INDEPENDENT ENGAGEMENTS · RED SUMMIT CONSULTING
Gore Insurance Company
CurrentTechnology Delivery Lead
May 2026 – Present
M&A IntegrationGuidewireData Migration
Technology delivery lead for an integration migrating an acquired book of business from a legacy platform onto Guidewire Cloud PolicyCenter.
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- Own end-to-end data migration delivery: extraction from the legacy platform, transformation, and landing into the Guidewire Cloud target state.
- Direct migration testing and full dry runs of the data cutover ahead of production.
- Coordinate target-state system configuration readiness so converted data lands correctly at cutover.
- Ensure policyholder documents and rate change communications align with FSRA expectations through the transition.
- Hold delivery to the integration timeline across all migration workstreams.
Ayr Farmers Mutual Insurance Company
CurrentTechnology Advisor
Mar 2026 – Present
AdvisoryCloud UpgradeGuidewire
Advising leadership on sequencing the technology decisions ahead of a potential Guidewire Cloud upgrade.
Definity Financial
M&A Program Director
Jun 2025 – May 2026
M&A IntegrationGuidewire
Directed the Personal Insurance integration stream of Definity's acquisition of Travelers Canada: a $1B book of business migrating into Definity's target policy systems.
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- Owned end-to-end policy data conversion delivery across a multi-vendor model of consulting SIs and internal delivery pods, managing dependencies across 10+ concurrent workstreams spanning claims, finance, BI, and regulatory reporting.
- Oversaw a renewal-based conversion engine migrating policies at point of renewal, minimizing customer disruption and go-live risk.
- Worked directly with Personal Insurance business leaders to translate product appetite, jurisdictional rules, and consolidation decisions into executable technical requirements.
- Managed pre-close data acquisition under strict legal constraints while the companies remained separate competing entities, securing critical datasets ahead of deal close.
- Built executive business cases quantifying post-close synergies and application sunsetting opportunities for senior leadership investment decisions.
- Kept the migration strategy and jurisdictional handling aligned with FSRA obligations across the transferred book.
Travelers Canada
Technology Program Director
Apr 2024 – Jun 2025
Cloud UpgradeGuidewire
Led the enterprise Guidewire Cloud upgrade program from planning through stabilization, across internal engineering, offshore delivery centres, and SI teams.
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- Coordinated directly with Guidewire on migration strategy and cutover, running full rehearsals of the minute-by-minute cutover plan with every delivery party before go-live.
- Set predefined success criteria for each dry run that had to be met before production was authorized. Result: zero P1 incidents and 11 post-production defects, all resolved within SLA.
- Chaired the senior technology and business forums defining the target-state Cloud data access and migration approach.
- Led month-end financial testing cycles across claims, finance, and GL teams, producing like-for-like reconciliations between on-prem and Cloud baselines that gave the business auditable confidence to proceed.
- Contributed to Travelers Canada's inaugural AI platform team, evaluating AI-assisted delivery tooling and responsible-use guidelines for a regulated insurance environment.
Definity Financial
Senior Program Manager
May 2022 – Apr 2024
Cloud UpgradeGuidewire
Accountable program lead for a $50M+ Guidewire Cloud transformation impacting 3,000+ users, owning scope, governance, delivery cadence, and executive reporting across all phases.
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- Designed and enforced a governance framework spanning 12 interdependent workstreams and 200+ resources.
- Built an enterprise cross-program delivery view consolidating release activity across underwriting, claims, data, integrations, and regulatory workstreams. It surfaced code collision risks before they materialized and remains in active use at Definity.
- Operationalized a portfolio management model governing 20+ concurrent initiatives, contributing to a 25% reduction in cloud spend.
- Established the operational readiness framework: business training, incident simulations, cutover rehearsals, and Go/No-Go criteria.
- Led warranty Command Center operations to 100% SLA compliance on P1/P2 incidents.
- Delivered bi-weekly program health reporting to executive sponsors and steering committees, translating delivery data into decision-ready business terms.
Trillium Mutual Insurance Company
Program Manager
Jan 2021 – May 2022
GuidewireTransformation
Single point of accountability for a full-suite Guidewire v10 transformation at a $120M GWP mutual insurer, coordinating internal SMEs and four system integrators.
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- Owned policy, claims, and document data migration strategy, achieving 95% conversion accuracy at production cutover.
- Led Broker Management System integrations supporting 40+ broker partners with 100% uptime through go-live.
- Chaired focus groups with principals from 16 brokerages to build broker-driven requirements into solution design.
- Met FSRA obligations to disclose system-driven rate adjustments in plain language at renewal, building parallel renewal letter templates so the business stayed compliant regardless of rate filing approval timing.
- Served as primary escalation point for SI delivery issues through a successful production cutover weekend.
Tradition Mutual Insurance Company
Advisor to Program Manager
Jan 2022 – Mar 2022
AdvisoryGuidewireTransformation
Advised delivery leadership on full-suite Guidewire implementation strategy, drawing on peer mutual insurer programs.
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- Defined phase-level entry and exit criteria to support governance decisions at critical milestones.
- Advised on FSRA policyholder communication obligations and contingency approaches for rate filings pending approval, protecting the go-live schedule from regulatory timing uncertainty.
Germania Mutual Insurance Company
Implementation Consultant
Nov 2021 – Feb 2022
AdvisoryData MigrationGuidewire
Designed the conversion strategy migrating legacy claims and policy data into ClaimCenter and PolicyCenter.
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- Documented 400+ ClaimCenter test scenarios across all lines of business and claim lifecycle events, including FSRA-required policyholder communication workflows.
- Delivered retrospective analysis that cut non-value-add testing effort by 20%.
Heartland Farm Mutual
Project Manager
Jun 2020 – Jan 2021
GuidewireTransformation
Program delivery lead for a $15M Guidewire v10 modernization at a $160M GWP insurer.
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- Accountable for end-to-end UAT across core systems, portals, and integrations: 1,200+ test cases at a 97% pass rate.
- Ran sprint planning and Scrum ceremonies across eight sprints with 100% on-time delivery.
- Acted as the single technical delivery contact for EY, and delivered executive dashboards and RAID reporting that reduced realized delivery risks by 20%.
EARLIER ROLES
Ernst & Young LLP
Implementation Consultant, Guidewire Delivery Practice
Jan 2019 – Jun 2020
GuidewireTransformation
Engagement Manager across three concurrent full-suite Guidewire InsuranceSuite implementations, from inception through warranty and handoff to managed services.
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- Managed delivery spanning PolicyCenter, ClaimCenter, BillingCenter, digital portals, and integrated third-party systems including SmartCOMM for policyholder document generation.
- Owned product model and submission wizard requirements, authoring 20+ user stories per sprint with UI mock-ups and legacy-to-Guidewire data mappings across three client engagements.
- Oversaw the BI and analytics layer: premium and loss analysis reporting by line of business and regulatory statistical submissions to IBC Canada.
- Directed multi-time-zone testing teams through 2,000+ test cases, improving first-pass success by 12% over prior programs.
- Managed warranty operations and formal transition to managed services with no unresolved critical issues at handoff.
Technical Sales Consultant, Keyence Canada · May 2018 – Jan 2019
SetUnit Solutions
Technology Consultant
May 2017 – May 2018
Data Migration
Technology Delivery Manager on a $5M insurance data migration program, owning delivery from extraction through production cutover.
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- Built standardized migration accelerators, including reusable extraction templates and automated validation scripts, that reduced migration timelines by 40%.
- Delivered executive dashboards for real-time visibility into migration status, accuracy rates, and go-live readiness.
