Portfolio Delivery Leader (AI & Cloud)

Location: Chicago, United States; other listed locations include Orlando, Raleigh, Dallas, Atlanta Metro Area, Denver Downtown, and Minneapolis. Hybrid workstyle aligned to an hirify.global office, with in-person collaboration based on client, team, development, or relationship-building needs.

Compensation range: $158,600–$281,600, plus eligibility for a discretionary performance-based bonus.

Company

hirify.global is a professional services firm serving middle-market clients globally.

What you will do

• Shape and maintain prioritized portfolio roadmaps with business stakeholders, aligning technology investments to strategic objectives and measurable value.
• Lead client-facing product teams and internal and third-party delivery teams developing, implementing, supporting, and maintaining custom solutions across cloud and hybrid platforms.
• Establish collaborative delivery processes and standardize Agile and SAFe practices in partnership with Scrum Masters, Release Train Engineers, and Agile Coaches.
• Oversee advanced product, AI, cloud platform, governance, security, privacy, data integrity, service quality, scalability, disaster recovery, monitoring, and risk-management activities.
• Lead continuous improvement, AI and automation initiatives, delivery workflow optimization, performance management, and operational efficiency efforts.
• Build trusted relationships with business and technology leaders, resolve competing priorities, and improve delivery predictability and transparency.

Requirements

• Bachelor of Science or equivalent experience in software engineering, cloud, or technology leadership; a Master of Science is preferred.
• At least 5 years of experience leading matrixed delivery teams, building strategic roadmaps, and aligning delivery with business needs.
• At least 10 years of experience building enterprise-class on-premise, off-premise, and hybrid solutions.
• At least 5 years of experience developing and maintaining policies, procedures, standards, and guidelines.
• Required experience delivering complex enterprise integrations across cloud, SaaS, custom, and third-party platforms, including Workday, ServiceNow, CRM, ERP, data and analytics, and finance systems.
• Deep knowledge of middleware, iPaaS, API management, reusable services, lifecycle and version management, observability, secure data exchange, privacy, data quality, access controls, testing, and production reliability.
• Ability to translate end-to-end business processes and enterprise priorities into scalable integration strategies and roadmaps, with accountability for reliability, adoption, risk, cost, cycle time, reduced manual effort, and measurable business value.
• Exceptional communication and influence skills, including explaining complex concepts, risks, tradeoffs, and decisions; building alignment; influencing without direct authority; and resolving competing priorities.
• Demonstrated success building accountable teams, developing technical and delivery leaders, managing capacity, and guiding stakeholders through technology, governance, and operating-model change.

Nice to have

• Leadership experience in a large, complex integration environment spanning business-critical platforms such as Workday, ServiceNow, CRM, ERP, data and analytics, and finance systems.
• Experience in regulated or data-sensitive environments involving security, privacy, data governance, compliance, and third-party risk.
• Experience advancing reusable integration patterns, developer enablement, intelligent automation, or AI-enabled workflows across internal teams, vendors, and managed service providers.
• Strong executive presence, negotiation, relationship-building, adaptability, and learning agility.
• Relevant certifications or advanced training in integration architecture, API management, cloud platforms, middleware, iPaaS, security, data governance, or leading enterprise applications.

Culture & Benefits

• Hybrid workstyle with office alignment and in-person connection based on role and client needs.
• Competitive benefits and compensation package.
• Discretionary bonus based on firm and individual performance.
• Equal employment opportunity and reasonable accommodation for applicants with disabilities.