In this fascinating conversation, Perplexity's Chief Business Officer Dmitry Shevelenko reveals how a company barely three years old is mounting the first credible challenge to Google's search dominance in two decades. Shevelenko shares the counterintuitive distribution strategy that led Perplexity to partner with mobile carriers and device manufacturers rather than chasing browser deals, explaining how creating mutual value with partners became their path to 22 million monthly active users. The discussion centres on execution velocity as Perplexity's primary competitive advantage, with Shevelenko openly admitting that six months from now he'll have a top priority he can't even imagine today. From eliminating internal presentations entirely to making hiring decisions "physically hurt," he paints a vivid picture of how Perplexity maintains startup intensity while competing against trillion-dollar tech giants, offering invaluable lessons for anyone navigating the AI transformation.

In this candid anniversary conversation, Hg's leadership team of Matthew Brockman and Nic Humphries reflects on 25 years of building one of Europe's most focused software investors. Humphries shares the challenge of convincing colleagues to abandon multiple sectors for pure software focus, while Brockman opens up about his leap of faith in 2010, leaving Apax Partners for an uncertain bet on Hg's vision and the turbulence of 2012 that eventually led to success. The conversation hones in on AI as the next major platform shift and Brockman's concept of the "last mile"—the deep understanding of customer workflows required to transform AI capability into practical business solutions. Their discussion reveals a firm that has spent 25 years accumulating the pattern recognition, operational capabilities, and entrepreneurial culture perfectly suited for an era where success depends less on investment judgement and more on building products that solve real workflow problems—making this milestone feel less like a celebration of the past and more like preparation for the defining challenge ahead.

In this compelling conversation, Tidemark Capital founder Dave Yuan shares his journey from Bain consultant to building one of the most thoughtful voices in vertical SaaS investing. Yuan reveals his "control point" philosophy—identifying the mission-critical systems that small businesses would turn off last before going bankrupt—and explains how this approach has guided Tidemark's investments in category leaders like ServiceTitan, Toast, and OneStream. His insights into workflow gravity, data gravity, and account gravity provide a masterclass in understanding what creates defensible market positions in software. The discussion takes a provocative turn as Yuan explores AI's dual nature as both opportunity and existential threat for established software companies. He introduces the concept of "integrate surround"—how AI point solutions can gradually subsume control points by becoming the system of action rather than just record—and shares his framework for "fast waters" versus "slow waters" in AI adoption. With characteristic humility and intellectual curiosity, Yuan offers practical advice for navigating today's volatile market while building the Vertical SaaS Knowledge Project community that has become an industry touchstone for founders and investors alike.

Orbit 48 sees Dr Amr Ellabban sit down with Des Traynor, co-founder and CSO of Intercom, to explore how AI requires revolutionary thinking from businesses. Des shares the pivotal moment when ChatGPT emerged in November 2022, spurring Intercom's bold 15-day pivot to develop Fin, their AI customer support agent. The conversation reveals how successful AI transformation demands complete organisational commitment—from reimagining pricing models to restructuring teams—rather than incremental changes: "It's not a cherry on top. It's the only game that matters." Drawing from his experience at Intercom and as an angel investor, Des outlines the three-phase evolution of AI in business: from augmenting human work to handling portions of jobs to eventually performing entire roles. For leaders navigating similar transformations, he offers unflinching advice on the necessity of decisive action and clear communication, predicting that AI may soon handle 60-80% of support volume in what will be "the largest change in how labour is applied in most businesses." His insights on product boundaries and avoiding "MiniDisc" solutions in rapidly evolving technology landscapes provide a compelling roadmap for organisations embracing this inevitable shift.

What happens when AI can code? In this illuminating conversation with Cognition's Founding President Russell Kaplan, we explore how AI is fundamentally transforming the landscape of software development. Drawing from his journey through Tesla's Autopilot team and Scale AI, Kaplan shares profound insights on leadership in rapid technological change, emphasizing that "talent is everything" and that exceptional outcomes come from "small teams of highly technical people." His perspective challenges conventional thinking about software engineering's future, suggesting we're entering an era of "software abundance" where customer expectations will rise dramatically. The discussion moves beyond theoretical AI potential to practical implementation, with Kaplan revealing how his philosophy of speed as strategy guides decision-making in a world where AI capabilities in software development are doubling every 70 days. Rather than fearing job displacement, Kaplan envisions a future where "way more people are shaping the creation of software" as the nature of engineering evolves. With refreshing optimism, he suggests we're approaching a time when "software is good by default" and shares his excitement for what may be "the most exciting time to be a software engineer" in history.

In this episode of Orbit, Matthew Brockman, Managing Partner at Hg, sits down with renowned AI pioneer Andrew Ng to explore the rapidly evolving AI landscape. Andrew, who has led ground-breaking initiatives at Stanford AI Lab, Google Brain, and Coursera, shares fascinating insights on building in the AI era, including how the falling costs of prototyping (just $55,000 to create a working prototype) are democratising innovation and allowing companies to take more shots at goal with minimal risk. The conversation delves into practical advice for software leaders navigating this technological revolution, with Andrew emphasising that the real value lies in the application layer rather than foundation models themselves. He challenges conventional thinking about AI "kill zones," advocates for creating innovation sandboxes within organisations, and offers a compelling perspective on why professionals across all domains—from lawyers to doctors to marketers—should learn coding to effectively harness AI's potential. Andrew's prediction of the rise of "10x professionals" who can masterfully direct AI to accomplish tasks presents both an exciting opportunity and imperative for business leaders to embrace this transformative moment.

As AI beds into the business world, a new breed of company is being born where the latest technology is built-in. Helping them to grow is an equally new breed of investor. In the first Orbit of 2025, Nic Humphries hosts sits down with Zoe Zhao and Annalise Dragic, co-founders of Azlin Software. With backgrounds in venture capital, M&A, and Hg's own Saturn investment team, Zhao and Dragic share their journey from investing in B2B software companies to creating their own investment platform. They delve into their unique approach to acquiring and nurturing vertically specialized young businesses, emphasizing a long-term, sustainable growth model that leverages AI and automation for efficiency. The co-founders discuss the importance of community within their portfolio, fostering innovation, and the balance between nurturing product development and a vibrant company culture. Their entrepreneurial spirit shines through as they explain how Azlin Software plans to support founders at the smaller end of the market, where businesses may not yet have the resources to fully realize AI's potential. Whether discussing their own entrepreneurial leap or the future of software investment, Zhao and Dragic offer a fresh perspective on the intersection of technology and business growth.” azlinsoftware.com zoe@azlinsoftware.com annalise@azlinsoftware.com

In our latest episode Hg’s Managing Partner, Matthew Brockman, presses two CEOs and an AI insider on how a business leader can usefully integrate generative AI into their business workflows. David Carmona, a VP and CTO at Microsoft, Avaneesh Marwaha, CEO of US legal tech producer Litera, and Soeren Brogaard, CEO of Danish construction innovators, Trackunit, cover the swift advancements in AI that are redefining industry workflows. These experts explore the journey from AI incubation to mass adoption, the balance between internal efficiency and customer-centric product enhancements, and the need for data-rich, insight-driven business strategies. They also consider the future of AI in reshaping the legal and construction sectors and the importance of fostering an organizational culture that embraces continuous innovation.

Hg’s Joe Jefferies sits down with Sukhinder Singh Cassidy, the CEO of Xero, to unravel the intricacies of leading a global software company and the personal journey that brought her to the helm. With a history of bold moves at tech behemoths like Amazon and Google, Singh Cassidy shares her philosophy on risk-taking, revealing how a series of strategic bets rather than any singular decision shaped her illustrious career. From a father's entrepreneurial spirit; to navigating a rocky job market post-college on the eve of a tech boom; to Xero's remarkable growth across 180 countries: Singh Cassidy reflects on fostering a culture of inclusivity and the importance of authenticity in leadership all whilst thriving on the continuous pursuit of impactful risk-taking.

In this enlightening episode of the Hg podcast series Orbit, host Joe Jefferies converses with Nick Mehta, the long-standing CEO of Gainsight, about the intersection of vulnerability and leadership in building a successful software company. Nick candidly describes his philosophy of "human-first" leadership, which has become a cornerstone of Gainsight's culture. He recounts his journey from childhood ambitions instilled by his father to the challenges he faced fitting in, and how these experiences shaped his transparent and authentic approach to leadership, coining the term "Nick 2.0" to signify his evolution. This transformation involved embracing openness and candidness, not just personally but also at the organisational level with "Gainsight 2.0," fostering a culture where honesty is valued, and employees are encouraged to embrace their own personal growth narratives.

As the CEO of Scandinavian software success story, Visma, this is Merete Hverven's second appearance on Orbit. Last time she pondered the reasons behind the Nordics' outsized contribution to the world of software, this time the same values of openness, competency over hierarchy and willingness to experiment come into play when running a scaled multinational conglomerate. With the complete opposite of a one-size-fits-all approach, Visma has partnered with companies across 32 different countries, collecting what they do best and disseminating it across the group. The key is to be humble to as you enter each new marketplace: "don't try to be interesting, be interested".

A veteran of the software industry for 25 years, Darren Roos is a disciple of the wisdom that failure breeds success. Battlescars that bring perspective and greater awareness of how to guard against the pitfalls of tough economic environments. He assures Hg's Nic Humphries that his abilities are not a result of intellect but rather hard-won experience; over two decades of seeing the same patterns reappear. Now the Chairman of enterprise software giant, IFS, he looks back at his arrival as CEO - a South African in a Scandinavian company - and how his work to transform the business required some transformation of his own; before discussing tips around succession planning and the reluctant addition of 'author' to his CV.

As CEO of IRIS Software, Elona Mortimer-Zhika has been a valued part of the Hg Orbit for 8 years and counting. In Orbit 39, she speaks to long-term friend and Hg's Senior Partner, Nic Humphries, about her unusal path to tech leadership: from Communist Albania to retail jobs in the UK and on to an audit career for Deloitte. Tracking the stratospheric progress of IRIS over the last decade and considering the effects of private equity investment, Nic and Elona discuss whether or not you need to be a techie to master the constantly moving goalposts of a highly successful software business.

In the final Orbit recorded at Hg's recent 'Software Leadership Gathering', we brought together three perspectives all investigating the AI wave through a business lens. With the technology in an early phase, it can be viewed as an existential threat for businesses but without a clear path to commercialisation. Brent Hayward of Salesforce, David Carmona of Microsoft and Nagraj Kashyap of Touring Capital discuss what’s actually working today for businesses, where they should be focusing their attention and what will be the likely opportunities in the future.

Inspired by watching the surge in space exploration during his childhood in 70s India, through the 80s microchip era and on into the internet boom and a 25-year career innovating software at a large enterprise scale - Netscape, Bang Networks and finally VMware – Raghu Raghuram can claim authority and perspective on close to the entirety of our industry. He has seen epochal change before and grown with it. Speaking at Hg's recent 'Software Leadership Gathering', Raghu tells Hg’s Alan Cline about the similarities and differences between our current shift and those that came before: comparing the economic and technologic circumstances and digging into the business angle from code to pricing to value proposition.

Born of the same crucible as Reid Hoffman, Peter Thiel and Elon Musk, Joe Lonsdale and Eric Poirier have been building and investing in software for over two decades. As the General Partner of 8VC and the CEO of Addepar respectively, they have seen industries evolve and innovate. Speaking at Hg's recent 'Software Leadership Gathering', Matthew Brockman asked them how - since software has allowed new entrants to compete with the old guard - what areas could AI open up? Applying AI to existing technologies and services is one approach but it is one that comes with a level playing field and broad competition. Ask yourself the question: what's only just become possible now that hasn't been possible over the last few years and invent something new.

Time for a conversation with one of the greats. As Professor of Finance and Economics at Columbia, former senior banker at both Morgan Stanley and Goldman Sachs, and currently Senior Advisor at Evercore Partners, Jonathan Knee’s thinking is held in high regard across the business world. His recent book, ‘The Platform Delusion’, dismantles the long-held belief that a platform business which provides connections rather than creating products is inherently valuable. So how should we assess business quality in this new era of AI & platforms? Mr Knee outlines the fundamental drivers which haven’t changed in the face of new technology and applies them to assessments of Uber vs Airbnb, Etsy vs Amazon and, of course, how does this all relate to vertical software where we at Hg spend our time.

The advances in technology on the clinical side of healthcare were shown convincingly in the speed of our response to Covid and in the new discoveries and improvements we continue to see. Covid may have also had a part to play on the administrative side - breaking down old habits and prompting the green shoots of innovation - but there is still a long way to go as legacy systems continue to be expensive, opaque and inefficient. In both cases, there is a huge opportunity for new ideas, new entrants and new investment. This expands from the traditional centre to prevention and lifestyle change too. Hg’s Nick Crowne speaks to Rod O’Reilly, a new advisor to the Hg team. Rod has been a leading figure in almost every aspect of the healthcare ecosystem for many years and is a strong advocate of change, disruption and the quest for greater affordability, access and outcomes.

After a year when the sudden leap forward of Gen AI and LLMs took almost everyone by surprise, it’s a good time to ignore the hype, take a step back and look at what we have. Guido Appenzeller is a special advisor to a16z, a former CTO at Intel and VM Ware and a leading voice in the current wave of software and technology. In part two of our conversation with Guido, we look at the ways the new generation of AI applications will effect the business world. How do you best capture the value of this wave, how to prepare for it and how to enable your teams to experiment from the bottom up.

After a year when the sudden leap forward of Gen AI and LLMs took almost everyone by surprise, it’s a good time to ignore the hype, take a step back and look at what we have. Guido Appenzeller is a special advisor to a16z, a former CTO at Intel and VM Ware and a leading voice in the current wave of software and technology. In part one of our conversation with Guido, we discuss where AI fits into the existing software universe, what phase 2 might look like, the potential limitations – regulatory and infrastructural - and what it means for developers when you have an additional fundamental system building block with which to work.