Will Thomas

Legal AI GTM

New York2.5k followers

Legoraex-Pignatto and Underwood, P.A.

ex-Northstar

I'm an Enterprise Sales Leader with over a decade of experience, specializing in driving business transformation and revenue growth.
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My approach is rooted in the belief that the modern seller must be a GTM Engineer and I am passionate about leveraging AI to multiply my work and empower my teams. I have extensive experience leading teams and taking startups to scale-ups and beyond. My current mission at Syndio is to help large enterprise companies use more data in all pay decisions, adopting a strategic, AI-first approach. I'm using AI to sell AI. I've pioneered the use of AI agents and LLMs to form the dynamic, modern sales playbook of the future. Examples: * Go-to-Market Engineering: I build and implement AI-native tech stacks, integrating tools like ChatGPT, Gemini, Perplexity, and Gong into every sales touchpoint. This allows me to automate and optimize workflows, from prospecting to deal closure. * Customized Pitches and Demos: I use AI to rapidly generate and tailor content, including presentations and proposals. I've built custom GPTs and agents, such as a customized demo flow using Google’s Agent Development Kit, to help prospects visualize how a product fits into their unique workflows. I use tools like Figma Make to create personalized landing pages in minutes. * Team Enablement: I'm committed to making everyone around me better. I regularly post to educate my team on AI best practices, fostering a culture of continuous improvement and empowering them to elevate their own performance. Throughout my career, I've lead teams and consistently succeeded in building new territories and GTM motions from the ground up, whether it was pioneering wallet messaging technology at Dispatch or leading the expansion into enterprise markets at Northstar. My passion lies in using technology to solve complex business problems, driving efficiency, and delivering exceptional value for clients. I've sold to a wide range of teams—from finance and marketing to HR—across diverse industries including non-profits, and to companies of all sizes, from SMBs to global multinationals.

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GTM Index

PAVILIONJOB
1. Executive Member
  3Y
LEGORAJOB
1. GTM Mgr
  4M
SYNDIOJOB
1. Enterprise Account Executive
  1Y 2M
QA NORTH AMERICAJOB
1. Account Executive
  1Y 2M
DISPATCHJOB
1. Sales Dir
  11M
NORTHSTARJOB
1. Founding Account Executive
  1Y 10M
JUSTWORKSJOB
1. Account Executive II
  10M
2. Account Executive
  1Y
ONEHOPEJOB
1. Senior Relationship Mgr
  5M
2. Major Gift Officer
  1Y 5M
3. Dir of Partner Engagement
  4Y 3M
VALICJOB
1. Financial Advisor
  1Y 2M
PIGNATTO AND UNDERWOOD, P.A.JOB
1. Tax Associate
  1Y
FLORIDA STATE UNIVERSITYSCHOOL
1. Bachelor of Science, Accou…
  4Y 11M

Job: Pignatto and Underwood, P.A. — Tax Associate · 2011-08 – 2012-08 · 1y
Job: Northstar — Founding Account Executive · 2021-04 – 2023-02 · 1y 10mo — At Northstar, I was a Founding Account Executive, a pivotal role that involved far more than just closing deals. My primary mission was to advance the company beyond founder-led sales and establish a repeatable, scalable go-to-market motion. My responsibilities included: * Building out a new territory from scratch: I was the key initial AE hire responsible for penetrating and growing our presence in the mid-market, enterprise, and large enterprise segments. I personally closed early-stage deals with major companies like eHealth, Netflix, and Workday, which served as foundational case studies. * Scaling the sales process: I was instrumental in crafting the sales playbook, from the initial…
Job: OneHope — Senior Relationship Manager · 2019-01 – 2019-06 · 5 mo
Job: VALIC — Financial Advisor · 2012-08 – 2013-10 · 1y 2mo
Job: OneHope — Major Gift Officer · 2018-01 – 2019-06 · 1y 5mo
Job: Syndio — Enterprise Account Executive · 2025-04 – 2026-06 · 1y 2mo — Attainment: 190% to goal, #1 of 10 AEs to-goal globally Winner: Agile Change Award 2026 for excellence in AI adoption As an Enterprise Account Executive at Syndio, an AI-native platform powering compensation intelligence at the point of decision, I help enterprise companies combine relevant data from various sources to make smarter choices. My work has evolved beyond traditional B2B SaaS into AI-native Go-To-Market. My work focuses on the AI-native transformation and sale of our products, particularly the new Intelligent Pay platform. My responsibilities include: Driving new revenue by winning strategic logos in the enterprise space, including a Fortune 50 company, while also building n…
Job: OneHope — Director of Partner Engagement · 2013-10 – 2018-01 · 4y 3mo
Job: Pavilion — Executive Member · 2023-10 – present · 2y 10mo — Pavilion is a private membership for high-growth leaders to achieve their professional potential.
Job: Justworks — Account Executive II · 2020-06 – 2021-04 · 10 mo — At Justworks, I was an Account Executive responsible for building out a new territory from the ground up. I took ownership of the full sales cycle, focusing on building strong relationships and closing initial logos in a previously untapped market. My responsibilities included: * Building a new territory: I was tasked with establishing our presence and driving revenue in a new market segment. I consistently led the team in new meetings and meetings booked, demonstrating a knack for market penetration and pipeline generation. * Selling to HR and finance leadership: I built relationships with C-suite executives and HR leaders, employing a consultative sales process to understand their pain…
Job: Dispatch — Sales Director · 2023-02 – 2024-01 · 11 mo — At Dispatch, I led a 3-person team in building out the initial go-to-market (GTM) for a state-of-the-art crypto technology: wallet messaging. This required pioneering a completely new sales process for messaging between digital wallets, a nascent field with no established best practices. I was the Head of Business Development, and I worked hand-in-glove with the founders, product, and design teams to power the full revenue motion. My primary responsibilities included: Pioneering a new GTM motion: I developed and implemented a streamlined process for our messaging-between-wallets technology. I was responsible for bringing on the initial customers for this and other product lines, including…
Job: Justworks — Account Executive · 2019-06 – 2020-06 · 1y
Job: QA North America — Account Executive · 2024-02 – 2025-04 · 1y 2mo — #2 Account Executive of 19 globally Leading AI-Driven Go-To-Market Adoption As an Account Executive at QA, I was at the forefront of the company's digital transformation, specifically in pioneering the adoption of GenAI technology within our GTM motion. Beyond my core sales responsibilities, I was a GTM engineer, building the foundational use cases that would enable our team to sell more effectively and efficiently. This was a critical step in modernizing our sales process and demonstrating the value of our own GenAI curriculum to clients. I led the initial adoption of three primary AI use cases for our GTM team: 1. Prospecting and Research Automation: I implemented AI tools to analyze…
Job: Legora — GTM Manager · 2026-06 – present · 2 mo — Working with in-house legal teams to put collaborative AI to work on contract review, research, and drafting, the stuff that eats their days. Legora is the collaborative AI platform for lawyers and the fastest sales-led company to $100M ARR. Always happy to talk with corporate legal teams figuring out where AI is returning value.
School: Florida State University — Bachelor of Science, Accounting · 2007 – 2011

Skills

SalesforceMakeAccountingFinanceBusinessRevenue Cycle ManagementReporting & AnalysisSales ManagementSales ProcessesAIGTM EngineeringGo-to-Market StrategyCommercial DevelopmentInvestment AdvisoryStrategic Financial PlanningWealth ManagementSeries 7InvestmentsSpanishSalesStrategic Account Development

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Will Thomas

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