Align your teams, upskill & close capability gaps, and empower agile leadership
Evolve Your Organization
Who This Is For
AI transformation isn’t just a technical challenge, it’s an organizational one.
Your people and structure must evolve as dramatically as your tools. True AI transformation breaks traditional hierarchies, rewrites roles, and demands a new way of thinking—collaborative, adaptive, and ethically aligned. Our Fractional CAIO leadership aligns people, roles, and ethics with the same urgency as the tech itself.
This is for leaders who recognize that capabilities, decision-making, and workforce design are just as critical as the tech stack.
Upskill engagements are ideal for organizations:
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Facing internal misalignment across product, engineering, and business functions
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Struggling with hiring, capability gaps, or distributed team cohesion
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Preparing to scale new lines of business or integrate AI across workflows
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Needing executive coaching, change leadership, or a new operating model
Use Cases
Upskilling isn’t about workshops—it’s about redefining how organizations operate, lead, and grow.
We’ve done this inside some of the most complex and distributed environments in business.
Healthcare Transformation (Global Hybrid Org)
Transitioned 65+ internal engineers through a full rebadging process, aligning leadership, retraining delivery teams, and standing up a new global domain model. Unified 11 disparate teams into four customer-centric domains. Led agile maturity effort—replacing misaligned processes with lean, test-validating delivery pipelines.
Identity & Consumer Platform (Post-Split Buildout)
Built a new global product and engineering organization from scratch following an organizational split. Oversaw hybrid delivery across the U.S. and Latin America. Realigned product and engineering around shared outcomes, hired and developed key leadership roles, and created a culture of aligned velocity.
Mobility Platform (From Concept to Scale)
Designed and built the entire product and engineering org for a venture-backed mobility arm inside a global enterprise. Recruited every team member, oversaw dual-location operations (U.S. and Germany), and established product-engineering operating rituals that supported real-time systems and service scale.
Global Media SaaS Org (Agile Consolidation at Scale)
Unified a globally distributed 170+ person product and engineering org spanning four continents. Consolidated functions, introduced career pathing, and established a new center of gravity in Canada while continuing to lead globally dispersed teams. Implemented agile structures and embedded team-wide training and upskilling to ensure performance continuity and growth through transformation. Designed and mentored the entire leadership layer from the ground up.
Value Outcomes
Our goal isn’t to add more process—it’s to build organizational velocity.
With ISS driving your Organization Evolution & Upskilling Strategy, you'll gain:
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A restructured organization built for speed, clarity, and ownership
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Teams aligned on outcomes, not just outputs
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Leaders equipped to drive transformation at every level
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Reduced attrition, increased cohesion, and improved hiring focus
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A culture ready to adopt and scale intelligent technology
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Deepened cross-functional trust and transparency
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A leadership team aligned not just on goals, but on ethics and intent
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A culture of psychological safety that supports intelligent experimentation
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A mentoring-first mindset that scales leadership capacity across teams
What We Deliver
We work across executive, departmental, and team levels to realign organizations around the skills, roles, and structures needed for transformation, and grow leadership capacity through embedded mentorship and executive development.
We focus on:
→ Org design for AI-native operating models
→ Capability mapping, role definition & hiring strategy
→ Leadership enablement & executive coaching
→ Agile transformation & product/engineering alignment
→ Workforce upskilling, training, & learning paths
→ Change management strategy & cultural integration
→ Mindset reorientation & adaptive learning programs
→ Psychological safety & change readiness coaching
We help organizations upgrade not just their tools—but their people, mindset, and momentum—emphasizing leadership growth and the scalable development of executive capacity at every level. That includes building trust in change, coaching adaptive leadership, and fostering cultures that learn in real time.