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Outbyte PC Repair FREEClear out junk files and repair common Windows errorsFree Scan →Outbyte Driver Updater FREEFix the driver behind crashes, sound loss and screen glitchesFind Drivers →Smartsheet disclosed on November 10, 2021, that Gene Farrell, its chief strategy and product officer, planned to resign effective December 10 and become CEO of Vanilla, an early-stage financial-technology company focused on estate planning. The move took Farrell from a public software company to a venture-backed business building estate-planning tools for financial advisors and wealth-management firms.
What Smartsheet announced—and when
Smartsheet’s November 10, 2021 SEC filing said Farrell had notified the company of his intent to resign as chief strategy and product officer. His departure was effective December 10, not the day the filing appeared. The filing said he was leaving to become CEO of an early-stage financial-technology company; contemporaneous reporting identified that company as Vanilla.
The filing describes a resignation, not a termination. It also does not suggest that Smartsheet was being acquired or facing financial trouble. The company was making a broader leadership transition at the same time.
How Smartsheet reorganized its leadership
Smartsheet did not appoint a like-for-like successor to Farrell’s combined strategy and product remit. Instead, it shifted product and engineering leadership to Praerit Garg, who moved from CTO and executive vice president of engineering to chief product officer and EVP of engineering. The company also named its first COO, Stephen Branstetter, and appointed Jolene Marshall chief legal officer and Andrew Bennett chief marketing officer.
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CEO Mark Mader credited Farrell and other executives with work spanning Smartsheet’s IPO, revenue growth, four acquisitions and international expansion. Those were Mader’s comments about the leadership team, not an independent accounting of Farrell’s individual contribution. GeekWire’s contemporary report also noted that Smartsheet raised its quarterly guidance around the announcement.
Farrell’s path from Coca-Cola and AWS to Smartsheet
Farrell’s career brought together consumer product development and enterprise software. According to his Vanilla biography, he founded and led Coca-Cola Freestyle, the customizable beverage platform. The biography says that work received Forbes recognition and Edison Gold Innovation and Catalyst Design awards.
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He then spent about five years as a vice president at Amazon Web Services, responsible for enterprise computing and involved in developing businesses including Amazon WorkSpaces and Amazon Chime. He joined Smartsheet in 2017, with responsibilities across strategy, corporate development, product management, product marketing, experience design and strategic alliances. Vanilla says he spent four and a half years there and describes Smartsheet’s revenue as growing from $100 million to more than $500 million during that period; that company account does not establish that Farrell alone caused the growth. Vanilla’s biography also says he holds an MBA from Emory University’s Goizueta Business School and a bachelor’s degree in business administration from the University of Washington.
His 2017 move from AWS to Smartsheet had drawn legal scrutiny: Amazon sued to block the move under a non-compete agreement, then dropped the case after reaching an agreement that imposed temporary work restrictions, according to GeekWire. The 2021 move to Vanilla was reported as an executive transition, not a dispute with Smartsheet.
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Vanilla is a business-to-business estate-planning platform for financial advisors, planners, attorneys and wealth-management firms—not simply a consumer app for buying a will. Its product descriptions include estate-plan visualizations, client reports, document creation, financial-data integrations, projections and scenario analysis. More advanced offerings describe document abstraction, AI-assisted summaries and review, and enterprise tools such as permissions, assignments and customized workflows.
The distinction matters. The platform is intended to help professionals organize estate information and support planning conversations and workflows. Software-generated summaries or document analysis should not be treated as legal or tax advice, nor as a substitute for qualified counsel on a client’s specific circumstances.
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Why an early-stage fintech would hire a SaaS executive
Vanilla was founded in 2019 by Steve Lockshin, a wealth-management entrepreneur; Farrell joined as CEO, not as a founder. At the time, the company had recently closed a $14.3 million Series A led by Venrock. WealthManagement.com reported that Vanilla had about 25 employees, was piloting with large wirehouses and investment banks whose names Farrell did not disclose, and expected to roughly double headcount in the first half of 2022, with most hires planned for engineering and development.
Vanilla’s January 2022 announcement introduced Farrell alongside CTO Amjad Hussain and SVP of Revenue Robin Melnick. Farrell had worked with Hussain at AWS. The appointment pointed to a practical scaling challenge: a specialist estate-planning product would need to develop its technology and operating capacity while earning adoption from financial institutions with demanding integration and procurement processes.
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- Transferable experience: Farrell had worked across enterprise products, strategy, partnerships and organizational growth at AWS and Smartsheet.
- Different market: Estate planning brings legal, tax and jurisdictional complexity that collaboration software does not. SaaS operating experience is relevant, but it is not itself estate-planning expertise.
- Longer sales and trust requirements: Wealth-management firms may require security reviews, integrations and internal approvals before adoption; pilots alone do not prove broad commercial traction.
The strategic bet was that software could make parts of estate planning more repeatable: helping advisors visualize plans, identify planning opportunities and organize documents rather than leaving each step to manual preparation. That is an interpretation of Vanilla’s product direction, not a claim that software replaces attorneys, tax professionals or fiduciaries.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.What changed at Vanilla after Farrell joined
Vanilla’s later announcements show an effort to broaden both its product and institutional reach. In 2024, the company announced a $35 million funding round led by Insight Partners, with participation from Venrock, Vanguard, Edward Jones Ventures, Nationwide, Allianz and Alumni Ventures. Vanilla said the round brought total funding above $85 million. It also reported more than 10,000 end clients and more than 12,500 estate documents mapped. These are company-reported figures, not independently verified measures of revenue, profitability, valuation or market share. See the company’s funding announcement.
The company has also described AI-assisted estate-plan review and document-related features, including V/AI Automatic Profiles. In April 2025, Vanilla announced a partnership with Mariner Wealth Advisors, saying it covered more than 700 advisors managing $560 billion in assets. Those figures describe the scale of the partner relationship as Vanilla presented it; they are not Vanilla’s assets under management or proof of its own financial performance. Vanilla’s announcement also names other relationships, including Vanguard, Balentine and Avantax.
Vanilla has extended its offering to smaller practices through Starter. The company’s Starter page, accessed in August 2026, lists monthly prices of $99 for up to 10 clients, $159 for up to 25 and $199 for up to 50; annual options are also listed. Larger firms seeking tailored workflows and enterprise capabilities are directed toward Vanilla’s other offerings and demo or pricing process. Pricing and product availability can change.
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Where Farrell and the move stand now
Vanilla’s leadership page currently lists Farrell as president and CEO. His move is notable because it placed an executive with public-company and enterprise-SaaS experience in charge of a much younger company working at the intersection of wealth management and estate planning. The opportunity was to build more scalable advisor tools; the harder test is whether those tools can fit the legal complexity, professional judgment and institutional requirements that estate planning demands.
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