Five Minutes With: Sheryl Hoskins, CEO at Litera

Sheryl Hoskins, CEO at Litera
Sheryl Hoskins, CEO at Litera, discusses the importance of serving as a role model for young women and fostering a more inclusive work environment

Sheryl Hoskins' first job, as an active-duty officer in the US Army, seems a far cry from her current role as a CEO.

The experience put her in a strong position, however, to progress through the ranks at General Electric and McKesson Corp, where she served in various domestic and international leadership roles up until 2012. 

Hoskins, who grew up in the Chicago area and has a degree in electrical engineering, as well as an MBA, subsequently took up senior positions at Global Payments, before leading the hospitality software company, Upserve.

With two decades of experience in the global technology industry under her belt, Hoskins is now CEO at Litera, a leading provider of workflow, collaboration and data management solutions for law firms and legal teams across the world. 

For those unfamiliar with Litera, how would you describe its main activities?

Litera has been at the forefront of legal technology innovation for more than 25 years, crafting legal software to amplify impact and maximise efficiency for law firms across the globe. 

The company has strategically leveraged a team of people with tech and legal experience to create a comprehensive suite of tools, and we simplify the way modern firms manage core legal workflows, secure collaboration and organise firm knowledge and experience. Today, we work with more than 99% of the AmLaw 100 and 90% of global large firms. 

I was drawn to the opportunity of working at Litera because of the strength of its products. Ultimately, lawyers are our first line of defence when it comes to true justice in the world, so it was appealing to me to have an impact on the industry and how this important work gets done.  

What are the biggest challenges you face in your role as CEO at Litera?

When I joined Litera in 2022, I was really focused on growing the business, ensuring value for our customers and engaging our global teams. To do that, I needed to understand what was going well and what wasn't from employees and customers around the world, so I sought out their feedback and advice.

My approach and strategy in the following months were grounded in what I heard in my initial listening tour. Since then, I’ve remained focused on communication, quality (core products, M&A and integration) and innovation. That means making sure our employees and customers feel heard and understand what our strategy is, shoring up the quality of not only our products, but our customer support as well. And then really investing in innovation so we can lead in the market and take advantage of new technology like generative AI, which is having a massive impact on the legal profession.

My proudest accomplishment is how quickly we have improved our customer experience. As well as having a customer retention rate of 99%, we’ve improved our net promoter score by 29 points our response time by 64%.  

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How important is it for public figures and business leaders to serve as role models for young women in the legal field and beyond?

I think it’s important for everyone to see themselves in key roles across industries, whether that’s starting a business, running a business or being one of the crucial leaders that make that business run successfully. 

Throughout my career, I found opportunities to mentor women, particularly those early on in their career when they are still finding their voice. Simple things like giving them a seat at the table makes a difference.

Ultimately, I want to have the best minds and the best teams in my organisation, and that diversity of thought and experience is crucial. I want my daughter and young girls all over the world to believe they can do anything they put their minds to if they work hard enough.

Tell us how Litera is promoting and celebrating diversity and inclusion

At Litera, we actively invest in building an inclusive culture where we have DE&I as a lens across the work we do, with a strong strategy that operates across functions and ensures we hold ourselves accountable and with integrity.

We are proud to have a C-Suite that is 40% female and strong representation across our senior leadership team in gender, orientation and racial diversity. I am also proud of the investment I have seen in leaders across the organisation in support of our DE&I strategy, creating an organisation where we respond to equity challenges with courage, transparency and, most importantly, action.

What do you feel companies must do to foster more inclusive work environments?

The environment and culture need to focus on empowering all underrepresented communities and providing them with equitable opportunities to develop and grow.

My passion is advocating and motivating more women to join STEM, and encouraging girls to explore the benefits of the industry and the impact they can make across a variety of potential career paths.

Therefore, companies must focus on ensuring employees feel supported in their career journey.  

What are your personal and professional goals for the next 12 months?

Over the next year I plan to continue to grow our business and create the best products in the legal technology market that are not only innovative, but easy and delightful to use. I also plan to stay laser-focused on our customer experience and how we deliver value to our firms every day.

Personally, I am always trying to find the right balance between work and taking care of myself and my family, so I can also be present for them and grow in my personal life as well. 

What's the best piece of advice you've ever received?

PIE: performance, image and exposure. This is a theory on professional development from Harvey Coleman that I really love and share with everyone when I talk about growing your career.

The idea is that you need to think about these three things to get ahead: performance is the results of the output in your role; image is what your immediate co-workers think about you; and exposure is what the rest of the company, particularly the C-level, think about you.

Especially for women, performance is not always enough to get ahead. It’s crucial that you actively manage how your work is perceived, but also how your role and actions are perceived throughout the company. Beyond your day-to-day tasks, how are you advocating for your image? Your team? Your passion projects?

And as CEO, these three elements are more important than ever. PIE is a great compass for prioritising your actions throughout your career. 


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