Associate Vice President (AVP) of PMO and Delivery

Accountabilities:: Own performance, quality, and delivery outcomes across the PMO and Delivery Lead functions. Lead, coach, mentor, and evaluate PMO leaders and Delivery Leads through strategic direction and performance management. Partner with senior leadership to establish and execute annual strategic objectives for both departments. Serve as a trusted executive advisor to clients, aligning delivery solutions with business objectives and influencing key decisions. Own PMO strategy, including staffing models, resource planning, and methodology standards across Agile, Scrum, SAFe, and Waterfall environments. Ensure delivery assurance programs and project playbooks are appropriately adapted to different implementation types, platforms, and SOW structures and consistently followed. Develop, monitor, and communicate enterprise-level KPIs and delivery metrics, translating performance trends into actionable improvement plans. Manage combined PMO and Delivery Lead budgets, ensuring effective financial management and resource allocation. Act as the executive escalation point for high-priority engagements, resolving complex delivery risks and issues. Foster a culture of accountability, innovation, and continuous improvement, including the adoption of AI and emerging delivery tools. Lead succession planning, talent development, and 360-degree feedback initiatives for department leadership. Partner with sales, account management, and delivery leadership to align resources, pipeline requirements, and project outcomes. Represent PMO and Delivery in growth initiatives, pre-sales activities, and strategic partner discussions. Ensure delivery practices remain aligned with applicable data privacy, security, and compliance requirements. Lead interview, onboarding, and training strategies for the PMO and Delivery Lead leadership pipeline. Requirements: 15+ years of experience in the technology services industry, including at least 7 years in senior leadership overseeing multiple teams or departments. Bachelor’s degree in Business, Technology, or a related field required; a Master’s degree is preferred. Proven track record leading project and program delivery alongside delivery quality, governance, or PMO functions. Experience managing budgets of $10M+ and enterprise-level KPI or reporting programs. Deep knowledge of project management methodologies and delivery governance frameworks. Advanced proficiency with Microsoft 365, including MSP, and delivery tools such as JIRA, Azure DevOps, or similar platforms. Strong analytical, risk management, and strategic problem-solving skills, with the ability to turn delivery and KPI data into actionable strategies. Executive-level communication and presentation skills, with the ability to engage senior leaders, clients, and strategic partners. Extensive experience leading, coaching, mentoring, and developing teams across multiple management levels. Servant leadership mindset combined with strong integrity, accountability, and sound judgment. Results-oriented approach and demonstrated ability to lead organizational change. Certifications across multiple project management disciplines, such as CSM, ACP, PMP, or SAFe, are preferred. Experience with Duck Creek Technologies and Property & Casualty insurance delivery is strongly preferred. Ability to work outside standard Monday–Friday, 8 AM–5 PM local hours when required. Willingness to travel as needed. Benefits: Competitive salary package with an annual bonus. Comprehensive and inclusive health benefits. Flexible working arrangements. Remote work options, with opportunities to work from offices in Springfield, Missouri or Puerto Rico. Opportunities for internal advancement and professional development. Relaxed office environment with casual dress. Company-sponsored activities and team-building events. Paid time off and company holidays. Traditional and Roth 401(k) plans with a 5% company match. Physical and mental wellness programs. Collaborative culture focused on knowledge sharing, continuous learning, and professional growth. Opportunity to shape delivery strategy, develop leadership talent, and influence complex technology engagements.