which is something I value tremendously.

Harley Finkelstein

President, Shopify

for Executive Coaching

About a decade ago, I was thrust into a position that would eventually become the most important role of my professional life. The problem was that I had very little experience. At the time, I was fortunate enough to have had a number of people helping advise, guide and support me - which made a huge difference. Throughout the challenges of building a company from a small handful of people to one of the world’s leading technology businesses, there was one person in particular that really stood out, his name is Cam Gregg.

Through a colleague I was introduced to Cam, who was a “coach”. I had no experience with a coach, and wasn’t sure what to expect. In fact, I was skeptical. I was unsure if this was someone I could trust and whether the investment of my time would create a real return for me. It turned out that those concerns were completely unfounded, and in fact coaching would become one of the greatest catalysts for my managerial abilities. Early on Cam helped me identify the transition that I wanted and needed to embark on in order to realize my full potential and add as much value as possible. From that point on, we worked tirelessly on that endeavour. Cam and I spent the next 4 years meeting on a bi-weekly basis. It wasn’t always easy, but it was always valuable. Cam didn’t give me the answers, rather he taught me how to find them for myself when I was unsure, a skill that would be critical to my future and to that of my company’s. But the benefits of working with Cam extended well beyond the office. This month, I became a father for the second time. Having children has helped me reflect upon my priorities—and the need to find a better work-life harmony. That’s hard when you’re in startup mode and working 80- or 90-hour weeks. I also stopped filling my calendar with back-to-back meetings and blocked out two hour-long slots each day to think, to physically move around the office, meditate and to connect with people serendipitously. That’s something I worked on with Cam, and it’s made me a better leader, husband and, I hope, father. This is one of the greatest references I’ve ever had the honour of writing. But it’s also one of the most difficult ones to properly articulate. It’s difficult to describe the experience of exponential personal growth. But that is truly what Cam Gregg helped me do, and I’m forever grateful.

Working with Deb

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Harley Finkelstein

President, Shopify

for Executive Coaching

Deb's superpower was asking thought-provoking questions that sharpened my ideas and, occasionally, flipped my opinion entirely. She helped me see where I was on track with outcomes that mattered, and where I might think or act differently in future opportunities. Deb also knew when to push me away from the familiar and back into the healthy tension that's required for growth. Our chats honed my instincts but also helped me see problems from completely new angles and perspectives. The highest compliment I can give is that I learned something new from each session.

I started working with Deb back in 2016. From early on, she became a trusted ally who deeply understood our executive team, the Shopify culture, the challenges we faced in the business, and what was required from us as leaders. Year after year, as Shopify continued its hypergrowth, the stakes were raised across the board. Every one of my decisions became more complex, and the impact was now felt across thousands of employees and millions of merchants. The trajectory of a leader must keep pace with the company they serve, and at Shopify, that’s no small order. The honest, vulnerable conversations I had with Deb kept me clear-sighted about how things were going and where I could continue to grow. Deb’s superpower was asking thought-provoking questions that sharpened my ideas and, occasionally, flipped my opinion entirely. She helped me see where I was on track with outcomes that mattered, and where I might think or act differently in future opportunities. Deb also knew when to push me away from the familiar and back into the healthy tension that’s required for growth. Our chats honed my instincts but also helped me see problems from completely new angles and perspectives. The highest compliment I can give is that I learned something new from each session. Deep care, wise counsel, and an always-pragmatic point of view—that’s Deb. She had my back but never hesitated to tell me the uncomfortable truth. She’s played an important role in my journey to be the best leader, husband, father, and human I can be, and I’m grateful for the five years we worked together.

Brittany Forsyth

Founder, Backbone Angels | Former Chief Talent Officer, Shopify

for Executive Coaching

My journey from Office Manager to Chief Talent Officer was over a decade long and full of ups and downs. It was a journey of growth, success and many failures along the way. I can honestly say that I wouldn't be where I am today, or have the success I've had at Shopify or in my life without Deb. The impact she's had is truly unmeasurable.

We started our coaching relationship in 2016 and focused heavily on a strategic mindset and my role on the executive team. Throughout the years, this focus evolved to both professional and personal growth opportunities. Always melding all aspects of me, as a human, to better myself and therefore my impact on the organization. Over the past six years Deb has been my partner and guide on this journey. Our practices flowed from specific skill building homework to new perspective building exercises (I could always count on Deb to be a source of truth, whether I wanted to hear it or not) to being a shoulder to confide in. She was the perfect combination of heart and head.

Jean Michel

Founder, Build Right Side | Former CTO/SVP Engineering, Shopify

for Executive Coaching

Deb worked as my coach for over 5 years. She’s brutally honest when you need it the most, but also strikes a balance of knowing when to let you discover yourself at your own pace. She helped me grow faster than Shopify was growing and that kept me on my toes and confident in leading in a complex and fast moving environment.

Loren Padelford

Chief Commercial Officer, Bill | Former VP/GM of Revenue & GM Shopify Plus

for Executive Coaching

Deb changed my career, and my life. She has been my coach for about 5 years, both during my time at Shopify and after. Deb's ability to cut through the noise and identify the areas for improvement has enabled me to develop new leadership skills, helped me to navigate challenging situations, and has helped me to better understand my own weaknesses, opportunities and risks.

Her own experiences and career give her a unique and highly valuable set of perspectives that helped me see things through different lenses. I would not have progressed to this stage in my career or managed to survive the hyper growth of Shopify had it not been for Deb. She is incredible.

Solmaz Shahalizadeh

Founding Partner, Backbone Angels | Board Member, Fullscript | Former VP, Head of Data, Shopify

for Executive Coaching

I had the pleasure of working with Deb as my coach for the past five years after I transitioned to my role as Head of Data at Shopify, a position I was equally ecstatic about and terrified to be thrust into. It was what I had always wanted to do, and yet I had very little experience doing it. Deb helped me understand and evolve from the leader of a 50 person group, to becoming the voice of data at Shopify, internally and externally, overseeing 500+ people with a seat at the executive table.

The coaching meetings were the ones I always looked forward to. I knew I’d get new perspective and insights about how I operate in my best times and when I’m under extreme pressure, and how to show up as my best for the company, my team and myself, at all times. That came from the immense trust I had in Deb and knowing that while she didn’t give me the answers, she would give me the tools to find the answers on my own. Growth companies are this beautiful chaos of many forces pushing up and to the right but the path isn’t always straight. At every setback, being able to take a step back and revisit the environment and our role in it, allows us to think of the best next step. Deb’s coaching offered me the unique space to better understand my own patterns of decision making, and ability to more fully understand the environment and as a result become a more effective leader, partner and friend. For all of these and much more, I’m forever grateful for Deb.

Lynsey Thornton

Founding Partner, Backbone Angels | Former VP UX, GM Core, Shopify

for Executive Coaching

Deb was my coach for 6+ years of extremely rapid growth and change at Shopify. It was my first coaching experience and I was skeptical. As a young leader, being catapulted from manager level to VP was a huge challenge. Deb increased the stability, pragmatism, and structure of my decision making processes. Her coaching can prompt very tough personal realizations, in a remarkably non-judgmental way that leaves her clients motivated and confident.

She contributed enormously to my effectiveness by helping me increase my confidence and improving my work approach. She coached the majority of Shopify’s executive team, as well as most senior women in the company, and was renowned for her thoughtfulness and insight. If you choose to work with Deb, she will adapt her approach to meet you where you are, and help you get where you need to be.

Atlee Clark

Director Shop, Shopify | Founding Partner, Backboneangels | Co-Founder, Pikalayers

for Executive Coaching

Working with Deb fundamentally altered the trajectory of my professional career. Her coaching has enabled me to become more self-aware, grounded and confident as a leader and decision maker. There is no better investment I could have made to ensure not only my success, but success in the way that feels authentic to me.

I had the opportunity to work with Deb for more than six years. Over that time I had many opportunities, successes, challenges and setbacks in my career and professional development. Deb helped me through each of these phases while also giving me the tools and skills to navigate the next one with more purpose and intentionality. I came to understand my blind spots, patterns and the impact I was having on those who worked with me much more clearly. Being able to see these things enabled me to change so that I could show up to situations the way I wanted to instead of the way I was used to. Through this work, Deb helped me embrace my strengths with more conviction and with a deeper understanding of how to teach what I am good at to others. Deb has a unique ability to be compassionate while also holding you accountable to your goals. She cares deeply about your professional development and goals as well as you as a person. If you are looking to seriously invest in yourself and your career, there is no better person to work with.

Janeen Speer

Chief People Office, Benevity | Former VP Talent, Shopify

for Executive Coaching

I had the pleasure of receiving coaching from Deb during my tenure as VP of Talent at Shopify. Deb has an incredible blend of business acumen and intuitive coaching ability that allows her to have significant impact. I found that she was able to connect concepts and "name" the trends that she saw happening in an effective way, giving us common language amongst our team to discuss things we saw happening.

Personally I felt that Deb challenged me to look deeply into the impact I was having and make thoughtful adjustments to raise my own performance. I would recommend Deb to any leader who is willing to engage in authentic discovery and take their performance to the next level.

Maryse LePage

Leadership Coach, Shopify

for Coaching Supervision

Working with Deb over the years has been a significant contributor to the coach - and human being - I am today. My passion for the craft of coaching is renewed every time I meet with Deb. She embodies learning, growth and the drive toward excellence in service of her clients.

Deb has facilitated my development in many ways. Important and often unexpected insights are revealed and new understanding takes shape. Then a firm and caring invitation to turn the possibilities into action. She has an uncanny ability to recognize patterns of thought and action in order to get to the very heart of challenges and issues – and reflects them back with clarity, precision and very deep care. She ultimately challenges and encourages me to reach for my highest potential. It is inspiring to know that she is walking the path of development and excellence with me.

Yasminka Kresic

Co-Owner, Human Capital | Former Leadership Coach, Shopify

for Coaching Supervision

I asked Deb to coach me when she and I were both at Shopify, after she had declared her passion for coaching coaches. What a phenomenal experience for me! She offered powerful metaphors to shift my way as a coach, with accompanying practices (not for the faint-hearted!) and learning sessions. She consistently showed up with presence, wisdom, compassion, and a willingness to challenge.

One of Deb’s gifts that I especially value is her deep curiosity about what drives people to act the way they do – which means that she will unearth uncomfortable but important patterns, and do so in a way that is fiercely accepting of you and in service of your growth. She is also a voracious learner – you can rest in knowing that she is constantly optimizing her skills and knowledge, out of love for her craft and her passion for her own personal growth. Without reservation, I highly recommend Deb as a masterful coach of coaches, and I predict that with her, you are in for a challenging, stimulating, and revelatory ride – in your evolution both as a human being and as a coach!

Donna Winfrey

Director of Learning & Development, Autodesk | former Coaching Lead, Shopify

for Coaching Supervision

My life has been forever changed thanks to Deb's expert coaching. Deb has a way of gently cutting through the fog, often a very dense fog that has hung around for years and contributed to my feelings of "stuckness", with the perfect, most relevant, most soul-connected, well-timed question.

She “sees” me and helps me see me with kindness, patience, and persistence. I am always on a self-development journey and have spent years in introspective work. However Deb’s coaching has been more transformative than all of that. She provides a safe and challenging space to help me move toward the life I am looking to create and the person I am becoming, which is a true gift.

Amandah Wood

Professional Coach | Founder of Ways We Work

for Coaching Supervision

Deb has this incredible ability to get right to the root of what is going on - specifically she is able to see patterns between how I'm showing up for my clients and my own personal areas for growth. I have truly learned the meaning of "coach as instrument" through our work together, and the deep connection between my own growth and that of my clients.

Deb has this great balance of being direct and helping uncover the pieces you might not be able to see just yet, while also holding such a supportive and compassionate space that it feels safe to try out new capabilities and new “ways of being”. As a result of our work together my coaching practice feels more spacious, and I feel more confident entering coaching sessions than I have ever felt before. More importantly, my clients have started to see increasing results since we began working together and many clients have decided to sign on to continue coaching with me as a result. I can’t recommend working with Deb enough if you’re ready to seriously level up as a coach – she is an absolute gamechanger.

Sylvie Daigle

Integral Coach and Facilitator

for Coaching Supervision

Working with Deb as my coaching supervisor in 2020, had a huge impact on my coaching practice. Before, working with Deb, I had a more conventional way of coaching, leaning on many years of experience and training as a senior manager and integral coach. Because of her exceptional quality of presence, in 6 sessions, Deb modeled a way of coaching where the coach is in resonance moment by moment with the client.

This showed me to really focus on what has potential in the moment, for my clients’ development. My coaching is more effective in terms of results but above all, it is much more satisfying, because I have now an internal reference for what it means to use myself as an instrument in the coaching process. I highly recommend working with Deb to bring your coaching practice at a new and unexpected level.