Senior Director, Technology - HR, Legal & Compliance

Transamerica•Cedar Rapids, IA

1d•Hybrid

About The Position

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.

Requirements

12+ years of progressive technology leadership experience, including 5+ years managing large, complex technology organizations (30+ FTE) and multi-year budgets exceeding $50M.
Demonstrated experience leading technology for corporate/enabling functions such as HR, Legal, Compliance, Audit, or Finance.
Direct experience with core HR technology platforms (Workday strongly preferred) and familiarity with the broader HCM/talent technology ecosystem (e.g., talent marketplace, engagement, culture platforms).
Experience with compliance/risk technology platforms (e.g., financial crime, sanctions/AML screening tools such as FinScan, or comparable) is a strong plus.
Familiarity with audit management platforms (e.g., TeamMate) a plus.
Proven track record of strategic planning translated into disciplined execution — able to operate at both the vision level and in delivery detail.
Exceptional stakeholder management and executive communication skills; able to build trust and influence across senior leaders with diverse priorities.
Strong financial acumen: budget planning, portfolio prioritization, vendor negotiation, and capacity/demand management.
Bachelor's degree required.
Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment Visa at this time.

Nice To Haves

MBA or advanced degree preferred.
Executive presence with the gravitas to represent technology in front of senior business leaders and, at times, the Board.
Comfortable operating in ambiguity, driving structure and clarity where it doesn't yet exist.
Strong people leader with a track record of developing talent and building high-performing, resilient teams.
High integrity and discretion, given exposure to sensitive HR, legal, and compliance matters.
Skilled at balancing competing priorities across multiple functions without losing sight of the bigger picture.

Responsibilities

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.
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.
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/leadership presentations, and briefing materials.
Serve as a key liaison between the executive's office and other business/technology leaders, ensuring alignment and follow-through on commitments.
Help shape organizational strategy, workforce planning, and culture initiatives across the broader technology organization.
Exercise discretion and sound judgment in handling confidential and sensitive information.

Benefits

Competitive Pay
Bonus for Eligible Employees
Pension Plan
401k Match
Employee Stock Purchase Plan
Tuition Reimbursement
Disability Insurance
Medical Insurance
Dental Insurance
Vision Insurance
Employee Discounts
Career Training & Development Opportunities
Paid Time Off starting at 160 hours annually for employees in their first year of service.
Ten (10) paid holidays per year (typically mirroring the New York Stock Exchange (NYSE) holidays).
Be Well Company holistic wellness program, which includes Wellness Coaching and Reward Dollars
Parental Leave – fifteen (15) days of paid parental leave per calendar year to eligible employees with at least one year of service at the time of birth, placement of an adopted child, or placement of a foster care child.
Adoption Assistance
Employee Assistance Program
Back-Up Care Program
PTO for Volunteer Hours
Employee Matching Gifts Program
Employee Resource Groups
Inclusion and Diversity Programs
Employee Recognition Program
Referral Bonus Programs