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Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

I am a semi-active angel investor with a portfolio of 14 investments, 2 highly positive exits and counting.

In my spare time, I am a passionate CrossFit athlete and electronic music producer/ DJ.

Services

As soon as you raise capital, you are committing yourself and your company to a one-way path of accelerated value creation. The leaders of high growth companies face tremendous pressure and expectations to grow themselves in order to keep up and remain relevant. The biggest outcomes are most often founder-led, start to finish. The highest leverage thing that you can do as a CEO is invest in your performance through coaching.

 

I work with the CEOs of venture and PE- backed technology companies to help them scale faster than their businesses so that they can be the best possible leaders and achieve the biggest outcomes.

 

In addition, I offer deal advice to companies that need help getting deals done but don’t want or need an investment bank.

CEO Coaching

1 on 1 coaching designed to maximize your effectiveness as a business leader and become a more fulfilled, complete human being.

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Deal Advice

Highly specific, tactical, behind-the-scenes deal advice based on over 20 years of doing venture capital, private equity and merger & acquisition deals.

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Investments

These are my personal angel investments. Some came through my involvement as an advisor to these companies. Others are more traditional investments. I invest first and foremost in people: in particular a founding leader that I believe can become a great CEO. The best outcomes are founder-led. Back the right founder and he or she will figure out the rest. Beyond the people filter, I only invest in sectors where I have deep knowledge and can be helpful, such as B2B SaaS and e-commerce.

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Testimonials

FAQ

What is exec coaching? How does coaching differ from mentoring or consulting?

Coaching is a deep 1 on 1 relationship designed to help you generate your own insights, growth and path forward. We work through personal and company issues to remove blockers and unlock performance. It is not about me giving you the answers. It is about helping you unlock the answers within you.

 

Mentoring is about sharing past experiences and lessons learned. Consulting can take many forms such as advice or actual project work.

 

Our sessions will sometimes touch on mentoring as clients look to leverage my experience. But, for the most part, we will be focused on coaching.

Why do clients choose to work with you?

My clients are looking for both personal growth and to maximize their personal and company performance. They realize what is at stake and what it will take for them to deliver on their own and their investors’ expectations.

 

They choose me because I have sat in their shoes. I have operated venture-backed startups and scale ups. I have been a VC. I have been funding, growing and exiting technology companies since 1999.

What topics can be discussed?

Anything is fair game. Whatever you or your business is going through, I have probably encountered it before.

Can I speak with references?

As you can imagine, I have private, intimate relationships with my clients. While I ask for testimonials and have shared them liberally on this site, the specific identity of my clients and the nature of what we work on together is highly confidential. As a result, I do not ask clients to do reference calls.

How does coaching work?

If we don’t know each other already, then I recommend a more immersive session upfront so that I have a deep understanding of you and your business.

 

From there, we move to ongoing calls. Usually twice a month, 50 minutes per call. I am available for spot coaching / special issues as needed.

 

Coaching sessions are remote over Zoom for the most part. Ideally the upfront immersive sessions are done in person so we can better get to know each other.

 

It is important that we set clear goals for coaching upfront. That way we will know when we have succeeded.

What is the cost?

I charge a monthly retainer and ask for a standard advisor option grant. 

 

I strongly believe that a CEO of a venture-funded company is like a pro athlete. He or she needs to have the best team around them to enable elite performance. I work with CEOs and CFOs who realize what is expected of them and invest in themselves to exceed these expectations.

How long does coaching last?

Individual sessions are 45 – 50 minutes long. The duration of the relationship is dependent on what you are trying to achieve.

 

My hope is that through coaching and my deal work that I will become a close friend of the company and an objective, trusted advisor over many years. That doesn’t mean you are a client the whole time, but that we come together as needed to make things happen and bring you and your business to the next level.

Latest Blog Feed

How to think about exit strategy

In my discussions with CEOs we often talk about exit strategy. Either because the company has current inbound interest or just thinking about the future. There is no one ‘right’ answer for when to sell your business. I often bring […]

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Why now?

Why now? This is perhaps the most strategic question for a startup investor. You can have an amazing team with an amazing product, but if they don’t get the timing right, it won’t be a win. There were search engines […]

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Nothing to hide: The benefits of being fully open

It is a truism that we fear what we don’t know. Left to our own devices, what we imagine is often worse than the reality. This is a hard-wired fight or flight survival mechanism. i.e. it won’t change. If staff […]

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Contact

Email : me@markmacleod.me

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