Director, Portfolio Lead & Agile Coach

Job Summary: 
The Hartford is seeking a high-energy, highly organized Portfolio Lead/Coach who combines expertise in Agile coaching, program delivery, lean portfolio management, and generative AI knowledge to support Enterprise Agile Lean Governance and Tech Strategy and Enablement initiatives.

The Portfolio Coach will partner with leaders across business and IT to align initiatives with strategic objectives, optimize the flow of value across the organization, and leverage modern tools (including AI) to inform decision-making and drive outcomes. Reporting to the AVP of the Agile Center of Enablement, this is an excellent opportunity for a dynamic leader passionate about lean governance, continuous improvement, and guiding teams and leaders to deliver superior business results in a scaled Agile environment. 

This role will have a Hybrid work schedule, with the expectation of working in Hartford, CT 3 days a week (Tuesday through Thursday). Candidate must be authorized to work in the US without company sponsorship. The company will not support the STEM OPT I-983 Training Plan endorsement for this position.

Key Responsibilities: 

• Leverage strong program management and Agile execution experience to structure and break down complex initiatives (epics, capabilities, features) into manageable components. Use program management practices to monitor scope, timelines, and budgets, ensuring that programs stay on track and deliver intended outcomes. 

• Support lean governance frameworks at the portfolio level to ensure Initiatives or Epics align with enterprise strategy. Oversee the portfolio backlog, and drive strategic prioritization to balance demand with capacity. 

• Drive innovation by identifying opportunities to leverage generative AI and other emerging technologies within portfolio management and delivery processes. Implement AI-driven tools or practices (e.g., predictive analytics for risk management, automated reporting) to enhance decision-making and team efficiency. Coach teams on adopting these solutions responsibly, ensuring that AI augments our processes while aligning with Agile values and business objectives.  

• Coach and mentor executive sponsors, portfolio managers, and Agile leaders in lean-agile practices and mindset, focusing on portfolio-level application. Educate leaders on principles of Lean Portfolio Management (e.g., prioritization, WIP limits, adaptive funding) and guide them in applying lean-agile practices to governance and strategy execution. Provide Agile coaching with an emphasis on scaling practices and sustaining Agile transformations across the enterprise.  

• Identify, track, and mitigate risks and impediments that could hinder the flow of value across teams and programs. Collaborate with senior leadership to escalate and remove systemic blockers, improving overall organizational throughput and delivery predictability. 

• Act as a liaison among business and IT stakeholders to maintain alignment and transparency. Communicate portfolio progress, risks, and achievements in a clear, timely manner, managing stakeholder expectations and fostering strong partnerships. Ensure feedback loops with stakeholders to course-correct and reinforce support for portfolio outcomes. 

• Define and measure meaningful productivity and flow metrics in addition to standard Agile metrics. Track indicators like flow efficiency (work time vs. wait time) and reliability (e.g., system uptime, incident recovery time) alongside team health, delivery performance, and business outcomes. Use these data-driven insights to coach teams and leadership, aiming for continuous improvement at the portfolio level.  

• Demonstrate thought leadership in Agile and Lean Portfolio Management. Lead and contribute to training sessions, workshops, and communities of practice on topics such as lean portfolio governance, agile metrics, program execution excellence, and emerging best practices. Share success stories and industry insights (via blogs, forums, presentations) to inspire a culture of continuous learning and improvement across the organization.  

Qualifications & Requirements: 

• Minimum of 5–7 years of experience in Agile coaching or related roles (e.g., Scrum Master, RTE, Product Owner) within a scaled Agile environment, with a demonstrated ability to coach multiple teams or programs and meet them where they are in their Agile journey.  

• Proven experience in program management, including managing complex dependencies and risks across large initiatives. Familiarity with coordinating multiple teams or ARTs and using program management tools and techniques (PMP, SAFe LPM or similar certifications are a plus).  

• Strong knowledge of lean-agile frameworks and Lean Portfolio Management practices. Experience establishing or participating in lean governance structures or an Agile PMO at the enterprise level is highly desirable. Successfully launching or steering Agile Release Trains is a plus.  

• Hands-on experience defining, tracking, and analyzing Agile and productivity metrics (velocity, cycle time, flow efficiency, etc.). Comfortable with data—able to derive insights from metrics to drive discussions on improvement, and translate metric trends into actionable recommendations for teams and leadership.  

• Exceptional communication and stakeholder management skills, with experience engaging all levels of the organization including executives. Strong influencing and negotiation skills to guide decision-making and foster adoption of new practices across diverse stakeholder groups.  

• Pragmatic, solution-oriented mindset. Proven ability to anticipate and address risks, cross-team challenges, or governance issues proactively. Adaptable and resilient in the face of organizational change; champions continuous improvement and can lead change management efforts to help teams embrace new ways of working.  

• Solid understanding of both business and IT perspectives. Comfortable discussing technology delivery (e.g., software development, DevOps, reliability engineering concepts) as well as business strategy and outcomes.  

• Proficiency with Agile project management tools and the Microsoft Office suite. 

• Bachelor’s degree or equivalent work experience in a related field. Experience in the insurance or financial services industry is a plus, as is experience in leading and managing a team. 

• Familiarity with emerging technologies, especially generative AI tools and methodologies. Proven interest or experience in applying AI-driven solutions or data analytics to improve processes and decision-making is an advantage.