InView Magazine: Issue 8 out now!
Craig Segal’s role as Chief Legal and Global Procurement Officer for social media management company Hootsuite utilizes both his legal and business skills. Having a clear vision and a willingness to make intentional choices have defined his career path and has transformed him from a traditional corporate lawyer into a business-minded lawyer who thrives at the intersection of legal, strategy, business operations, and technological innovation.
Like many of his peers, Craig’s career began in private practice, where he honed his skills in corporate law, M&A, banking and restructuring. “Private practice gave me a deep understanding of corporate transactions and an ability to think critically under pressure,” he says. “But I also realized that my passion extended beyond pure legal issues – I wanted to be part of the larger decision-making ecosystem.”
The variety of work, particularly in the restructuring space, was a pivotal point in his career and helped him to develop versatile skills; he was proud to be considered a generalist lawyer. Yet, despite being on track to make partner, he was keen to explore other options. Being able to apply his legal skills directly within a business context was top of his list.
Craig’s move from private practice wasn’t a straight line and moving to a company should have occurred earlier in his career. “It was a good lesson for my younger self – go with your gut,” he says. “At the time I wanted to go in-house but I thought it would be a good experience to focus on banking and financing work and something I could grow to love. Instead, it was something I grew to hate.”
The experience strengthened his resolve to find an in-house role, which led him to Canon as Senior Legal Counsel. This role was transformative, exposing him to the complexities of advising on business operations across sales, finance, marketing, product, HR and procurement. “Being embedded in the business taught me the importance of speaking the language of the organization,” he explains. “You can’t confine yourself to legal jargon; connecting with internal stakeholders and understanding the business’s heartbeat is critical.”
This transition marked the beginning of Craig’s philosophy as a business-minded lawyer. “I came to see legal strategy as inseparable from business strategy,” he explains. At Canon, his ability to align legal solutions with corporate goals became his signature skill.
Craig’s desire to lead a legal department then brought him to the software space, where he assumed the role of Vice President of Corporate Affairs and General Counsel at Dundas Data Visualization (now insightsoftware). Here, he tackled the unique challenges of managing legal matters for a SaaS company while also driving operational improvements and technological adoption within legal processes, an early sign of his penchant for innovation.
Joining Hootsuite in 2017 meant that Craig initially took a smaller-scope role compared to his previous experience. “It was a step back from running the mothership,” he says. But the move has more than paid off, as today he leads a global team responsible for corporate/commercial, privacy, employment, compliance, procurement, and more.
“Moving to Hootsuite has definitely been one of the best decisions I’ve made,” he says.
What sets Craig apart is his ability to blend his legal oversight with driving business forward, while maintaining operational efficiency. Procurement has also become one of his key responsibilities at Hootsuite. He views procurement as a strategic function in cost control and an enabler of the business. This holistic view mirrors his belief that in-house lawyers must evolve beyond traditional confines. “Modern lawyers need to wear multiple hats – not only to solve legal problems but to pre-empt them by fully understanding the organization’s goals and pressures,” he says.
Craig is a steadfast advocate for redefining how in-house legal professionals interact with their organizations. For him, legal advisors must be deeply integrated into business strategy, not just as a legal adviser but as decision-making partners. “Having a seat at the table is non-negotiable. Legal needs to be part of the strategic dialogue from the outset, not an afterthought,” he asserts.
He believes this requires both skill and intention and says effective relationship building is foundational to this evolution. “Trust and communication matter. Building relationships across the enterprise, not just with leadership but throughout all levels of the organization, is what transforms legal from a reactive function to a proactive partner.”
He stresses that relationships are probably the most important aspect of being successful. “I often tell my team, and I remind myself of this as well, that things aren’t always going to go right. There are going to be hurdles – it’s the nature of what we do. Sometimes we don’t get it get right, and sometimes we make mistakes. But mistakes are generally forgivable and it’s possible to get past them if relationships have been built.”
In a post-pandemic “remote world”, Craig emphasises that good relationships have never been more necessary than now. The seismic changes that occurred since 2020, have created unforeseen challenges. “It’s all doable,” he says, “but when you’re in the trenches, it’s a lot easier to work through things when you have built those relationships.
“When the stresses are high and there’s a lot going on, that’s the time to step up because that’s the time when individuals remember that legal was there, we were by their side, and we were being a help and not a hindrance.”
Craig regards himself as a business minded lawyer – a term he favors. “I’m practical. While crossing T’s and dotting I’s is important, it’s not what excites me. I like to look at things from a business perspective.
“The fortunate part of being in legal, is that you see the big picture; it’s about being able to see the big picture and being practical. Which means there needs to be an appetite for risk. You cannot see the world in black and white, you need to see grey.
“You go to the business and talk about wonderful redlines you’ve done with an indemnity clause, and the businessperson will roll their eyes and fall asleep. You say ‘hey, I just saved you a few million bucks on the contract and this impacts EBITDA’ and all of a sudden there’s a light in the businessperson’s eyes with an appetite for discussion.”
In a nutshell, it’s about showing the value legal brings to the business – having a legal department that is viewed as a value add.
Craig says that in the past, legal could often get away with “we’re a compliance function” – it’s impossible to measure success. Legal was protecting the company and there was no way to measure its effectiveness. Legal was regarded as doing its job if there were no lawsuits and the organization’s name wasn’t making newspaper headlines for the wrong reasons.
But adopting a business mindset, using metrics, makes it possible to show value. “For a long time, I struggled in terms of different iterations of leaders pushing metrics and KPIs and OKRs and trying to fit that square peg in a round hole. But if you think about it and do it well, and you look at the company strategy, there are ways to come up with metrics that can be measured and that can move the needle in the right direction, that can show your objective value to the business. And that’s when you start being viewed as a business function versus a cost center.”
Ultimately, Craig’s philosophy is simple yet profound: lawyers are at their best when they facilitate business rather than inhibit it.
