Industry Veteran with Deep Enterprise and FinTech Leadership Joins as Zenwork Scales Its AI-First Tax Compliance Platform
DALLAS, TX AND FAYETTEVILLE, AR / ACCESS Newswire / May 28, 2026 / Zenwork Inc. today announced the appointment of Barrett Boston as President. In this strategic role, Boston joins the technology company behind Tax1099 and Compliancely to lead commercial strategy, accelerate enterprise market expansion, and drive execution of Zenwork’s ambitious AI-first growth roadmap.
Most recently, Boston served as Chief Executive Officer of Ottimate (formerly Plate IQ), where he led the transformation of the company into a fully AI-driven accounts payable automation and vendor payments platform serving seven industries. . Prior to Ottimate, Boston served as Chief Revenue Officer at TriNet, a leading Professional Employer Organization, where he drove revenue growth at the intersection of compliance, HR technology, and financial services, a domain directly complementary to Zenwork’s core market.
Earlier in his career, Boston served as Vice President at IBM’s Software Group, where he led worldwide sales for the Big Data & Analytics division and shaped competitive go-to-market strategy for one of the world’s largest enterprise software portfolios. He also held the position of President of the Americas at TravelClick, overseeing sales and operations across the region. Boston holds an MBA from Harvard Business School and a Bachelor of Arts in Economics from Duke University.
A Strategic Appointment for an AI-First Future
Zenwork is at an inflection point, redefining tax compliance in the age of artificial intelligence. With more than 1.2 million businesses and CPA firms nationwide, the company has established itself as the definitive platform for IRS-compliant e-filing and tax regulatory reporting. Zenwork recently launched an Agentic AI solution suite that includes Zenwork AI Co-pilot, Diagnostic AI, Zenwork AI Assist, and the industry’s first Tax1099 MCP Server.
Barrett Boston’s appointment signals Zenwork’s intent to match this technological momentum with enterprise-grade commercial leadership. His track record of scaling AI-driven fintech platforms, building large enterprise sales organizations, and raising institutional growth capital makes him uniquely qualified to lead Zenwork’s next chapter: expanding into new enterprise markets, deepening CPA firm partnerships, and accelerating revenue growth.
Leadership Perspectives
“Barrett brings exactly the caliber of leadership we need as Zenwork enters its next phase of growth. His background scaling AI-powered platforms in adjacent compliance and financial technology markets, combined with his enterprise go-to-market expertise, makes him the ideal partner to expand our reach and deepen our impact for businesses and accounting professionals across the country.”
Sanjeev Singh, Founder & CEO, Zenwork Inc
“Zenwork has built something truly special, a platform that sits at the nexus of AI, tax compliance, and the digital transformation of accounting. The opportunity to serve more than 1.2 million businesses with intelligent, agentic tools that take the complexity out of regulatory filing is enormous. I am excited to partner with Sanjeev and the entire Zenwork team to scale that impact across enterprise markets and bring next-generation compliance technology to even more businesses nationwide.”
Barrett Boston, President, Zenwork Inc.
About Zenwork Inc.
Zenwork Inc. is the technology company behind leading AI-powered digital tax compliance and regulatory reporting platforms Tax1099 and Compliancely. Trusted by more than 1.2 million businesses and CPA firms nationwide. Zenwork automates the e-filing and e-delivery of 40+ IRS and state-compliant tax forms, including 1099s, W-2s, 1095s, and more. Backed by Spectrum Equity, Zenwork is pioneering the next generation of agentic AI for tax compliance. Learn more at http://www.zenwork.com.
Media Contact
Ed Pratt
Co-founder, Zenwork Inc.
[email protected]
SOURCE: ZENWORK INC
