“The life of the law has not been logic; it has been experience.”

— Oliver Wendell Holmes Jr.

Law does not evolve in isolation. It evolves through experience, pressure, and leadership. Today, some of the most transformative experiences shaping the legal industry are being led by women who are willing to challenge convention, embrace technology, and redefine how legal teams operate. 

SpotDraft is excited to spotlight a powerful group of founders, operators, educators and system-builders who are rethinking everything from contracting and legal operations to access to justice, legal design and responsible AI. These are women who have lived the pain points inside legal teams, courtrooms and businesses, and then chosen to build better systems, smarter workflows and more human ways of working.

What connects every story in this edition isn’t disruption for the sake of it. It’s something far more meaningful: a deep commitment to judgment, usability, trust and real-world impact. From practical contracting education and legal ops maturity, to people-centred legal services and thoughtful AI adoption, each of these leaders is shaping the future of legal work. One grounded, deliberate decision at a time.

As we build what’s next for legal, it’s worth pausing to recognise the women who are already designing it.

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Alessandra Colaci 

AI curiosity is everywhere in legal teams. Real adoption is not. And that gap is exactly where Alessandra Colaci chose to build.

Alessandra is the Founder and CEO of Legal+AI, a consultancy created to help legal teams move from interest in AI to meaningful, day-to-day use. With a background in SaaS and technology, she built Legal+AI around what she consistently identifies as the biggest challenge in the market today: not a shortage of tools, but a lack of structured, practical capability inside legal teams.

She knows that successful legal AI adoption is driven by people, not platforms. She speaks openly about the fear and hesitation many lawyers feel when it comes to experimentation, and makes a strong case for leadership creating psychological safety and clear guardrails, so teams can test, learn, and build confidence without putting quality or security at risk.

Alessandra advocates for prompt libraries, real use cases, and fast, low-risk wins, giving lawyers immediate value while maintaining professional standards.

Alessandra positions AI as an operational enabler, not a strategic checkbox. Her message is refreshingly grounded: legal teams do not need more hype or abstract strategy, they need hands-on workflows, shared standards, and leadership support to embed AI into everyday legal work.

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Alma Asay

Alma is a legal tech Founder best known for building and leading Allegory Law, a litigation management platform. Trained as a lawyer, she made an early and deliberate move away from traditional practice and into technology. She is currently the Chief Innovation and Value Officer at Crowell & Moring. 

Alma addresses the uncertainty of starting a legal tech company, learning to treat mistakes as part of leadership, and navigating the steep learning curve that comes with fundraising quite candidly in her conversations. 

She is focused on why litigation management should be seen as a strategic capability for legal teams, as better systems create visibility, accountability, and stronger collaboration across legal and the wider business.

Alma has become a recognised voice in the legal innovation community, regularly sharing insights on career transitions, founder resilience, and what it really takes to build technology for lawyers.

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Basha Rubin

Founder and CEO of Priori Legal, she is one of the sharpest voices rethinking how companies actually find and hire legal talent.

Basha keeps coming back to one stubborn truth about the legal industry: great legal talent is everywhere, but getting the right lawyer, at the right time, is still opaque, relationship-driven, and inefficient.

That’s exactly why she built Priori.

Priori was created to bring structure, data, and transparency to a process that has long relied on informal networks and personal referrals. The platform matches companies with vetted, high-quality lawyers and law firms based on real needs, experience, and outcomes, not who happens to be in someone’s contact list. 

Basha’s leadership perspective is shaped by what it really takes to build a two-sided marketplace in one of the most conservative industries in the world. She stresses the importance of trust, quality control, and long-term relationships between clients and legal professionals, while making one thing very clear: technology should strengthen human judgment, not replace it.

Beyond building a platform, Basha is equally candid about what it takes to build a sustainable legal tech business. Her advice is refreshingly grounded: stay relentlessly customer-focused, test assumptions quickly, and resist the temptation to build technology for novelty instead of real impact.

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Carolyn Elefant

MyShingle is one of the longest-running and most influential platforms dedicated to solo and small-firm law practice, and it was founded by none other than Carolyn. 

A former energy and environmental lawyer, she created MyShingle to give independent lawyers something they were rarely offered: practical, honest guidance on how to build sustainable legal practices. Today, Carolyn works as a self-employed AI in law expert, advising and educating lawyers on how to adopt technology responsibly and confidently.

In The Solo Trailblazer podcast, she consistently reframes AI not as a shiny disruption, but as a potential competitive equaliser for solo and small-firm lawyers, when used responsibly.

Her focus is firmly grounded in real-world practice, putting internal policies in place, managing risk and confidentiality, understanding ethical obligations, and helping lawyers use AI to improve client service, not replace professional judgment.

Alongside her speaking and interview work, Carolyn is also a regular contributor to industry publications such as The National Law Review, where she writes on legal innovation, practice management, and professional responsibility. 

Carolyn is very steadfast in her idea that the future of legal work, especially outside big law, will belong to lawyers who combine independence, business literacy, and thoughtful use of technology.

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Erin Levine

Most legal tech stories start with a big idea. Erin Levine’s started with a hard reality.

Before becoming an entrepreneur, Erin was a family law attorney who saw, up close, just how confusing, expensive, and emotionally exhausting the traditional divorce process really is. She’s been clear about what pushed her to build a company: not ideology, not disruption for the sake of it, but a very practical realisation.

Most people don’t need a high-conflict, courtroom-driven experience.

They need clarity. Structure. And reliable guidance at one of the most stressful moments of their lives.

This led Erin to create Hello Divorce along with Heather MacKensie. A technology-enabled, human-centred alternative to conventional legal services that combines self-service tools with access to expert support.

Erin believes that technology should streamline how legal services are delivered, not replace expertise. She often speaks openly about being sceptical of early DIY legal tools herself. That scepticism became the foundation of her product philosophy: design for real people, real emotions, and real complexity.

Rather than treating lawyers as barriers, Erin reframes their role as guides and problem-solvers, stepping in exactly where judgment, nuance, and empathy matter most. This hybrid model, software plus professional support, is central to how Hello Divorce makes divorce more accessible, while still protecting quality and trust.

In doing so, Erin has helped reframe family law as a space where thoughtful product design, simpler processes, and empathetic legal delivery can genuinely coexist. It shows how legal tech can modernise deeply human legal problems without ever losing sight of the people at the centre.

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Hannah Konitshek

As the Co-founder and COO of Legal.io, Hannah is one of the builders helping reshape how legal professionals and legal teams find and trust each other in today’s market.

Her path into legal tech didn’t follow a traditional playbook. Legal.io evolved from an early, experimental idea into a trusted global marketplace for legal talent, anchored in a simple belief: the legal industry needs better ways to discover, evaluate, and access the right expertise at the right moment.

Hannah is crystal on one stance: community before platform. Hannah has always been candid about how Legal.io’s growth hasn’t been driven by chasing scale alone. It has been by intentionally building trust with legal professionals and creating a network that genuinely serves both lawyers and in-house teams.

She has also been recognised for her leadership as a female founder in legal tech, highlighting not only her operational role in scaling the business, but her broader commitment to representation and inclusion in a traditionally closed industry.

Long before these topics became mainstream, Hannah was already writing about legal marketing, lawyer visibility, and how startups should think about in-house legal support on the Legal.io blog. Those early articles reveal a founder who understood from the start that legal innovation isn’t only about technology, it’s also about access, storytelling, and being seen.

Today, Hannah continues to play an active role in the global legal innovation ecosystem, championing a future where legal work is more open, more connected, and far more human.

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Heather MacKenzie

Heather MacKenzie is the kind of founder who makes legal tech feel… human. 

As Co-Founder and President of Hello Divorce, she helps people navigate one of life’s most emotionally loaded moments with clarity, calm and real support. What drives her isn’t disruption for disruption’s sake, it’s removing the confusion, paperwork panic and hidden costs that so often make divorce feel impossible to manage. 

Before Hello Divorce, Heather built and scaled fast-growing digital businesses, including playing a key role in growing BestReviews into a major consumer platform. That background in product, content and customer experience shaped how she approaches family law today, starting with real user problems, not legal complexity. 

In interviews and conversations, Heather often speaks about how broken and inconsistent the divorce process can feel across states, and why technology, when paired with expert support, can radically reduce stress, time and cost for families.

A trained storyteller at heart, Heather brings a rare blend of journalism and startup leadership to the world of legal services. That perspective shows up in how Hello Divorce explains the law, clearly, accessibly and without intimidating language. 

On shows like The Divorce Survival Guide Podcast, she breaks down practical barriers people face during divorce, from financial disclosures to filing confusion, and reframes the process as something people can understand, and manage, with the right support.

Heather MacKenzie isn’t just modernising divorce technology. Along with her co-founder Erin, they are rebuilding trust in how legal services can show up for people when they need them most.

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Laura Frederick 

Meet Laura Frederick, a legal tech entrepreneur, educator, and one of the clearest, most refreshing voices rethinking how contracting is actually taught and practised in the modern legal world.

A former BigLaw and in-house lawyer, Laura built her career right inside fast-moving businesses, the kind where contracts are about making smart calls, moving fast, and helping teams make better decisions.

That real-world experience is exactly why she built How to Contract.

Laura goes straight after a gap, almost every lawyer feels early in their career: traditional legal education rarely shows you how to negotiate, draft, and manage contracts in real situations. How to Contract exists to close that gap. It delivers practical, structured training that helps lawyers and legal teams build confidence, consistency, and clarity in their contracting work, without leaning only on templates or institutional memory.

At the heart of Laura’s work is a simple belief: contracting is a skill, not an instinct.

Laura is someone who champions the notion that AI isn’t here to replace legal thinking; it’s a force multiplier. And that means lawyers need sharper judgment, not less of it. 

Whether she’s teaching a junior lawyer, supporting in-house teams, or speaking about the future of legal work, the focus never changes: empowering lawyers to do better contracting by design is what Laura swears by.

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Lucy Bassli

When it comes to a refreshingly no-nonsense voice on contract lifecycle management, Lucy Bassli is hard to beat. As the Founder of InnoLaw Group, she is widely recognised as one of the most practical and grounded leaders in legal operations. 

Drawing on her experience building and scaling contracting operations inside large organisations, Lucy is very clear about why so many CLM programmes struggle. It’s rarely because of the tools. It’s because teams underestimate just how important process design, ownership, data readiness, and internal alignment really are. 

Her message is simple and sharp: great contracting programmes start by understanding how work actually flows across legal, sales, and procurement, and only then choosing technology that supports those realities.

Through her writing and speaking, including her book CLM Simplified, Lucy consistently advocates for a more human, commercially connected legal function, one that treats contracts as strategic business infrastructure, not administrative artefacts.

She positions AI as an accelerator for visibility, consistency, and prioritisation, not as a replacement for legal judgment. She also encourages organisations to resist “feature-driven” buying and instead focus on what outcomes really matter, such as faster deal cycles, stronger compliance tracking, and a better experience for stakeholders.

That outcome-first mindset runs through much of the guidance she shares with in-house teams starting, or rethinking, their CLM journeys.

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Margaret Hagan

If there’s one person quietly reshaping how the legal system is built around real people, it’s Margaret Hagan.

As the Executive Director of the Stanford Legal Design Lab, Margaret is one of the most influential voices bringing human-centred design into law. And she’s consistently clear about what legal design isn’t. 

It’s not a visual refresh. It’s not an innovation trend. It’s a practical way to improve how people actually experience the legal system.

Margaret focuses on redesigning legal services, court processes, and digital tools so they are understandable, usable, and rooted in real human needs. Rather than treating technology as the answer, she puts the emphasis where it belongs: careful problem framing and deep collaboration between lawyers, designers, technologists, and community partners.

More recently, she has also become a leading voice on the responsible use of AI in legal help systems. Her position is refreshingly grounded: evaluation, transparency, and stewardship matter just as much as technical capability. For Margaret, AI should be judged on real user outcomes, like whether people make better decisions or get help faster, not simply on performance metrics. 

Through the Lab’s research, teaching, and open resources such as her Law by Design work, Margaret continues to advocate for a future where lawyers are trained not only in doctrine, but also in experimentation, collaboration, and systems thinking, so the profession can actively build fairer and more effective legal infrastructure.

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Stephanie Corey

She is widely recognised as one of the foundational voices behind modern legal operations.

Stephanie has played a defining role in shaping how in-house legal teams think about structure, technology, and operating models, at real scale. She is also a co-founder of the Corporate Legal Operations Consortium (CLOC), the global community that helped formalise legal operations as a recognised discipline. 

Today, Stephanie works independently as an advisor and speaker and is also the co-founder of UpLevel Ops. Here, she supports legal leaders through large-scale change and technology adoption. 

Across everything she does, one message comes through clearly: legal transformation is not about tools alone. It’s about creating clarity in how work happens, building cross-functional trust, and removing everyday friction so lawyers can spend more time on higher-value judgment.

That perspective lands strongly with teams navigating growth and complexity, particularly as AI and automation become part of everyday legal workflows.

Through her speaking, advisory work, and community leadership, Stephanie continues to shape how in-house legal teams move beyond reactive service models and grow into deeply business-embedded partners.

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Innovation has found its leaders

Innovation in legal rarely arrives with a dramatic breakthrough or a bold headline. It shows up in classrooms where contracting finally clicks, in legal teams moving from chaos to clarity, and in founders who refuse to automate broken workflows. It lives in systems designed for real people, real judgment, and real responsibility.

The future of legal isn’t being handed down by technology; it is being built, deliberately and creatively, by women who understand the work and the weight of changing it.

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