By Sheryl Hoskins, CEO at Litera

As the CEO of a leading legal technology company, with twenty years of experience in the global technology industry, I’m proud to lead a diverse team. But that isn’t just an ethical decision or one based on my own experience, it’s a business decision.

I know that when our leaders have diverse perspectives – whether those come from their racial, gender or sexual identity – they collectively bring more to the table than a group with similar backgrounds and points of view. When you have a diverse workforce who feel comfortable showing up as themselves every day, you get to better ideas faster with numerous perspectives and inherent trust in the company. According to a recent study, companies with a broad range of diverse board members consistently outperform those with less diversity.

Cementing your place in the industry

Before I stepped foot into the technology sector, I started my career as an active-duty officer in the US military. Who I am as a leader and how I lead is rooted in my military background. As you can imagine, it was an incredibly male-dominated workplace. I learned to always be prepared. Sometimes I’m overly prepared, and the military taught me to have a primary plan but also have a plan B and C for when plans don’t go the way you expect.

To add to this, I’m disciplined and rigorous in my execution – as a leader in the Army, the lives of my soldiers were my responsibility. I had to be disciplined and rigorous with my strategy and work. I learned early on as a Platoon Leader that gaining the trust of my soldiers was critical to accomplishing our mission. I was genuine, full of integrity, honest, and trustworthy. Because of this, I learned how to greet challenges willingly and prove that anything’s possible, both of which apply to everyday life at any company. All these attributes are rooted in my military experience and have stayed with me throughout my career. It is something I continue to be proud of.

Planting equal opportunities

After leaving the military, I worked for Fortune 15 companies and in software technology holding multiple roles. Working in technology, once again I was frequently the only woman in the room, and certainly often the only Asian woman. But I’ve always been able to grow and succeed based on hard work and dedication. Another key to my success was to always seek out mentorship or observe to learn from those above me while identifying the best opportunities to propel my career forward. This allowed me to cement my place in the industry and I encourage others to do the same if they are able.

Being the only female in a professional setting has taught me many things, including the importance of a diverse team. It has been proven that having women in leadership roles at equal numbers improves profits and outcomes. The Ready-Now Leaders report from the Conference Board shows that organisations with at least 30% of women in leadership roles are 12x more likely to be in the top 20% for financial performance.

Having robust DEI initiatives in place fast forwards these outcomes and ensures a diverse company from the board down. But it is also about the work you do day to day. My passion for equity drives the mentorship I provide at Litera as well as the technology we build that champions fairer ways of working: Litera Foundation helps firms ensure they are providing attorneys equal opportunities when it comes to high-profile work, and Kira, our AI-powered contract review tool where we hope to address bias in the legal world, ensuring documents are being reviewed fairly.

Creating change in tech

Surprisingly, it is only in the past thirty years that we’ve begun to see dramatic gender shifts in the workplace thanks to a growing chorus of role models, initiatives, and advocates. However, across all industries, we still have a long way to go. It is only in the past ten to fifteen years that there has been a core focus on encouraging women to get into STEM career paths.

Even though businesses have a large part to play in hiring women in tech, it ideally starts at the root with schools investing in training, mentoring, and resources that highlight the various career paths you can achieve with technology.

Companies must also hold themselves accountable when it comes to a diverse workforce and creating accessible opportunities is a first step. I recall, early in my career, being “tapped on the shoulder” to take on a project or initiative. Another memorable event for a female colleague was when I invited her to sit at the table during a meeting (versus sitting in the back row). Little gestures like these can have a big impact in creating these “accessible opportunities”. To make this shift, more business leaders need to be aware and advocate for their team members.

It’s all well and good saying that the onus sits with businesses and schools, but that means the people in charge need to take a stand. The shifts we’ve seen across industries in recent years give me hope that change is upon us. I am proud that Litera’s leadership team is 40% female and that we have strong representation across our senior leadership team in gender orientation as well as racial diversity.

Luckily, I’ve had the opportunity to work with some incredible leaders, colleagues and friends who have taught me and proved that the unimaginable is possible. It is so empowering to see the industry change in ways we never would have dreamed and the future looks incredibly bright.


About the author

Sheryl Hoskins is CEO at Litera and has experience within the military as an active duty officer that shaped her leadership style going into the world of tech. She had roles at both General Electric and McKesson Corp until 2012 and has an electrical engineering degree. She also has two decades of experience in the global tech industry and is set to transform the legal industry, empowering professionals to upskill – she is extremely passionate about DEI and this is also reflected in her role. and has experience within the military as an active duty officer that shaped her leadership style going into the world of tech. She had roles at both General Electric and McKesson Corp until 2012 and has an electrical engineering degree. She also has two decades of experience in the global tech industry and is set to transform the legal industry, empowering professionals to upskill – she is extremely passionate about DEI and this is also reflected in her role.