Boston, MA
Ironside Insurance Group's Logo of an anchor in a blue square

We’re always looking for great people

We’ve made the Inc. 5000 list of America’s fastest growing companies every year, since 2021!  Do you think you have what it takes to be part of a fast-paced, rapidly growing insurance agency?  Located in downtown Boston’s financial district, Ironside Insurance Group is looking for the best of the best to join us.

At Ironside Insurance Group, we offer a well-rounded benefits package to include:

  • Competitive salary based on experience, plus bonus opportunities
  • Medical benefits to include a family plan with cost share
  • Generous flexible time-off plan
  • Group life insurance
  • Accidental Death & Dismemberment insurance
  • Short-Term and Long-Term Disability
  • 401K with company matching (after 90 days)

 

Current Openings:

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Client Executive – Commercial Lines Middle Market

Job Description:

Ironside is looking for a Commercial Lines Account Executive to help lead the client experience for a growing book of Mid-Market Commercial Clients. This is a senior, client-facing role for someone who can manage strategy, drive renewals, support producers, work with carriers, and help elevate the overall team.

The ideal candidate likes to be in the middle of the action: solving problems, advising clients, organizing strategy, helping producers win, pushing carriers, and making sure clients feel like they are in good hands. The right person will be polished but not stiff, technical but not robotic, and organized enough to manage complexity inside a fast-growing company.

While this opportunity is hybrid, the ideal candidate must be based in Massachusetts, Rhode Island or Connecticut as travel to attend meetings in and around Boston will be occasionally required.

Core Responsibilities:

  • Collaborate on Middle Market service strategy and client experience for largest, VIP clients.
  • Lead renewal planning, including exposure review, timeline management, carrier strategy, proposal development, and client presentations.
  • Work with producers to retain and grow key accounts, while providing leadership in industry specialty education and growth.
  • Review coverage programs and identify gaps, improvements, and account-rounding opportunities.
  • Coordinate with client managers to ensure service work, documentation, certificates, endorsements, audits, and policy checking are handled accurately.
  • Build strong relationships with carriers and advocate for clients during marketing, underwriting, claims, and renewal negotiations.
  • Help manage complex service issues, coverage questions, claims concerns, billing problems, and client escalations.
  • Support and mentor internal team members as Ironside continues building a polished, proactive commercial service model.

Required Skills:

  • At least five years direct commercial insurance experience in an independent agency or brokerage environment, managing larger, more complex commercial accounts.
  • Property & Casualty license required, specialty designations and CPCU or CIC preferred.
  • Strong technical knowledge of property, general liability, commercial auto, umbrella/excess, workers compensation, builders risk, professional liability, management liability, and related coverages.
  • Strong understanding of carrier appetites, submission quality, underwriting questions, and coverage negotiation.
  • Experience with real estate, construction, advanced industries, life science and loss sensitive & captive programs a plus.
  • Ability to lead renewal strategy, not just react to renewal terms.
  • Confidence communicating with business owners, real estate operators, developers, controllers, CFOs, underwriters, and producers.
Apply Online
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Client Manager – Commercial Lines Middle Market

Job Description:

Ironside is looking for an experienced Commercial Lines Account Manager to support a growing book of Mid-Market commercial clients. This role is ideal for someone who knows commercial insurance, takes pride in clean service work, and wants to be part of a fast-moving agency with a strong reputation and a great culture.

The ideal candidate will be organized, responsive, detail-oriented, and confident enough to own your work. We move quickly and value people who bring solutions, communicate clearly, and care about doing things the right way.

While this opportunity is hybrid, the ideal candidate must be based in Massachusetts, Rhode Island or Connecticut as travel to attend meetings in and around Boston will be occasionally required.  

Core Responsibilities:

  • Manage day-to-day service for an assigned commercial book, including client questions, policy changes, certificates, endorsements, audits, billing issues, and general account support.
  • Coordinate renewal workflows by gathering updated information, preparing applications, reviewing renewal terms, tracking timelines, and keeping producers and clients informed.
  • Review policies, endorsements, proposals, binders, applications, and carrier documents for accuracy.
  • Support remarketing efforts by organizing submissions, exposure data, carrier correspondence, and proposal information.
  • Communicate directly with clients, carriers, producers, and internal team members in a professional and helpful way.
  • Maintain accurate documentation in the agency management system and help improve workflows as the agency continues to scale.

Required Skills:

  • At least two years direct experience as a middle market commercial lines account manager in an independent agency environment.
  • Property & Casualty license required
  • Strong knowledge of property, general liability, commercial auto, umbrella/excess, workers compensation, and related coverages.
  • Experience supporting larger or more complex commercial accounts preferred.
  • Experience with real estate, construction, advanced industries, life science and non-profits is a plus.
  • Ability to manage competing deadlines without letting details slip.
  • Clear communication skills and a client-first mindset
Apply Online
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Commercial Lines Account Manager / CSR

Job Description:

Within this role you will be a key point of contact for our policyholders. This will include but not be limited to, answering phones, and responding to e-mails to address customer questions & concerns. You will also be supporting Ironside Insurance Group’s goal of providing our clients with appropriate levels of protection through an array of available insurance products.

As a Commercial Lines Account Manager, you will perform a full range of consultative activities to ensure a positive customer experience. This role is available as an in-office (Boston, MA) or fully remote, work from home position only for candidates living in the following states:

  • Massachusetts
  • Connecticut
  • Florida
  • New Hampshire
  • North Carolina
  • Pennsylvania
  • Rhode Island

 Core Responsibilities:

  • Assist prospects and clients with gathering information, completing applications and working closely with underwriters to determine appropriate policy solutions, pricing and product eligibility.
  • Provide exceptional customer service and follow-up by promptly responding to client calls and e-mails.
  • Aid in customer retention via multiple methods of contact and annual insurance policy reviews.
  • Proactively identify and process policy transactions and explain any resulting customer impact.
  • Assist with policy billing, including invoicing and tracking of agency billed payments.
  • Manage and utilize your time effectively to ensure the department meets required service levels for improved customer satisfaction results.
  • Cross-selling additional insurance solutions as appropriate.

Required Skills:

  • Associate’s degree in business-related field or minimum 2-year equivalent training/work experience
  • Prior customer service experience is a must.
  • Prior commercial lines insurance experience is required.
  • Excellent communication and interpersonal skills combined with the ability to work both independently and as part of a team.
  • Currently holds and maintains required insurance licenses.
  • Ability to both prioritize, as well as review, record and organize data from a variety of sources.

Preferred Skills:

  • Bachelor’s degree
  • Working familiarity of Agency Management Systems and MA Registry of Motor Vehicles System a plus.
  • Fluency in Spanish also a plus.
Apply Online
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Commercial Lines Inside Sales / Licensed Agent

Job Description:

At Ironside, we differentiate roles that are aligned with new business vs. renewal and remarketing.  The ideal candidate for this role will be responsible for providing superior service specifically to our new business commercial insurance policyholders, who come to us directly from our internal group of producers.  You will be advocating Ironside Insurance Group’s goal of providing our clients with appropriate levels of protection through an array of affordable commercial insurance products.

While this role is available as a fully remote, work from home position, we are only considering candidates living in the following states: Massachusetts, New Hampshire, Connecticut, and Rhode Island.

Core Responsibilities:

  • Quotes and binds new business policies, quoting directly on multiple Carrier rating platforms, completing new business applications for the surplus lines market, working closely with our producers and carrier underwriters to assess risks and determine pricing and product eligibility.
  • Provides exceptional customer service and follow-up by responding to client calls and e-mails in a prompt manner.
  • Aid in customer retention via multiple methods of contact and annual insurance policy reviews.
  • Proactively identifies and process policy transactions and explains any resulting customer impact.
  • Assists with policy billing, including invoicing and tracking of agency billed payments.
  • Manage and utilize your time effectively to ensure the department meets required service levels for improved customer satisfaction results.
  • Cross-selling additional insurance solutions as appropriate.

Required Skills:

  • Minimum of three years in an independent agency environment with a focus on commercial lines.
  • Experience with excess and surplus lines
  • Currently holds and maintains required insurance licenses.
  • Acquire and maintain a Massachusetts non-resident license if not already licensed in Massachusetts.
  • Excellent communication and interpersonal skills combined with the ability to work both independently and as part of a team.
  • Ability to both prioritize, as well as review, record and organize data from a variety of sources.

Preferred Skills:

  • Well versed in the intricacies of Massachusetts commercial lines insurance.
  • Working familiarity of Agency Management Systems (QQ is a plus)
  • Active P&C Insurance licensed in the State of Massachusetts 
  • Familiarity with the Massachusetts Registry of Motor Vehicles (RMV) system
  • Fluent in Spanish
Apply Online
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Outside Sales / Producer

 Job Description:

Ironside Insurance Group is seeking a dynamic, results-oriented individual to join our rapidly growing Agency as an Outside Sales Producer. This individual should possess strong relationship-driven attributes, as new business development via referrals from professional networking partners will be your primary responsibility. This position is the key point of contact for our policyholders, providing them with the best level of protection through Ironside Insurance Group’s wide array of insurance carriers and products.

Candidate Qualifications:

  • The ideal candidate will be based in Massachusetts and can work out of our downtown Boston office when necessary
  • Possess a solid network of strong referral sources
  • Associates degree in a business-related field or minimum 2 years equivalent direct sales experience
  • Prior insurance experience with a basic knowledge of industry principles and products
  • Hold or acquire and maintain required insurance licenses
  • Excellent communication and interpersonal skills combined with the ability to work independently and as part of a team
  • Ability to review, prioritize, record, and organize data from a variety of sources

Core Responsibilities:

  • Generate leads, prospects, and referrals through various channels
  • Identify opportunities, contacting same via outbound calls and emails
  • Quote new business across all carriers, asking for and closing the sale of additional products and services
    • Advising and educating prospects/clients on coverage, options, and features
    • Accurate input of information to ensure correct risk assessment and premium calculation
    • Field underwrites to ensure binding types of risk that fit within agency appetite

Preferred Skills:

  • Bachelor’s degree
  • Active P&C Insurance license in the State of Massachusetts
  • Experience with carriers in the Massachusetts and New England area
  • While not required, a working familiarity of Agency Management Systems and MA Registry of Motor Vehicles System a plus.
  • Fluency in Spanish also a plus.
Apply Online
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Personal Lines Account Manager / CSR

Job Description:

Within this role you will be a key point of contact for our policyholders. This will include but not be limited to, answering phones, and responding to e-mails to address customer questions & concerns. You will also be supporting Ironside Insurance Group’s goal of providing our clients with appropriate levels of protection through an array of available insurance products.

As a Personal Lines Account Manager, you will perform a full range of consultative activities to ensure a positive customer experience. This role is available as an in-office (Boston, MA) or fully remote, work from home position only for candidates living in the following states:

  • Massachusetts
  • Connecticut
  • Florida
  • New Hampshire
  • North Carolina
  • Pennsylvania
  • Rhode Island

Core Responsibilities:

  • Provide exceptional customer service by promptly responding to inbound calls and e-mails.
  • Aid in customer retention via multiple methods of contact and annual insurance policy reviews.
  • Proactively identify and process policy transactions and explain any resulting customer impact.
  • Assist with policy billing issues, including evaluating and making decisions regarding payment plan exceptions and any applicable fees, including initiating alternate payment arrangements.
  • Cross-sell additional insurance solutions as appropriate, as well as assist in policy rewrites/remarkets.
  • Process personal lines E&S policy renewals and collect payment for agency bill accounts.
  • Manage and utilize your time effectively to ensure the department meets required service levels for improved customer satisfaction results.

 Required Skills:

  • Associate degree in business-related field or minimum 2-year equivalent training/work experience.
  • Prior customer service experience is a must.
  • Prior personal lines (auto & home) insurance experience with a basic knowledge of industry principles and products.
  • Active Property & Casualty Insurance licensed
  • Comfortable with identifying opportunities, asking for and closing the sale of additional insurance products & services.
  • Excellent communication and interpersonal skills combined with the ability to work independently and as part of a team.
  • Ability to both prioritize, as well as review, record and organize data from a variety of sources.
  • Background check upon job offer (if applicable) 

Preferred Skills:

  • Bachelor’s degree
  • While not required, a working familiarity of Agency Management Systems and MA Registry of Motor Vehicles System a plus.
  • Fluency in Spanish also a plus.
Apply Online
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Personal Lines Inside Sales / Licensed Agent

 Job Description:

Within this role you will be the initial point of contact for our future policyholders. Quoting new business prospects for predominantly personal lines and occasional small commercial lines policies. You will also be supporting Ironside Insurance Group’s goal of providing our clients with appropriate levels of protection through an array of affordable insurance products.

As a Personal Lines Licensed Agent, you will perform a full range of consultative activities to ensure a positive customer experience. This role is available as an in-office (Boston, MA) or fully remote, work from home position only for candidates living in the following states:

  • Massachusetts
  • Connecticut
  • Florida
  • New Hampshire
  • North Carolina
  • Pennsylvania
  • Rhode Island

Core Responsibilities:

  • Manage incoming leads provided by our producers and internal agency referrals
  • Make outbound calls & e-mails to these prospective clients
  • Quote new business across all carriers
  • Advise and educate prospects/clients on coverage, options and features
  • Input accurate information to ensure correct risk assessment and premium calculation
  • Field underwrites to ensure only binding appropriate types of risk for agency appetite
  • Track leads and progress throughout the quoting process and maintain appropriate follow-up
  • Cross-sell additional lines of business
  • Obtain referrals

Required Skills:

  • Associate degree in business-related field or minimum 2-year equivalent training/work experience.
  • Prior sales experience is a must.
  • Prior personal lines (auto & home) insurance experience with a basic knowledge of coverage, industry principles and products.
  • Comfortable with identifying opportunities, asking for and closing the sale of additional insurance products & services.
  • Excellent communication and interpersonal skills combined with the ability to work independently and as part of a team.
  • Active P&C Insurance licensed
  • Ability to both prioritize, as well as review, record and organize data from a variety of sources.

Preferred Skills:

  • Bachelor’s degree
  • Commercial lines insurance knowledge and experience
  • Working familiarity of Agency Management Systems, Single Point / Boston Software and MA Registry of Motor Vehicles system a plus.
  • Fluency in Spanish also a plus.
Apply Online