Full-Time

Director of Artificial Intelligence

Hybrid

Posted on 11/1/2025

TruStage

TruStage

11-50 employees

Co-branded insurance and investment solutions

Compensation Overview

$163.8k - $304.6k/yr

+ Annual Incentive Plan

Company Does Not Provide H1B Sponsorship

United States

Hybrid

Hybrid role; specific on-site days not stated.

Category
AI & Machine Learning (3)
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Requirements
  • Bachelor’s degree in computer science, data science, engineering, or related technical discipline, or equivalent combination of education and/or related professional work experience.
  • 12+ years of progressive experience in data, analytics, or AI leadership roles, with at least 5 years in senior management driving enterprise-scale AI initiatives.
  • Deep expertise in modern AI/ML techniques, including predictive analytics, prescriptive modeling, LLMs/generative AI, and agentic applications, with demonstrated success in operationalizing AI at scale.
  • Proven track record delivering AI-enabled solutions that drive measurable business outcomes, improve operational efficiency, and create competitive advantage.
  • Experience defining and executing AI roadmaps aligned to business strategy, including prioritization, ROI measurement, and value realization.
  • Hands-on knowledge of MLOps, AIOps, cloud-native AI deployments, hybrid architectures, and model lifecycle management.
  • Demonstrated ability to lead multidisciplinary teams of data scientists, engineers, governance specialists, and vendors, fostering a high-performance and innovation-oriented culture.
  • Strong communication and storytelling skills, capable of translating complex AI concepts into relatable business applications for diverse audiences.
  • Proven experience in AI governance, ethics, and compliance, particularly within regulated or risk-sensitive environments.
  • Collaborative leadership style with high emotional intelligence, adept at stakeholder engagement, change management, and building enterprise AI literacy.
Responsibilities
  • Evolve and communicate the enterprise AI strategy in collaboration with business, technology, and risk stakeholders.
  • Proactively identify, shape, and evaluate high-value AI opportunities with clear ROI and strategic relevance.
  • Translate emerging AI capabilities into tangible, scalable business applications that create competitive advantage.
  • Prioritize and sequence AI initiatives to maximize enterprise value, alignment, and adoption.
  • Direct the design, development, deployment, and integration of AI products and capabilities into core business workflows to ensure adoption and sustained value.
  • Define and track key performance indicators (KPIs) for AI programs, including ROI, adoption rates, productivity improvements, and customer satisfaction.
  • Establish continuous improvement processes to monitor, retrain, and optimize AI models and solutions post-deployment.
  • Ensure AI capabilities are scalable, reliable, and embedded effectively into operational processes.
  • Build, lead, and mentor a multidisciplinary team of AI professionals, including data scientists, engineers, governance specialists, and external vendors.
  • Foster a high-performance culture that emphasizes innovation, collaboration, and responsible AI development.
  • Manage strategic partnerships and vendor relationships supporting AI product delivery and platform evolution.
  • Partner with business and enablement teams to drive AI literacy and upskill associates through structured training and engagement programs.
  • Lead change management activities facilitating AI adoption across diverse business units.
  • Inspire and influence stakeholders by demonstrating the art of the possible with AI, translating complex capabilities into relatable, actionable business opportunities.
  • Implement and maintain AI governance frameworks that address ethical, legal, regulatory, and security considerations.
  • Develop and oversee AI risk management processes to ensure compliance with evolving regulatory requirements and corporate standards.
Desired Qualifications
  • Graduate degree in data science, computer science, or relevant quantitative field.
  • Prior success scaling and maturing business-focused AI, analytics, or data science teams.
  • Familiarity with Azure AI/ML tooling and platform services.
  • Demonstrated thought leadership in AI adoption, emerging technology, and responsible innovation.

TruStage partners with credit unions to offer co-branded insurance and investment products to their members. Its products include life, auto, and home insurance, plus retirement and investment options, sold through the credit unions. The model uses the trust and relationships of credit unions to reach everyday consumers, especially middle-income families. Its goal is to help people achieve financial security by making insurance and investment products accessible through trusted credit unions.

Company Size

11-50

Company Stage

N/A

Total Funding

N/A

Headquarters

Madison, Wisconsin

Founded

1935

Simplify Jobs

Simplify's Take

What believers are saying

  • SavvyMoney integration yields 40% applicant interest in loan protection products since December 2024.
  • Tangenesis Version 3.0 enables real-time quoting and instant purchases in Temenos Virtual Capture.
  • ZoneChoice Advantage Annuity launches innovative RILA crediting strategies for retirement flexibility.

What critics are saying

  • Demopolis acquisition strips TruStage's digital storefront, eroding B2B2C distribution by Q3 2026.
  • Only 40% interest despite 80% demand exposes weak loan protection product-market fit in 2026.
  • NCUA vendor oversight mandates diversified providers, dismantling exclusive credit union partnerships by 2027.

What makes TruStage unique

  • TruStage partners exclusively with credit unions for co-branded insurance distribution.
  • Manages $36.1 billion AUM as of 2025, ranking fourth largest US life insurer by policy count.
  • Compliance Hub Alerts tracks 18,000+ legal citations across all 50 states and federal agencies.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Life Insurance

Disability Insurance

Parental Leave

Paid Vacation

401(k) Retirement Plan

Hybrid Work Options

Tuition Reimbursement

Company News

The Associated Press
Mar 26th, 2026
TruStage generates $6.1B revenue, becomes fourth largest US life insurer by policy count

TruStage reported strong 2025 financial performance with over $6.1 billion in revenue, $312 million in net income and $36.1 billion in assets under management. The insurance and financial services provider maintained strong ratings from AM Best (A), S&P (A+) and Moody's (A2). The company paid over $2.6 billion in total benefits across 42 million consumers and became the fourth largest life insurance provider in the US by policy count. TruStage Ventures expanded to 67 portfolio companies with over $400 million in total investment. The TruStage Foundation invested $3.9 million in communities through more than 100 non-profits, whilst employees registered 8,600 volunteer hours and raised $640,000 for charitable organisations. The company has been named to Forbes' Best Insurance Companies list for four consecutive years.

Yahoo Finance
Mar 9th, 2026
TruStage launches automated compliance tool tracking 18,000+ legal citations across US states and federal agencies

TruStage Compliance Solutions has launched Compliance Hub Alerts, a regulatory tracking tool that monitors over 18,000 legal citations across state and federal levels, agency rules, case law and regulatory guidance. The web-based application automatically notifies compliance officers of regulatory changes affecting their operations. The platform uses customisable filters to deliver tailored alerts and allows users to assign specific changes to team members. Each alert includes a summary of the update, potential impact, legal references and implementation guidance. A centralised dashboard provides visibility into tracked legislation and generates audit reports. Compliance Hub Alerts covers all 50 US states, Washington DC and federal bodies including the Consumer Financial Protection Bureau, Federal Reserve, FDIC, IRS and NCUA. The tool aims to automate previously manual compliance monitoring processes for financial institutions.

Credit Union League of Connecticut
Dec 10th, 2025
Committed Partners in a Changing World

Committed partners in a changing world. For 90 years, TruStage has stood shoulder-to-shoulder with the credit union movement. As Connecticut's credit unions continue to navigate change, TruStage remains a trusted and essential partner, offering support, innovation, and stability in every environment we face together. In its most recent annual report, TruStage delivered more than $2.5 billion in benefits to members across the country, helping families weather uncertainty, build resilience, and plan for the future. They were again named one of America's Best Insurance Companies by Forbes and have now become a Top 5 life insurer in the U.S. by policy count. These accolades underscore what credit unions already know: TruStage delivers for people. Their commitment to credit unions goes well beyond product delivery. In 2024 alone, TruStage generated more than $5.6 billion in revenue and $200 million in net income - enabling continued reinvestment into the system and our communities. Their $3.5 million in philanthropic pledges through the TruStage Foundation and over $159 million invested into the credit union system over the past five years prove that they're more than a vendor; they are aligned with our mission. In Connecticut, TruStage has partnered with the League to empower innovation, promote advocacy, and support financial well-being initiatives. Their voice is present alongside ours on issues like data privacy, interchange, and consumer protection. Their national perspective, combined with local support, helps our credit unions stay ahead of change and focused on impact. * Trusted by 93% of credit unions nationwide * Over 39 million consumer relationships * $400+ million invested in 67 FinTechs, creating 1,800 partnerships through TruStage Ventures * Products and services that span every stage of the financial life journey - from first car to retirement Looking forward, we are excited to continue our collaboration with TruStage and our joint investment in partnerships like Clutch, which help position credit unions as FinTech-forward institutions without sacrificing what makes us unique: people-first service and local trust. In a rapidly changing financial services environment, TruStage remains steady, forward-thinking, and true to the credit union mission. We are proud to work with them, and we know their future-focused vision will continue to benefit our members and communities for generations to come.

PEI Group
Oct 7th, 2025
Demopolis Acquires TruStage Platform

Demopolis has acquired TruStage's digital storefront platform.

TruStage
Jun 24th, 2025
TruStage(TM) launches ZoneChoice Advantage Annuity, offering more flexibility for retirement planning

MADISON, Wis. - TruStage, a leading insurance and financial services provider, today announced the launch of a new retirement solution, the TruStage ZoneChoice Advantage Annuity, underwritten by MEMBERS Life Insurance Company, a registered index-linked annuity (RILA) with new, innovative crediting strategies for end-investors.

INACTIVE