Senior Director, Technology - HR, Legal & Compliance

Transamerica; Cedar Rapids (IA); On-site; USD 180,000 - 240,000; Full time

Job summary

Transamerica is seeking a Senior Director of Technology to lead the technology organization supporting HR, Legal, Compliance, Audit, and Communications. You will guide strategic planning, portfolio governance, and staffing for a 30–40 person team with a $50M+ annual budget.

You will balance run-the-business with strategic initiatives, build multi-year roadmaps, and drive AI/automation opportunities while ensuring data security and regulatory compliance across platforms.

Qualifications

• Proven experience leading enterprise technology teams.
• Experience managing multi-function technology portfolios and budgets.
• Ability to partner with senior executives and drive strategic initiatives.

Responsibilities

• Own end-to-end technology strategy, roadmap, and delivery for HR, Legal, and Compliance.
• Lead HR technology ecosystem with Workday as core HRIS and integrate ancillary tools.
• Oversee Audit/Compliance tech with FinScan to meet regulatory requirements.
• Provide governance, tooling, and support for Legal and Communications tech.
• Manage a $50M+ annual technology portfolio, including capex/opex and vendor contracts.
• Develop multi-year roadmaps and oversee AI/automation initiatives and risk reduction.

Skills

Technology leadership

Strategic planning

Budget management

People management

Stakeholder management

Data governance

Regulatory/compliance

Tools

Workday HRIS

FinScan

Job description

Job Family

IT - Development

About Us

At Transamerica, hard work, innovative thinking, and personal accountability are qualities we honor and reward. We understand the potential of leveraging the talents of a diverse workforce. We embrace an environment where employees enjoy a balance between their careers, families, communities, and personal interests.

Ultimately, we appreciate the uniqueness of a company where talented professionals work collaboratively in a positive environment — one focused on helping people look forward and plan for the best life possible while providing tools and solutions that make it easier to get there.

Who We Are

We believe everyone deserves to live their best life. More than a century ago, we were among the first financial services companies in America to serve everyday people from all walks of life.

Today, we’re part of an international holding company, with millions of customers and thousands of employees worldwide. Our insurance, retirement, and investment solutions help people make the most of what’s important to them.

We’re

What We Do

Transamerica is organized into three distinct businesses. These include 1) World Financial Group, including Transamerica Financial Advisors, 2) Protection Solutions and Savings & Investments, comprised of life insurance, annuities, employee benefits, retirement plans, and Transamerica Investment Solutions, and 3) Financial Assets, which includes legacy blocks of long term care, universal life, and variable and fixed annuities. These are supported by Transamerica Corporate, which includes Finance, People and Places, General Counsel, Risk, Internal Audit, Strategy and Development, and Corporate Affairs, which covers Communications, Brand, and Government and Policy Affairs.

Transamerica employs nearly 7,000 people. It’s part of Aegon, an integrated, diversified, international financial services group serving approximately 23.9 million customers worldwide. * For more information, visit transamerica.com.

Job Description Summary

We are seeking a strategic and execution-oriented Senior Director of Technology to lead the technology organization supporting our HR, Legal, Compliance, Audit, and Communications functions. This is a highly visible role for a leader who can operate equally well in strategic planning sessions with senior executives and in the operational details of platform roadmaps, budgets, and staffing. The ideal candidate has deep experience leading enterprise technology teams supporting corporate/enabling functions, has managed large budgets and diverse platform portfolios, and has the executive presence and organizational savvy to act as a trusted extension of leadership across the broader organization. This role leads a team of 30–40 technologists and manages an annual technology portfolio budget exceeding $50M, spanning core platforms, ancillary systems, and change/run investment across multiple business functions.

Job Description

Responsibilities

Technology Leadership

• Own the end-to-end technology strategy, roadmap, and delivery for the HR, Legal, and Compliance functions, ensuring platforms and capabilities align with business priorities and enterprise architecture standards.
• Serve as the primary technology leader for Human Resources technology, with Workday as the core HRIS platform, alongside a broader ecosystem of ancillary tools ensuring integration, adoption, and ongoing optimization.
• Lead technology for Audit and Compliance, with FinScan as the primary platform for financial crime/sanctions screening, ensuring the platform scales with regulatory and risk requirements.
• Provide technology oversight and support for Legal and Communications functions; ensure appropriate governance, tooling, and support model is in place.
• Manage the full technology portfolio budget ($50M+ annually), including capital and operating spend, vendor contracts, licensing, and resource allocation across all supported functions.
• Own capacity and demand management across the portfolio — balancing run-the-business needs with strategic initiatives, prioritizing investment against business value, and ensuring transparent trade-off decisions with stakeholders.
• Build and maintain a multi-year technology roadmap for each function, incorporating platform modernization, AI/automation opportunities, risk reduction, and regulatory change.
• Ensure strong data governance, security, and compliance posture across all platforms, particularly given the sensitivity of HR, Legal, and Compliance data.

Organizational Leadership

• Lead, develop, and grow a team of 30–40 technology professionals (direct and matrixed), including managers, engineers, product/platform leads, and business analysts.
• Build a high-performing, engaged organization; establish clear career paths, performance management practices, and succession plans.
• Foster a culture of accountability, continuous improvement, and customer-centric delivery.
• Manage vendor and partner relationships, including systems integrators and platform providers, to ensure quality delivery and cost efficiency.

Stakeholder Management

• Serve as the primary technology partner and trusted advisor to senior business leaders across HR, Legal, Compliance, Audit, and Communications (typically SVP/EVP level and their leadership teams).
• Build strong, credible relationships across a diverse set of stakeholders with differing priorities, translating business needs into technology strategy and vice versa.
• Represent technology in business planning, budget reviews, and steering committees; communicate complex technical topics in clear, business-relevant terms.
• Manage escalations and competing priorities across functions with diplomacy and sound judgment.
• Partner closely with enterprise technology leadership (architecture, security, infrastructure, data) to ensure alignment with broader technology strategy.
• Act as a strategic partner and force multiplier for the Head of Corporate Systems and Data, driving key organizational initiatives, executive communications, and cross-functional coordination.
• Manage the operating rhythm for the executive's organization: leadership meetings, offsites, town halls, business reviews, and reporting cadences.
• Lead or coordinate special projects and strategic initiatives on behalf of the executive, often requiring rapid synthesis of ambiguous problems into clear plans.
• Prepare executive-level communications, board/lead