These three words have been rolling around in my brain for months. What does it take to operate a finance department in 2022? Is it any different than 2002?
The answer of course is yes. While finance professionals are known for their logic and reason, they are not immune to change. A new generation of finance leaders is making waves in Canada — rethinking how they build their teams, navigate career paths, implement technology, and steward their companies through the inevitable peaks and valleys they will face.
Retained Learnings was dreamt up as a way to put a spotlight on these forward-thinking finance leaders in Canadian startup and midmarket companies. People like Mark MacLeod, one of Canada’s most interesting finance leaders, and now executive coach, who shares advice from his long and successful career with companies including Shopify and Freshbooks. Or accounting leader Angela Gill, who is brave enough to explore the world of TikTok as a means of reaching new audiences.
This monthly digital publication will also take conversations about Canadian finance operations out of the 1:1 realm into a more public sphere where information is accessible to anyone. Whether you need real-world tips on navigating a migration to NetSuite or insights on how other teams are planning and executing their budget cycles, you can look for it here, or by listening to the Retained Learnings podcast, available on your favourite podcasting platform.
Welcome to the inaugural edition of Retained Learnings. Enjoy reading!
Like many finance professionals, Angela Bierman, Finance Manager at Calgary West Central Primary Care Network, considers herself a recovering perfectionist.
“I’m an accountant,” she recently explained in an interview with CPA Alberta, “I used to think I don’t have the luxury of ‘good enough.’ Numbers are black and white, and they have to be perfect, but I’ve come to understand that even accountants have to embrace the grey.”
This perspective has led her to develop a specialty in building systems that support complex operations.
“I like being able to support a business in having a more strategic focus,” she shared with the Float team. “Whether we’re in good times or bad, someone always needs to count and report on the money. What’s been really exciting is not just looking backwards, but helping with analysis and projections to help businesses figure out where they’re going.”
Since beginning her career in 2008 at Fitzpatrick & Company, a local public accounting firm in Prince Edward Island, Bierman has built up a reputation as a finance powerhouse who champions innovation, embraces change, and always puts people first. In this interview with the Float team, she shares advice for fellow accountants who are looking to evolve in their careers.
What led you to pursue a career in finance? How did you get your first job?
AG: I love things that are organized and in neat and tidy boxes. I was always very good at math. It’s funny, everyone would always tell me I should be an actuary but I didn’t want to go that route. After studying engineering and psychology, that’s when I found accounting and it was home for me. I actually didn’t find accounting until my third year of university. But once I did, I knew right away it was what I was meant to do.
I worked with a local public accounting firm in Prince Edward Island called Fitzpatrick & Company for about three years. I went through the process to get my CPA designation while I was there as well. When I started with the company, it was actually their first year of operations, so I was able to see a lot of growth firsthand.
Was the job what you expected?
AG: No! A lot of people think there is monotony in accounting but working at a public accounting firm was just the opposite. Our clients were diverse; they ranged from dairy farmers to restaurants. There was so much opportunity to learn and I was really able to expand my skill set there.
At the end of the day, a business always needs a financial system and the finance team is critical in weathering that storm. A lot of organizations see finance and accounting as a cost center, something that they have to do and can’t get away from. Being able to sell leadership and management on the value that finance can bring is a lot easier when we have smart tools to help us automate and integrate our financial processes. It gives us a more strategic lens, while helping us better showcase our value.
What was the first step that you took to advance your career, personally?
AG: Any time someone asks what I’m most proud of, I always tell them it’s my Chartered Professional Accountant Designation. My journey to obtaining my CPA designation was very challenging, but it taught me a lot. I learned how to effectively prioritize and make the best use of my time. I also discovered that critical thinking is not only about what you know today, but how you approach what comes your way tomorrow.
More importantly, my CPA designation has given me the confidence to believe in my skills. Each day, it serves as a reminder that I am capable of overcoming challenges, learning difficult things, and that I deserve to be where I am. This reminder is especially helpful when imposter syndrome creeps in.
As soon as I got my CPA, I moved across the country to Calgary and have loved every second of being out West since. I jumped feet first, moved with a lease, and three interviews lined up, and the rest is history!
What other steps have you taken to level up in your career?
AG: I research software and trends as a hobby. I’m always learning new apps and follow a bunch of creators in the realm of finance business partnering on LinkedIn. For me, I really see technology as the tool that is going to make our lives easier and elevate us to do our best work. Technology is designed to eliminate and reduce data entry and prevent us from making silly mistakes. If we can have system controls that will protect us from ourselves, that’s just the way to go! I’ve been really passionate about learning more and I’m always on the lookout to grow and understand tools and technology that I can introduce to my team. I’ve also been reading about leadership, change management, and how technology serves as a tool to impact people.
What’s challenging about being a leader in finance right now?
AG: It’s a balancing act between building and generating the data and analyzing that data in a way that’s useful to tell stories. When it comes to being more innovative, I am very aware of the pace of change in which new technology is introduced. While the goal is to make everyone’s lives easier, it can also make things harder if we’re changing too much, too fast.
I’ve had to regularly assess priorities and check in on where my team and the organization is at. In my job, I try to maintain three priorities: current financial reporting, strategic focus on how I can help budget holders and leadership make better decisions, and revamping the systems that underpin the first two priorities. Any leader needs to be in the driver’s seat of their own priorities. This keeps you in a proactive instead of reactive mindset, allowing you to move the needle on what’s important to you and the organization as a whole.
What would you say are the toughest decisions finance leaders are making today?
AG: I think deciding where to make long-term investments is one of the toughest decisions. The world has changed so much in the last two to three years and when you’re making a financial decision, it’s hard to hypothesize what the conditions are going to be like in five, 10, or 15 years. Recognizing that, I think it’s important to have wider frames of acceptable risk. If you need a very narrow set of circumstances for something to succeed, your time frame needs to be short. If you’ve got a wider set of circumstances where you can envision success, then you can go a little bit longer term.
What are some of the most interesting projects that you’ve been working on?
AG: I’m really passionate about digital transformations – transforming accounting systems, new applications and innovative processes – I get so excited by all of it! Testing out new technologies and apps allows me a sense of play. Recently, I’ve been involved in several projects related to going paperless, moving to a digital invoicing system, and implementing new apps and processes.
At my current job, we changed accounting systems from a legacy ERP to cloud-based Xero and integrated several apps, including Float, which has been a lot of fun for me. It was a real game changer for my team in terms of simplifying our process, adding greater consistency, and just making our lives easier by reducing the burden of data entry. Now, we’re able to spend more time on analysis, which is where we can bring greater value to the organization.
What have been some of the boldest decisions you’ve made lately?
AG: Our previous system was not user-friendly. I really struggled with it. I couldn’t even figure out how to get my general ledger exported for Excel and do some basic analysis. Despite my level of comfort with technology, I couldn’t get what I needed out of our old system and I grew very frustrated because I knew there was a better way.
I have a healthy appetite for change and innovation, which always go hand-in-hand. When it comes to introducing new technology to my team, I like to collect data on what’s out there and observe what everyone else is doing – which is one of the reasons I initiated our switch to Xero. It had a great reputation and so many cloud-based accounting firms recommended it. There are established gold standards when it comes to apps, so I wanted to go with something that was highly reviewed.
In some ways, it feels like we’re in new finance terrain with so much technology, market volatility, changes to regulation, and other challenges. In your opinion, what steps do you take to ensure you’re making your best possible decision?
AG: Assessing risk head on is key. It’s crucial to critically examine which risks you’re willing to accept and which ones you’re going to actively mitigate. It’s also important to understand your own values and the organization’s values, so that no matter what comes your way, you can use that as a framework to make the right decisions.
Another is pulling the plug on a project I’ve spent money on that’s not working. Sometimes you need to try things out in order to fully understand if it’s going to work and benefit the business. If I spend money and it doesn’t work out, I have no qualms letting it go. I’ve paid to learn something I might not have otherwise known, which has given me direction to look at alternative options. I’m not paralysed by waiting to find the perfect solution. Instead, I move quickly and sometimes that means failing forward.
Don’t get me wrong, I’m not flippant with spending money, but it’s critical to take a step back and assess if what we’re doing is really working. Something I always tell my team is to take the hiccups and mishaps as lessons, and make different mistakes, not the same ones.
Being able to sell leadership and management on the value that finance can bring is a lot easier when we have smart tools to help us automate and integrate our financial processes. It gives us a more strategic lens, while helping us better showcase our value.
Are there any mentors who have helped you level up into leadership? What is some of the best advice or guidance that you’ve ever received?
AG: I have an executive coach – her name is Dr. Wilma Slenders. She works for a company called Transcend Management and has been instrumental in my growth as an individual and leader. It’s hard to get that independent lens of what you’re struggling with at work. There’s confidentiality concerns, and seeing somebody that’s completely outside of your organization is really valuable.
Dr. Wilma Slenders has an ability to ask me the right questions and is so helpful with communication. Personally, I want to be more direct in the way I communicate and she’s taught me how to use the correct language and has even recommended great articles and books. She listens and validates, and is able to give me a new perspective on things – because often, the problem is not what we think it is.
What are some of your future aspirations?
AG: I love working in an environment that is collaborative, innovative, and psychologically safe. I’ve been having a tremendous amount of fun with software implementation and systems improvement. I recently started a TikTok channel for tech and productivity tips to help others beat burnout. It has really scratched my creative itch! I’m very eager to share my passion and enthusiasm for technology in ways that help make people’s lives easier.
What words of advice or encouragement do you have for aspiring finance leaders?
AG: Assess your people and leadership skills. A lot of finance leaders are incredible with numbers, it’s where our training was focused and where our skill and comfort level lies. Since obtaining my CPA and going into leadership and management, I’ve made mistakes and I’ve learned a lot of lessons, so I’ve invested in improving my skills in that area.
I don’t work in isolation. To achieve, I need a team that is aligned, I need collaboration from peers, and I need support from leadership and management. I don’t have it figured out 100%, but I continue to work on it everyday.
I also think the finance industry can be prone to burn out. We have a lot of deadlines, a lot of expectations, and a lot of manual work that has to happen. I would encourage everybody – especially those early in their careers – to set healthy boundaries and have balance. Understand that the work is going to be there tomorrow.
In the world of finance and accounting, every detail matters. There’s absolutely no wiggle room for error. But there also aren’t enough hours in the day to do everything that needs to get done. That means finance teams often have no choice but to deprioritize more meaningful (and enjoyable) strategic initiatives.
One of our goals at Retained Learnings is to help finance professionals get ahead of this dynamic and gain more control over their careers as a result. Throughout 2022, we’ve been conducting research with a focus group to better understand common pain points and time sinks. An issue that inevitably comes up is expense management, particularly in remote work contexts.
To help explore this issue in greater depth, we commissioned a survey of 427 Canadian finance decision makers at companies with 15-300 employees. All respondents were members of the online Angus Reid Forum. Here are some key findings.
1. Challenges tracking real-time spending
Finance leaders are increasingly focused on tracking spend and finding opportunities for cost savings. Unfortunately, the reality is that much expense management is done retroactively after the expenses have been incurred.
It’s common for business expenses to be incurred on credit cards, and yet this is an area of spend that is rife with operational bottlenecks.
38% of businesses are unable to track corporate card spending in real time
36% of businesses have difficulty keeping track of access to corporate cards
51% of businesses with remote workforces say receipt tracking has become more complicated
2. Requiring employees to incur business expenses on their personal cards
Whether an employee is traveling for a conference or picking up supplies for a virtual social, most companies are expecting the employee to outlay this expense on their personal credit card and get reimbursed in the future.
Why is this a problem?
As the economy worsens, individuals are being stretched more than ever – rising interest rates causing higher mortgage payments and inflation causing prices of everything to go up from rent to groceries.
In addition, 51% of companies with remote workforces agree that time spent reporting expenses negatively impacts their ability to accomplish work.
3. Time spent on closing books and expense reconciliation
As companies look to conserve cash, employee headcount is under extra scrutiny. Finance departments must evaluate all expenses with a critical eye, and look for ways to support the business without hiring new staff.
Expense management is an area that traditionally involves a high degree of manual data entry and time-consuming repetitive tasks.
4. As companies increasingly shift to remote or hybrid workforces, finance leaders need to consider new measures to prevent security risks and operating bottlenecks.
Security and fraud risks are rising across the board. The best way to address these challenges is to address and identify potential issues head-on, before they have a chance to bubble up. Here are some of the problem areas that came up in our research.
57% of businesses where employees use their personal credit cards for business expenses also share company credit cards across multiple employees
63% of businesses with remote workforces share credit card details over Slack or email (3x that of companies who are not fully remote)
5. Remote workforce challenges
Virtual socials, work from home stipends, the list goes on. As companies increasingly moved to a remote or hybrid workforce during the Covid pandemic, this resulted in new or more pronounced issues around expense management.
The most time-consuming expense reporting tasks for companies that have shifted to remote work are: ensuring expenses are accurate (64%), fixing human errors (56%), tracking down employees for receipts (56%) and manually reconciling and entering data (55%).
Almost half (48%) of businesses with most or all employees shifting to remote work are seeing increased paperwork from expense reporting
30 percent of businesses who have most or all of their employees working remotely use 6 or more different finance software and tools for accounting-related work
The ripple effect of heavy manual expense tracking is that it leaves businesses unable to scale up without increasing overhead. It’s important to tackle expense management issues as early on as possible. Take a look at the full report to help with identifying issues that may be impacting your organization.
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Methodology: These are the findings of a survey conducted by Float from May 26-30, 2022 among a nationally representative sample of 427 Canadian finance decision makers at companies with 15-300 employees. All respondents were members of the online Angus Reid Forum. For comparison purposes only, a probability sample of this size would yield a margin or error of +/- 4.7 percentage points, 19 times out of 20. The survey was offered in both English and French.
Retained Learnings reached out to a group of Canadian venture capitalists (VCs) for their expert insights on how founders and finance leaders can best navigate these questions. Here are some highlights from our interviews:
Tactics for finance leaders to empower their organizations
1. Don’t underestimate the power of focus
Eliminate the noise, reexamine what your company needs now to grow, and stay focused on the outcome.
“In challenging environments like these, a ruthless focus on the thing that matters most for the business is required to succeed. What is the one thing you need to get right in order to win? Apply all your resources and energy to that thing, and tune everything else out because it’s noise.”
Cash flow is always foundational, but in this market, it has taken on new meaning.
“Our advice to founders in this environment has two approaches. The first is to make time your friend by ensuring enough cash runway exists to enable businesses to succeed, and the second is more nuanced depending on the sector or company. In markets where growth is accelerating, we are telling our founders to seize the opportunity. In those cases where growth is slowing, we are asking them to focus on efficiency and finding gritty ways to grow. A one-size-fits all advice policy isn’t always appropriate. Your customers should be telling you how you are doing.”
3. Lean into tailwinds, and be courageous about headwinds
Take stock of what opportunities can accelerate your growth or productivity. Make tough calls to reduce the impact of headwinds.
“If you provide your customers with real and immediate productivity tools or mission-critical applications, this investment may become a tailwind for your business. You will have opportunities to gain market share, innovate, and accelerate your growth. It is during recessions that Google and Facebook have emerged as leaders. So there! It’s not all bad news.
If you are in a tailwind situation, this is surely a good time to accelerate your product agenda, or even buy a competitor if you happen to be blessed with a sufficient pool of resources. Understanding your competitor’s cash and competitive position, as well as your own, will be more important than ever.
In contrast, if a recession sends headwinds your way, it is crucial for you to have the courage to recognize your position and make tough decisions. Only then will you buy the option to make it through to see the next up cycle.”
Understand that the details matter. Now is the time to be more intentional about the small details that have the potential to scale up.
“There’s a misconception about a trade-off that exists between focusing on growth at all costs, and profitable growth, because doing both a little bit often doesn’t work super well. You should always be steering a tight ship.
Consider every dollar spent as an experiment that requires justification for continued investment. Measure everything and you’ll know exactly where to double down. Is there low-hanging fruit optimizing conversion rates? Can you reduce customer acquisition costs (CAC) with viral product strategies? Lengthen long-term value (LTV) with customer success or re-engagement campaigns? How do you justify a new full-time salary?
Growth leadership during an economic downturn isn’t just about go-to-market, it’s a full-company effort. Capital is best raised if you know exactly how to spend it.”
5. Find the middle ground between growth and profitability
Remember that success is a spectrum. Balanced thinking has the potential to be your company’s competitive advantage.
“You’re certainly not going to win in raising capital just by showing that you’re profitable but not growing. And then on the flip side now, I don’t think you can just be growing and not demonstrate some level of potential for a profitable, healthy unit economic business. So you have to find the middle ground of, you know, really strong growth and proof points around your unit economics. Now, this always depends on stage and the type of business, but it’s finding that middle ground.”
As the saying goes, we can’t change the world around us — but we can take action to ensure that we are optimally prepared. Every business has its own unique story, and it’s up to finance leaders to support leadership in making the right judgment calls. Now more than ever, founders, executive teams, investors, and finance teams need to be working closely together to ensure the best possible outcomes for their organizations. The bottom line is to never underestimate the power of self-stability as a force of forward progress.
Introducing The F Word, a new comic that puts the spotlight on the inner workings of the finance department. Whether it’s chasing employees for receipts or nerding out on Excel jokes, we’ll show you that finance isn’t as dry as people think. If Dilbert and The Office had a baby, and that baby was really good with numbers, it would be The F Word.
Have a funny finance anecdote to share with us? Let us know by Tweeting @floatcard .
Jennifer McNamee and her team weren’t worried. They hadn’t heard the horror stories. There was a general “We’ve got this” vibe. It didn’t last long, though.
“We told ourselves, ‘We’ve implemented software platforms before, and we’ll do it again,’” McNamee, Float’s Senior Finance and Accounting Manager, recalled, harkening back to a project with a previous employer. “But then, halfway through, it was like, ‘Okay, actually, this is a huge beast.’
The beast, of course, was NetSuite, an integrated suite of applications that spans enterprise resource planning (ERP), customer relationship management (CRM) and e-commerce.
This is not necessarily a criticism of the product itself. It’s just that any time a company moves from technology with basic functionality to something more advanced, there is going to be a learning curve. Too often, people have to pursue that learning on their own.
With that in mind, Retained Learnings drew upon McNamee’s experience, prior to joining Float, to create a high level NetSuite upgrade playbook and help streamline this journey for fellow finance professionals.
Step 1: Review your business case for a NetSuite upgrade
It’s easy to understand why growing companies don’t start off with a platform like NetSuite. It would be like a single person buying a mansion as a first home: their life probably hasn’t got enough going on to fill all those rooms.
In a similar way, many companies typically set up their finance and accounting teams with tools that allow them to handle everyday transactions and keep costs down at the same time. QuickBooks is a great example of a product that’s suited for small businesses and early-stage startups. In the case of the company where McNamee worked previously, the finance team had been working with Xero.
Everything was going fine until the organization grew to the point where it had a U.S. subsidiary and consolidation was becoming more onerous.
“If you have multiple entities, you have to download both sets of financials, put them into a Google sheet and then do that consolidation manually,” she explained. “It just takes a lot and it’s pretty error prone.”
As a company takes on more subsidiaries, manual consolidation simply isn’t scalable. There are also multiple currencies to consider: McNamee’s company, for instance, was suddenly dealing not only with U.S. dollars but Euros.
If you’re still not sure if you’re ready to upgrade to NetSuite, think long-term. Jen recalls being in meetings about a possible exit strategy for her former employer and, whether you go public or private, NetSuite is a common thread among companies that move to the next level.
“It’s just a much more robust and trustworthy accounting tool. That’s something that investors in the market really like to see,” she said. “We had to step it up.”
Step 2: Budget for the time it takes to get NetSuite running
In addition to your company’s IT department, upgrading to NetSuite will need to draw upon the insights and experience of multiple stakeholders in your organization. This can create tension within some teams, where the time spent advising on a software deployment and participating in user testing means less time for the regular day-to-day tasks associated with managing finance.
As McNamee suggested earlier, however, sticking with manual consolidation can be an even bigger time suck. Depending on how often you’re closing the books – and many firms are moving to a continuous close – you might need finance and accounting team members working late, or even losing their weekends to get the job done.
Though the exact timeline for a NetSuite migration will vary from one organization to another, it’s probably better to err on the side of having the right stakeholders available for more hours than you initially expect.
“If I could redo it, I would not try and chip away at this project,” Jen said. “I would just say, ‘Okay, no – we’re working on this project full time for the next four or five months and then we’re done.’ Don’t try and just do it on the side of your desk. It will drive you crazy.”
Step 3: Bring on third-party experts who know how to customize
Consultants get a bad rap sometimes because they can be expensive. The reason those costs skyrocket in many cases, though, is because the consultants don’t fully understand the needs of their clients and aren’t prepared to ensure the technology is probably aligned with the nuances of a particular business.
McNamee has seen this challenge first-hand. When her former company moved to NetSuite, a team of consultants were initially brought on to guide the implementation. It became clear, however, that their approach was out-of-the-box and failed to meet the project’s goals.
On a daily basis, for example, the company would bring in all the batch transactions, including a deferred revenue component. That meant NetSuite had to be configured so that it could parse a daily batch of more than 1,000 transactions and automate the revenue recognition process.
Unfortunately, the initial migration led to ongoing errors in the reconciliations, which meant a lot of time going back and forth to the consulting team. Eventually she and her team found an independent contractor through word of mouth who was able to approach the NetSuite migration with the specific use cases in mind.
“We wasted all this money and time with those people, and we didn’t finish what we wanted to finish,” McNamee recalled. “(The independent contractor) cost lots of money, but she was really good. She developed a whole customized plan for us. And then we ended up finishing the project because of her.”
Step 4: Minimize business disruption – and remember the people
After four months with the initial consulting team, McNamee estimates working with the independent contractor took approximately another six months. There’s obviously no way to simply put consolidation and other finance/accounting tasks on hold, but switching over everything at once risked causing even greater disruption if anything went wrong.
That’s why, as with so many other projects, Jen’s firm decided to have Xero and NetSuite running in parallel. That way, as the ability to produce new reports using NetSuite went live, the team was able to evaluate whether they were getting the results they wanted and then continuing until NetSuite was fully operational.
“Don’t take on too much,” McNamee advised. “Take baby steps. Get a basic version going that you can live with.”
A project like this is never purely about technology, of course. It also represents change for all those who have been doing manual work or using tools with less functionality. Though they may appreciate moving to NeSuite, make sure you work with team members to understand their needs in transitioning to a new platform, including any ongoing support following initial training.
McNamee had been leading a team of two. One of those people had never used NetSuite, but she caught on fast. And the other one? “We actually specifically hired him because he had that NetSuite experience so we knew he would have no problems day to day,” she said.
If you’re a controller who’s considering or in the midst of moving to NetSuite, this may be a time to consider the skill sets you look for as you bring on more talent.
Step 5: Think beyond the go-live
As one of the early entrants in cloud-based finance software, NetSuite is constantly getting updated with new features and capabilities. At the time this playbook was being produced, Oracle had just introduced tools to manage rebates and trade promotions, as well as improvements to the way users can track estimated or proforma claims and disbursements.
Within your company, meanwhile, there may be an equal or even greater number of changes going on. Before she joined Float, McNamee said her former company had moved into a new business vertical. That led to taking another look at NetSuite to ensure the team knew how to track all the new data associated with the change. “As the business evolves, our use of NetSuite just became more and more sophisticated,” she said.
In some cases, you should even be prepared to walk through the entire planning, deploying, testing and go-live process to avoid any performance issues.
It’s about the destination, so embrace the journey
The good news is that McNamee has only good things to say about life after a NetSuite migration. She found, for example, that the technology not only brought time savings and improved accuracy, but greater comfort over the numbers when the time came for audits to be conducted.
Best of all, McNamee said she would even consider doing it all over again. Beyond the business benefits, she said she learned a lot and has come to recognize the game-changing opportunities that modern technology can bring to finance and accounting.
“It’s almost like it’s like a strategy game, because you have all these different objects,” she said. “And it’s all about how you assemble them in the most efficient way to get to the end goal. I like that about NetSuite.”
Spoken like someone who not only played that strategy game, but came out a winner.
Mark MacLeod has seen the finance world from just about every angle, and he’s got no time for B.S.
“I’m 52, I know exactly who I am, I don’t feel like compromising, and I have no time for a**holes,” he said in an interview with Retained Learnings. “Life’s too short.”
MacLeod also knows exactly what it takes to build a winning company. He began his career as a CPA in auditing and then moved into corporate finance before making his way into the tech industry. After a series of finance lead and CFO roles he eventually landed the top finance jobs with some of the country’s biggest names in tech, including FreshBooks and Shopify, before dabbling in investment banking.
In this interview, he reflects on his lifelong experiences in accounting and finance, career transitions to becoming a coach to CEOs, and best recommendations for finance leaders to level up in their performance.
From music to mathematics to moneyman
MacLeod says he first fell into accounting as a high school student trying to make sense of a world that couldn’t be more different than the one he knew growing up. MacLeod was born and raised on a small island in Scotland, and immigrated to Canada at the age of 11. As a kid from a poor family with a funny accent he spent much of his high school years seeking logic, patterns and things that just made intuitive sense, which initially led to music. At the time the longhaired drummer, like many aspiring rock stars, had little interest in academics.
That all changed during the final year of high school when MacLeod took an accounting class and immediately saw parallels with what was then his primary passion. “I’ve often felt those two worlds were very aligned,” he said. “Music is highly mathematical, and highly structured.”
Accounting also came with another perk; unlike most academic pursuits the university program included a co-op, which allowed MacLeod — the first in his family to attend postsecondary — the opportunity to earn tuition money from articling while pursuing his degree.
MacLeod graduated from Brock University in 1995 and earned his CPA designation in 1995, then spent a few “boring and painful” years in auditing before transitioning into corporate finance. He’s been studying what makes businesses successful, or not, ever since.
“That’s what made it interesting for me,” said MacLeod, who recalls taking his clients’ paperwork to restaurants after work to study their financials, challenging himself to determine their break-even.
MacLeod got his first opportunity to join the high growth start-up world in 1999. “I ended up helping a client raise a Series A funding round, and then joined them as their first finance leader,” he said. While working for the start-up MacLeod also pursued his MBA at McGill University, a decision he came close to reversing at least three times before eventually graduating in 2003.
During the pandemic MacLeod, like many, took some time to reflect on his career, and concluded the aspect he most enjoyed were the one-on-one coaching and advisory conversations with business leaders. That is ultimately what inspired his latest career transition.
“I bought my first book on coaching back in 2002 and concluded that I lacked the gray hair and moral authority to crush it as a coach,” said MacLeod. “You can be the judge on moral authority, but I’ve got some white hair now, so I can check that box.”
Now, as an executive coach, he’s sharing his more than 30 years of experience, a series of battle-tested guiding principals and his no-nonsense attitude with those who need it most. MacLeod says his role as an investor and coach has provided insight into how expectations of finance leaders have evolved since.
The role of the CFO is expanding: Here’s what to expect
“There’s been a huge expansion of the CFO role over the last few years, and it’s something I welcome,” he said. “More and more businesses are data-driven, and I think the CFO’s role is to be that one source of truth for all the different functions of the business, and help them make more data-driven decisions.”
At the same time MacLeod says finance leaders are under greater pressure today, especially given the current state of the market. He explains that start-ups and tech companies are under more financial scrutiny, particularly those that raised capital in the overinflated pandemic market. The cooling of capital markets, coupled with the rising cost and competitiveness of talent, has put an onus on finance leaders to improve operational efficiency across the board.
“There’s a huge imperative now to find ways to do more with less,” he said. “Reduce headcount, eliminate things that aren’t adding value, automate, streamline and generate more revenue per employee than you had done in the past in order to rationalize your business model and get the margins back.”
MacLeod adds that such responsibilities go well beyond those of finance leaders of the relatively recent past. In fact, when he began his career professionals like himself were expected to stay in their bean-counting lane, which usually didn’t include a seat at the decision-making table.
“Finance used to be quite distant from the business, and didn’t deeply understand how the business works,” he said. “Now finance needs to deeply understand how the business works so it can be a trusted advisor to every function.”
Crafting a distinct leadership edge: It’s about guiding principles
MacLeod is accustomed to balancing his responsibilities as both a departmental leader and a top advisor. Using that influence responsibly is also something he takes from his side-career as a DJ, which he developed in parallel with his day job.
“When I’m DJ-ing I am in complete control of that room; I decide when we go up, I decide when we go down, I will look at a track and instantly know ‘yeah, that’s going to work,’” he said. “As a CFO you need to have deep command and mastery over the business; you know all the knobs and levers, you’ve got the early warning signals, you know exactly how it works so you can be a sounding board to the executives of the company.”
Whether making music, practicing yoga, martial arts or cross fit training, serving as CFO, running a venture capital firm, or coaching business leaders, MacLeod doesn’t believe in putting in any less than his full effort. He continues to preach the value of mastery — and the idea that all pursuits are a journey with no final destination — to the executives he coaches and the artists he signs to his record label, Deep Down.
As someone who has always sought out logic, structure and predictability — and as someone who has been entrenched in the startup world for over 30 years — MacLeod has developed a few guiding principles that, when applied correctly, can be instrumental to a business’s success.
At a very basic level he says companies die when they run out of money, simple as that; everything else in an organization’s early days should therefore come second to literally buying time. “You can keep screwing up as long as you have money,” says MacLeod, adding that having more runway allows the business to keep working towards developing a winning formula. “When you have a proven repeatable machine and the market is pulling you, go as aggressive as you can.”
MacLeod adds that CEOs and executives can’t unlock the full potential of their business until they develop that repeatable recipe for ongoing revenue growth, the importance of which can’t be overstated.
“In my experience, the rate of revenue growth is the single biggest driver in valuation — it is the thing that attracts investors, it attracts ambitious talent, it attracts strategic partners and buyers — it’s a magnet,” he said. “Unlock revenue growth in your business, and hang on for dear life.”
MacLeod adds that his responsibility as a coach is, in part, to teach executives how to cling to the rocket ship as it’s taking off. Specifically, he says CEOs and executives must learn to grow their own expertise at a pace equal to or greater than the growth rate of their business, or risk dragging it down.
“If your business is doubling every year, then you need to at least double as a leader, so that you are as effective in a year from now as you are today,” he said. “You look at all the biggest outcomes in the start-up world and they tend to be founder-led start to finish, so there’s a 100% correlation between your performance as CEO and the outcome of the business. That, to me, is the purpose of coaching.”
“In my experience, the rate of revenue growth is the single biggest driver in valuation — it is the thing that attracts investors, it attracts ambitious talent, it attracts strategic partners and buyers — it’s a magnet,” he said. “Unlock revenue growth in your business, and hang on for dear life.”
The power of professional coaching
When MacLeod left his job in corporate finance to help a start-up raise its Series A he had high hopes for the company, which he describes as “DocuSign, but two decades too early.” Its ultimate struggles demonstrated the importance of timing, a lesson MacLeod carries with him to this day.
That’s why, despite having an interest in coaching for much of his career, he felt the timing was finally right in 2020. Not only was he confident in his own potential as a coach, but MacLeod says he had also witnessed how the industry’s attitude towards the practice has evolved since he began his career.
“Back then it was a stigma; If your board said ‘hey, I think you would benefit from working with a coach’ it was perceived as ‘you have a deficiency or are lacking in some way,’” he said. “What CEOs are coming to realize is this is actually just a key tool, given the expectations on their shoulders.”
MacLeod explains that the CEO who raises a $30 million funding round should dedicate the same resources towards their own development as a professional athlete that earns $30 million in salary. They should also strive to put in professional sports-level care when building out their team.
The CEO-CFO partnership
When it comes time to pick their finance leader — which MacLeod believes shouldn’t be given a CFO title until the company is mature enough to truly need one — he advises CEOs to find someone with complementing strengths. He explains that there are two kinds of finance leaders: “technicians” like himself, who typically come from a CPA background and have a strong understanding of accounting and finance rules; and “deal makers,” who typically come from a venture or investing background, and are more focussed on strategy.
MacLead advises CEOs to pick their finance leaders based on the kind of expertise they need at their disposal, and to help fill any gaps in their own expertise. “Either persona can work,” he said. “It’s about assembling a complete team around the strengths of the leader.”
Beyond numbers: What it takes for finance leaders to master their role
No matter their background, however, MacLeod believes all finance leaders need to master more than just finance, and seek to really understand how the business works. That, he says, will eventually enable them to create a dependable, repeatable formula, akin to a math equation or a piece of sheet music, that just makes sense.
“You need to understand, for example, that for every 1,000 customers we add we need a new customer support rep — you need to figure out that formula so that you can turn the business into a recipe,” advises MacLeod. “That’s why it’s not enough for a finance leader to only know finance; you actually need to have some base level understanding of all the other functions.”
Being a well-rounded finance leader isn’t limited to business operations, either. MacLeod knows how hard it can be for executives to pull themselves away from their work, but cautions against that sort of isolation. He explains that the industry has long maintained an unhealthy culture of fetishizing work, but has some hope that the pandemic gave everyone, including those at the top, the opportunity to re-evaluate what’s important in life.