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Senior Director Circle Lead (Canada Personal Lines Auto)

Toronto (Region), Ontario

Company Information

Solid reputation, passionate people and endless opportunities. That's Travelers. Our superior financial strength and consistent record of strong operating returns mean security for our customers - and opportunities for our employees. You will find Travelers to be full of energy and a workplace in which you truly can make a difference.

Target Openings


Job Description Summary

Travelers is seeking a Senior Director, Circle Lead to drive the execution of our Canada PI - Auto business strategies in an agile fashion. In this position, you will be responsible for implementing the strategy and portfolio of deliverables and capabilities spanning a medium number of agile product teams primarily within a single business unit or product. You will apply business acumen and leadership in partnership with technology counterparts to enable teams to achieve their goals, and drive end-user value while delivering results in service to business strategy. You will drive towards innovative solutions, while making trade-off decisions related to funding and resource allocation.

Primary Job Duties & Responsibilities

  • Lead, define, communicate and champion the work of a small number of agile teams (i. e. Team of Teams) working toward common business outcomes generally within a specific business segment.
  • At this level, you generally lead:
  • Less than 8 teams (less than 100 total people)
  • multiple business units or product lines/assets that may cross Circles, Value Streams and/or organizations
  • products with interdependencies with other systems/products
  • less established applications
  • Work with most senior levels of the organization
  • systems may be used across the entire enterprise
  • Partner with Technology Circle Lead to implement multi-team vision and strategy, ensuring alignment to overall value stream outcomes, including the business architecture and roadmap for achieving the strategy, vision and business outcomes; articulate the Circle/Team of Teams vision and strategy effectively to teams and stakeholders.
  • Effectively drive, manage, implement and track one or more portfolios of deliverables and capabilities as well as 'test and learn'/experimentation targeted at defining/refining future deliverables, measuring performance and adjusting the overall roadmap of deliverables as needed.
  • Prioritize interdependent team backlogs addressing risks and dependencies within and outside the Circle to defined outcomes and ensuring overall alignment with business strategy; Make trade-off decisions to balance quality, cost, and timelines to maximize value.
  • Identify innovative solutions both internally and in the external marketplace; ensure competitive and industry benchmarking of critical capabilities.
  • Oversee and make data driven decisions related to funding and resource allocation, and prioritization of work in alignment with circle and value stream objectives.
  • Lead positive team dynamics, encourage collaboration and drive appropriate levels of self-organization; assess, utilize, and partner with external resources and partners to meet agreed upon expectations, as needed.
  • Manage multi-team dynamics; remove impediments to teams' success and assist in conflict resolution, issue and dependency management.
  • Build and foster collaborative relationships across other Circles and with key partners.
  • Share best practices with peers across the value stream to ensure alignment and consistency in ways of working.
  • Help grow agile maturity within and across teams.
  • People-management responsibilities for team members and may manage other Circle Leads as well.

Minimum Qualifications

  • Six years of relevant business experience required.
  • Three years of people leadership/ management experience required.

Education, Work Experience, & Knowledge

  • Six years of experience in an agile/execution leadership role delivering business solutions on a demanding schedule preferred.
  • Four years of people leadership/ management experience preferred.
  • Strong business acumen and a deep strategic mindset preferred.
  • Proven analytical skills and experience making decisions based on hard and soft data preferred.
  • Strong knowledge of the Line of Business with the ability to develop and leverage business and/or vendor partnerships, consult on business priorities, and optimize value through solution identification aligned with business objectives preferred.

Job Specific Technical Skills & Competencies

  • Agile Mindset: Embody Agile core values of openness, courage, respect, focus, and commitment. Infuse Agile principles, practices and methodologies to achieve team success.
  • Product Mindset: Focus on defining a product value proposition that aligns with and supports the circle/value stream objectives and which is the north star for the Circle.
  • Change Agent: Expert change leadership skills including the ability to create an inclusive environment, manage conflict and develop solutions to mitigate risk.
  • Influence: Ability to influence behaviors of leaders at all levels and without traditional hierarchy.
  • Servant Leadership: Foster an environment where individuals thrive as empowered and equal members of a team.
  • Communication: Ability to communicate thoughts, concepts, practices effectively at all levels, adjusting as needed to a target audience.
  • Collaboration: Expertise working with others in a cross-functional multi-team environment.
  • Continuous Improvement: Demonstrate a commitment to continually improve, share learning with others and encourage team development.

Equal Employment Opportunity Statement

Travelers is an equal opportunity employer. We are committed to providing accommodation to persons with disabilities. If you require accommodation during the recruitment or interview process we will work with you to accommodate your needs.

If you are a candidate and have specific questions regarding the physical requirements of this role, please send us an email so we may assist you.

About Travelers

The Travelers Companies, Inc. (NYSE: TRV) is a leading property casualty insurer selling primarily through independent agents and brokers. The company's diverse business lines offer its global customers a wide range of coverage in the auto, home and business settings. A component of the Dow Jones Industrial Average, Travelers has more than 30,000 employees and generated revenues of approximately $25 billion in 2010.