Leadership hiring trends in insurance tech

What do CEO departures signal for the future of InsurTech? You may have noticed a growing trend of startups announcing leadership changes. Back in March, I recorded a podcast analyzing this shift when ManyPet’s and then Wefox’s CEO were replaced. Since then, Clark and Tractable have joined them in making similar moves within the unicorn club. These back-to-back announcements made me think there’s something deeper to explore, as there are several ways to interpret these changes. The analysis I shared then still holds true today, so I’m publishing it here. 1/ Growth phases and leadership shifts As companies grow, their needs evolve. The early stages of a startup require innovation and vision, but as businesses scale, the focus shifts to operations, profitability, and expansion. It’s common for founders to step aside once the company reaches a certain size. Wefox, for instance, has processed over €1.5 billion in insurance premiums and generated €800 million in revenue last year (according to the founders’ announcements). With over 860 employees, the challenges are now different from its early days. Similarly, ManyPets has grown to over 400 employees and insures hundreds of thousands of pets. As companies scale, founders often move into advisory roles, bringing in CEOs with commercial expertise to manage the next phase of growth. This pattern is typical across the tech industry. 2/ Adapting to a changing market The market environment has also shifted. Venture capital funding has slowed, especially in InsurTech, with an emphasis now on profitability over growth. This requires different leadership skills and strategies. For example, Element’s new CEO, with extensive insurance experience, was chosen to focus on technical profitability, reflecting the new priorities in the sector. Leadership changes can signal that a company is adapting to these market conditions, acknowledging the end of the "growth at all costs" era. 3/ Potential challenges ahead? These leadership shifts may also hint at underlying challenges. Wefox reduced its workforce by 13% last year, and ManyPets exited the Swedish market despite strong demand there. Additionally, mental health concerns among startup leaders are rising, with nearly half of CEOs considering stepping down due to stress (according to Sifted’s report). These moves suggest that more leadership changes in InsurTech could be on the horizon, driven by both market forces and personal pressures. The leadership transitions at InsurTech startups are likely a mix of natural growth and response to market realities. As the sector matures, more companies may face similar decisions in the months ahead. #insurance #insurtech #venturecapital 

𝗧𝗵𝗶𝗿𝘁𝘆 𝘆𝗲𝗮𝗿𝘀 𝗶𝗻 𝗲𝘅𝗲𝗰𝘂𝘁𝗶𝘃𝗲 𝘀𝗲𝗮𝗿𝗰𝗵 𝘁𝗮𝘂𝗴𝗵𝘁 𝗺𝗲 𝘀𝗼𝗺𝗲𝘁𝗵𝗶𝗻𝗴 𝘂𝗻𝗰𝗼𝗺𝗳𝗼𝗿𝘁𝗮𝗯𝗹𝗲: 𝗺𝗼𝘀𝘁 𝗶𝗻𝘀𝘂𝗿𝗮𝗻𝗰𝗲 𝗰𝗼𝗺𝗽𝗮𝗻𝗶𝗲𝘀 𝗮𝗿𝗲𝗻'𝘁 𝗵𝗶𝗿𝗶𝗻𝗴 𝗳𝗼𝗿 𝘁𝗿𝗮𝗻𝘀𝗳𝗼𝗿𝗺𝗮𝘁𝗶𝗼𝗻. 𝗧𝗵𝗲𝘆'𝗿𝗲 𝗵𝗶𝗿𝗶𝗻𝗴 𝗳𝗼𝗿 𝘁𝗵𝗲 𝗶𝗹𝗹𝘂𝘀𝗶𝗼𝗻 𝗼𝗳 𝘁𝗿𝗮𝗻𝘀𝗳𝗼𝗿𝗺𝗮𝘁𝗶𝗼𝗻 𝘄𝗵𝗶𝗹𝗲 𝗵𝗼𝗽𝗶𝗻𝗴 𝘁𝗵𝗶𝗻𝗴𝘀 𝘀𝘁𝗮𝘆 𝗺𝗼𝘀𝘁𝗹𝘆 𝘁𝗵𝗲 𝘀𝗮𝗺𝗲. I've placed over 100 C-suite executives in this industry. This year, the Chief AI Officer trend started in earnest. I just launched one for a large mutual P&C carrier, and I'm in discussions with several others across all lines of insurance. 𝗕𝘂𝘁 𝗵𝗲𝗿𝗲'𝘀 𝘄𝗵𝗮𝘁 𝗜'𝘃𝗲 𝗹𝗲𝗮𝗿𝗻𝗲𝗱 𝘀𝗶𝘁𝘁𝗶𝗻𝗴 𝗶𝗻 𝘁𝗵𝗼𝘀𝗲 𝗹𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽 𝗺𝗲𝗲𝘁𝗶𝗻𝗴𝘀: 𝘁𝗵𝗲𝘆 𝗱𝗼𝗻'𝘁 𝗮𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝗸𝗻𝗼𝘄 𝘄𝗵𝗮𝘁 𝘁𝗵𝗲𝘆 𝘄𝗮𝗻𝘁. What they want is someone who looks like they're leading AI transformation but doesn't disrupt how the business operates. Someone who can say "machine learning" in investor calls without making anyone uncomfortable. 𝗕𝗼𝗮𝗿𝗱𝘀 𝘀𝗮𝘆 𝘁𝗵𝗲𝘆 𝘄𝗮𝗻𝘁 𝘁𝗿𝗮𝗻𝘀𝗳𝗼𝗿𝗺𝗮𝘁𝗶𝗼𝗻𝗮𝗹 𝗹𝗲𝗮𝗱𝗲𝗿𝘀. 𝗧𝗵𝗲𝗻 𝘁𝗵𝗲𝘆 𝘀𝗰𝗿𝗲𝗲𝗻 𝗼𝘂𝘁 𝗮𝗻𝘆𝗼𝗻𝗲 𝘄𝗵𝗼 𝗺𝗶𝗴𝗵𝘁 𝗮𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝘁𝗿𝗮𝗻𝘀𝗳𝗼𝗿𝗺 𝘀𝗼𝗺𝗲𝘁𝗵𝗶𝗻𝗴. I understand why. Insurance is low-margin, high-risk. One bad bet costs billions. Regulators are watching. The incentive structure rewards stability over speed. 𝗕𝘂𝘁 𝘁𝗵𝗲 𝗺𝗮𝗿𝗸𝗲𝘁 𝗶𝘀 𝗺𝗼𝘃𝗶𝗻𝗴 𝗳𝗮𝘀𝘁𝗲𝗿 𝘁𝗵𝗮𝗻 𝘁𝗵𝗲 𝗵𝗶𝗿𝗶𝗻𝗴 𝘁𝗶𝗺𝗲𝗹𝗶𝗻𝗲𝘀. (𝗥𝗲𝗮𝗱 𝘁𝗵𝗮𝘁 𝗮𝗴𝗮𝗶𝗻.) Twenty years ago, you could hire a CEO in nine months because the industry moved slowly. In 2026, nine months is long enough for a competitor to deploy AI-powered underwriting, steal market share, and establish a distribution advantage you'll spend three years clawing back. The candidates who make it through are the ones who've learned to sound transformational while signaling they won't change too much too quickly. It's a performance. Everyone knows it. But the performance gets the offer. The best placements I've made broke this pattern. They happened when a board finally admitted "𝘸𝘦'𝘳𝘦 𝘥𝘺𝘪𝘯𝘨 𝘴𝘭𝘰𝘸𝘭𝘺, 𝘢𝘯𝘥 𝘴𝘢𝘧𝘦 𝘪𝘴𝘯'𝘵 𝘴𝘢𝘧𝘦 𝘢𝘯𝘺𝘮𝘰𝘳𝘦." The Chief AI Officer wave is the test case for 2026. Every carrier creating this role is making a choice: 𝘈𝘳𝘦 𝘺𝘰𝘶 𝘩𝘪𝘳𝘪𝘯𝘨 𝘴𝘰𝘮𝘦𝘰𝘯𝘦 𝘵𝘰 𝘢𝘤𝘵𝘶𝘢𝘭𝘭𝘺 𝘵𝘳𝘢𝘯𝘴𝘧𝘰𝘳𝘮 𝘩𝘰𝘸 𝘺𝘰𝘶 𝘰𝘱𝘦𝘳𝘢𝘵𝘦, 𝘰𝘳 𝘢𝘳𝘦 𝘺𝘰𝘶 𝘩𝘪𝘳𝘪𝘯𝘨 𝘴𝘰𝘮𝘦𝘰𝘯𝘦 𝘵𝘰 𝘮𝘢𝘬𝘦 𝘵𝘳𝘢𝘯𝘴𝘧𝘰𝘳𝘮𝘢𝘵𝘪𝘰𝘯 𝘭𝘰𝘰𝘬 𝘭𝘪𝘬𝘦 𝘪𝘵'𝘴 𝘩𝘢𝘱𝘱𝘦𝘯𝘪𝘯𝘨 𝘸𝘩𝘪𝘭𝘦 𝘦𝘷𝘦𝘳𝘺𝘵𝘩𝘪𝘯𝘨 𝘴𝘵𝘢𝘺𝘴 𝘵𝘩𝘦 𝘴𝘢𝘮𝘦? 𝗪𝗵𝗮𝘁 𝘀𝗲𝗽𝗮𝗿𝗮𝘁𝗲𝘀 𝗰𝗼𝗺𝗽𝗮𝗻𝗶𝗲𝘀 𝘁𝗵𝗮𝘁 𝘀𝘂𝗰𝗰𝗲𝘀𝘀𝗳𝘂𝗹𝗹𝘆 𝗵𝗶𝗿𝗲 𝗳𝗼𝗿 𝘁𝗿𝗮𝗻𝘀𝗳𝗼𝗿𝗺𝗮𝘁𝗶𝗼𝗻 𝗳𝗿𝗼𝗺 𝘁𝗵𝗲 𝗼𝗻𝗲𝘀 𝘁𝗵𝗮𝘁 𝗵𝗶𝗿𝗲 𝗳𝗼𝗿 𝘁𝗵𝗲 𝗶𝗹𝗹𝘂𝘀𝗶𝗼𝗻 𝗼𝗳 𝗶𝘁? #Insurance #ExecutiveSearch #ChiefAIOfficer #Transformation #Leadership #CEO #CHRO #AIinInsurance

The best technology leaders I've placed in insurance weren't the most technically impressive candidates on the shortlist. They were the ones who understood the operating environment before they tried to change it. I've placed enough of these leaders to see the pattern from both sides. The failure mode isn't competence. It's context. Two versions of the same problem: Version 1: The tech leader who arrives with a Silicon Valley playbook, moves fast, breaks things, and discovers that "things" in a regulated insurer include compliance frameworks, actuarial models, and distribution relationships that took decades to build. They lose credibility with the operating team within 90 days. By month six, they're isolated. By month twelve, they're gone. Version 2: The tech leader who gets handed a mandate to "transform" the organization but is given so much authority and so little institutional guardrails that they charge ahead with approaches that put the company at genuine risk. Regulatory exposure. Carrier relationship damage. Production systems rebuilt without the people who actually understand what they do. Both versions start with the same hiring mistake: evaluating the candidate's technical capability without evaluating their respect for the operating environment they're walking into. Insurance is not a slow industry because the people in it are slow. It's a deliberate industry because the consequences of moving wrong are severe. The best technology leaders I've placed in insurance understood that on day one. They didn't try to override it. They learned the system, earned trust, and then changed it from a position of credibility. The question isn't "can this person build?" It's "can this person build here?" If you're hiring a tech leader into a regulated environment, what's the one interview question that actually reveals whether they'll respect the operating context? #insurance #leadership #executivesearch #futureofwork

The market is shifting, quietly yet meaningfully. Over the past few weeks, I’ve observed trends that signal change: - Requisitions reopening - Budgets getting approved faster - Hiring managers engaging earlier - Fewer “let’s wait another quarter” conversations Is it a full rebound? No. Is it momentum? Yes. Companies are hiring more intentionally, focusing on adding capability rather than simply increasing headcount. Key areas of growth include AI enablement, data strategy, cybersecurity hardening, operational efficiency, and revenue-driving roles. For candidates: Now is the time to refine your positioning. Be specific about your impact, quantify your outcomes, and know your story. For hiring leaders: The market still favors discernment, but top talent is no longer sitting still. The best candidates are moving quickly and carefully evaluating culture, stability, and leadership quality. We are not in 2021. We are not in 2023. We’re in a more disciplined, strategic hiring cycle — and that’s not a bad thing. The door isn’t wide open, but it is opening. Stay sharp. Stay visible. Stay ready. #lgirondajobs

AI and regulation are shaping the Insurtech landscape in 2025 and if you’re hiring or raising, you can’t afford to ignore either or just focus on one! Insurtech funding rebounded in Q1 and Q2 this year, but investors are zeroing in on AI-native roadmaps. The bar is high and they want to see traction, defensible tech, and a clear AI moat. On the policy side, the mood has shifted from loose principles to hard proof. Nearly half of U.S. states have adopted the NAIC’s Model AI Bulletin, which means insurers and their vendors are expected to have written governance programs and auditable AI controls. Colorado’s rules on algorithmic decision making are already influencing carriers nationwide. Globally, the EU AI Act is now in motion. Many global insurers will align to the strictest standard to simplify operations which means even U.S. only players will feel the ripple effects. 👉🏼 What this means for hiring: Demand is growing for AI governance leads, model risk specialists, ML platform engineers, and hybrid actuary/ML talent. Designers and PMs who can make AI decisions explainable will stand out. 👉🏼 What this means for fundraising: Show a compliance-ready AI pipeline, not just model accuracy. Prove you can scale across geographies and regulatory regimes. Partnerships move faster when you walk in with governance already baked in. Basically in 2025, AI is the growth engine but policy is the gatekeeper and always will be! The companies that hire for both will be the ones still standing in the years to come and attract the better talent on the market! #insurtech #funding #naic #ai #startups #scaling

What is the next phase of evolution for the Insurance COO? Is today's COO more of a COO/CIO hybrid? Today’s COO is increasingly at the helm of technology, data and transformation - acting as a critical connector between the board’s strategic ambition and the actual capability to deliver it. In my most recent Beyond the Desk Podcast interview with Ketan Motwani, COO at Arch Insurance (UK) Limited we spoke about this exact topic in detail. Ketan agreed that today, a COO absolutely MUST be close to tech and data to thrive in the coming years. And we're seeing this firsthand at Invecta. Since we started the business 6 months ago, we’ve been retained on multiple COO searches where the brief has moved well beyond traditional operational leadership into areas like: ✅ AI deployment and automation ✅ Platform modernisation ✅ Data-driven transformation ✅ Digital operations and customer journeys ✅ Cyber and resilience oversight In short, the modern COO is becoming a role that’s as much about shaping the future as it is running the present. If you'd like more insights, I'm happy to share what we’re seeing in the market. The full episode with Ketan is now available on Apple, Spotify, and YouTube - links to check it out are in the comments below.

There is a shift happening in InsurTech hiring, and it is worth paying attention to.   Companies that launched five to seven years ago with a bold vision to rethink insurance from the ground up are entering a new stage. They led with innovation. That mattered. It still does.   But in the last 18 months, hiring patterns have started to tell a new story. Those same companies are now reaching out for savvy product professionals, experienced underwriters, and claims leaders. Not just to support growth, but to stabilize it.   Here is the tension I keep hearing: Traditional insurance professionals are still asking - will my skills be valued in a tech-first culture? Is the opportunity here worth the risk? Will I have a voice?   For InsurTech leaders, now is the time to answer those questions with action. Transparency about your vision and financial health. Clear roles that link expertise to business outcomes. Respect for how the work gets done in the real world.   Insurance is not being replaced. It is being reimagined by the companies willing to blend innovation with experience.   Ready to explore what this means for your career? Book a call or share this with a colleague navigating the same questions.

🚨 Hiring for AI leadership? You're not alone — and you're not imagining the difficulty. Across industries, companies are racing to harness AI, but some roles are proving exceptionally hard to fill — especially at the leadership level. Over the past few months, I've seen growing demand for strategic AI talent in research, engineering, product, and governance — yet the available talent pool remains incredibly tight, particularly for those who can lead cross-functional AI initiatives that deliver real impact. Here’s a quick snapshot of the most difficult AI-related roles to hire for — by industry — with a spotlight on the leadership positions in highest demand: 🔹 Tech/SaaS: → Head of ML/AI → Director of MLOps / AI Infrastructure 🔹 Healthcare: → Chief AI Officer → Director of Responsible AI 🔹 Financial Services & Insurance → Head of AI Risk & Governance → Chief Data & AI Officer 🔹 Industrial / Supply Chain: → VP of AI & Automation → Director of AI/ML for Smart Manufacturing 🔹 Retail / eCommerce: → VP of Personalization / AI Strategy → Director of ML for Recommender Systems 🔹 Media / Content: → Head of Generative AI / Creative AI Lab Leadership → Director of Ethical AI 🔹 Autonomous Vehicles: → VP of Autonomous Systems / AI → Director of Perception & Sensor Fusion 🔎 These aren’t just technical roles — they require strategic vision, strong cross-functional leadership, and domain fluency. The bar is high, and the best candidates are often deeply embedded in high-impact roles already. If your organization has similar talent needs, I would be happy to discuss how we can partner with you to identify the ‘best in class’ talent in the space. #AILeadership #ExecutiveSearch #MLOps #GenerativeAI #ResponsibleAI #TechLeadership #HiringTrends #FutureOfWork #CDAO #VPofAI