Chief Digital

1 month ago


Boston, United States 20Twenty Search Full time

20Twenty Search are retained with a leading reinsurance consulting firm, a global firm who provide strategic consulting & managed services, technology, data sciences and blockchain solutions to insurance organizations globally.


Domiciled in Bermuda, with offices in the United States, United Kingdom and other international locations, this firm helps insurers launch new products, drive operations, implement intelligent technology, deploy advanced analytic capabilities, and achieve business process optimization.


This leading consulting firm work with all reinsurance counterparties and enable insurers, reinsurers, brokers & agents, and program administrators worldwide to enhance policyholder service, enter new markets, boost workflow productivity, and improve profitability.


Reporting to executive leadership in a matrix organization, the Chief Digital Officer is a highly visible role in the driver’s seat of delivering impeccable digital strategy and spectacular customer experience.


The ideal candidate will be able to apply deep insurance operations know-how to identify viable digitalization opportunities with scalable technology implementation. The suite of digital interventions would comprise of homegrown assets, innovative partnership engagements and acquired assets through M&A. These digital assets should enable the firm to offer superior and differentiated AI powered, digital-enabled service offerings to different insurance market segments across the globe.


The ideal candidate will bring together Insurance industry talent, domain knowledge, agile, lean and six sigma capabilities, proven methodologies, frameworks, AI/ML and hyper automation assets to simplify processes, enhance operating environments, mitigate operational risks, modernize operating models and increase process efficiency and effectiveness.


Given the transformation agenda impacting the entire Insurance industry, this is arguably a career-defining opportunity for an ambitious and talented individual with a long and well documented track record of challenging status-quo and delivering change in a consultative fashion with empathy for the customers as well as service delivery teams.


You are, quite simply, an Insurance Expert with the deep domain skills, knowledge, and industry networks to navigate the opportunity identification and implementation. This will probably mean a combination of at least 2 or 3 of following experiences:

  • Strong consulting experience with a top tier consultancy or a similar time at senior management level within the insurance industry where you have showcased strong problem solving and consulting competencies and developed granular affinity with the very DNA of the specialized domain.
  • Leading a large transformation agenda/program of works or deployed a range of packaged solutions supporting the Insurance value chain whilst working judiciously within a matrix reporting environment across industry vertical, discipline and geographic lines.
  • Exposure to scalable and trusted product buildout and support
  • Led an innovation lab for (re)insurance business.


The Role / Demands:


  • Formulate digital strategy to drive value by understanding micro and macro level datapoints (industry trends, competitive differentiation, process/people/tool challenges, whitespace, growth segments etc)
  • Bridging business and technology to spearhead pragmatic AI transformations and build high impact applied machine learning capabilities across organizations.
  • Shaping enterprise AI vision and advising business stakeholders on maximizing value from AI investments. Advocating responsible AI development with ethics, interpretability, and governance in mind.
  • Create and refine a digital roadmap based on digital strategy, identifying processes to optimize, and choosing right technologies and platforms.
  • Find optimal solutions against the roadmap (build or buy)
  • Coordinate with available Insurance domain experts at within the firm and Industry experts externally to validate digital opportunities.
  • Record, publish and market the wins and augment the successful use cases.
  • Collaborate with Strategic Account Leaders, Delivery, Solutioning, Business development teams internally to create a market leading differentiation for the firm
  • Managing and tracking the digital initiatives budget and the qualitative/quantitative value released.
  • Represent the firm at different forums, seminars, conferences and drive their positioning as a digital managed service provider.


Experience Required

  • 20+ years of experience in leading large insurance transformation/product innovation initiatives
  • Strong operational experience of more than one Insurance market segment (carrier/broker/reinsurer/MGAs) with proven transformative leadership impact
  • Excellence in strategic and analytical problem solving -Quantitative, fact-based approach to team-based problem solving and addressing issues and offering solutions.
  • Candidate should have an aptitude for analytical concepts and thinking.
  • Business acumen and IT knowledge - Must understand current market trends, risks and prevalent technologies used in the global Insurance industry.
  • Good understanding of practical adoption of AI/ML technology in solving modern business challenges.
  • Outstanding leadership and communication skills - Polished verbal and written communication style.
  • Ability to confidently build a strong rapport with internal and external stakeholders.
  • Personal drive - Entrepreneurial drive with a can-do attitude, a strong desire to learn and shape your own career path. Commitment to making a positive lasting impact.
  • Self-guided attitude - The ability to succeed in a professional environment where problem statement is not always well defined.


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