Discover Xero's leadership team, from CEO Sukhinder Singh Cassidy to key executives shaping the future of cloud accounting for millions of small businesses.
Written by Laura Bouttell • Sun 4th January 2026
When a New Zealand startup founded in a Wellington office transforms into a global platform serving nearly four million subscribers, the calibre of leadership behind that growth merits serious examination. The Xero leadership team represents a fascinating blend of Silicon Valley veterans, seasoned telecommunications executives, and homegrown Antipodean talent, each bringing distinct perspectives to the challenge of modernising small business finance.
What distinguishes exceptional leadership from merely competent management? In Xero's case, the answer lies in a collective commitment to what founder Rod Drury termed "beautiful accounting"—the radical notion that financial software need not be a necessary evil but rather an elegant tool that genuinely serves its users. This philosophy permeates every level of the organisation's leadership structure.
The Xero leadership team operates through a carefully orchestrated hierarchy designed to balance global strategic vision with regional market expertise. At the apex sits Chief Executive Officer Sukhinder Singh Cassidy, who assumed the role in February 2023 following a distinguished career spanning Google, StubHub, and multiple successful ventures.
Beneath the CEO, Xero maintains a classic C-suite structure augmented by regional managing directors who possess significant autonomy to address local market conditions. This distributed leadership model reflects the company's origins as a challenger brand that succeeded by understanding accountants' needs better than entrenched competitors.
The executive leadership team comprises functional heads overseeing technology, finance, legal affairs, human resources, and product development, whilst regional leaders manage operations across Australia and New Zealand, the United Kingdom, the United States, and emerging markets. This matrix structure enables rapid decision-making at the local level whilst maintaining strategic coherence globally.
Perhaps no appointment better illustrates Xero's evolution from scrappy disruptor to mature global platform than the selection of Sukhinder Singh Cassidy as Chief Executive Officer. Born in Dar es Salaam, Tanzania, to parents of Punjabi Sikh heritage, Singh Cassidy brings to Xero a career trajectory that reads like a masterclass in technology leadership.
Her credentials are formidable:
Singh Cassidy advocates for what she terms "risk-taking and resilience"—the notion that meaningful progress requires embracing uncertainty rather than avoiding it. Her leadership style emphasises data-driven decision-making combined with genuine empowerment of team members. As she articulated to investors, "Our strategy is simple, focused, and purpose driven."
This approach represents continuity with Xero's founding ethos whilst bringing greater operational discipline. Where founder Rod Drury championed creative chaos and rapid experimentation, Singh Cassidy has introduced structured frameworks for prioritisation—notably the "Win the 3x3" strategy focusing on accounting, payroll, and payments across Australia, the United Kingdom, and the United States.
Understanding Xero's current leadership requires appreciating the foundation laid by Sir Rod Drury, the New Zealand entrepreneur who founded the company in 2006 with Hamish Edwards. Drury's unconventional decision to list Xero on the New Zealand Stock Exchange in 2007—with fewer than 100 customers and no meaningful revenue—established the company's appetite for bold strategic moves.
Drury's leadership philosophy centred on several distinctive principles:
Now a Knight Companion of the New Zealand Order of Merit, Drury stepped down as CEO in March 2018 and departed the board entirely in 2023, though he remains an adviser to the business. His induction into the New Zealand Business Hall of Fame cements his legacy as one of the country's most significant technology entrepreneurs.
The Xero leadership team extends well beyond the chief executive, encompassing specialists who collectively possess expertise spanning global technology giants, major consultancies, and innovative startups.
| Executive | Role | Background |
|---|---|---|
| Sukhinder Singh Cassidy | Chief Executive Officer | Google, StubHub, Joyus founder |
| David Thodey AO | Chairman | Former Telstra CEO, CSIRO Chair |
| Claire Bramley | Chief Financial Officer | Former CFO of Teradata, HP Inc veteran |
| Diya Jolly | Chief Product & Technology Officer | Former CPO at Okta, Google VP |
| Damien Coleman | Chief Legal Officer & Company Secretary | Former Telstra Deputy General Counsel |
| Jeff Ryan | Chief People Officer | Former CPO at McAfee, Zynga, GoPro |
| Angad Soin | MD Australia & NZ, Global Chief Strategy Officer | Former Deloitte Partner |
| Kate Hayward | Managing Director, United Kingdom | Former EY, Deloitte, KPMG |
Several patterns emerge when examining the leadership cohort:
Global technology experience: Multiple executives hail from household names including Google, Microsoft, Amazon, and HP, bringing enterprise-scale operational knowledge to a platform primarily serving small businesses.
Financial services pedigree: The presence of former Telstra executives David Thodey and Damien Coleman reflects the telecommunications industry's parallel journey through digital transformation—lessons directly applicable to Xero's evolution.
Consulting backgrounds: Leaders including Angad Soin (Deloitte) and Kate Hayward (EY, Deloitte, KPMG) understand the accountant community that forms Xero's crucial partner channel.
As Chairman since February 2020, David Thodey AO brings to Xero governance experience few can match. His tenure as Telstra's Chief Executive Officer from 2009 to 2015 saw Australia's largest telecommunications company navigate the transition to the National Broadband Network—a transformation requiring precisely the blend of strategic patience and operational intensity that cloud platform evolution demands.
Thodey's current portfolio speaks to his standing in Australian business circles:
His presence signals to institutional investors that Xero maintains governance standards befitting its market capitalisation and global ambitions.
The appointment of Diya Jolly as Chief Product and Technology Officer represents Xero's most significant statement about its technological ambitions. Jolly joined in April 2023 as Chief Product Officer and was elevated to her current expanded role in April 2024, assuming responsibility for engineering, security, and data alongside her existing product portfolio.
Her credentials are exceptional:
Jolly now leads a globally distributed team of 2,500 professionals across product, design, engineering, data science, and security—talent drawn from Amazon, Apple, Meta, Google, Uber, Intuit, and Square.
Under Jolly's leadership, Xero has launched "JAX" (Just Ask Xero), an AI assistant designed to automate accounting tasks and deliver personalised insights. The vision extends beyond simple automation:
Xero's global presence requires leaders capable of adapting the platform to local regulatory requirements, cultural expectations, and competitive dynamics.
Angad Soin serves as Managing Director for Australia and New Zealand whilst retaining his role as Global Chief Strategy Officer. A former Deloitte Partner with thirteen years at the consultancy, Soin joined Xero in 2021 and was elevated to his current dual role in October 2024. Australia and New Zealand remains Xero's largest market and the foundation of its "Win the 3x3" strategy.
Kate Hayward leads Xero's UK operations, having assumed the managing director role in March 2024 after five years with the company across strategy and operations functions. A chartered accountant who trained with EY before holding strategy roles at Deloitte Australia and KPMG, Hayward understands intimately the accounting profession that forms Xero's crucial partner channel in Britain.
Andrew Tokeley oversees Xero's North American expansion, bringing experience from leadership roles at both Intuit and PayPal—direct competitors whose playbooks he now deploys against them.
The Xero leadership team has cultivated a distinctive organisational culture that balances innovation with accountability. Their articulated values include:
Senior executives characterise their leadership style as "data-driven, outcome-oriented and grounded in accountability, while also empowering people with the autonomy and support they need to succeed." This balance between measurement and empowerment reflects the company's maturation from startup to established platform.
The cultural emphasis on celebrating failure—established by founder Rod Drury—persists under current leadership. Mistakes acknowledged and learned from are valued over risk-averse decision-making that prioritises individual career protection over organisational progress.
Recognition of these cultural investments includes:
The Xero leadership team has articulated a focused strategy for the medium term, encapsulated in the "Win the 3x3" framework: strengthening three core product areas (accounting, payroll, and payments) across three priority markets (Australia, the United Kingdom, and the United States).
Key strategic initiatives include:
Platform expansion: Building on the existing ecosystem of over 1,000 connected applications and more than 300 banking integrations
Artificial intelligence integration: Deploying AI to automate routine tasks whilst generating actionable insights for small business owners
Mobile-first development: Enabling complete accounting management through smartphone interfaces
Strategic partnerships: Collaborations with BILL, Stripe, and Amazon Web Services extend platform capabilities without requiring internal development
Selective acquisitions: The September 2024 acquisition of Syft Analytics for up to US$70 million enhances reporting and analytics capabilities
Sukhinder Singh Cassidy serves as Xero's Chief Executive Officer, having assumed the role in February 2023. She brought to the position extensive technology leadership experience from Google, where she built revenue operations across Asia Pacific and Latin America, and StubHub, where she served as President overseeing the platform's US$4 billion sale. Singh Cassidy is also the author of the Wall Street Journal bestseller "Choose Possibility."
Sir Rod Drury co-founded Xero in 2006 with Hamish Edwards in Wellington, New Zealand. Drury served as CEO until March 2018 and remained on the board as a non-executive director until 2023. He now acts as an adviser to the business. A Knight Companion of the New Zealand Order of Merit, Drury was inducted into the New Zealand Business Hall of Fame in recognition of his contributions to the technology sector.
Xero's leadership philosophy centres on balancing data-driven accountability with genuine empowerment of team members. The company values transparency, celebrates learning from failure rather than punishing it, and emphasises collaboration across functions and regions. Leaders describe their approach as "outcome-oriented" whilst providing autonomy for teams to innovate and challenge established thinking.
Xero's executive leadership team comprises approximately ten senior leaders overseeing functions including technology, finance, legal affairs, human resources, product development, and marketing. This is supplemented by regional managing directors for Australia and New Zealand, the United Kingdom, the United States and Canada, and EMEA markets including South Africa and Ireland.
Xero executives typically bring experience from major global technology companies including Google, Microsoft, Amazon, and Okta, combined with backgrounds in professional services firms such as Deloitte, EY, and KPMG. Several leaders have telecommunications experience from Telstra, reflecting parallels between that industry's digital transformation and cloud platform evolution. Many hold advanced degrees from institutions including Harvard Business School.
Xero's board is chaired by David Thodey AO, former Chief Executive Officer of Telstra and current Chairman of CSIRO. The board provides strategic oversight whilst allowing management significant operational autonomy. Governance structures reflect the standards expected of a company listed on both the Australian Securities Exchange and New Zealand Stock Exchange with a market capitalisation exceeding NZ$20 billion.
Xero invests significantly in leadership development through its people experience function, now led by Chief People Officer Jeff Ryan. The company has been recognised for workplace culture initiatives including gender equality (ranked 41st globally by Equileap) and employee wellbeing (included in the Top 10 Global Healthy Workplaces). Internal promotion, as evidenced by Diya Jolly's elevation and Angad Soin's expanded responsibilities, demonstrates commitment to developing leadership talent from within.
The Xero leadership team exemplifies what happens when talented individuals from diverse backgrounds unite around a compelling mission. From Rod Drury's founding vision of beautiful accounting to Sukhinder Singh Cassidy's disciplined execution of the "Win the 3x3" strategy, the company has assembled leaders capable of navigating the complexities of global expansion whilst remaining true to its roots serving small businesses and their advisers.
For students of corporate leadership, Xero offers valuable lessons in cultural continuity through executive transition, the balance between innovation and operational discipline, and the construction of leadership teams that combine complementary rather than duplicative capabilities. As the cloud accounting market matures and competition intensifies, the quality of this leadership cohort will ultimately determine whether Xero maintains its position as a category leader or cedes ground to better-resourced rivals.