Chief information officer
Caldermere Mutual
- Sector
- Property and casualty insurance
- Ownership
- Policyholder-owned mutual
- Company scale
- USD1.82bn direct written premium in 2025
- Employees
- 2,400
- Geography
- Madison, Wisconsin headquarters; eight Midwestern states
- Reporting to
- Chief executive officer
- Team
- 186 employees through seven direct reports; sixty contractors counted separately
- Financial scope
- USD96m 2026 technology authority: USD61m continuing operations and USD35m change
Mandate
Maintain insurance services and govern technology change with clear ownership of the decisions supported.
Outcomes
- Restricted the claims assistant to supervised drafting after testing 1,800 closed files.
- Retained human release authority for all 900 letters in a subsequent pilot, including eighty-three substantive rewrites.
- Funded USD540,000 of assisted renewal capacity alongside the online service.
- Separated twenty-four observed daily minutes of net task reduction from any staffing-saving claim.
Decisions in context
My appointment combined the technology functions I had previously encountered through individual programmes. I now lead architecture, applications, operations, delivery and information services across the mutual. The chief executive expects me to explain the operating consequence of a technical choice, including costs retained when an ambitious release is narrowed. I work through seven direct reports and keep contracted resources separate from the employee count. Recent decisions have included limiting claims correspondence automation and preserving assisted renewal capacity. Neither decision was solely a technology preference: claims and operations leaders retained the authority over the service being provided. I present these matters to the board risk committee without holding a director seat. My current focus is the design of exception routes, especially where ordinary evidence cannot be supplied immediately. A future appointment would need to value that connection between enterprise technology and the insurer's accountability to its members.
Reason for the move
Current remit; open to a future CIO mandate or one compatible external board contribution.
Vice president, enterprise delivery
Caldermere Mutual
- Sector
- Regional property and casualty insurance
- Ownership
- Policyholder-owned mutual
- Company scale
- USD1.02bn annual direct written premium at appointment
- Employees
- 1,550
- Geography
- Madison headquarters; six Midwestern states
- Reporting to
- Chief information officer
- Team
- Eighty-eight employees through five direct reports
- Financial scope
- USD29m annual technology programme portfolio
Mandate
Coordinate enterprise change across claims, underwriting, finance and agent service within available delivery capacity.
Outcomes
- Introduced a cross-function review for twenty-two proposed initiatives.
- Sequenced six projects later when business training capacity was unavailable.
- Required named operating owners for fourteen approved programme benefit statements.
Decisions in context
This appointment moved me beyond one operating function and into the conflicts between several legitimate priorities. Claims wanted better case handling, agents wanted simpler transactions and finance needed dependable information. My task was to make their proposed changes work together within the delivery and training capacity available. I asked sponsors to describe the activity their programme would add as well as the activity it would remove. That made some benefit statements smaller and some schedules longer. It also gave the executive team a more credible basis for sequence. Six projects were moved later because business colleagues could not absorb the required training alongside their existing work. I did not treat that as a technical delay alone. The period prepared me for the CIO role by making enterprise dependencies visible and by teaching me to explain a portfolio choice without dismissing the need behind the deferred request.
Reason for the move
Promoted to CIO after responsibility expanded from programme delivery to continuing technology service.
Director of claims technology
Caldermere Mutual
- Sector
- Personal and small commercial property insurance
- Ownership
- Policyholder-owned mutual
- Company scale
- USD710m annual direct written premium at appointment
- Employees
- 1,040
- Geography
- Wisconsin headquarters; five-state regional service
- Reporting to
- Chief information officer; delivery priorities agreed with the chief claims officer
- Team
- Fifty-four employees through five direct reports
- Financial scope
- USD14m annual claims technology expenditure
Mandate
Improve the systems through which claims colleagues receive evidence, manage work and explain the status of a file.
Outcomes
- Consolidated seven separate intake queues into a common supervised work view.
- Introduced explicit ownership for twelve recurring missing-evidence situations.
- Tested two catastrophe intake exercises with claims supervisors and service colleagues.
Decisions in context
Working beside claims management changed how I thought about an incomplete record. The missing item might be necessary before a final decision, yet impossible for a member to supply at the first contact. I led the technology work to show that condition clearly rather than allowing colleagues to hide it in a note or invent a value that satisfied the screen. The claims officer determined the professional process; I was responsible for making the supporting systems usable and reliable. Our work on seven intake queues exposed differences in who believed they owned a pending request. We brought those decisions into the common work view and rehearsed unusual conditions with supervisors. The role gave me practical experience of technology during periods of heightened demand. I moved on because the most persistent obstacles increasingly involved policy systems, agent service and enterprise priorities rather than claims applications alone.
Reason for the move
Moved into enterprise delivery to address dependencies beyond the claims function.
Policy platforms manager
Caldermere Mutual
- Sector
- Regional personal-lines insurance
- Ownership
- Policyholder-owned mutual
- Company scale
- USD420m annual direct written premium at appointment
- Employees
- 700
- Geography
- Madison headquarters; Wisconsin and neighbouring states
- Reporting to
- Head of applications
- Team
- Twenty-six colleagues through four direct reports
- Financial scope
- USD6m annual policy applications budget
Mandate
Maintain policy administration and improve the evidence passed between agent transactions and member service.
Outcomes
- Mapped eighteen transaction types with agent and policy service representatives.
- Established a release review involving four operating departments.
- Replaced three local status lists with a shared account of pending policy requests.
Decisions in context
Joining the mutual gave me my first substantial people-management responsibility. I inherited applications that had been shaped by successive product and service changes, each with an understandable local purpose. Agents and service colleagues could sometimes describe the same request differently because they saw different stages of it. I worked with them on eighteen transaction types and on the evidence needed to explain a pending instruction. The work was less visible than a new customer feature, but it reduced the need for private status lists that became unreliable when somebody was absent. I also introduced operating representatives into release review, so that training and member communication were considered before installation. I learned to balance the urgency of an agent's immediate problem with the need for a coherent system that other colleagues could support. The move into claims technology extended that concern to the consequences of a loss.
Reason for the move
Appointed to lead claims technology after gaining experience across policy and service dependencies.
Systems analyst
Vellorin Assurance
- Sector
- Regional property and casualty insurance
- Ownership
- Privately owned insurer
- Company scale
- USD210m annual direct written premium at entry
- Employees
- 460
- Geography
- United States Midwest
- Reporting to
- Policy applications team manager
- Team
- Individual contributor in a ten-person team; no direct reports
- Financial scope
- Analysis and testing assignments within the manager's application budget; no independent spending authority
Mandate
Document policy processes, test application changes and connect technical records with the documents used by insurance colleagues.
Outcomes
- Documented the purpose and timing of sixteen policy document types.
- Prepared test examples for eleven policy transaction changes.
- Supported three releases with service-desk guidance and issue follow-up.
Decisions in context
I entered the insurer four months after completing my information systems degree. My responsibilities were analysis, test preparation and follow-up on application issues. I did not manage a team, approve policy terms or control a separate budget. Much of my learning came from asking experienced colleagues why two apparently similar documents could lead to different actions. Sixteen document types formed the basis of an early analysis assignment, and I learned to preserve their purpose and timing when describing a proposed system change. I also saw how incomplete service guidance transferred the cost of a release to the colleagues answering calls. Supporting three releases taught me to stay with an issue after the code had been installed. The later opportunity at Caldermere offered a larger management remit, but I carried forward the habit of asking for the underlying insurance example before accepting a technical description as complete.
Reason for the move
Accepted a policy platforms management role at Caldermere Mutual with direct responsibility for people and delivery.
What I am looking for next
I would consider a CIO appointment in an established insurer whose next technology phase needs a clearer connection to operating responsibility. A mutual or privately held enterprise may be particularly relevant where management is modernising service without assuming that every member will follow the same digital route. I would want the remit to include continuing service, architecture and delivery, with claims, underwriting and operations leaders actively involved in priorities. A role limited to promoting a predetermined tool would not make good use of my experience. I also remain interested in one external board contribution where technology dependence and customer service deserve closer oversight. That would require employer consent, an assessment of current relationships and agreement on time, including periods of unusual demand. I have twenty days annually available for ordinary preparation and meetings, subject to those discussions. I would judge either opportunity by the decisions I could help the organisation make more clearly, not by the scale of its announced programme.