Our Lead Toasters

Chris Comparato

Chief Executive Officer & Director

Chris Comparato is the chairman and chief executive officer of Toast. He has led Toast through several significant stages of growth in its mission to empower the restaurant community to delight their guests, do what they love, and thrive. In 2020, Chris (along with Toast’s founders) was the overall national winner for the E&Y Entrepreneur of the Year Award, recognizing the team’s effort to help the industry adapt, innovate, and transform. Chris has an extensive background in leading high-growth SaaS, software, and consulting companies with a focus on building strong teams and a passion for customer happiness. 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 platforms to diverse industries started. He holds a BS in mechanical engineering from Union College.

Steve Fredette

President, Co-Founder & 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.

Jon Grimm

Co-Founder & Chief Technology Officer of Toast.org

Jon Grimm is co-founder of Toast, Inc., and CTO of Toast.org, the philanthropic branch of Toast. After holding the CTO role at Toast, Inc. for 10 years, he now leads efforts to leverage Toast product capabilities to advance the Toast.org mission. 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. Jon holds a BS in computer science from MIT.

Aman Narang

Co-President, Co-Founder, Chief Operating Officer & Director

Aman Narang is chief operating officer, president, and co-founder of Toast, where he leads Sales, Marketing, Customer Success, Business Development, and Fintech initiatives. Aman’s various roles over the past decade have given him an expansive understanding of the business. Prior to Toast, Aman worked at Endeca, now Oracle, where he led their mobile business unit. Aman holds BS and MS degrees in computer science from MIT.

Jen DiRico

Senior Vice President & General Manager of International

Jen DiRico is SVP and general manager of International at Toast, where she leads the company’s international strategy and commercial expansion. She is also responsible for leading Corporate Finance. 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 Finance. 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 Places team efforts as Toast's chief people officer. She has led organizations through rapid growth as the chief people officer at Moderna, VistaPrint, and Digitas and led both Talent and Corporate Strategy teams at Iron Mountain. Annie also spent time as an operating partner at Bain Capital. She started her career in finance and strategy roles. Annie is a published author, having written a book and several articles about trust and leadership. Annie serves on the board of directors of the Posse Foundation. She has a bachelor’s degree in chemical engineering from Bucknell University, where she serves as vice chair of the board of trustees. She also has an MBA from the Tuck School at Dartmouth College. Annie is inspired by the passion all Toasters have for our restaurant community and is driven to create a career-defining experience for every Toaster.

Brian Elworthy

Senior Vice President & General Counsel

Brian Elworthy is SVP and general counsel at Toast. In this role, he leads a team of attorneys and compliance professionals responsible for all aspects of Toast’s legal and regulatory affairs around the world. Before joining Toast, he served as assistant general counsel in the corporate headquarters of a global provider of commercial and clinical solutions to the life sciences industry. Brian began his legal career at Ropes & Gray, spending six years practicing in the firm's Corporate department. Brian earned his JD from Georgetown University Law School and his BA from Middlebury College.

Elena Gomez

Chief Financial Officer

Elena Gomez is the chief financial officer at Toast where she oversees global finance, investor relations, and corporate development. Under her leadership, Toast launched its initial public offering in 2021. Prior to Toast, Elena was the CFO of Zendesk, growing market cap over $15B. Over her 30-year career, Elena has also held finance leadership roles at Fortune 500 companies, including Salesforce, Visa, and Charles Schwab. Elena has a passion for helping organizations drive scale through cycles of massive growth. She was named to the list of Most Influential Women in Business in 2017 by the San Francisco Business Times. In addition to her operator role, Elena serves on the board of directors, as audit committee chair, for both Smartsheet and PagerDuty. Elena is an advocate for diversity, equity, and inclusion within the global business community, serving the Haas School of Business as a founding member of the Haas Center for Gender, Equity, and Leadership Advisory Council. Elena also serves on the board of the Boys and Girls Club of San Francisco. Elena graduated with a business degree from the University of California, Berkeley Haas School of Business.

Megan Anderson

Senior Vice President of Global Care

Megan Anderson is the SVP of Global Care, responsible for leading the customer support functions at Toast. Before coming to Toast, Megan scaled and led the Global Customer and Partner Services team at Booking.com in Amsterdam, where she elevated the customer experience, drove automation and self-service, and oversaw a team of 9,000, providing 24/7 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 BS in business administration and Spanish from the University of California, Berkeley and an MBA from Stanford Graduate School of Business.

Yi Chen

Senior Vice President & General Manager of Guest

Yi Chen is SVP and GM of Guest at Toast where he is responsible for leading digital ordering, restaurant marketing platforms, guest data platforms, the 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 start-ups and entrepreneurs. Yi holds a bachelor’s degree in computer engineering from Cornell University and an MBA from Harvard Business School.

Debra Chrapaty

Chief Technology Officer

Debra Chrapaty is the chief technology officer, consolidating the leadership of technical planning and operations, architecture, infrastructure, data, AI, and product engineering. Debra brings decades of experience in large-scale technical infrastructure, cloud, operations management, and product management for many brands, including the National Basketball Association (as CTO), E*TRADE (as CIO), Microsoft (as corporate VP of Infrastructure and Cloud), CISCO (as SVP of Collaboration Software), and ZYNGA (as CIO). Most recently, Debra served as the CTO of Wells Fargo, building services stability, scalability, developer productivity, speed, security, and compliance for the nation’s fourth-largest bank. As the VP and COO of Amazon Alexa, she led product growth and monetization, third-party skills and devices, and international product expansion. Throughout her career Debra has been a valued board member and advisor for many well-known companies. She holds an undergraduate degree in Economics from Temple University and an MBA in Information Systems from New York University’s Stern School of Business.

Dean Crutchfield

Chief Information Security Officer

Dean Crutchfield 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

Senior Vice President 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% and following its merger with Citrix’s GoTo business, Matt was appointed GM of Emerging Growth Products. Prior to LogMeIn, Matt 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

Senior Vice President of Operations & Hardware

Emmanuelle Skala leads operations across the company and is responsible for the hardware P&L as the senior VP of Operations and Hardware. She is a member of a group of directors for several high-growth companies, such as Emerald Holding, Inc. (NYSE: EEX) and Electric.ai, as well as lectures at MIT Sloan School of Management. Prior to Toast, she led Sales and 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 salesperson at Endeca and Vertica and was fortunate to see both through rapid growth and successful acquisitions. She holds a BS in industrial management and French from Carnegie Mellon University and an MBA in marketing and finance from New York University’s Stern 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

Anisha Vaswani brings more than 25 years of experience executing technology strategies to drive mission-critical transformation, digitization, and scale at a variety of companies. Prior to Toast, Anisha was chief information officer at Box, where she scaled the function to support the company in its journey from IPO to over $700M in ARR. Prior to Box, Anisha held several leadership roles at VMWare, Agilent, and Hewlett-Packard. In her role as CIO, Anisha is responsible for the business systems, IT operations, end-user services, and program management of technologies that power operations at Toast. Anisha received a bachelor’s degree from San Jose State University.