Erin Wiley’s journey from private practice to in-house legal leadership wasn’t a straight line – it was a deliberate, strategic pivot. After nearly a decade in big law, she realized what she valued most wasn’t the prestige of private practice but the deep engagement with clients – the ability to understand their businesses, guide them through legal risk, and help shape strategic decisions.
“In a law firm, you sort of parachute in, help with one thing, and then you’re out,” she says. The transactional nature of firm work left little room for the creativity and pragmatism she craved. That realization led her to move in-house, placing her at the intersection of law, strategy, and business – first in FinTech, then at major banks, Shopify, and now at Hiive, where she serves as vice president and deputy general counsel.
Hiive is no ordinary tech company. It operates in the private securities trading space, a complex and deeply regulated world. “We live and breathe our legal and compliance posture in everything that we do,” she says. Unlike other tech companies where legal might be an afterthought, Hiive’s very existence hinges on robust legal and compliance functions. “Rather than being a blocker or an afterthought, we are very much linked arms with our key business stakeholders every step of the way,” she says.
The company’s platform facilitates the trading of private securities, a historically opaque and manual process. “There was really this gap in the market,” she says, explaining how the traditional private securities market relies on old-school brokerage methods – phone calls, limited transparency, and restricted access. Hiive’s founders saw an opportunity to bring efficiency and trust to this space. “We operate a marketplace platform,” she says. “What we do is connect buyers and sellers of stock in venture-backed pre-IPO “unicorn” companies, allowing for liquidity in the market.”
For many employees at these companies, that liquidity is a game changer. “All of a sudden, they have this part of their compensation that may or may not be realized depending on if a company goes public or is acquired,” she says. “Now, through this platform, they can actually realize liquidity if they want to.”
Of course, operating at the crossroads of tech and securities law means Wiley and her team face no shortage of legal challenges. “Securities law is one of the reasons why I came to Hiive,” she says. “Our broker-dealer is FINRA and SEC-registered in the United States. It is also an exempt market dealer in Ontario and BC. And we’re growing quickly, which means we’re highly attuned to the securities laws in other jurisdictions as well.”
Beyond securities, the legal team handles privacy, employment law, commercial contracts, and product counselling. “One of the areas I’m excited about building at Hiive is a really robust product counselling function,” she says. In a tech company, she notes, legal teams must be involved from the earliest stages of product development, not just as a final check before launch.
Wiley takes a nuanced approach when it comes to balancing legal risk with innovation. “I had somebody ask me a few months ago, ‘What kind of lawyer are you? Are you a deal junkie?’” she says. “I think I would characterize myself as someone who is obsessed with risk.”
For her, the key to effective legal counsel is framing issues in terms of risk rather than rigid legal constraints. “It’s not just about spotting risk but helping the business understand how likely something is to happen and, if it does, how bad it would be,” she says. “And then figuring out: Are there mitigation strategies we can apply? What’s the residual risk after those mitigations? Because ultimately, business leaders want to know – so what? What does this mean for us, and is the risk worth it?”
That ability to translate legal risk into business terms makes in-house lawyers indispensable. It’s also why regulatory engagement is key to Hiive’s legal strategy. “I always consider our regulators to be one of our key stakeholder groups,” she says. While some companies view regulatory bodies as adversaries, Wiley sees them as essential partners. “We welcome engagement with regulators because we are a compliant business,” she says.
That proactive approach is critical in an industry where regulation often lags innovation. “Tech moves really quickly, and legislation doesn’t always keep up,” she says. “There can be an inherent tension there. But we want to be partners with our regulators, to help them understand how we’re thinking about the industry.” Sometimes, this means advocating for changes that would benefit both Hiive and the broader market. “If there are gaps in regulation or areas that need to evolve, we want to be part of that conversation,” she says.
Managing risk, regulation, and rapid growth means Wiley also relies on external counsel, though she has clear expectations for what makes outside lawyers effective. “One of the challenges with external counsel is they will never know your business as well as you do,” she says. “That can create a disconnect – a lack of pragmatism in the legal advice you’re getting.”
She recalls a particularly unhelpful experience when she asked for an overview of a regulatory issue across multiple jurisdictions. “The work product I got back was basically a chart with cut-and-pasted sections of legislation,” she says. “That’s one of the least helpful things I could ever receive.”
What she needs isn’t raw legal text – it’s interpretation. “What does this actually mean for us?” she says. “I think really great external counsel take the time to ask questions, to understand the risk tolerance and the business context before they even start billing. That way, they can frame their legal advice in a way that’s actually useful.”
For young lawyers interested in making the leap in-house, Wiley has three key pieces of advice: curiosity, creativity, and attention to detail. “Being a constant learner, being willing to jump into any area and just be a sponge – that’s critical,” she says. She also believes legal work requires a surprising amount of creativity. “A lot of what I do is problem-solving,” she says. “How do we achieve what the business wants to achieve while still staying within the legal and compliance frameworks? That requires thinking outside the box.”
And finally, she emphasizes the importance of precision. “Attention to detail should flow through every aspect of your practice,” she says. “Whether it’s drafting, issue-spotting, or risk assessment – it all matters.”
For Wiley, moving in-house isn’t just a career shift; it’s a move toward a practice that aligns with her strengths and passions. At Hiive, she’s found a space where law isn’t just about rules – it’s about strategy, collaboration, and building something new.