Sales professionals in Legal technology
Large law firm deals, matter management and legal spend tools, and AI products for firms are the ground these legal technology sales professionals cover, with two at Litera, including its Global Vice President of Sales, Enterprise and Large Law, and others at Intapp, Filevine, ContractPodAi, Smokeball, Supio, Bloomberg Law, Logol AG and Paradigm. Three work in England and Switzerland, useful for anyone judging how a legal software purchase gets made.
Professionals to explore
Addy Spearman
LinkedInExperience: Director of Sales · ContractPodAi
From London, Addy Spearman has been Director of Sales at ContractPodAi since 2025, after Enterprise Sales Director at Onit (2024–2025). Addy was Manager, Key Accounts Management Team, UK at LinkedIn (2022–2023), Regional Sales Director EMEA at Wolters Kluwer ELM Solutions (2017–2021) and Manager, Legal Solutions- Europe eDiscovery at Epiq (2016–2017), and describes helping organizations use technology and AI to improve matter management and reduce legal spend.
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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, Anamika Das held Vice President of Sales, Large Law North America (2025), Vice President, Global Solution Sales (2024–2025) and Senior Director of Sales (2023–2024) there, and was Senior Director of Sales at Thomson Reuters (2022–2023). Anamika recently led a team of 120+ supporting a set of US law firms and advises firms on legal market trends and ROI.
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Brian Milanese
LinkedInExperience: Sales Director (LollyLaw & MerusCase) · Paradigm
Since 2014, Brian Milanese has been Director of Sales at MerusCase, and since 2023 Sales Director (LollyLaw & MerusCase) at Paradigm; Milanese was also Sales Manager at Paradigm (2014–2023). At Gemini Legal, Brian was Regional Sales Manager (2013–2014) and Product Manager Corporate Trainer (2011–2013), and lists product demonstration and litigation management among skills, a fit for questions on demos and adoption at law firms.
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Chris Jefferson
LinkedInExperience: Sales Director · Litera
In Maidenhead, England, Chris Jefferson has been Sales Director at Litera since 2025 and describes helping law firms get more from client relationships and deliver legal services using Microsoft and the Peppermint platform. Chris was Director of Sales and Marketing (2023–2025) and Senior Sales Executive (2017–2023) at Peppermint Technology, Sales Consultant at OneAdvanced (2015–2017) and Client Manager at O2 (Telefónica UK) (2013–2015).
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Clement Quessette
LinkedInExperience: Sales Director B2B SaaS & AI-Powered Legal Solutions · Logol AG
Based in Zug, Clement Quessette has been Sales Director B2B SaaS & AI-Powered Legal Solutions at Logol AG since 2023, leading its commercial strategy and DACH expansion. Clement was 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), so customer success and new market entry for legal AI both fit.
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Donna Bailey
LinkedInExperience: Vice President, North America Legal Industry Sales · Intapp
Donna Bailey has been Vice President, North America Legal Industry Sales at Intapp since 2021, after Managing Director there (2019–2021). Donna was 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), and describes a focus on enterprise AI solutions for compliant growth in the legal industry.
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Ken Brajevich
LinkedInExperience: National Director of Sales · Supio
National Director of Sales at Supio since 2025, Ken Brajevich says the work is helping law firms modernize and scale with AI solutions. Ken was a Business Consultant at KBBC (2023–2025), Global Head of Partner Development at Vertex Inc. (2021–2023), National Director Of Sales Emerging ERP at Avalara (2013–2021) and National Accounts Manager, West Coast at Kyocera (2011–2013), a fit for selling AI tools to law firms.
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Michela DiGioia-Nuño
LinkedInExperience: Vice President of Sales · Smokeball - Legal Software
Michela DiGioia-Nuño has been Vice President of Sales at Smokeball - Legal Software since 2025, after Senior Sales Director there (2025), and a member of Pavilion since 2024. Michela was Sr. Director of Sales- Commercial NAMER (2022–2023) and Director of Sales- Commercial (2021–2022) at ActiveCampaign, and describes 20+ years in sales with 10 in sales leadership in software.
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Rob Midson
LinkedInExperience: Director, Enterprise and Mid-Market Sales · Filevine
Director, Enterprise and Mid-Market Sales at Filevine since 2024, Rob Midson was briefly a Consultant at Foxit eSign (2024) and Head of Sales at LineLeader by ChildcareCRM (2023–2024). At Centerbase, Rob was Director of Sales (2022–2023) and Sales Manager (2021–2022), and suits questions on enterprise and mid-market deals with law firms.
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Rob Recklaus
LinkedInExperience: Director, Legal Enterprise Sales · Bloomberg Law
Rob Recklaus has been Director, Legal Enterprise Sales at Bloomberg Law since 2023. At Bloomberg Government, Rob was Vice President Sales and Customer Engagement (2016–2023), Sales Account Management Industry Lead (2010–2016), Director of Government Relations (2008–2010) and Chief of Staff Communications Director (2002–2008), and describes building teams in corporate, government and nonprofit settings, a fit for enterprise legal sales questions.
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Choose the right perspective
For a large law firm purchase, Anamika Das and Donna Bailey hold large law and legal industry sales titles at Litera and Intapp, and Chris Jefferson, in England, sells to law firms for Litera. Addy Spearman fits matter management and legal spend questions from Onit and Wolters Kluwer ELM Solutions; Michela DiGioia-Nuño, Brian Milanese and Rob Midson cover sales at Smokeball, Paradigm and Filevine; Ken Brajevich and Clement Quessette cover AI legal tools in the US and Switzerland, and Rob Recklaus enterprise sales at Bloomberg Law.
Questions to take into the conversation
- 01How does a law firm's innovation or IT committee decide which software pilots go firm-wide?
- 02What do partners need to see before they will change how their team records time or manages matters?
- 03How do you price AI legal tools when firms bill by the hour?
About this directory
This is a professional research starting point based on business profile data retrieved on . Titles and companies reflect that source snapshot; roles marked former had ended by then. Check the linked profiles for current details. Inclusion does not imply Instant Expert membership or availability.