Director Guidewire Testing Practice

| Chicago, IL, USA +80 more | Remote | Hybrid
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You have a clear vision of where your career can go. And we have the leadership to help you get there. At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential.
CNA seeks to offer a comprehensive and competitive benefits package to our employees that helps them - and their family members - achieve their physical, financial, emotional and social wellbeing goals.
For a detailed look at CNA's benefits, check out our Candidate's Guide .
The Director, Guidewire Testing Practice is a key strategic role responsible for the overall testing strategy and execution spanning multiple Guidewire PolicyCenter implementations. The role has direct ownership and accountability for testing and testing teams spanning multiple products and teams partnering with Portfolio Leads, Product Owners, Architects, RTEs and other stakeholders. Collaborates closely alongside other Test Leaders to ensure integrated systems consistently meet or exceed the quality standards expected by our customers and internal partners. Ensures all Guidewire migrations, greenfield implementations and on-going enhancements are tested effectively and efficiently and high quality outcomes are maintained. Responsible for influencing broader QE policy decisions as they apply to the design, development, testing and delivery of application software across the CNA Enterprise. Ensures that products, applications, and systems are built and maintained in a manner that consistently meets or exceeds the quality standards expected by our customers and internal partners.
This role utilizes broad Quality Engineering and Software Engineering expertise needed to drive our testing engagements and to contribute to the ongoing evolution and roadmaps supporting broader Test Engineering practices. Drives and takes ownership of the testing roadmaps, projects and deliverables supporting the Portfolios they oversee. Directly engages and builds collaborative relationships with IT Partners, Business Stakeholders and Quality Engineering vendor(s). Ensures quality governance standards are being consistently adhered to and delivered in a cost-effective fashion. This Quality Leader will be a strong advocate and champion of Agile delivery supported by "Shift Left" testing, optimized test automation, Test Data Management (TDM) and integrated testing supporting CI/CD pipelines.
Essential Duties & Responsibilities
Performs a combination of duties in accordance with departmental guidelines:
Actively contributes and provides input and oversight into IT Quality Engineering/Quality Assurance strategy, decisions and execution across supported areas.
Actively participates in defining and implementing the TCOE Tooling & Practices Roadmap supporting functional and non-functional test automation frameworks, application life cycle, test data management, environment provisioning, defect tracking and quality metrics. Stays informed on new and trending technology, tooling and practices supporting QE and related practices.
Engages with internal and external partners/vendors to advise, promote and measure adherence of Quality Engineering best practices, policies, tooling, governance and reporting.
Works with vendor partners supporting CNA's technology environment to ensure reliable, cost effective and optimized business operations and customer support.
Promotes and facilitates expanded use of Automated Testing, Test Data Management, integrated testing supporting CI/CD and Test Driven Development (TDD) across supported areas.
Is a champion of SAFe Agile and provides influence and engagement expertise. Ensures testing teams are properly integrated within agile scrum teams utilizing quality engineering principles, tooling and techniques that are appropriate to the supported platforms.
Provides input into key decision-making activities with IT Leadership by advising on best practices and providing alternative solutions to complex issues during project execution as needed to ensure adequate quality and governance. Leads projects with moderate to large resource requirements, risk, and/or complexity in area of responsibility. Works independently with guidance in only the most complex situations.
Ensures effective administration of, and compliance with, all applicable CNA processes, procedures, and controls related to IT Quality Assurance through active monitoring, reporting and governance. Drive action on improvement priorities by summarizing trends identified, actions taken, and results defined by key metrics.
Oversees estimation and staffing exercises and assists in the management of budgets across Quality Engineering Services.
Skills, Knowledge & Abilities
Possesses multiple areas of specialization spanning software quality practices & principles, testing standards & best practices, integrated tooling, test case management, automated testing, test data management (TDM), testing governance and quality analytics. Possesses broad IT experience spanning development, testing and release management.
Hands-on expertise with Guidewire PolicyCenter and associated testing patterns and strategies is REQUIRED. Experience on Guidewire ClaimsCenter and BillingCenter are a plus.
Solid technical experience and strategical knowledge of multiple test automation disciplines and models spanning API, Web, Data, Comparative, Distributed, DDT and BDD etc. Previous experience building and leveraging automated testing supporting Guidewire is mandatory and experience on Guidewire's GT Framework is as plus.
Previous experience supporting an enterprise-wide, metrics driven quality governance practice. Possesses expertise and experience optimizing software testing and improving overall quality by embracing technology, tooling and analytics. History of promoting a "Shift Left" and "Automate First" culture and mindset.
Knowledgeable and current on technologies and tooling supporting integrated testing as part of CI/CD Pipeline and release progression practices. Hands-on experience with Google Cloud and/or AWS a plus
Solid ability to influence and collaborate with CNA business and IT leadership to define service goals, objectives, and metrics through the application of specialized knowledge of concepts, principles and practices in IT QE.
Has developed cross-team roadmaps and facilitated the planning through execution while monitoring progress and results against strategic goals.
Acts as a thought leader in researching and presenting innovative ways to solve complex QE/Testing issues. Ability to think analytically, critically and creatively in an outcome-based model to identify viable options from conception to execution
Excellent project management skills and ability to organize and plan effectively to meet project goals in an Agile environment and working through multiple IT vendors across disciplines.
Proactively engages and collaborates with other leaders across CNA Technology to ensure needed business subject matter expertise and skillsets are in place for testing design, development and execution.
Strong interpersonal, presentation, verbal and written communication skills, with the ability to interact effectively with internal and external business partners at all levels.
Proven ability to work well under pressure while maintaining a professional image and approach. Acts with a sense of urgency while achieving quality results and identifying and resolving problems and issues within the scope of responsibility.
Education & Experience

  • Bachelor's Degree in Computer Science, Information Technology, or related work experience. Advanced degree preferred.
  • Typically 5+ years in a Leadership/Management role within Quality Engineering/Quality Assurance
  • 5-7 years of experience supporting Guidewire PolicyCenter with experience on Ver10 and/or Cloud
  • 10+ years of Information Technology experience spanning IT Applications Development, or Quality Engineering
  • Experience managing and maximizing IT vendor partner relationships.
  • Extensive knowledge of testing frameworks and practices supporting functional, performance, security and accessibility testing in a dev/ops culture. GT Framework experience a plus.
  • Extensive Quality Engineering experience supporting Agile, Scrum and/or SAFe delivery methodologies.
  • Experience supporting Commercial Lines is a plus
  • IT Quality Assurance & Guidewire certifications are a plus.

CNA is committed to providing reasonable accommodations to qualified individuals with disabilities in the recruitment process. To request an accommodation, please contact [email protected] .

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Candidate Location Eligibility:
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Technology we use

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An Insider's view of CNA

How would you describe the company’s work-life balance?

Work-life balance has always been a priority for me. It always will be. CNA’s hybrid working model allows me to not only maximize collaboration with my peers but also take advantage of increased flexibility by combining remote and in-office work. I’m empowered to take control of my schedule based on what works best for me and my team.

Alison Massey

Agile Scrum Master Consultant

How do you collaborate with other teams in the company?

On the Security Advisory team, collaboration is key to what we do. We sit at a unique intersection of security goals and business objectives. By working across nearly every IT team at CNA, we balance the need for maintaining secure initiatives and keeping projects on track. It’s our job to find the best, secure path to ‘Yes’ for business requests.

Zach Jones

Director, Security Advisory

How has your career grown since starting at the company?

I joined CNA as a contractor and became a full-time employee after an eight-year contractor journey. I’m passionate about solving technical challenges and CNA allows me to foster that passion. Every day, I learn about emerging technologies. I’m empowered to develop, grow, and create a career that works for me and my lifestyle.

SenthilKumar Asokan

Applications Engineer Senior Specialist

How do your team's ideas influence the company's direction?

Enterprise Architecture creates foundations for IT expectations across CNA. I’m on a team that builds reusable IT assets, communicates best practices, and decides standards for tooling, and more. I influence CNA outside of my role, too, specifically through CNA’s Employee Resource Groups. I’m empowered to influence both IT and our culture of inclus

Lisa Smith

Architecture Senior Specialist

What does career growth look like on your team?

Career growth can take on many different forms at CNA, and that’s because there are always opportunities to acquire transferrable skills. On my team specifically, we’re encouraged to identify and work toward development opportunities that matter to us. We’re empowered to make a difference while advancing our careers.

Josie Lee

Director, HR Business Partner

What are CNA Perks + Benefits

CNA Benefits Overview

One of the many advantages of working at CNA is the benefits program we offer you and your eligible dependents,
beginning on the first day of your employment. The program features a variety of plans that provide health care
benefits, well-being, disability and survivor protection, and 401(k) savings, among others. Below are highlights
of the offerings.

Volunteer in local community
Partners with nonprofits
Open door policy
OKR operational model
Open office floor plan
Flexible work schedule
Remote work program
Dedicated diversity and inclusion staff
Diversity employee resource groups
Health Insurance + Wellness
Flexible Spending Account (FSA)
Disability insurance
Dental insurance
Vision insurance
Health insurance
Life insurance
Pet insurance
Wellness programs
Mental health benefits
Financial & Retirement
401(K) matching
Company equity
Employee stock purchase plan
Performance bonus
Charitable contribution matching
Child Care & Parental Leave
Generous parental leave
Family medical leave
Adoption Assistance
Vacation + Time Off
Generous PTO
Paid holidays
Paid sick days
Office Perks
Commuter benefits
Some meals provided
Relocation assistance
Onsite gym
Professional Development
Job training & conferences
Tuition reimbursement
Lunch and learns
Online course subscriptions available
Paid industry certifications

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