Rajneesh Chhabra: Disrupting Legal Tech through a Security-First Approach

Rajneesh Chhabra | CEO and Founder of Secure Engage
Rajneesh Chhabra | CEO and Founder of Secure Engage

Leading Legal Innovation!

The legal industry is indispensable in ensuring the smooth functioning of societies and businesses by upholding justice, maintaining order, and safeguarding rights. As the world becomes increasingly digital, the industry faces new challenges, particularly in data privacy, cybersecurity, and regulatory compliance. Legal professionals now must steer intricate digital fields where protecting sensitive information is paramount. As a result, the integration of technology into legal workflows is accelerating, with AI-assisted audits and automated compliance tools transforming traditional practices. This evolution reflects the industry’s need to mitigate risks while enhancing efficiency and ensuring that client trust remains intact.

Rajneesh Chhabra, CEO and Founder of Secure Engage, is leading this transformation, bringing visionary leadership to the legal tech. His approach centers on simplifying cybersecurity for law firms, enabling them to address pressing risks without requiring deep technical expertise. Under his guidance, the focus remains on creating solutions that cater specifically to the legal industry’s unique challenges, particularly those related to confidentiality, privilege, and client relationships. Rajneesh’s leadership is defined by his ability to inspire innovation, build cohesive teams, and prioritize practical, results-oriented strategies that advance the legal sector’s cybersecurity standards.

Secure Engage has emerged as a trusted partner in the legal industry, delivering advanced solutions to address cybersecurity and compliance challenges. The company’s flagship product offers AI-driven audits tailored to the specific needs of law firms, helping them manage risks, streamline processes, and ensure alignment with evolving regulatory frameworks. By automating compliance checks and offering comprehensive cybersecurity assessments, Secure Engage empowers legal professionals to focus on their core responsibilities while minimizing vulnerabilities. Through its commitment to innovation, Secure Engage is reshaping how law firms engage with cybersecurity, ultimately fostering a safer, more efficient legal environment.

Let’s explore his transformative leadership journey in Legal Tech:

Innovating Within a Large Corporation

Secure Engage developed its flagship product at one of the top five banks in Canada after the Panama Papers cybersecurity incident, where a law firm was breached. This breach had a catastrophic ripple effect on many banks and their clients. Rajneesh and his team were brought in to create a solution that would help banks prevent or stay ahead of such situations in the future.

Innovating within a large corporation was challenging; they faced considerable pushback and skepticism. Fortunately, several executives and team members supported him in taking the product outside the bank and commercializing it. Some of them are now part of his team at Secure Engage, including his co-founder, Jolie Lin.

Aligning Legal Workflows with AI-Assisted Audits

Secure Engage is designed to assess risks and manage law firm relationships in the legal sector, offering tools like its Cyber Risk Assessment (CRA) and the Preferred Accredited Network of External Law Firms (PANEL). Its focus on legal expertise, continuous monitoring, and fostering collaboration sets it apart.

It is crucial to understand that risks in legal engagements extend beyond cybersecurity; they include branding, reputation, confidentiality, privilege, and contractual obligations. Secure Engage’s key differentiator is its deep understanding of the unique challenges law firms face in cybersecurity assessment and business alignment.

Unlike generic platforms, the company addresses compliance issues, conducts cybersecurity scans, and provides AI-assisted, streamlined audits with actionable recommendations tailored to legal workflows. On the PANEL side, it creates alignment on pricing, culture, diversity, expertise, and experience. Overall, it helps both corporate legal and law firms to have a smooth engagement experience, nurturing trust and confidence.

Automating Compliance Checks for Efficiency

Secure Engage has introduced several key innovations. Its CRA tool helps law firms assess and enhance their cybersecurity posture with minimal disruption, evaluating risks comprehensively while providing actionable insights.

PANEL serves as a trusted network that allows law firms to engage vetted external legal service providers, ensuring their partners meet the same high cybersecurity standards. Secure Engage is also automating compliance checks to streamline often cumbersome processes, allowing firms to focus more on their legal work rather than administrative burdens.

Focusing on Relevant Threats and Vulnerabilities

While SOC 2 is an important standard, it can be time-consuming and costly, especially for smaller firms. Secure Engage offers a more streamlined and cost-effective alternative without compromising security. Its solution is specifically tailored to the legal industry, focusing on the most relevant threats and vulnerabilities.

Secure Engage prioritizes practicality and speed—its assessments can be completed in a fraction of the time it takes for a full SOC 2 audit. Ultimately, it provides firms with an actionable, risk-based approach that helps them secure their operations efficiently, avoiding extensive overhead.

Integrating Security into Daily Operations

According to Rajneesh, one of the most significant challenges law firms face is the increasing complexity of cybersecurity threats alongside strict regulatory compliance requirements. Many firms, especially smaller ones, lack the resources for dedicated cybersecurity teams, making them more vulnerable.

Additionally, managing data privacy, secure communication, and protecting sensitive client information is paramount. Secure Engage simplifies this process by providing user-friendly tools that empower firms to assess and mitigate their cybersecurity risks without requiring deep technical expertise. The platform integrates security into daily operations, reducing breach risks and ensuring compliance with industry standards.

Simplifying Remediation for High-Risk Businesses

Due to the confidential nature of the business, Rajneesh can only refer to general experiences without naming specific firms. Secure Engage has had the privilege of working with a well-known law firm that has engaged with clients for many years. CRA assessments revealed significant gaps in their security approach that could have led to risky and costly breaches. Additionally, external scans uncovered stealth breaches.

It is common for law firms to fly under the radar of third-party risk management systems that clients usually have in place, given the unique nature of their “high-risk, high-trust” business. Remediation becomes easier when the assessment is legally focused, understands unique challenges, and offers straightforward assistance in addressing issues.

Automating Threat Monitoring and Response

Rajneesh believes cybersecurity threats are evolving rapidly, especially with the rise of AI-driven attacks. At Secure Engage, the threat detection algorithms are continuously updated to stay ahead of these developments. The company is also exploring AI-based tools to automate threat monitoring and response, ensuring that law firms can react to emerging threats in real-time.

Education is another cornerstone of the strategy; clients are kept informed about new risks and mitigation strategies. By remaining proactive and continually evolving the platform, Secure Engage ensures that clients are protected against the latest threats.

Investing in Continuous Learning and Development

Innovation is at the heart of Secure Engage company culture. Rajneesh encourages the team to think beyond immediate challenges and anticipate future needs. The company has cultivated a collaborative environment where experimentation is welcomed and no idea is too small.

Secure Engage also invests in continuous learning, whether through attending industry conferences or conducting internal workshops. As CEO, he leads by example, staying curious and open to new ideas. The company’s agility comes from a flat organizational structure that allows for swift decision-making, enabling quick pivots based on client feedback or market changes.

Vision for Global Cybersecurity Leadership

In the next 5-10 years, Rajneesh and his team envision Secure Engage becoming a global standard-bearer for cybersecurity in the legal sector. However, the company is also exploring opportunities in other industries, particularly those that handle sensitive data and face stringent compliance requirements, such as healthcare and finance.

As Secure Engage expands, the focus will remain on developing practical, user-friendly solutions that help businesses efficiently manage cybersecurity risks. The company also plans to grow the PANEL network into a global standard for law firms seeking secure legal services. Innovation and client-centric development will guide Secure Engage’s growth.

Time Management Philosophy

In Rajneesh’s opinion, maintaining a work-life balance is always a challenge. He is sold on the work-life harmony approach he heard Jeff Bezos talk about once. His ability to hyper-focus while staying connected and aware of personal and professional matters allows him to be available to his family and team members, making it easier.

For him, all time is work time, and all time is family time; he doesn’t box them. Time is time, and he likes to use it for the best use possible for whichever section of his life has the priority. It’s not perfect, but it does the job for him.

He believes that having a capable team allows him to trust them to manage tasks when he’s not available, which is crucial. He also practices mindfulness and tries to disconnect and recharge on a regular basis, both mentally and physically.

Cultural Inclusion and Value

Secure Engage believes in looking for the right attitude and potential rather than just credentials and experience. He seeks individuals who are curious, adaptable, and passionate about solving complex problems. Diversity is central to Secure Engage’s hiring philosophy because it understands that different perspectives drive innovation.

The company strives to understand cultural nuances and ensure everyone feels included and valued, regardless of their background. Additionally, it focuses on the continuous learning and development of the current staff, ensuring that team members grow alongside the company.

Multicultural and Globally Minded Operations

As a Canadian company, Secure Engage sometimes encounters challenges related to scale and access to capital compared to U.S. or European competitors. There is also a perception issue where Canadian tech companies may not be viewed as aggressive market players compared to their American counterparts.

However, he sees their Canadian base as an advantage; they operate in a multicultural, globally minded environment. Canada’s strong reputation for privacy protection and ethical technology development aligns well with its mission. Navigating various regulatory environments globally can be challenging, but it also drives them to innovate.

Empowering Others to Find Solutions

In Rajneesh’s view, transitioning to the CEO role required him to shift from focusing on specific tasks to thinking strategically about the company’s overall vision. In previous roles, he was more hands-on, but as CEO, he has had to learn to trust others to lead operational tasks while he concentrates on long-term goals, partnerships, and culture building.

The biggest adjustment has been managing his expectations of what success looks like and recognizing that leadership is about empowering others to find solutions rather than having all the answers himself.

Guiding with Authenticity and Listening

Rajneesh has been fortunate to have several mentors who have significantly influenced his career. Early on, his family instilled the values of hard work and perseverance, which have guided him throughout. In the professional realm, mentors taught him the importance of listening and leading with authenticity, principles he incorporates into his leadership style.

His wife has been a constant source of support, especially during demanding times for the business, helping him stay grounded. Lastly, his team at Secure Engage has played a crucial role in shaping his collaborative leadership approach.

Lessons from the Harvard Experience

Harvard was an eye-opening experience for him, exposing him to leaders from various industries. He learned valuable lessons about organizational behavior, leadership under pressure, and fostering innovation within a team. The most important takeaway was the value of critical thinking and systematically approaching complex problems.

At Secure Engage, these lessons have helped him structure the company to encourage creativity while maintaining clear goals. The network he built at Harvard and the alumni community have been incredibly valuable, providing not only advice but also opening doors to partnerships and collaborations that have facilitated Secure Engage’s growth.