Waymaker Wednesday: Women in LegalTech – Meet Dolvi Oswal

This week, we’re spotlighting, Dolvi Oswal, a LegalTech professional who works at the intersection of legal workflows, AI, and product enablement. Currently part of the Legal Tech and Innovation team at Zensar Technologies, she focuses on implementing AI-enabled Contract Lifecycle Management (CLM) systems, streamlining contract intake, automation, and collaboration across legal, business, and technology teams.

With over six years of experience in LegalTech, her work centres on translating complex legal requirements into scalable, tech-driven solutions that actually get adopted by users. Prior to Zensar, she spent several years at Klarity, a Y Combinator-backed company, where she played a key role in leading GenAI-powered document review operations. Working closely with product and engineering teams, she helped shape features based on real user pain points, scaled review workflows, improved data accuracy, and supported product-led growth through enterprise pilots.

Her career journey spans legal operations, AI-enabled review processes, team leadership, and product collaboration, grounded in a strong understanding of how legal teams work in practice. What sets her apart is her ability to bridge law and technology with operational clarity, ensuring that legal tools are not just intelligent, but intuitive and impactful for the teams using them.

Here’s a peek into her world:

1. What inspired you to join the Women in LegalTech community?

When I started working in LegalTech, it was still a relatively new and evolving space, especially in India. At that point, I didn’t really know who to connect with or whether there were others navigating similar roles, challenges, and uncertainties. LegalTech as a career path wasn’t clearly defined, and there were very few reference points.

When I discovered the Women in LegalTech community, it immediately felt like I had found my people. It became a space where meaningful conversations could happen about tools, impact, leadership, and the real dilemmas we face while building and implementing technology in legal environments. Being able to learn from others, share experiences, and grow together in a space that truly understands this work is what inspired me to join, and I’m genuinely grateful to be part of this community.

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2. If you could solve one problem in the legal world (or beyond) with technology, what would it be?

One of the biggest challenges I see is the sheer amount of administrative and repetitive work lawyers deal with on a day-to-day basis. This operational burden takes time away from strategic thinking and meaningful legal work. Beyond automation, I believe there is also a need to help legal teams understand which technology actually works for them. Today, many organisations adopt tools through trial and error, only to abandon them later because they weren’t the right fit. If technology could guide legal teams toward the right solutions for their specific workflows, reducing friction, confusion, and fatigue, it would significantly improve adoption and long-term impact.

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3. What’s one book, podcast, or resource that’s made a big impact on how you think about work or life?

Atomic Habits by James Clear. It fundamentally changed how I think about growth by focusing on small, consistent actions rather than dramatic changes. In fast-moving and evolving fields like LegalTech, this mindset has helped me stay grounded while continuously improving.

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4. Outside of work, what’s something you’re passionate about or love spending time on?

Having worked closely with startups, I’ve developed a genuine interest in understanding how businesses are built and scaled across industries. I enjoy learning about operations, strategy, and decision-making, regardless of the domain.

In my free time, you’ll often find me watching interviews and conversations on platforms like Bloomberg or listening to podcasts like Nikhil Kamath’s, where founders and operators share their journeys. Learning from how different businesses think and evolve has become a passion in itself.

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5. What’s the best piece of advice you’ve ever received as a woman in your career journey?

That skills matter more than formal labels or backgrounds, and that you should never hesitate to ask questions. Coming from a legal background and working in a technology-driven industry taught me that curiosity, continuous learning, and skill-building can take you far. Asking questions is not a weakness; it’s often the fastest way to grow.

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6. If you weren’t working in law/legaltech, what’s another path you could totally see yourself in?

I could see myself working in strategy or advisory roles, helping organisations solve complex problems, build systems, and navigate transformation. At the core, I enjoy understanding how things work and helping create clarity in moments of change.

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Her journey reflects how deep legal understanding, paired with tech fluency and execution, can create real impact. She continues to shape how legal teams adopt AI, not as a buzzword, but as a meaningful enabler of better legal work.

Are you a woman shaping the future of legal tech? We’d love to hear your story. Our Women in LegalTech community is a space to connect, inspire, and spark conversations that matter. Click here