Insurance
10 Cigna engineering leaders
These ten people hold or have held engineering leadership roles at Cigna, including senior vice presidents of engineering, managing directors of software engineering and senior directors of software engineering and engineering management. A reader can learn how engineering leaders build and run their teams in insurance companies.
Professionals to explore
01—10Bill Phillips
LinkedInExperience: Senior Director, Engineering Management · Cigna Healthcare
Former Senior Director, Engineering Management at Cigna Healthcare (2017–2020); the profile says the role led enterprise-wide solution delivery and oversaw a 200+ global solution train of business, operations and IT resources, and managed two large Agile Experience Groups. Former Director, Value Based Reimbursement at Cigna Healthcare (2010–2016).
Koshy Cherian
LinkedInExperience: Managing Director of Software Engineering · The Cigna Group
Managing Director of Software Engineering at The Cigna Group, a current role listed from January 2014; the profile headline cites 500+ engineers and a $100M+ portfolio across The Cigna Group / Evernorth, along with platform modernization work. Former IT Principal at Staples (2013–2014) and former Information Systems Consultant at MetLife (2005–2013).
Krishna Kumbum
LinkedInExperience: Software Engineering Senior Director · Cigna Healthcare
Software Engineering Senior Director at Cigna Healthcare since July 2026, listed at Director level in the Engineering and Technical department. Former Software Engineering Director (2020–2026) and former Architecture Senior Manager (2011–2020) at Cigna Healthcare, and former Associate Director at Babson Capital Management LLC (2008–2011).
Mansey Amin
LinkedInExperience: Software Engineering Senior Director · The Cigna Group
Software Engineering Senior Director at The Cigna Group since June 2025, a title also listed there for November 2023 to June 2025; the profile describes the role as Engineering Leader for Pharmacy Benefit Services, driving innovation, AI tooling and quality across large programs. Former Application Development Director (2020–2023) and former DevOps Engineering Senior Manager (2018–2020) at The Cigna Group.
Raul Cariboni
LinkedInExperience: Software Engineering Managing Director · Cigna Healthcare
Former Software Engineering Managing Director at Cigna Healthcare (2022–2026) and Information Technology Managing Director there since July 2026, a role the profile ties to Platform Intelligence, Security Products and Technology Delivery for Infrastructure. Former Engineering Management Sr. Director (2019–2022) and former Engineering Management Director (2017–2018) at Cigna Healthcare.
Raymond Gillett II
LinkedInExperience: Senior Director of Software Engineering · The Cigna Group
Senior Director of Software Engineering at The Cigna Group since September 2025, listed at Director level in the Engineering and Technical department. Former Strategy and Architecture Senior Director at The Cigna Group (2025), former Software Engineering Senior Director (2022–2025) and Software Engineering Director (2020–2022) at Evernorth Health Services, and former Software Engineering Senior Manager at Cigna Healthcare (2011–2020).
Sachin Joshi
LinkedInExperience: SVP Data, AI and Platforms Engineering · Cigna
SVP Data, AI and Platforms Engineering at Cigna since June 2025 and Senior Vice President, Data and Analytics Engineering at Cigna since January 2022; the profile says the role has led data and analytics engineering for The Cigna Group since 2022, with responsibility for a 3,000+ person technology organization. Former Vice President Technology Solutions at Cigna (2019–2022) and former Vice President Software Engineering at Express Scripts Pharmacy Benefit Services (2017–2019).
Scott Oshima
LinkedInExperience: SVP Engineering · Cigna-Digital
Former SVP Engineering at Cigna-Digital (2010–2018) and Vice President Digital Technology at Cigna Healthcare since January 2018, listed at President/Vice President level in the Engineering and Technical department. Former Director, Search Product at Dex One Corp. (2009–2010) and former Senior Manager Engineering at business.com (2000–2009).
Stephen Shepler
LinkedInExperience: Engineering Management Senior Director · Cigna Healthcare
Former Engineering Management Senior Director at Cigna Healthcare (2022–2025); the profile describes being technology lead for the Client, Customer, and Data Movement Services organization within the US Employer business, with application responsibility for eligibility, client installation, document generation and workflow management. Former Application Development Director at Cigna Healthcare (2013–2021).
Vinay Mogali
LinkedInExperience: Sr. Director Software Engineering · Cigna Healthcare
Sr. Director Software Engineering at Cigna Healthcare since January 2019, listed at Director level in the Engineering and Technical department, and Data & Analytics Director at Cigna Healthcare, a current role listed from 2017. Former Application Technology Director (2014–2017) and former Program Director (2010–2013) at Dow Jones.
Choose the right perspective
Match the person's area to your question, since data and platform engineering, pharmacy systems and employer business applications teams work on different systems and constraints. Check each role's dates and the person's other employers, since experience gained elsewhere may not reflect how Cigna works today.
Questions to take into the conversation
- 01How does a large health insurer split engineering between data platforms, digital products and core business applications?
- 02What has worked and what has not when scaling agile delivery across large insurance engineering organizations?
- 03How should an insurer's engineering leaders decide where AI tooling fits into software delivery?
Reaching Cigna engineering leaders
How can I contact one of these Cigna engineering leaders?
Pick one of the 10 people on this page and choose "Book a paid call", or describe your project to find others. You offer a fee for a 15-minute call or a written answer, Instant Expert finds the person's work email and sends the invitation, and they decide whether to accept. The list covers 4 companies, including Cigna Healthcare, The Cigna Group and Cigna, based on profile data retrieved on October 5, 2026. Being listed here doesn't mean someone has agreed to take calls.
How much does it cost to reach Cigna engineering leaders?
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About this directory
This is a professional research starting point based on business profile data retrieved on . Titles and companies reflect that source snapshot and may describe past or present roles. Check the linked profiles for current details. Inclusion does not imply Instant Expert membership or availability.
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