The Team

Art Shaikh

Founder & CEO

Art has over 20 years of experience building and maintaining relationships while effectively managing high-functioning teams. He’s always had an entrepreneurial drive and his mission to bring DigitalWill.com to the masses was made a reality in early 2018. Since then, he’s put together a diverse team of dedicated individuals that share his passion and drive. He’s the fearless leader of DigitalWill.com and the man behind the idea.


Rafi Sayyed

Chief Technology Officer

Rafi has over 25 years of experience in the fintech, telecomm, insurance, and legal/regulatory industries and is skilled in end-to-end application development. At DigitalWill.com, he leads a high-performing team of developers that have spent countless hours bringing DigitalWill.com to life. He plays a major role in the ideation, development and implementation of new features while ensuring our platform is reliable and secure.


Sami Sayyed

VP of Engineering

Sami has over 20 years of experience with Motorola in a myriad of capacities ranging from Engineering Manager to Business Development Manager. In his role here at DigitalWill.com, Sami works closely with our entire design and tech teams to ensure all aspects of our app development remains on track and on schedule. He thrives under pressure, has strong attention to detail and problem solving capabilities.


Joe Karasin

Head of Growth Marketing

Joe has over 10 years experience in SEO, PPC, social media, and email marketing. Here at DigitalWill.com, Joe enjoys working with the creative and marketing teams to develop comprehensive marketing strategies that deliver results. He’s innovative, passionate, and an expert at executing data-driven strategies for business growth and has been an integral part of DigitalWill.com’s growth.


Samantha Ruffolo

Lead Designer

Samantha is a super talented designer with over 7 years experience in the industry. She’s a true creative that loves the ideation process. From designing our digital assets to coordinating our branded swag, Samantha truly wears multiple hats here at DigitalWill.com. Her amazing designs have boosted engagement across platforms and ensured that DigitalWill.com is being shared with the world.


Teresa Duckworth

VP of Brand Communications

Teresa has over 20 years of branding experience and has confidently built and led creative and communication teams throughout her career. Here at DigitalWill.com, she’s responsible for ensuring our brand image and voice is consistent across all outlets. Teresa is truly a strategic thinker with the unique ability to understand and implement the psychology behind successful communications.


Elizabeth Michals

Lead Product Designer

Liz is a well-rounded designer with over 5 years experience across a wide range of design disciplines. Here at DigitalWill.com, she’s our UI/UX design master behind our Generational Platform and has an impeccable eye for detail and extraordinary work ethic. Liz has the uncanny ability to put herself in the shoes of our members and understand how they think and navigate through our platform.


Ian Winans

Product Designer

Ian is a recent Cum Laude DePaul graduate specializing in user experience design. Ian views UI/UX design as an opportunity to build modern and innovative experiences based on users' unique needs. Here at DigitalWill.com, he is truly a hands-on member of our product design team aiding in interactive design for our website and mobile product.


Tim McCarter

Product Manager

Tim has over 25 years experience in project leadership and team management. Here at DigitalWill.com, he ensures that all aspects of our generational platform are built with our members' needs first. With his diverse history as a process engineer, he works hard designing, developing and testing new procedures and tracks metrics to discover areas for improvement.


Lisa Roti

VP of Marketing & Partnerships

Lisa has over 10 years of experience in creative strategy and cultivating strategic partnerships. Lisa’s role at DigitalWill.com is to communicate and connect people’s stories with DigitalWill.com mission - her passion to deepen understanding and create community is completely in line with this objective. You may also recognize her, on camera, in DigitalWill.com online videos and ads.


Cortland Gillespie

Producer & Director

Cortland has over 5 years experience in the film industry and is the official Steven Spielberg of DigitalWill.com. Producing and directing high quality videos is his specialty and he brings his unique creativity to every project. Cortland creates all of our marketing videos to help new users discover the app and educational videos to help them make the most out of their experience.


Orissa Claver

VP of Human Resources

Ori has over 13 years experience leading diverse teams and is a master organizer that excels under pressure. She’s a people person and puts her interpersonal skills to great use here at DigitalWill.com. Ori maintains our vendor relationships, company financials, and internal HR needs. Ori really is the backbone of the DigitalWill.com team and is always willing to lend a hand – no matter the need.


Aisha Nawab

Finance & Operations

Aisha has 15 years of experience working in a myriad of roles and industries and currently holds a Doctorate in Chinese Medicine. From her efforts helping people heal to her administrative roles in fortune 500 companies, she comes to DigitalWill.com with amazing organizational and managerial skills and is truly a balancing force here at DigitalWill.com.