Legal technology
10 legal operations experts
These ten professionals have led or managed legal operations inside in-house legal departments, with titles ranging from legal operations manager to head of legal operations. A reader can learn from them how corporate legal teams manage outside counsel, choose and roll out legal technology and improve how the legal department works.
Professionals to explore
01—10Akiko Kakihara
LinkedInExperience: Head of Legal Innovation, Strategy, & Operations · MUFG
Head of Legal Innovation, Strategy, & Operations at MUFG since June 2026. At MUFG the other roles are Head of Legal Operations (2024–2026), Legal Operations Manager (2018–2024) and Analyst - Legal Operations (2013–2018). The profile describes managing a complex corporate legal department, including outside counsel management, legal technology management, reporting and analytics.
Carol Gelman
LinkedInExperience: Head of Legal Operations · HERE Technologies
Head of Legal Operations at HERE Technologies since April 2022, with Legal Operations roles at the company in 2018 and from 2021 to 2022 and a Contract Specialist role there from 2016 to 2018. The profile describes overseeing the day-to-day operations of the HERE Technologies Law and IP Department, reporting to the General Counsel and acting as an interface between the General Counsel and the legal department.
Christina Jackson
LinkedInExperience: Head of Legal Operations · WEX
Head of Legal Operations at WEX since November 2024. Other roles include Legal Operations Manager at Guardian (2021–2023) and Legal Operations Manager, Vice President at State Street (2017–2020). The profile describes a legal operations leader specializing in technology, finance, outside counsel management, knowledge management and project management.
Daniela Dwyer
LinkedInExperience: Head of Legal Operations at BILL · BILL
Former Head of Legal Operations at BILL (2021–2026), where the profile describes also serving as Chief of Staff to the CLO and driving strategy, execution and transformation across Legal and Compliance. Other roles include Head of Legal Operations at eBay (2015–2021) and Legal Operations Manager at VMware (2007–2012).
Heather Cruz
LinkedInExperience: VP, Head of US Legal Operations · Lockton
VP, Head of US Legal Operations at Lockton since June 2024. Other roles include Legal Operations Manager at Yellow (2022–2024) and Paralegal Legal Operations Manager at Compass Minerals (2020–2022). The profile describes managing business critical projects and strategic initiatives, multi-million-dollar budgets, complex litigation, vendor relationships and cross-functional teams.
Hope Cannon
LinkedInExperience: Director of Legal Operations · HighLevel
Director of Legal Operations at HighLevel since January 2026, after serving as Director of Legal Operations & Global Lead of Mental Health & Wellbeing ERG at Diligent from 2024 to 2025. At HighLevel the profile describes leading change and continuous improvement initiatives to strengthen governance, increase adoption of legal technologies and position Legal as a strategic business partner.
Jeremy Gilbert
LinkedInExperience: Director, Legal Operations · The New York Times
Director, Legal Operations at The New York Times since March 2026. Other roles include Senior Director, Legal Operations and Strategic Enablement at Gartner (2018–2026) and Operations Leader Law & Policy at GE Capital (2012–2017). The profile describes leading legal department transformation through operational excellence, advanced legal technology implementation and AI and metrics programs.
Kevin Behan
LinkedInExperience: Senior Director, Legal Operations · Centene Corporation
Former Senior Director, Legal Operations at Centene Corporation (2020–2021) and Sr. Director, Legal Operations at WellCare Health Plans, Inc. (2017–2020). The profile describes managing all external legal vendors, including outside counsel, as a legal operations executive and reducing external legal spend through strategies including Alternative Fee Arrangements.
Linda Swan
LinkedInExperience: Director of Legal Operations · JFrog
Director of Legal Operations at JFrog since April 2024 and former Director of Legal Operations at Ciena (2019–2024). Other roles include Legal Operations Manager at Extreme Networks (2017–2018) and Manager, Legal Operations at Atmel Corporation (2006–2017). The profile describes recommending, implementing and managing cost effective legal tools as a legal technology and operations advisor.
Sandy MacDonnell
LinkedInExperience: Senior Director and Head of Legal Operations · Docusign
Senior Director and Head of Legal Operations at Docusign since February 2026. At Docusign the other roles are Head of Legal Ops Lead Legal Operations Manager (2024–2026), Senior Manager, Legal Operations (2022–2024) and Senior Legal Operations Manager (2021–2022). The profile also mentions legal ops roles at FireEye and NetApp and an early role at the Corporate Legal Operations Consortium.
Choose the right perspective
Match the person's company size and industry to your own, since a legal operations function at a regulated bank or health plan works differently from one at a fast-growing software company. Also decide whether your main need is outside counsel and vendor management or legal technology and process work, since legal operations leaders often focus more on one than the other.
Questions to take into the conversation
- 01How do you decide which legal operations work to tackle first in a legal department that has never had the function?
- 02How do you manage outside counsel and legal vendors so that cost and quality both stay under control?
- 03How do you choose legal technology and get lawyers to actually adopt it?
Reaching legal operations experts
How can I contact one of these legal operations experts?
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 10 companies, including MUFG, HERE Technologies and WEX, based on profile data retrieved on October 3, 2026. Being listed here doesn't mean someone has agreed to take calls.
How much does it cost to reach legal operations experts?
You choose the offer, starting at $5 per person. It includes Instant Expert's 20% fee, so an offer that pays the person $100 costs you $125. You're charged only when the person books the call or sends the answer.
What if they don't reply?
You pay nothing. Instant Expert sends follow-up reminders, and if the person hasn't booked or answered within 7 days, the request expires and any hold on your card is released. You can invite several of the 10 people on this list at once and cap your total spend, so you pay only for the ones who accept.
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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