Head of Delivery-IT Services Consulting

Cyclotron, Inc.-posted 11 days ago
Full-time • Mid Level
Remote • Chicago, IL
101-250 employees
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We’re a global Microsoft partner consultancy (~200 employees) delivering complex, high-impact Generative AI programs through our AI Innovation & Strategy and AI Engineering teams, as well as our Azure, M365, Security, and Change Leadership practice areas, supported by our PMO. The Head of Delivery is accountable for delivery excellence, portfolio performance, continuous process improvement, people leadership, and end-to-end PMO oversight, including engagement management, software development, and AI initiatives. This leader partners with Change Leaders, Sales, Presales, and Practice Leads to ensure we consistently deliver on time, on budget, and with exceptional client satisfaction. The ideal candidate is an industry veteran who has held a similar Director/VP delivery role and thrives in a data-driven, client-centric, growth environment.

  • Own the delivery portfolio across practices; set standards for predictable, high-quality execution and proactive risk management.
  • Establish and enforce delivery playbooks (planning, execution, QA/controls, change control, cutover, and hypercare) and ensure consistency across global teams.
  • Serve as the senior escalation point for complex programs; drive recovery plans and executive stakeholder communication.
  • Champion client advocacy and measurable outcomes from sales handoff through delivery completion and adoption.
  • Define and own delivery KPIs and dashboards, including utilization, profitability/margin, schedule adherence, forecast accuracy, backlog health, client satisfaction/NPS, and delivery risk profile.
  • Perform portfolio-level capacity planning and quarterly outlook; align resourcing with demand, skills, and billability targets.
  • Review trends and operational data to identify improvement opportunities; convert insights into action via quarterly OKRs.
  • Lead the PMO and community of practice for project/program managers; define methodologies, governance, stage gates, and standards (Agile, PMI/PMBOK, SAFe where applicable).
  • Oversee engagement management, software development, and AI delivery responsibilities within PMO scope.
  • Maintain a robust portfolio management process (intake, prioritization, approvals); ensure compliance to policy, documentation, and controls.
  • Implement project financial discipline: baseline, EAC, burn, change control, and invoicing cadence; partner with Finance on revenue recognition and margin improvement.
  • Work directly with Sales and Presales to ensure an efficient closed feedback loop on delivery gaps to strengthen SOW quality, estimates, and assumptions.
  • Standardize handoffs from sales to delivery and improve estimation accuracy.
  • Optimize use of Microsoft partner programs and funding (e.g., ECIF, MCI) to maximize delivery efficiency and client value.
  • Manage and develop delivery managers, PMO team leads, and project/program managers; set role clarity, expectations, and growth paths.
  • Build a high-performing, accountable, and inclusive delivery organization with strong coaching, performance management, succession planning, and workforce planning.
  • Partner with Practice Leads on staffing models, skills development, certifications, and billability targets across global teams.
  • Partner with Sales/Accounts on pursuit strategy, solution shaping, and seamless sales-to-delivery transition; strengthen client relationships and outcomes.
  • Work with Operations/Finance on forecasting, pricing guardrails, margin levers, and delivery cost controls.
  • Collaborate with Technical Practice leadership on methodologies, standards, and innovation to improve delivery efficiency and client value.
  • 12+ years in IT professional services/consulting, including 5+ years leading multi-disciplinary delivery teams at Director or VP level.
  • Proven success overseeing a PMO and delivery portfolio spanning enterprise cloud and GenAI programs.
  • Deep familiarity with Microsoft partner ecosystem, including ECIF and MCI funding programs.
  • Strong financial acumen (utilization, margin, revenue forecasting), executive stakeholder management, and client-success orientation.
  • Demonstrated experience improving delivery processes, tooling, and data to achieve measurable results at scale.
  • Delivery & Governance: Expert in project/program delivery models, controls, and risk management.
  • Data-Driven Leadership: Comfortable owning KPIs, building dashboards, and making decisions from insights.
  • Client Advocacy: Builds trust with executives; ensures outcomes that drive adoption and loyalty.
  • People & Culture: Coaches high-performers, sets clear expectations, and fosters accountability and inclusion.
  • Continuous Improvement: Simplifies processes and deploys automation to scale quality and profitability.
  • Certifications preferred: PMP, Agile methodologies, including Scrum.
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