Leadership Team

Chief Executives & Advisors
Jessica Ewing
CEO & Founder

An unapologetic lover of literature, Jessica Ewing is Founder and CEO of Literati. Jessica began her career as a product manager at Google, where she worked directly for both Marissa Mayer and Sundar Pichai for five years developing consumer products. She was featured in Fast Company as one of “Google's 12 Most Innovative Minds” in 2007, and she is the co-owner of five different patents in consumer technology design. Ewing left Google in 2009 to pursue a lifelong dream of writing. A graduate of Stanford University, Jessica previously served as special assistant to the Director of the National Economic Council in the White House. She is also an instructor at the Boulder Outdoor Survival School, where she teaches courses on primitive and traditional wilderness survival in the deserts of southern Utah. In 2016, Jessica founded Literati, with a mission of igniting a love of learning and a love of life in people everywhere.

Stewart Pickard
Chief Operations Officer

Stewart Pickard, a seasoned executive with a proven track record in growth-oriented environments, is Chief Operating Officer at Literati. He brings extensive leadership experience from various roles across SaaS, eCommerce, and tech-enabled sectors within Austin's vibrant startup landscape. Prior to Literati, Stewart was COO at Dropoff, a prominent last mile logistics firm. During his tenure, he led successful initiatives enhancing on-time delivery rates to over 90%, expanding service reach to 40+ markets, and implementing effective cost containment strategies leading to positive EBITDA performance. His prior key roles at Bazaarvoice, as Client Partner and Director of Commercial Relations, involved fortifying relationships with global top-tier brands and retailers, further bolstering his portfolio of impactful executive responsibilities. Stewart earned his Bachelor's degree from the University of Missouri School of Journalism and dual Masters degrees in Communications and Business Administration from the University of Texas at Austin. His impressive professional and academic pedigree is complemented by his commitment to personal growth and love of music, fitness and family.

Daragh Sibley
Chief Algorithms Officer

Daragh is the leader of Literati’s Analytics and Algorithms team. This team works to optimize all the company’s high value decisions. For instance, they build algorithms that pick which books get sent to each client, how each book is priced, and what/when/how much inventory is purchased to balance client and financial outcomes. Moreover, the Analytics and Algorithms team creates and enables a culture of data driven strategic decision making throughout the company. Prior to Literati, Daragh spent 8 years leading multiple algorithms teams at Stitch Fix, which operates a model very similar to Literati’s Clubs. Daragh joined Stitch Fix when it was smaller than Literati and helped grow it to a profitable public company generating over $1.5B of revenue a year. Daragh earned a PhD in Applied Experimental Psychology, by developing large scale neural network simulations of language acquisition and then testing these models’ predictions in neuro-imaging studies. These studies yielded dozens of peer reviewed articles and conference papers.

Aydin Senkut
Board of Advisors, Felicis Ventures

Aydin Senkut is an investor, serial entrepreneur and executive, as well as Founder and Managing Partner of Silicon Valley VC firm Felicis Ventures. Early in his career, he was Google's first product manager. An original “super-angel” investor, he was named to Forbes’ 2014-2021 Midas Lists. He was also named among the New York Times’ Top 20 Venture Capital investors in 2016, 2017, 2018 & 2019. Aydin is well-known as an early backer of a number of iconic companies including Adyen, Shopify, Pluralsight, Credit Karma, Fitbit, Rovio, Meraki, Guardant Health & Soundhound. Besides his impressive track record building many of the world’s most well-known companies, Aydin is an avid pilot, skier and tennis player.

Nikhil Basu Trivedi
Board of Advisors, Footwork

Nikhil is an investor and entrepreneur focused on discovering, investing in, and mentoring the next generation of entrepreneurs. Born in the UK, Nikhil was raised in three countries on three continents. He discovered a love of entrepreneurship while a student at Princeton University. In 2008, during his sophomore year, Nikhil co-founded Artsy, an online platform for discovering and collecting art. Nikhil’s investments include Canva, Whisper, Doctor on Demand, Survios, Bloc, Hinge, Eero, Imperfect Foods, The Pill Club, Lattice, and Literati. In 2015, Nikhil was named to Forbes Magazine’s 30 Under 30 list for Venture Capital. Today, he serves as Co-Founder and General Partner at Footwork, and brings deep expertise in consumer-oriented businesses to Literati.