Smartsheet vs Xero: Founders, CEOs and History
Smartsheet was founded in 2005 by Brent Frei, Mark Mader, Eric Browne and is led by Rajeev Singh. Xero was founded in 2006 by Rod Drury, Hamish Edwards and is led by Sukhinder Singh Cassidy.
Company facts
Smartsheet
- Founded
- 2005
- Headquarters
- Bellevue, Washington, USA
- Current CEO
- Rajeev Singh
- Employees
- 3,300
Xero
- Founded
- 2006
- Headquarters
- Wellington, New Zealand
- Current CEO
- Sukhinder Singh Cassidy
- Employees
- 4,400
Founders
Smartsheet
Brent Frei
Brent Frei co-founded Smartsheet in 2005 in Bellevue, Washington, after founding Onyx Software, a CRM vendor he took public. He led Smartsheet in its first year before Mark Mader became CEO in 2006, and later served on the board. Brent Frei was born in 1966.
Mark Mader
Mark Mader joined Smartsheet as CEO in 2006, a year after its founding, and is counted among its founding team.
Eric Browne
Eric Browne co-founded Smartsheet in 2005. Providing absolutely critical early technical leadership, he helped design the platform's initial architecture, heavily focusing on ensuring the cloud-based application could instantly sync massive spreadsheets across…
John Creason
John Creason co-founded Smartsheet in 2005. Working closely with the technical founding team, he played a massive role in building the early prototype.
Xero
Rod Drury
Rod Drury is a New Zealand software entrepreneur who co-founded Xero in Wellington in 2006 and served as its chief executive until 2018. Before Xero he built software businesses including AfterMail, which he sold to Quest Software.
Hamish Edwards
Hamish Edwards co-founded Xero in 2006 alongside Rod Drury. Working as an accountant, he was deeply furious at how incredibly terrible, slow, and outdated legacy desktop accounting software was.
CEOs and their tenures
Smartsheet
- Brent Frei2005–2006
Co-founder and Chief Executive Officer
As the visionary Co-Founder (who previously founded Onyx Software), he provided the massive initial capital and strategic direction to launch the company.
Source - Mark Mader2006–2025
Chief Executive Officer & President
As Co-Founder and CEO, he navigated the company through its difficult early years, guided its highly successful IPO, and established it as a dominant player against aggressive rivals.
Source - Rajeev Singh2025–present
Chief Executive Officer
As a highly experienced tech executive and board member, he provides absolutely critical guidance on scaling enterprise SaaS operations.
Source - Sunny Gupta2025–2025
Executive Chair and Acting CEO
As an influential board member and enterprise CEO, he advises on highly complex enterprise sales strategies.
Source
Xero
- Rod Drury2006–2018
Co-Founder & Former Chief Executive Officer (2006-2018)
As Co-Founder and legendary CEO, he was the absolute visionary who completely revolutionized the deeply boring accounting software industry by making the software beautiful, cloud-native, and highly integrated with banking APIs.
Source - Sukhinder Singh Cassidy2023–present
Chief Executive Officer
Under her leadership revenue grew from ~$812 million (NZ$1.40 billion) in FY23 to ~$1.59 billion (NZ$2.75 billion) in FY26, and Xero moved from a net loss to a net profit.
Source
Timeline: Smartsheet and Xero side by side
2005Smartsheet
Smartsheet founded in Bellevue, Washington: Brent Frei and a small founding team start Smartsheet to make spreadsheets collaborative.
2006Xero
Rod Drury and Hamish Edwards found Xero in Wellington, New Zealand.
2007Xero
Xero lists on the NZX.
2010Xero
Peter Thiel Invests
Peter Thiel's Valar Ventures invested in Xero in 2010.
2012Xero
Xero lists on the ASX.
2014Smartsheet
Series E Funding
Smartsheet raised $35 million in a Series E round led by Sutter Hill Ventures in May 2014.
2017Smartsheet
Series F Funding
Smartsheet raised $52 million in a round led by Insight Venture Partners in 2017.
2018Smartsheet
NYSE IPO (SMAR): Smartsheet lists on the NYSE at $15 per share, raising about $150 million.
2018Smartsheet
Acquired Converse.AI
Smartsheet acquired Converse.AI. Smartsheet acquired chatbot and automation startup Converse.AI in 2018; terms were not disclosed.
2018Xero
Steve Vamos succeeds Rod Drury as CEO; Xero buys Hubdoc and delists from the NZX.
2019Smartsheet
10,000ft and Slope Acquired
Smartsheet bought the resource-management company 10,000ft and the collaboration company Slope in 2019.
2020Smartsheet
Brandfolder acquired for about $155 million: Adds digital asset management to Smartsheet workflows.
2020Xero
Waddle Acquired
Xero bought the invoice-lending platform Waddle in 2020.
2021Xero
Acquired Planday A/S
Xero acquired Planday A/S for $184 million.
2023Xero
Sukhinder Singh Cassidy becomes CEO.
2024Smartsheet
Passes $1 billion in ARR: Smartsheet crosses $1 billion in annualized recurring revenue in fiscal 2024.
2025Smartsheet
Blackstone and Vista complete $8.4 billion buyout: The take-private closes on January 22, 2025, and SMAR is delisted.
2025Smartsheet
Rajeev Singh named CEO: Singh succeeds acting CEO Sunny Gupta after Mark Mader's retirement.
2025Xero
Claire Bramley becomes CFO on 1 April; Xero completes the Melio acquisition on 15 October.
2026Xero
Matan Bar named CEO of Xero US; FY26 revenue reaches ~$1.59 billion (NZ$2.75 billion).
Acquisitions
Smartsheet
- Brandfolder Inc.2020$155M
- 10,000ft (Resource Planning)2019Undisclosed
- Converse.AI2018Undisclosed
Questions about Smartsheet vs Xero
Who is the CEO of Smartsheet and Xero?
Smartsheet is led by Rajeev Singh and Xero is led by Sukhinder Singh Cassidy. Both serve as the top executive responsible for the company's strategy, operations, and financial performance.
When was Smartsheet founded vs Xero?
Smartsheet was founded in 2005 — 1 year before Xero, which was founded in 2006. Smartsheet's longer operating history gives it a deeper track record but also potentially more institutional inertia compared to the younger Xero.
How many employees does Smartsheet have compared to Xero?
Smartsheet employs approximately 3,300 people, while Xero employs approximately 4,400. Xero has the larger workforce at 4,400 employees, compared to Smartsheet's 3,300. A higher headcount does not necessarily imply greater efficiency — it often reflects differences in business model (e.g., manufacturing vs. software).
Where are Smartsheet and Xero headquartered?
Smartsheet is headquartered in United States and Xero is headquartered in New Zealand. Their different home markets mean they may face different regulatory frameworks, tax regimes, and currency exposure.
Who founded Smartsheet and Xero?
Smartsheet was founded by Brent Frei, Mark Mader, Eric Browne, John Creason. Xero was founded by Rod Drury, Hamish Edwards.
Which company has a longer operating history — Smartsheet or Xero?
Smartsheet has been operating for approximately 21 years, making it the more established of the two companies. Xero has been in operation for around 20 years. A longer operating history often signals greater institutional resilience and brand recognition, though it can also mean slower adaptation to new market conditions.
Figures come from each company's filings and the sources linked beside them. Amounts reported in another currency are shown in US dollars at an approximate rate and marked with ~. Back to the Smartsheet vs Xero overview