Legal technology
Sales professionals in Legal technology
These ten professionals have held sales roles at legal technology vendors. A reader can learn how legal software is sold to law firms and corporate legal departments, and what drives adoption once a tool has been bought.
Professionals to explore
01—10Addy Spearman
LinkedInExperience: Director of Sales · ContractPodAi
Director of Sales at ContractPodAi since 2025, and former Enterprise Sales Director at Onit (2024–2025) and Regional Sales Director EMEA at Wolters Kluwer ELM Solutions (2017–2021). Also listed are Manager, Key Accounts Management Team, UK at LinkedIn (2022–2023) and Manager, Legal Solutions- Europe eDiscovery at Epiq (2016–2017). The summary describes long-standing experience in the legal tech space, helping organizations use technology and AI to improve matter management and reduce legal spend.
Anamika Das
LinkedInExperience: Global Vice President of Sales, Enterprise and Large Law · Litera
Global Vice President of Sales, Enterprise and Large Law at Litera since 2025. Other listed Litera roles include Vice President of Sales, Large Law North America (2025), Vice President, Global Solution Sales (2024–2025) and Senior Director of Sales (2023–2024); also listed is Senior Director of Sales at Thomson Reuters (2022–2023). Her summary describes leading a team of 120+ legal professionals supporting law firms across the United States and consulting on legal market trends.
Brian Milanese
LinkedInExperience: Sales Director (LollyLaw & MerusCase) · Paradigm
Sales Director (LollyLaw & MerusCase) at Paradigm since 2023, with an open-ended Director of Sales row at MerusCase since 2014; also listed is Sales Manager at Paradigm (2014–2023). Other listed roles include Regional Sales Manager (2013–2014) and Product Manager Corporate Trainer (2011–2013) at Gemini Legal. His summary describes a sales track record across the legal technology industry, with skills including product demonstration and litigation management.
Chris Jefferson
LinkedInExperience: Sales Director · Litera
Sales Director at Litera since 2025, and former Director of Sales and Marketing (2023–2025) and Senior Sales Executive (2017–2023) at Peppermint Technology. Also listed is Sales Consultant at OneAdvanced (2015–2017). His highlights describe helping law firms maximise the value of their client relationships and deliver legal services efficiently using Microsoft and the Peppermint platform.
Clement Quessette
LinkedInExperience: Sales Director B2B SaaS & AI-Powered Legal Solutions · Logol AG
Sales Director B2B SaaS & AI-Powered Legal Solutions at Logol AG since 2023. Other listed roles include Advisor at PK Labs (2024–2025), Customer Success Manager at PXL Vision (2023), Head of Growth at EDGE Empower® (2022–2023) and Director of Customer Success at inveox (2021). His summary describes leading commercial strategy at Logol, which it calls one of the leading enterprise legal technology providers in Switzerland.
Donna Bailey
LinkedInExperience: Vice President, North America Legal Industry Sales · Intapp
Vice President, North America Legal Industry Sales at Intapp since 2021, and former Managing Director at Intapp (2019–2021). Other listed roles include Sales Director - Central - IBM Solutions at Imagine Solutions (2017–2019), Account Executive at Aderant (2014–2017) and Director of Business Development at DocAuto, Inc. (2011–2013). Her summary describes leading sales executive teams focused on B2B enterprise AI solutions for the legal industry.
Ken Brajevich
LinkedInExperience: National Director of Sales · Supio
National Director of Sales at Supio since 2025. Other listed roles include Business Consultant at KBBC (2023–2025), Global Head of Partner Development at Vertex Inc. (2021–2023) and National Director Of Sales Emerging ERP at Avalara (2013–2021). His summary describes helping law firms modernize and scale by bringing AI solutions in legal tech to their operations.
Michela DiGioia-Nuño
LinkedInExperience: Vice President of Sales · Smokeball - Legal Software
Vice President of Sales at Smokeball - Legal Software since 2025, and former Senior Sales Director there (2025). Other listed roles include Sr. Director of Sales- Commercial NAMER (2022–2023) and Director of Sales- Commercial (2021–2022) at ActiveCampaign. Her summary describes more than 20 years in sales, including 10 years in sales leadership within the computer software industry.
Rob Midson
LinkedInExperience: Director, Enterprise and Mid-Market Sales · Filevine
Director, Enterprise and Mid-Market Sales at Filevine since 2024, and former Director of Sales (2022–2023) and Sales Manager (2021–2022) at Centerbase. Other listed roles include Head of Sales at LineLeader by ChildcareCRM (2023–2024) and Consultant at Foxit eSign (2024). His summary describes guiding Filevine's sales team through strategic negotiations and growth initiatives, with a mission in the legal tech industry.
Rob Recklaus
LinkedInExperience: Director, Legal Enterprise Sales · Bloomberg Law
Director, Legal Enterprise Sales at Bloomberg Law since 2023, and former Vice President Sales and Customer Engagement (2016–2023) and Sales Account Management Industry Lead (2010–2016) at Bloomberg Government. Also listed are Director of Government Relations (2008–2010) and Chief of Staff Communications Director (2002–2008) at Bloomberg Government. His summary describes building teams in corporate, government and nonprofit environments.
Choose the right perspective
Match the person's customer segment and product type to your decision, since selling to large law firms, small practices and corporate legal departments involves different buyers, budgets and sales cycles. Check whether their relevant role is current or past and which region it covered.
Questions to take into the conversation
- 01Who signs off on new software at a law firm, and how long does that process take?
- 02How do you show partners and legal operations leaders the return on a legal technology purchase?
- 03What usually stalls adoption after a firm buys a new tool, and how do you address it?
Reaching sales professionals in Legal technology
How can I contact one of these sales professionals in Legal technology?
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 9 companies, including ContractPodAi, Litera and Paradigm, based on profile data retrieved on October 1, 2026. Being listed here doesn't mean someone has agreed to take calls.
How much does it cost to reach sales professionals in Legal technology?
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.
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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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