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Plymouth Rock Assurance

Provides auto, home, renters, condo insurance

Lead Network Engineer

Full-Time
No salary listed
Senior
Bachelor's, Master's
Boston, MA, USA
In Person
IT OperationsNetwork Engineering & Administration

About the job

Requirements
  • A Bachelor of Science or Master of Science degree is required; Computer Science or Electrical Engineering is preferred, and an advanced degree is a plus.
  • A minimum Cisco Certified Network Professional certification is required.
  • Demonstrated experience with Cisco network product suites, including ISR routers, ASR 1001 routers, Nexus 9000-series switches, Catalyst switches, and ASA 5500-series firewalls.
  • Familiarity with Cisco wireless controllers and access points.
  • At least five years of routing and switching design and implementation experience with Cisco hardware and software, including Layer 1, Layer 2, and Layer 3 design principles.
  • Experience with the OSPF routing protocol.
  • At least five years of hands-on networking experience in a mission-critical production environment supporting more than 750 servers using Microsoft Windows and Linux technologies.
  • Knowledge of RADIUS server and authentication.
  • Experience with Cisco and Juniper firewalls, including hardware and software upgrades, migrations, rule additions, network address translations, routing, and troubleshooting.
  • Knowledge of load-balancing technologies, including installation, software upgrades, virtual IP creation, error handling, and Layer 4 concepts.
  • Experience designing and troubleshooting spanning tree, routing protocols, IP network address subnetting, and network address translations.
  • Hands-on experience with enterprise-grade network monitoring systems.
  • Experience with WAN and circuit technologies, including Ethernet Private Line and T1, and WAN routing protocols such as MPLS and BGP.
  • Ability to perform packet-level analysis with network protocol analyzer software tools.
  • Experience with Internet and networking technologies including DNS, DHCP, SMTP, SNMP, and NTP.
  • Strong oral and written communication skills.
Responsibilities
  • Maintain a complex wired and wireless network infrastructure supporting distributed business applications, e-commerce, voice over IP, and video.
  • Design, maintain, and manage an enterprise-wide network infrastructure hierarchy.
  • Develop and document system standards for computer and network devices.
  • Create and update networking-environment documentation, including equipment inventories and vendor-activity documentation.
  • Develop implementation plans, test plans, and project timelines for network projects.
  • Maintain knowledge of the network environment in conjunction with business applications and systems.
  • Actively monitor LAN and WAN traffic and capacity using available software reporting tools.
  • Evaluate network performance and utilization trends proactively.
  • Troubleshoot and analyze network communication failures and congestion.
  • Help resolve production problems in a large-scale environment affected by network issues.
  • Escalate network carrier issues as necessary.
  • Generate vendor quotes for network hardware, software, and support contracts.
  • Ensure the development and use of a preventive maintenance program supporting a 99.9% availability objective.
  • Respond to system problems on a 24-by-7 basis and participate in an on-call rotation.
  • Attend seminars and training to maintain proficiency with current network technologies.
  • Assist the telephony team with Avaya Communications Manager voice support and perform other assigned job-related duties.
Desired Qualifications
  • Experience with Cisco and Juniper firewalls is desired.
  • Experience with Netscaler is desired, and Radware App Director experience is a plus.
  • Experience with SolarWinds is a plus.
  • Expertise with quality-of-service network prioritization is desired.

About the company

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Plymouth Rock Assurance

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Plymouth Rock Assurance sells auto, home, renters, and condo insurance in the Northeast through employees and independent agents. Policies are underwritten and supported by claims and service teams with offices in Woodbridge, NJ and Boston, MA serving NJ, NY, NH, MA, CT, and PA. Customers access coverage through an agent network and in-house teams who match needs with appropriate policy options. The company differentiates itself with strong community involvement, recognized workplace culture, and a focus on reliable, high-quality service for families and communities.

Company Size

1,001-5,000

Company Stage

N/A

Total Funding

N/A

Headquarters

Boston, Massachusetts

Founded

1983

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Simplify Jobs

Simplify's Take

What believers are saying

  • AM Best upgraded outlooks positive on March 3, 2026, signaling improving credit profile.
  • July 2026 hires in data, claims, and service target faster underwriting and lower expense ratios.
  • September 2026 leadership renewal and ChatGPT quoting should deepen distribution and conversion through 2027.

What critics are saying

  • Regional concentration in six Northeast states exposes earnings to local catastrophe spikes.
  • Independent-agency reliance makes Plymouth Rock vulnerable if agents shift volume to Progressive.
  • Leadership turnover across 2026 signals execution risk while Taylor, McPhail, and Seaborn reset priorities.

What makes Plymouth Rock Assurance unique

  • July 2026: first U.S. insurer offering home quotes inside ChatGPT.
  • Northeast specialization across six states supports dense agent relationships and local brand recall.
  • September 2026: Chris Taylor returns with Hanover agency-channel and personal-lines operating experience.

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Company News

Plymouth Rock Assurance
Sep 29th, 2026
Plymouth Rock Home Assurance names Jared Stuckey VP of Customer Service and Underwriting.

Plymouth Rock Home Assurance names Jared Stuckey VP of Customer Service and Underwriting. BOSTON - Sept. 29, 2026 - Plymouth Rock Home Assurance Corporation has named Jared Stuckey Vice President of Customer Service and Underwriting, effective immediately. Stuckey led underwriting strategy and managed personal and commercial products for Plymouth Rock's Independent Agent auto business. He will now oversee both customer service and underwriting for the Home Insurance group. "Jared gets things done," said Bill Martin, President and CEO of Plymouth Rock Home Assurance Corporation, announcing Jared's promotion. "In 20-plus years across nearly every insurer function, he's built a track record of results. Our officers universally identified him as our highest potential manager. We are thrilled to have him here on the Home team." Before joining Plymouth Rock, Stuckey spent 16 years at Liberty Mutual, where he held a variety of senior roles in product management and customer experience. He is a graduate of Goshen College and holds an MBA from The Wharton School. "I'm excited for the opportunity to use my experience in customer experience and home insurance at a time when so much is evolving," said Stuckey. "The opportunities to innovate and enhance the customer experience are tremendous. Our agents are going to love the changes to come." About Plymouth Rock Plymouth Rock was established to offer its customers a higher level of service and a more innovative set of products and features than they would expect from an insurance company. Plymouth Rock's innovative approach puts customers' convenience and satisfaction first, giving them the choice to do business the way they want - online, using a mobile device, by phone or with one of Plymouth Rock's agents. Plymouth Rock Assurance(R) and Plymouth Rock(R) are brand names and service marks used by separate underwriting, managed insurance, and management companies that offer property and casualty insurance in multiple states pursuant to licensing arrangements. Taken together, the companies write and manage $2.5 billion in auto and home insurance premiums across Connecticut, Massachusetts, New Hampshire, New Jersey, New York and Pennsylvania. Each underwriting and managed insurance company is a separate legal entity that is financially responsible only for its own insurance products. Actual coverage is subject to the language of the policy as issued. You can learn more about Plymouth Rock Company by visiting plymouthrock.com.

GlobeNewswire
Sep 23rd, 2026
Plymouth Rock Assurance Corporation names Chris Taylor President and Chief Executive Officer.

Plymouth Rock Assurance Corporation names Chris Taylor President and Chief Executive Officer. Industry veteran returns to Plymouth Rock to lead its Independent Agency Group's next chapter of growth. September 23, 2026 11:00 ET | Source: Plymouth Rock BOSTON, Sept. 23, 2026 (GLOBE NEWSWIRE) - Plymouth Rock Assurance Corporation today announced that it has named Chris Taylor as President and Chief Executive Officer. He will lead Plymouth Rock's Independent Agency Group, effective Monday, October 12, 2026. The appointment reflects Plymouth Rock's continued investment in the independent agency channel, backed by Taylor's decade-plus track record of personal lines insurance leadership and deep experience in the agency channel. "We are thrilled to welcome Chris into his new role," said Jim Stone, Founder and Chairman of the Plymouth Rock Group. "Independent agents have always been central to Plymouth Rock's business, and Chris understands firsthand what it takes to build the strong, lasting partnerships that our business requires." Taylor brings personal lines leadership experience to the role, most recently as Vice President and Head of State Management at The Hanover Insurance Group, where he had P&L responsibility for auto, home, and ancillary lines. In that role, he built and strengthened independent agency relationships, expanded the company's portfolio, and led profitable countrywide growth. He helped bring several new products to market, including a successful high-net-worth offering. Before joining The Hanover, Taylor worked at Plymouth Rock, where he helped lead the company's entry into the New York and Pennsylvania auto insurance markets through the independent agency channel. He began his insurance career at The Hartford in Product Management. "Independent agents have been central to my career and to my view of how insurance is best delivered," said Taylor. "Agents know their clients, understand their communities and bring a level of personal guidance that is incredibly valuable to insurance shoppers. I'm excited to return to Plymouth Rock to work alongside a strong team and our agent partners, building on that strength and creating new opportunities to grow together." Taylor holds a BS in Chemistry from the University of Connecticut, an MS in Chemistry from the University of Illinois, and an MBA from the University of Connecticut. About Plymouth Rock Plymouth Rock was established to offer its customers a higher level of service and a more innovative set of products and features than they would expect from an insurance company. Plymouth Rock's innovative approach puts customers' convenience and satisfaction first, giving them the choice to do business the way they want - online, using a mobile device, by phone or with one of Plymouth Rock's agents. Plymouth Rock Assurance(R) and Plymouth Rock(R) are brand names and service marks used by separate underwriting, managed insurance, and management companies that offer property and casualty insurance in multiple states pursuant to licensing arrangements. Taken together, the companies write and manage $2.5 billion in auto and home insurance premiums across Connecticut, Massachusetts, New Hampshire, New Jersey, New York and Pennsylvania. Each underwriting and managed insurance company is a separate legal entity that is financially responsible only for its own insurance products. Actual coverage is subject to the language of the policy as issued. You can learn more about us by visiting plymouthrock.com.

Associated Press
Jul 30th, 2026
Plymouth Rock becomes first US insurer to offer home insurance quotes through ChatGPT

Plymouth Rock Home Assurance has become the first US insurer to offer home insurance quotes through ChatGPT. The company launched a plugin enabling homeowners to receive real-time quotes directly within the AI platform, creating what it describes as a faster and more accessible way to shop for coverage. "We've spent a decade offering the fastest, easiest way to buy home insurance," said Bill Martin, president and CEO of Plymouth Rock Home Assurance. "Today, customers can get answers instantly through ChatGPT." The plugin is available to homeowners across all states where Plymouth Rock operates, including Massachusetts, New Jersey, Pennsylvania, Connecticut, New York and New Hampshire. The Plymouth Rock group of companies writes and manages $2.5 billion in auto and home insurance premiums across these states.

II Reporter
Jul 13th, 2026
Plymouth Rock names three executives.

Plymouth Rock names three executives. The appointments strengthen leadership across enterprise data, claims and customer service for the Northeast personal lines insurer. Anthony R. O'Donnell // July 13, 2026 (Image credit: IIR/Gemini.) Plymouth Rock Assurance (Boston) has appointed Gavin McPhail VP and Chief Data Officer; Cornelius Young VP and Chief Claims Officer, Independent Agency Group; and Lindsay Mustard VP, Customer Service, Independent Agency Group. The appointments are intended to support Plymouth Rock's work in innovation, operational excellence and customer experience, according to a company statement. "These appointments reflect Plymouth Rock's ongoing investment in the leadership needed to drive our business forward," comments Andrew McElwee, President and COO, The Plymouth Rock Company. "Gavin, Cornelius, and Lindsay each bring deep industry experience and proven track records of leading transformation, improving customer outcomes, and delivering business results. Their leadership will help us continue to enhance the value we provide to our customers, agents, and partners." McPhail to Lead Enterprise Data Strategy As VP and Chief Data Officer, McPhail will lead Plymouth Rock's enterprise data strategy, including use of data, analytics, automation and AI to support profitable growth, operational excellence and customer experience. McPhail brings more than 20 years of leadership experience. He previously served as Executive VP and General Manager of Risk Intelligence at Fusable, where he led the company's insurance risk intelligence data-as-a-service business. Plymouth Rock says his experience includes enterprise-scale growth initiatives, data and analytics modernization, acquisition integration and operational transformation for Fortune 100 organizations. Young to Lead Independent Agency Claims As VP and Chief Claims Officer, Independent Agency Group, Young will lead the group's claims organization, with responsibility for operational excellence, claims customer experience and adoption of data, analytics and AI across the claims lifecycle. Young previously served as Chief Insurance Officer at Cambridge Mobile Telematics, where he led insurance strategy and helped develop AI-powered telematics, crash detection, digital claims workflow and risk-insight capabilities. Before that, he spent more than 13 years at Liberty Mutual Insurance in leadership roles across claims, strategy and analytics. Mustard to Lead Customer Service As VP, Customer Service, Independent Agency Group, Mustard will lead customer service operations across service center operations, underwriting, agency and sales operations, compliance, project management and customer experience. Mustard most recently held senior leadership roles at Jenius Bank, including Head of Strategy and Head of Product Engagement. She previously held Senior VP roles at Citizens Bank and earlier worked as a Project Leader at Boston Consulting Group. Plymouth Rock provides auto and home insurance across Connecticut, Massachusetts, New Hampshire, New Jersey, New York and Pennsylvania. The company says its underwriting, managed insurance and management companies write and manage $2.5 billion in auto and home insurance premium.

Plymouth Rock Assurance
Jul 13th, 2026
Plymouth Rock Assurance strengthens leadership team with strategic appointments.

Plymouth Rock Assurance strengthens leadership team with strategic appointments. BOSTON - July 13, 2026 - Plymouth Rock Assurance, a leading auto and home insurance provider in the Northeast, announced the appointments of three experienced insurance and financial services leaders to key executive roles, reinforcing Plymouth Rock's commitment to innovation, operational excellence, and exceptional customer experiences. Plymouth Rock has recently appointed Gavin McPhail as Vice President and Chief Data Officer; Cornelius Young as Vice President and Chief Claims Officer, Independent Agency Group; and Lindsay Mustard as Vice President, Customer Service, Independent Agency Group. "These appointments reflect Plymouth Rock's ongoing investment in the leadership needed to drive our business forward," said Andrew McElwee, President and Chief Operating Officer at The Plymouth Rock Company. "Gavin, Cornelius, and Lindsay each bring deep industry experience and proven track records of leading transformation, improving customer outcomes, and delivering business results. Their leadership will help us continue to enhance the value we provide to our customers, agents, and partners." Gavin McPhail Named Vice President and Chief Data Officer As Vice President and Chief Data Officer, McPhail will lead Plymouth Rock's enterprise data strategy, advancing Plymouth Rock's use of data, analytics, automation, and artificial intelligence (AI) to drive profitable growth, operational excellence, and exceptional customer experiences. He will partner with business and technology leaders to strengthen data as a strategic asset, accelerating innovation and delivering measurable value across underwriting, claims, risk management, and customer operations. McPhail is an accomplished executive with more than 20 years of leadership experience. He has a proven track record of leading enterprise-scale growth initiatives, modernizing data and analytics capabilities, integrating acquisitions, and delivering operational transformation for Fortune 100 organizations. Prior to joining Plymouth Rock, McPhail served as Executive Vice President and General Manager of Risk Intelligence at Fusable, where he led the company's insurance risk intelligence data-as-a-service business. He earned an MBA from the Haas School of Business at the University of California, Berkeley; a Master of Science in Information & Telecommunication Systems from The Johns Hopkins University; and a Bachelor of Science in Finance from the University of Maryland, College Park. Cornelius Young Named Vice President and Chief Claims Officer, Independent Agency Group As Chief Claims Officer, Young will lead the Independent Agency Group's claims organization, with responsibility for driving operational excellence, enhancing the claims customer experience, and accelerating the adoption of data, analytics, and AI across the claims lifecycle. Young brings more than two decades of insurance leadership experience spanning claims operations, analytics, product innovation, and technology transformation. Throughout his career, he has led initiatives focused on improving claim outcomes, creating exceptional customer experiences and leveraging data to drive results. Prior to joining Plymouth Rock, he served as the Chief Insurance Officer at Cambridge Mobile Telematics, where he led insurance strategy and developed AI-powered solutions that transformed how insurers leverage telematics, crash detection, digital claims workflows, and risk insights. Prior to Cambridge Mobile Telematics, Young spent more than 13 years at Liberty Mutual Insurance, where he held a variety of leadership positions across claims, strategy and analytics. During his tenure, he led claims transformation initiatives, including efforts focused on fraud detection, predictive analytics, operational efficiency, and policyholder experience improvements. Young holds an MBA from the Boston College Carroll School of Management and a Bachelor of Science in Business Administration from Northeastern University. Lindsay Mustard Named Vice President, Customer Service, Independent Agency Group As Vice President, Customer Service, Mustard will lead the Independent Agency Group's Customer Service organization, with responsibility spanning all customer service operations including Service Center Operations, Underwriting, Agency and Sales Operations, Compliance, Project Management, and Customer Experience. She will focus on elevating service delivery, driving operational efficiency, and advancing customer-centric initiatives across the organization. Mustard brings deep experience working at the intersection of customer experience, digital innovation, and operational excellence. Most recently, she held senior leadership roles at Jenius Bank, including Head of Strategy and Head of Product Engagement. Prior to Jenius, she held Senior Vice President roles at Citizens Bank, and earlier in her career was a Project Leader at The Boston Consulting Group. Mustard holds an MBA from the Tuck School of Business at Dartmouth College and a Bachelor of Science in Mathematics from Trinity College. About Plymouth Rock Plymouth Rock was established to offer its customers a higher level of service and a more innovative set of products and features than they would expect from an insurance company. Plymouth Rock's innovative approach puts customers' convenience and satisfaction first, giving them the choice to do business the way they want - online, using a mobile device, by phone or with one of Plymouth Rock's agents. Plymouth Rock Assurance(R) and Plymouth Rock(R) are brand names and service marks used by separate underwriting, managed insurance, and management companies that offer property and casualty insurance in multiple states pursuant to licensing arrangements. Taken together, the companies write and manage $2.5 billion in auto and home insurance premiums across Connecticut, Massachusetts, New Hampshire, New Jersey, New York and Pennsylvania. Each underwriting and managed insurance company is a separate legal entity that is financially responsible only for its own insurance products. Actual coverage is subject to the language of the policy as issued. You can learn more about Plymouth Rock Company by visiting plymouthrock.com.