About Litera

As Chief Executive Officer, Sheryl is responsible for leading Litera as it scales its enterprise software businesses, delivers the best legal technology ecosystem, and revolutionizes how legal teams and law firms use technology to drive digital transformation. She drives the entire team to deliver genuinely leading-edge legal technology solutions for our customers. She strives to serve the business and its customers by helping enable our leaders and people to fulfill their passion for making a difference.

Sheryl has more than twenty years of experience in the global technology industry and a proven track record managing global teams. She spent the first decade of her career at General Electric and McKesson Corp, where she held domestic and international leadership roles. Most recently, Hoskins served as CEO of Upserve. Sheryl received a BS Degree in Electrical Engineering, an MBA in Marketing, and is a US Army veteran.

As Chief Customer Officer, Chris Arellano is responsible for Customer Success, Professional Services, and Customer Support to ensure customers have a superior experience and can fully maximize the value of the solutions and services provided.

Chris has over 20 years of experience in executive leadership, operations, customer success, and continuous improvement. She has a proven track record as an exceptional leader and process expert in the industry, holding key leadership roles at Upserve, McKesson, American Express, FedEx Ground, Motorola, and Acoustic. She has successfully led global teams responsible for managing over $1 billion in annual revenue across 50,000+ customers.

Chris has a B.S. degree in Industrial Engineering from ASU and an MBA with an emphasis in Leadership from Grand Canyon University. She is also a Six Sigma Master Blackbelt.

As Chief Financial Officer, Carl Gillert is responsible for managing the financial health, performance, and strategy of the business to support Litera’s Value Creation Plan.

Carl’s experience is primarily in private equity-backed technology companies, where he has worked to achieve growth and operational efficiencies through partnering with key business stakeholders. His specialties include operational and commercial finance strategies and transformation, FP&A, pricing, sales operations, M&A, accounting, and treasury. Before Litera, Carl was at Exostar, a cyber security and secure collaboration firm, where he built a best-in-class finance team and accelerated the growth of the business as it transformed into a successful provider of SaaS solutions. Before Exostar, Carl was the CFO of parking technology provider T2 Systems, where he led successful M&A transactions enabling the company to accelerate their growth. Carl also spent nine years with telecom technology provider Syniverse in various finance roles.

Carl holds a Master’s Degree in Accounting from the University of Central Florida and a Bachelor’s Degree in Accounting from the University of South Florida. He is also a Certified Public Accountant.

As Chief Technology Officer, Greg Ingino is responsible for leading the engineering, dev ops, architecture, R&D operations, QA, IT, and Security teams across the company.

Greg brings more than 17 years of senior management experience in both PE backed and public companies, primarily focused on high growth, highly acquisitive, software companies across several different industries. Before Litera, Greg was CTO of WebPT, Greg was responsible for rebuilding and transforming the technology organization of the largest outpatient software provider in the industry to achieve enterprise scale through the integration of several acquisitions, delivering new enterprise platform capabilities, launching the companies first enterprise data offering, and improving overall scalability of the company’s technology assets. Prior to WebPT he served as the CTO of Vertafore, the largest provider of software to independent insurance agents, helping the company scale to $600M+ in revenue which led to a sale of the company to Roper Technologies for $5.35B. 

Greg holds a bachelor’s degree from California State University Northridge and an MBA from UCLA.

As V.P., Chief of Staff, Emily Legere is responsible for instilling cadence discipline, leading key programs and initiatives, and ensuring overall execution effectiveness with a focus on annual strategic planning and value creation.

Emily is an experienced Chief of Staff and motivated SaaS technology-industry professional with expertise in financial and business analysis, strategic planning, program management, and operations. Before joining Litera, Emily held similar positions with Acoustic, Bottomline Technologies, Sovos, and ClickSoftware.

Emily has a B.S. degree in Mathematics from the University of Massachusetts Lowell and an MBA from Babson College.

As Chief People Officer (CPeO), Michelle leads the People management team, which includes talent acquisition, Talent Management, Learning & Development, DE&I, and People Operations.

Michelle completed her undergrad work at Alma College in Michigan and attended the University of Alabama for law school. She was in private practice, specializing in employment law, for over a decade then moved into Human Resources. Michelle began her HR career with LexisNexis, later moving to Verint Systems (a B2B Enterprise software company) both highly acquisitive and rapidly growing organizations. 

Her most recent role was Chief People Officer with ServiceMaster Brands, a $4B franchise company where she was responsible for both the internal Human Resources organization and the customer-facing HR consulting and training groups.

As Chief Sales Officer, Sean is a seasoned sales professional with a stellar reputation for accelerating sales growth and cultivating dynamic teams that exceed expectations. His expertise in strategic sales initiatives and his passion for innovation make him the ideal leader to drive our sales operations to success.

As Head of Transformation, Rachael Rekart is responsible for driving cross-functional organizational change, focusing on maximizing business performance and enhancing efficiency.

Rachael has over 15 years of experience in the software industry, playing pivotal roles in sales, customer success, finance, and operations for various companies, including publicly traded, VC-backed, and PE-backed organizations. She is an expert in digital transformations, with a wealth of experience incorporating AI deployments and cross-functional strategic initiatives to optimize operations. Rachael has been featured in Vogue Australia and the Wall Street Journal for her work in AI and was named one of San Francisco Business Times’ ‘Most Influential Women in Bay Area Business.’ She is an evangelist of human-machine augmentation and has spoken on the topic world-wide.

Rachael has a Master’s in Psychology from Pepperdine University, along with a Bachelors’ in Marketing and Supply Chain Management from Arizona State University. 

Adam is a seasoned product and innovation leader with a proven track record in driving growth and delivering successful products. With over 18 years in the legal and tech industry, Adam has been at the forefront of driving product management and innovation in legaltech. He has a law and computer science background and was the Chief Legal Innovation Officer at Freshfields before joining Litera.