Head of Software Systems & Business Enablement

The Fedcap Group · Remote

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Title: Head of Software Systems & Business Enablement

Location: Remote 

Reports to: SVP, Enterprise Applications & Digital Platforms

Salary Range: $180,000 - $220,000/yr + $40,000 performance bonus

About The Fedcap Group

Founded in 1935, The Fedcap Group is a $425M global nonprofit organization focused on advancing economic well-being for individuals facing barriers to employment. Headquartered in New York City, Fedcap operates across 106 locations in 29 U.S. states, the U.K., Canada, and Australia serving nearly 332,000 people annually. Fedcap’s mission is to create opportunities for people facing barriers to achieve economic independence, dignity, and become contributing members of society. Through innovative programs, strategic partnerships, workforce development initiatives, and community-based services, Fedcap helps individuals build sustainable pathways to employment and long-term success.

Position Summary

The Fedcap Group (TFG) is seeking a strategic, business-oriented Head of Software Systems & Business Enablement to lead the management, optimization, and lifecycle of all software systems across TFG’s international footprint. This role will ensure our platforms are reliable, well-governed, cost-effective, and positioned to harness innovation and AI so the business can operate efficiently and scale.

Reporting to the SVP, Enterprise Applications & Digital Platforms, the Head of Software Systems & Business Enablement will serve as the bridge between business operations and technology, partnering with business leaders and technology peers to translate business needs into sustainable system capabilities.

Additionally, the Head of Software Systems & Business Enablement, will own a portfolio of 300+ systems and vendors, drive rationalization, adoption, and lifecycle discipline, while shaping the team needed to deliver.

Goals of the Position

The Head of Software Systems & Business Enablement will:

• Maximize Business Value Through Innovation & AI
  Ensure software systems are configured, adopted, and continuously improved, and identify opportunities to apply AI, automation, and emerging capabilities that improve efficiency, service delivery, and measurable business outcomes.

• Establish Strong System Ownership & Lifecycle Management
  Create disciplined ownership and lifecycle standards across the software portfolio, from selection through consolidation and retirement.

• Build a Business-Facing Partnership Model
  Establish trusted partnerships with business units, proactively identifying opportunities to improve processes, increase adoption, reduce manual work, and use technology more effectively.

• Strengthen Architecture, Integration & Standardization
  Lead the systems and application architecture function, aligned with enterprise-wide standards. Partner with Software Engineering and Data & Analytics to strengthen interoperability, API enablement, and data flows while reducing redundant or fragmented systems.

• Drive Adoption, Change & Service Excellence
  Establish consistent practices for onboarding, training, change management, service levels, user communications, and feedback so technology changes translate into sustained operational improvement.

• Cultivate a High-Performing, Business-Focused Team
  Invest in the capabilities and growth of a distributed, high-performing team. Foster a culture of business partnership, accountability, documentation, and continuous improvement.

Key Responsibilities

Systems Strategy & Leadership

• Partner with the SVP to define and execute a multi-year systems roadmap aligned with TFG’s growth. 
• Drive platform rationalization and consolidation in alignment with enterprise architecture and technology strategy. 
• Identify, evaluate, and scale AI, automation, and emerging capabilities within TFG’s software platforms, in alignment with enterprise AI governance and security standards.

Systems Oversight

Software Portfolio Management

• Lead system administration, configuration, and functional support across TFG’s software portfolio, including Oracle Fusion ERP and platforms supporting CRM, case management, student management, electronic health records, and fundraising.
• Own a portfolio of 300+ systems and vendors with named business and technical owners, documented business purpose, criticality, cost, dependencies, and lifecycle status.
• Establish standards for configuration, release management, testing, change control, documentation, and production readiness.
• Design and maintain application role and permission models in partnership with Security and Compliance.
• Coordinate application vulnerability remediation, upgrades, patches, and vendor-supported maintenance.
• Execute data archival and destruction in line with retention policy and ensure continuity and disaster recovery requirements for critical applications are documented and tested.

Business Partnership & Service Management

• Build and lead a business partnership function that serves as the primary relationship layer between technology and business operations.
• Create a consistent engagement model to understand business processes, pain points, and automation opportunities, and translate them into configuration, workflow, integration, reporting, or development needs.
• Establish a systems service catalog with standardized intake, prioritization, escalation paths, and measurable satisfaction targets, prioritizing requests with the SVP and business leaders by value, risk, cost, and capacity.

Implementation, Adoption & Change Management

• Lead software implementations, upgrades, and migrations from requirements through stabilization, including UAT, deployment readiness, training, and post-launch support.
• Drive change management so new capabilities are embedded in day-to-day operations, not treated solely as technology deployments.
• Monitor utilization and adoption and develop remediation plans where systems are underused or processes remain manual.

Architecture & Integration

• Lead the systems and application architecture function, including the systems landscape, application architecture, and integration patterns.
• Represent the systems domain on the Enterprise Architecture Review Board, providing systems-domain review and sign-off within delegated authority.
• Own business application integration requirements and interoperability standards, partnering with Software Engineering on technical delivery.
• Partner with Data & Analytics to improve data quality at the source and enable reliable enterprise reporting.
• Ensure system changes account for downstream data, reporting, identity, security, and infrastructure dependencies.

Vendor, Licensing, Financial & Compliance Oversight

• Manage the software vendor lifecycle, including onboarding, performance, licensing, and service levels.
• Manage the approved systems and software vendor budget in partnership with the SVP and Finance, including forecasting, analysis of license utilization, overlapping functionality, and total cost, and reporting realized savings separately from cost avoidance.
• Lead quarterly business reviews with strategic vendors and hold vendors accountable to contractual commitments.
• Partner with Procurement, Finance, and Legal on software negotiations, renewals, and purchasing decisions.
• Partner with Security and Compliance on logging and audit readiness to meet standards such as HIPAA, SOC 2, PIPEDA, GDPR, and ISO 27001.

Growth, RFP & M&A Support

• Provide systems expertise and solution architecture input to business proposals and RFP responses.
• Assess systems, applications, data dependencies, and contracts during pre-acquisition due diligence.
• Lead post-acquisition systems onboarding, migration, and harmonization using a repeatable integration playbook.

Team Leadership & Culture

• Build, coach, and lead a high-performing team, shaping the roles and capabilities needed to deliver the systems strategy.
• Establish clear ownership, service standards, priorities, and performance measures across the team.
• Develop team capability across business applications, business analysis, change management, and vendor management.

Qualifications

Education & Certification

• Bachelor’s degree in Information Systems, Business, Engineering, Computer Science, or related field (advanced degree preferred).
• ITIL, PMP, Prosci, business analysis, TOGAF, and/or relevant platform certifications preferred.

Professional Experience

• 10+ years in enterprise applications, business systems, or digital transformation roles, including 5+ years in leadership.
• Proven success leading major system implementations, migrations, adoption programs, and platform rationalization across multiple business units or entities.
• Experience managing distributed teams, business-facing technology functions, and third-party software vendors.
• Experience leading application architecture, integration standards, and architecture reviews across a complex, multi-entity organization preferred.

Technical Competencies

• Strong working knowledge of Oracle Fusion ERP and enterprise platforms spanning CRM, case management, student management, and EHR, with demonstrated depth in one or more major platforms and familiarity with modern SaaS administration.
• Understanding of application integrations, APIs, identity and access management, role-based permissions, release management, application security fundamentals, and AI and automation capabilities within software platforms.
• Strong capability in application portfolio management, software licensing, service management, and technology financial optimization.

Leadership & Communication

• Business-first leadership style with strong customer orientation and a focus on measurable operational outcomes.
• Adept at building trusted relationships with executives, operational leaders, technical teams, vendors, and end users.
• Comfortable operating in a federated, international organization undergoing significant transformation.

Benefits

• Medical, Dental & Vision | Life/AD&D & Long-Term Disability | Flexible Spending Account (FSA) | Commuter Benefits | 403(b) | Wellness Program

• May vary by location and business unit

Equal Opportunity Employer

The Fedcap Group is an Equal Opportunity Employer and is committed to fostering a diverse, inclusive, and respectful workplace. We provide equal employment opportunities to all employees and applicants and prohibit discrimination and harassment of any kind based on race, color, religion, sex, age, national origin, disability, protected veteran status, sexual orientation, gender identity or expression, genetic information, or any other characteristic protected by applicable federal, state, provincial, or local law.

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