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Director of Engineering, Stop Loss at Symetra Financial - Remote - Apply Now!

Symetra Financial

Director of Engineering, Stop Loss at Symetra Financial - Remote - Apply Now!

full-timePosted: Dec 3, 2025

Job Description

About Symetra Financial

Symetra Financial is a leading insurance and financial services company dedicated to providing innovative solutions in life insurance, retirement planning, and employee benefits. Headquartered in Bellevue, Washington, Symetra serves millions of customers across the United States with a commitment to sustainable growth, employee empowerment, and exceptional customer experiences. The company's Technology and Operations Benefits Division plays a pivotal role in delivering cutting-edge Stop Loss solutions, protecting employers from catastrophic healthcare claims while enabling efficient benefits administration.

Role Overview

As the Director of Engineering, Stop Loss at Symetra Financial, you will spearhead the development of a world-class engineering team in a fully remote capacity. Reporting directly to the VP of Engineering for the Technology and Operations Benefits Division, this leadership role involves setting technical priorities, driving strategic initiatives, and delivering end-to-end technology solutions for Stop Loss insurance products. With a salary range of $166,400 - $277,400 plus annual bonuses, this position offers significant impact on Symetra's growth in the competitive insurance sector.

Strategic Impact

You will shape the technical roadmap for AI-enabled products, microservices architectures on AWS, and scalable distributed systems, ensuring seamless integration with Symetra's broader life insurance and employee benefits platforms.

Key Responsibilities

In this high-visibility role, your responsibilities include:

  • Building and leading an inclusive, collaborative engineering team aligned with Symetra’s values and DEI commitments.
  • Defining technical strategy and partnering with stakeholders to deliver end-to-end business solutions for Stop Loss.
  • Fostering a culture of quality, agility, and continuous delivery with a DevSecOps mindset.
  • Coaching, mentoring, and developing engineering talent while recruiting and retaining top performers.
  • Driving large-scale initiatives to deliver modern, AI-enabled products and user experiences.
  • Ensuring secure, scalable, and high-performing solutions are delivered on time.
  • Managing vendor relationships and leading transitions to new services.
  • Reducing technical debt and operational risk while championing user-focused design.
  • Supporting production releases with off-hours availability for critical systems.
  • Contributing to departmental strategy and continuous improvement.

Qualifications & Requirements

Symetra seeks proven leaders with:

  • Bachelor’s or Master’s degree in Computer Science or a related field.
  • 8+ years of experience leading large, cross-functional engineering teams in remote-first environments.
  • Strong background in software engineering, AI, and solutions architecture.
  • Hands-on experience with AWS, microservices, serverless, and distributed systems.
  • Advocacy for CI/CD pipelines and modern engineering practices.
  • Expertise in data management, systems design, and agile methodologies.
  • Excellent communication, leadership, and problem-solving skills.
  • Ability to balance long-term technology investments with short-term business needs.
  • Passion for building shared services and solving complex integration challenges.
  • Comfort in fast-paced, high-visibility environments with ambiguity; some travel required.

All new people leaders must complete a comprehensive leadership development program within the first year, including in-person sessions at Symetra’s Bellevue headquarters (travel and accommodations covered).

Benefits & Perks

Symetra prioritizes employee well-being with tailored programs:

  • Flexible full-time or hybrid telecommuting arrangements for optimal work-life balance.
  • 401(k) plan with immediate vesting and company matching up to 6%.
  • Generous paid time away: vacation, sick time, flex days, and ten paid holidays.
  • Double your community impact through company matching for charitable giving.
  • Comprehensive health benefits at reasonable costs, as praised by employees.

Career Growth

Symetra invests in your professional development through mandatory leadership training, ongoing mentorship, and opportunities to influence strategic direction. Employees like Cindy J. G., Sr. Product Owner, highlight 'innovation, empowerment, and growth opportunities,' while Kerry S., Sr. Systems Analyst, notes the supportive culture where 'failure is seen as integral to the learning process.' Advance your career in insurance technology while enjoying remote flexibility and robust perks.

Why Join Symetra

Join Symetra Financial to lead transformative engineering in Stop Loss insurance, a critical component of employee benefits. Benefit from a culture that values DEI, agile practices, and employee success. With competitive compensation, remote work, and a focus on life insurance, retirement, and benefits administration, Symetra offers stability and innovation in the financial services industry. Employees rave about the work-life balance, incredible benefits, and empowerment to drive sustainable growth.

Role FAQs

Q: Is this role fully remote? Yes, it's a remote-first position across the United States, with some travel for training.

Q: What technologies are prioritized? AWS, microservices, serverless, AI, DevSecOps, CI/CD, and agile methodologies.

Q: What is the salary range? $166,400 - $277,400 base, plus annual bonus eligibility.

Q: Are there leadership development opportunities? Yes, a required program for new leaders, fully covered by Symetra.

Q: How does Symetra support diversity and inclusion? Through team-building aligned with DEI commitments and inclusive hiring practices.

Locations

  • United States (Remote)

Salary

Estimated Salary Range

166,400 - 305,140 USD / yearly

* This is an estimated range based on market data and may vary based on experience and qualifications.

Skills Required

  • AWSintermediate
  • Microservicesintermediate
  • Serverless Architectureintermediate
  • Distributed Systemsintermediate
  • CI/CDintermediate
  • DevSecOpsintermediate
  • AI-Enabled Productsintermediate
  • Agile Methodologiesintermediate
  • Data Managementintermediate
  • Systems Designintermediate

Required Qualifications

  • Bachelor’s or Master’s in Computer Science or related field (experience)
  • 8+ years leading large cross-functional engineering teams in remote-first environments (experience)
  • Strong background in software engineering AI and solutions architecture (experience)
  • Hands-on experience with AWS microservices serverless and distributed systems (experience)
  • Excellent communication leadership and problem-solving skills (experience)

Responsibilities

  • Build and lead an inclusive collaborative engineering team
  • Define technical strategy and partner with stakeholders for business solutions
  • Foster a culture of quality agility and continuous delivery with DevSecOps mindset
  • Coach mentor and develop engineering talent recruit and retain top performers
  • Drive large-scale initiatives for modern AI-enabled products and experiences
  • Ensure secure scalable high-performing solutions delivered on time
  • Manage vendor relationships and lead transitions to new services
  • Reduce technical debt and operational risk champion user-focused design

Benefits

  • general: Flexible full-time or hybrid telecommuting arrangements
  • general: 401(k) plan with immediate vesting and company matching up to 6%
  • general: Paid time away including vacation sick time flex days and ten paid holidays
  • general: Company matching for community giving
  • general: Comprehensive leadership development program with travel covered

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Symetra Financial logo

Director of Engineering, Stop Loss at Symetra Financial - Remote - Apply Now!

Symetra Financial

Director of Engineering, Stop Loss at Symetra Financial - Remote - Apply Now!

full-timePosted: Dec 3, 2025

Job Description

About Symetra Financial

Symetra Financial is a leading insurance and financial services company dedicated to providing innovative solutions in life insurance, retirement planning, and employee benefits. Headquartered in Bellevue, Washington, Symetra serves millions of customers across the United States with a commitment to sustainable growth, employee empowerment, and exceptional customer experiences. The company's Technology and Operations Benefits Division plays a pivotal role in delivering cutting-edge Stop Loss solutions, protecting employers from catastrophic healthcare claims while enabling efficient benefits administration.

Role Overview

As the Director of Engineering, Stop Loss at Symetra Financial, you will spearhead the development of a world-class engineering team in a fully remote capacity. Reporting directly to the VP of Engineering for the Technology and Operations Benefits Division, this leadership role involves setting technical priorities, driving strategic initiatives, and delivering end-to-end technology solutions for Stop Loss insurance products. With a salary range of $166,400 - $277,400 plus annual bonuses, this position offers significant impact on Symetra's growth in the competitive insurance sector.

Strategic Impact

You will shape the technical roadmap for AI-enabled products, microservices architectures on AWS, and scalable distributed systems, ensuring seamless integration with Symetra's broader life insurance and employee benefits platforms.

Key Responsibilities

In this high-visibility role, your responsibilities include:

  • Building and leading an inclusive, collaborative engineering team aligned with Symetra’s values and DEI commitments.
  • Defining technical strategy and partnering with stakeholders to deliver end-to-end business solutions for Stop Loss.
  • Fostering a culture of quality, agility, and continuous delivery with a DevSecOps mindset.
  • Coaching, mentoring, and developing engineering talent while recruiting and retaining top performers.
  • Driving large-scale initiatives to deliver modern, AI-enabled products and user experiences.
  • Ensuring secure, scalable, and high-performing solutions are delivered on time.
  • Managing vendor relationships and leading transitions to new services.
  • Reducing technical debt and operational risk while championing user-focused design.
  • Supporting production releases with off-hours availability for critical systems.
  • Contributing to departmental strategy and continuous improvement.

Qualifications & Requirements

Symetra seeks proven leaders with:

  • Bachelor’s or Master’s degree in Computer Science or a related field.
  • 8+ years of experience leading large, cross-functional engineering teams in remote-first environments.
  • Strong background in software engineering, AI, and solutions architecture.
  • Hands-on experience with AWS, microservices, serverless, and distributed systems.
  • Advocacy for CI/CD pipelines and modern engineering practices.
  • Expertise in data management, systems design, and agile methodologies.
  • Excellent communication, leadership, and problem-solving skills.
  • Ability to balance long-term technology investments with short-term business needs.
  • Passion for building shared services and solving complex integration challenges.
  • Comfort in fast-paced, high-visibility environments with ambiguity; some travel required.

All new people leaders must complete a comprehensive leadership development program within the first year, including in-person sessions at Symetra’s Bellevue headquarters (travel and accommodations covered).

Benefits & Perks

Symetra prioritizes employee well-being with tailored programs:

  • Flexible full-time or hybrid telecommuting arrangements for optimal work-life balance.
  • 401(k) plan with immediate vesting and company matching up to 6%.
  • Generous paid time away: vacation, sick time, flex days, and ten paid holidays.
  • Double your community impact through company matching for charitable giving.
  • Comprehensive health benefits at reasonable costs, as praised by employees.

Career Growth

Symetra invests in your professional development through mandatory leadership training, ongoing mentorship, and opportunities to influence strategic direction. Employees like Cindy J. G., Sr. Product Owner, highlight 'innovation, empowerment, and growth opportunities,' while Kerry S., Sr. Systems Analyst, notes the supportive culture where 'failure is seen as integral to the learning process.' Advance your career in insurance technology while enjoying remote flexibility and robust perks.

Why Join Symetra

Join Symetra Financial to lead transformative engineering in Stop Loss insurance, a critical component of employee benefits. Benefit from a culture that values DEI, agile practices, and employee success. With competitive compensation, remote work, and a focus on life insurance, retirement, and benefits administration, Symetra offers stability and innovation in the financial services industry. Employees rave about the work-life balance, incredible benefits, and empowerment to drive sustainable growth.

Role FAQs

Q: Is this role fully remote? Yes, it's a remote-first position across the United States, with some travel for training.

Q: What technologies are prioritized? AWS, microservices, serverless, AI, DevSecOps, CI/CD, and agile methodologies.

Q: What is the salary range? $166,400 - $277,400 base, plus annual bonus eligibility.

Q: Are there leadership development opportunities? Yes, a required program for new leaders, fully covered by Symetra.

Q: How does Symetra support diversity and inclusion? Through team-building aligned with DEI commitments and inclusive hiring practices.

Locations

  • United States (Remote)

Salary

Estimated Salary Range

166,400 - 305,140 USD / yearly

* This is an estimated range based on market data and may vary based on experience and qualifications.

Skills Required

  • AWSintermediate
  • Microservicesintermediate
  • Serverless Architectureintermediate
  • Distributed Systemsintermediate
  • CI/CDintermediate
  • DevSecOpsintermediate
  • AI-Enabled Productsintermediate
  • Agile Methodologiesintermediate
  • Data Managementintermediate
  • Systems Designintermediate

Required Qualifications

  • Bachelor’s or Master’s in Computer Science or related field (experience)
  • 8+ years leading large cross-functional engineering teams in remote-first environments (experience)
  • Strong background in software engineering AI and solutions architecture (experience)
  • Hands-on experience with AWS microservices serverless and distributed systems (experience)
  • Excellent communication leadership and problem-solving skills (experience)

Responsibilities

  • Build and lead an inclusive collaborative engineering team
  • Define technical strategy and partner with stakeholders for business solutions
  • Foster a culture of quality agility and continuous delivery with DevSecOps mindset
  • Coach mentor and develop engineering talent recruit and retain top performers
  • Drive large-scale initiatives for modern AI-enabled products and experiences
  • Ensure secure scalable high-performing solutions delivered on time
  • Manage vendor relationships and lead transitions to new services
  • Reduce technical debt and operational risk champion user-focused design

Benefits

  • general: Flexible full-time or hybrid telecommuting arrangements
  • general: 401(k) plan with immediate vesting and company matching up to 6%
  • general: Paid time away including vacation sick time flex days and ten paid holidays
  • general: Company matching for community giving
  • general: Comprehensive leadership development program with travel covered

Target Your Resume for "Director of Engineering, Stop Loss at Symetra Financial - Remote - Apply Now!" , Symetra Financial

Get personalized recommendations to optimize your resume specifically for Director of Engineering, Stop Loss at Symetra Financial - Remote - Apply Now!. Takes only 15 seconds!

AI-powered keyword optimization
Skills matching & gap analysis
Experience alignment suggestions

Check Your ATS Score for "Director of Engineering, Stop Loss at Symetra Financial - Remote - Apply Now!" , Symetra Financial

Find out how well your resume matches this job's requirements. Get comprehensive analysis including ATS compatibility, keyword matching, skill gaps, and personalized recommendations.

ATS compatibility check
Keyword optimization analysis
Skill matching & gap identification
Format & readability score

Tags & Categories

Symetra CareersInsurance JobsFinance CareersEngineering LeadershipStop Loss InsuranceRemote Tech JobsDevSecOpsAWS Engineering

Answer 10 quick questions to check your fit for Director of Engineering, Stop Loss at Symetra Financial - Remote - Apply Now! @ Symetra Financial.

Quiz Challenge
10 Questions
~2 Minutes
Instant Score

Related Books and Jobs

No related jobs found at the moment.