Our Lead Toasters

Chris Comparato

CEO and Director

Chris Comparato is Chief Executive Officer and a Director of Toast. He has an extensive background in leading high growth SaaS, software, and consulting companies with a focus on customer success and building strong teams. Prior to Toast, he led all customer success functions at Acquia (named Inc. 500 #1 fastest growing company) and Endeca (acquired by Oracle in 2011). He previously held roles at consulting firms Keane and Cambridge Technology Partners, where his track record of delivering innovative business technology to diverse industries started. He holds a BS in Mechanical Engineering from Union College.

Steve Fredette

President, Co-Founder and Director

Steve Fredette is President, co-founder and a Director of Toast, where he leads product and innovation initiatives. Prior to Toast, he worked on mobile app development before the iPhone came out, creating the first Flickr and Shoebuy.com apps. At Endeca, now Oracle, he co-founded their mobile commerce business, building the product team and driving sales, marketing, and services to over $10 million in revenue in two years. He also ran the Special Operations team at Endeca, creating new prototypes for various customer and business needs, including Endeca’s business intelligence platform. Steve holds a BS degree from MIT.

Jonathan Grimm

CTO & Co-Founder

Jonathan Grimm is CTO and co-founder of Toast. Prior to Toast, he held solution engineering and application development leadership roles at Endeca/Oracle, interacting with customers on a day-to-day basis and developing new frameworks for the development team. He now spearheads Toast’s software and technology efforts, focusing on scalable infrastructure and technology architecture. With a passion for startups, he leads initiatives to grow the business from a technology perspective. Jon holds a BS in Computer Science from MIT.

Aman Narang

Co-President, Co-Founder, COO and Director

Aman Narang is President, co-founder, Chief Operating Officer, and a Director of Toast. Prior to Toast, he worked on innovation initiatives at Endeca, now Oracle. Aman spearheaded the development of Endeca’s business intelligence platform as well as their mobile commerce platform, each of which became major business units. He holds BS and MS degrees in Computer Science from MIT and currently leads innovation and business development initiatives at Toast.

Jennifer DiRico

SVP, Finance and General Manager of International

Jen DiRico is SVP, Finance and General Manager of International at Toast, where she leads the company’s international strategy. She is also responsible for leading the finance and business intelligence teams. Jen has held several operational and finance leadership roles at Toast, including the company’s first Chief of Staff, where she built Toast's "Operating System" for running the company and also as VP of Financial Planning & Analysis, where she established the function. Jen comes to Toast having held various finance and consulting roles in the hospitality and SaaS space. She is a graduate of the University of Miami and holds an MBA from Simmons School of Management.

Annie Drapeau

Chief People Officer

Annie Drapeau leads our People and Culture efforts as Toast's Chief People Officer. She started her career in finance and strategy leadership roles. She has led organizations through rapid growth as Chief People Officer at Digitas, VistaPrint, and Moderna and led both Talent and Corporate Strategy teams at Iron Mountain. Annie also spent time as an Operating Partner at Bain Capital. Annie serves on the Board of Directors of the Posse Foundation. She has a Bachelors Degree in Chemical Engineering from Bucknell University, where she serves on the Board of Trustees. She also has an MBA from the Tuck School at Dartmouth College.

Brian Elworthy

SVP and General Counsel

Brian Elworthy is SVP and General Counsel at Toast, where he is responsible for managing all of the company’s legal affairs. Before joining Toast, he served as Assistant General Counsel at inVentiv Health, a global provider of commercial and clinical solutions to the pharma industry. Brian began his legal career at Ropes & Gray, spending six years practicing in the private equity/M&A groups. Brian earned his JD from Georgetown University and his BA from Middlebury College.

Elena Gomez

Chief Financial Officer

Elena Gomez brings more than 25 years of experience in leading companies at scale that are also category winners, including Salesforce and Zendesk. Since May 2016, she served as the Chief Financial Officer at Zendesk where she helped scale the global company to over $1B in annual revenue, managing growth across the enterprise and developing multi-year, long range plans for the global company. Prior to Zendesk, Gomez held senior finance roles at Fortune 500 companies including Salesforce, Visa, and Charles Schwab. She currently sits on the Board of Directors at Smartsheet and PagerDuty. Ms. Gomez holds a B.S. in business administration from the Haas School of Business at the University of California at Berkeley.

Megan Anderson

Chief Customer Officer

Megan Anderson is the Chief Customer Officer, responsible for leading the customer support functions at Toast. Before coming to Toast, Megan scaled and led the Global Customer & Partner Services team at Booking.com in Amsterdam, where she elevated the customer experience, drove automation and self-service and oversaw a team of 9000, providing 2/47 support in 32 languages. Also at Booking.com Megan launched the alternative accommodation business. Other prior roles include Operating Director at Berkshire Partners, a Boston-based private equity firm, and management consultant with Bain & Company. Megan holds a B.S. in Business Administration & Spanish from University of California, Berkeley and an MBA from the Stanford Graduate School of Business.

Yi Chen

SVP & GM of Guest

Yi Chen is the SVP and GM of Guest at Toast where he is responsible for leading digital ordering, restaurant marketing platforms, guest data platform, Toast consumer app, and other guest facing products and services. Prior to his current role, Yi was leading the product and design teams at Toast as the VP of Product for many years starting as the first product manager working in Aman’s basement. Prior to Toast, Yi was part of a leadership rotation program at General Electric and led a product engineering program to automate freight transportation for the Canadian National Railway with self driving locomotives. Yi is also an investor and advisor to early stage startups and entrepreneurs. Yi holds a bachelors degree in Computer Engineering from Cornell University and an MBA from Harvard Business School.

Debra Chrapaty

Chief Technology Officer

Debra serves as the the CTO, consolidating the leadership of technical planning, architecture, and engineering. Debra brings decades of experience in large scale technical infrastructure, cloud, and operations management; hardware & many brands, including the National Basketball Association (as CTO), E*TRADE (as CIO), Microsoft (as Corp VP Infra & Cloud), CISCO (as SVP of Collaboration Software), and ZYNGA (as CIO). Most recently Debra served as the CTO of Wells Fargo building stability, speed and security & compliance for the nation’s 4th largest bank. And as the VP & COO of Amazon Alexa, run devices design; software services, developer productivity and agile.

Dean Crutchfield

Chief Information Security Officer

Dean is a senior leader with over three decades of experience in technology companies that focus on vertical SaaS product development, hardware development and technology integration. Dean has held executive leadership positions at leading technology companies including Dell Technologies, Zebra Technologies and vertical SaaS provider CDK Global. At Toast, Dean serves as the Chief Information Security Officer responsible for commercial technology solution security, corporate security, technical compliance and security operations.

Kevin Hamilton

Chief Marketing Officer

Kevin Hamilton serves as the Chief Marketing Officer at Toast. An experienced sales and marketing leader, Kevin most recently served as the Senior Vice President of Marketing and Business Development for Benefitfocus (NASDAQ: BNFT). Prior to Benefitfocus, Kevin was an early employee at Opower where he served in a variety of sales and marketing leadership roles leading up to the company's successful initial public offering and subsequent acquisition by Oracle. Kevin is a graduate of the University of South Carolina and holds an MBA in Finance from The University of North Carolina's Kenan-Flagler Business School.

Matt Kaplan

SVP of Product

Matt Kaplan is SVP of Product at Toast, where he leads product strategy, product management, and design. Matt was recently the SVP of product at Acquia and served as chief product officer and GM at LogMeIn. During Matt’s six-year tenure at LogMeIn, revenue grew more than 800 percent and, following its merger with Citrix’s GoTo business, Matt was appointed GM of emerging growth products. Prior to LogMeIn, Kaplan was integral to driving online product and customer solutions for KnowledgeVision, PermissionTV, AGENCY.COM, AdValue Network, and Cambridge Technology Group. Matt holds a BS degree in Mathematics with Computer Science from MIT.

Emmanuelle Skala

SVP Operations & Hardware

Emmanuelle leads all the post-sale customer-facing functions at Toast as the Senior VP of Operations & Hardware. She sits on the advisory board of four startups and is a frequent industry speaker and blogger. Prior to Toast, she lead Sales & Customer Success at DigitalOcean, scaled Influitive 10x in two years leading Sales, and ran the Global Channel Sales at Sophos. She was also the first hired sales person at Endeca and Vertica and was fortunate to see both through rapid growth and successful acquisitions. She holds a B.S. in Industrial Management from Carnegie Mellon University and an M.B.A. in Marketing and Finance from New York University’s School of Business.

Jonathan Vassil

Chief Revenue Officer

Jonathan Vassil is Chief Revenue Officer for Toast. Previously, he led Toast’s Sales and Onboarding organizations. Jonathan has extensive experience in hyper-growth businesses and offers a deep background in SMB sales, operations, and marketplace development. He sits on the board of several early-stage startups. Prior to joining Toast, Jonathan held several senior leadership roles at GolfNow (Comcast), Orderup, and Groupon. He holds a BS in Behavioral Sciences from the University of Maryland and an MBA from the University of Virginia’s Darden School of Business, where he is also a guest lecturer.

Anisha Vaswani

Chief Information Officer

Vaswani joins Toast with more than 20 years of experience in the IT space, having most recently served as the Chief Information Officer at Box. In this capacity, she was responsible for global IT including enterprise applications, IT operations, end user services, and project management office (PMO). Her team led technology selection, solutions architecture, analysis, design, development, quality assurance, and project management of systems. Prior to Box, Vaswani held IT management roles at VMware, Agilent Technologies, and Hewlett-Packard. Vaswani received a bachelor's degree from San Jose State University.