IT Program Director (MA based or Fully Remote)

Our Information Technology (IT) team is currently seeking a Program Director in our Worcester, MA office or remote work arrangement.

This is a full time, exempt role.


POSITION OVERVIEW:



Reporting to a Delivery Leader within Specialty Lines, this Program Director will be responsible for leading and managing the execution of a strategic portfolio of IT projects. They will also be a matrixed-member of the Program Management Office (PMO) leadership team helping to ensure the overall success of initiatives undertaken. They will plan, drive, oversee, analyze, and report out on a wide range of technology projects of varying complexity.

The Program Director will create and lead Executive level presentations and discussions, in formats such as Steering Committee and Portfolio Management meetings. As part of the PMO, they may also lead internal initiatives, make process improvement recommendations, and drive and champion best practices. They will have accountability for growing our Agile capabilities within their portfolio and infusing Agile into our culture.


The Program Director is expected to assess, identify, classify, and report potential project risk with mitigation strategies and contingency plans, and to provide continuing leadership and direction to project teams. Candidate must have proven success delivering complex projects/programs, strong risk and financial management expertise, and the ability to work within a matrixed environment.



IN THIS ROLE, YOU WILL:

Lead strategic and program planning, estimating, scheduling, tracking, risk management, portfolio-level finances, trending and forecasting, reporting, and stakeholder communication.
Resolve interdependencies within the portfolio and across the Enterprise.
Directly manage a team of Project Managers and Business Analysts.
Build followership through strong relationships with both IT teams and business stakeholders.
Drive effective and proactive resource management across the Specialty portfolio, and with the Enterprise.
Continuously monitor project status and manage project resources, finances, and scope. Contribute to and may lead program governance and steering committees.
Develop strong partnerships within IT, strategic external partners and the Business functions.
Demonstrate an advanced understanding of Business Strategies, Products, and Organizations to ensure clarity of the business drivers and outcomes.
Excel at design and formation of effective teams. Apply talent development skills by constantly assessing talent across program.
Own or participate in selecting and developing strategic partnerships with vendors including contract negotiations, monitoring execution, and evaluating outcomes.
Contribute to and promote adherence to best practices as defined by the Project Management COE and Project Management Office (PMO).


WHAT YOU NEED TO APPLY:

Minimum of 8 years of IT Project and Program Management, and 2+ years leading a team of Project Managers and/or Business Analysts
Experience delivering projects using Agile and Waterfall methodology
Bachelor's degree in related field, specialized training, or equivalent work experience
Prior Property and Casualty experience a plus
Strategic and insightful in their thinking, with good judgment and an intuitive sense of where to look for opportunities to drive delivery success and effectively support the business
Promote teamwork, cooperation, respect, creativity, recognition, and provides ongoing coaching to employees
Demonstrated track record of leading high-performance teams toward the successful attainment of challenging goals in support of the corporate business strategy
Aptitude for learning and intellectual curiosity beyond immediate scope of responsibility
Able to establish credibility with and provide guidance to the CIO’s and Sr. Leaders within IT and the Business Areas
Decisive, but open-minded, innovative, and entrepreneurial thinker
Able to trade-off the risks and rewards while also considering the big picture of company-wide impact, industry trends, and strategic implications
Proven track record of working hand-in-hand with other leaders and rolling up their sleeves to get the job done
An aggressively collaborative, team player with strong results orientation and sense of urgency
Executive presence with effective oral and written communication targeted to Senior and above levels
Ability to develop a business case, evaluating overall benefits, costs, strategic alignment and risk