Rightworks team

Ian is responsible for defining and setting the company’s direction and working with the Rightworks leadership team on the execution of that strategy. He brings decades of experience driving transformation and profitability in technology-enabled businesses. His visionary leadership and track record of aligning teams around performance and customer centricity positions him to lead the company into its next chapter of growth.

Before Rightworks, Ian was CEO of DRB Systems, where he led the company through record growth by introducing a cloud-based platform that transformed their SaaS/hardware mix, achieving “Rule of 40” performance over multiple years. He has also held executive roles at Deluxe Corporation, Imation, Seagate, and Hewlett-Packard, where he demonstrated an ability to scale businesses from $10M to $3.2B in revenue across sectors, including fintech, data security, and cloud storage.

Jenny is responsible for leading Rightworks’ finance function as it continues to expand into new markets. With over 20 years of experience in senior finance leadership roles, Jenny supports the company’s goals and strategic initiatives with her extensive experience in driving financial performance, strategy implementation, corporate governance and risk management.

Before Rightworks, Jenny was the CFO at Cisive, where she built FP&A capabilities, implemented rigorous forecasting and KPI reporting, and led integration efforts for acquired companies. She also served as CFO at Captivate Communications and held finance leadership positions at eBay/PayPal, NBA, Knotel, and Discovery Communications, where she optimized growth and financial performance across diverse industries.

Jay is responsible for leading the Rightworks global go-to-market (GTM) strategy encompassing sales, marketing, partners, business development and customer success. With over 30 years of experience unifying processes across the customer journey, Jay drives growth through new customer acquisition, improved GTM team efficiency and helping customers realize the full value of their investments in Rightworks. He joins Rightworks with a proven record of building and unifying global GTM organizations in public and high-growth SaaS companies.

As former Chief Commercial Officer at Evolv Technology and Chief Marketing Officer at Kinaxis, Jay consistently delivered significant revenue growth and improved GTM effectiveness while improving customer experiences. He has previously held senior leadership roles at Intralinks, IBM, and PTC, scaling organizations from $75M to over $1B and spearheading international expansion. Jay earned both a Bachelor of Science and Master of Science in Engineering from the Massachusetts Institute of Technology and an MBA from the Harvard Business School.

Dana is responsible for advancing the company’s people strategy to support leadership and growth. She also leads innovative human resource programs for the company’s employees across the country. Programs include talent development, staffing, compensation, benefits and employee relations.

As an experienced HR executive, Dana brings a deep understanding of the necessity for a vibrant organizational culture. She also possesses a well-honed talent for attracting qualified, top-tier employees.

She has served in various senior leadership roles throughout her career and is an active member of SHRM.

Before joining Rightworks, Jon served as the Vice President for Tax Software Technology at Thomson Reuters. Jon has deep expertise and a passion for designing and operating large-scale software systems and creating and optimizing high-performing teams.

As Chief Technology Officer, he governs the development of the entire cloud and software product business line and the emerging technologies teams.

Anjan is responsible for leading Rightworks’ enterprise-wide cybersecurity strategy, overseeing security operations, governance, risk, and compliance across the organization. With deep expertise in protecting cloud platforms, SaaS environments, and large-scale technology systems, he drives a proactive, security-first approach that strengthens customer trust and safeguards the sensitive financial and business data entrusted to Rightworks. Anjan brings extensive experience leading company-wide cybersecurity programs, managing incident response, advancing secure development practices, and modernizing cloud defenses in highly regulated industries, including financial services and central banking.

As former Chief Information Security Officer at the Federal Reserve Bank of Boston, Anjan led enterprise security strategy, threat intelligence, vulnerability management, and emerging AI governance initiatives supporting national-scale financial infrastructure. Previously, he served as CISO at SS&C Intralinks and held senior security leadership roles at BNY Mellon – Eagle Investment Systems, EnerNOC, and the University of Rochester Medical Center.

Gayle is responsible for leading Rightworks’ marketing strategy and execution to accelerate revenue growth and strengthen the company’s global go-to-market performance. She builds and scales integrated marketing engines that drive customer acquisition, expansion, and brand leadership in close partnership with sales, product, and customer success, ensuring marketing is a strategic lever for profitable growth.

Prior to Rightworks, Gayle served as Chief Marketing Officer at COMPLY, where she led go-to-market strategy and product launches to expand into new FinTech markets and build a scalable revenue engine. At Litera Microsystems, she scaled and transformed a global marketing organization, increased brand awareness, and led marketing integration efforts tied to multiple acquisitions, aligning brand and go-to-market strategy across a growing portfolio while supporting the company’s private equity recapitalization. She has also held senior marketing leadership roles at SS&C Intralinks, Rocket Software, and Harte Hanks Trillium Software.

As Chief Customer Care Officer, Gary is accountable for creating outstanding customer experiences. Under his guidance, our team of technology professionals delivers award-winning assistance and support for the adoption and continued use of all our hosting, security, and productivity solutions.

Gary brings a blend of strategic vision and operational focus that helps ensure that accounting firms and small business professionals achieve the full benefits of digital transformation and cloud adoption.

Before joining the Rightworks team in 2018, Gary spent 14 years as Sr. Vice President of Customer Support at Endurance International Group (now Newfold Digital), growing the SaaS company from a start-up to a public company. Gary has also held senior leadership positions at GlowTouch (now UnifyCX) and eSupportNow, consistently focusing on Customer Care operations.

Adam oversees legal affairs and manages the company’s legal compliance and corporate governance. He joined Rightworks with more than 15 years of legal experience in corporate law and governance, M&A, SEC reporting, data privacy, intellectual property and commercial matters.

Adam most recently served as Deputy General Counsel and Assistant Secretary for Datto, a cybersecurity software company where he managed a team of nine and navigated the company through a successful IPO process in 2020. Prior to that, Adam served as Deputy General Counsel at EnerNOC, a publicly traded energy management technology company, and as a corporate attorney at Ropes & Gray LLP.

As the Vice President of Strategy and Corporate Development, Tom assesses new product and market opportunities, oversees mergers and acquisitions, and ensures operating plans align with the company’s overarching business strategy.

Before joining Rightworks, Tom spent nearly 10 years leading finance and business operations at multiple startups—in addition to several years in investment banking.