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Remote Chief Underwriter Jobs (NOW HIRING)

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Underwriter Portfolio Middle Market

Worcester, MA · On-site +1

This position reports to the Chief Operating Officer of Middle Market . This is a full time, exempt ... Position is eligible for Hybrid or Remote work arrangement. POSITION OVERVIEW: The Sr. Portfolio ...

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Underwriter Portfolio Middle Market

Worcester, MA · On-site +1

This position reports to the Chief Operating Officer of Middle Market . This is a full time, exempt ... Position is eligible for Hybrid or Remote work arrangement. POSITION OVERVIEW: The Sr. Portfolio ...

Ledgebrook

Inland Marine Underwriter

Ledgebrook is a fully-remote US based company backed by top venture investors including Brand ... Act as the internal CEO of your book, collaborating with leadership to refine appetite, respond to ...

NANO BANC

Chief Credit Officer

Irvine, CA · On-site +1

$300K - $375K/yr

This role focuses on managing all credit functions, including underwriting, loan reviews, credit ... This position is primarily office-based, with no regular remote work. Some travel may be required ...

Adlib Software

Account Executive, Insurance

CA · Remote

$125K - $145K/yr

... Remote, North America. Approximately 30% travel. Target start date September 15, 2026 Base salary ... Reach and hold the attention of Chief Claims Officers, Chief Underwriting Officers, COOs, CIOs and ...

Finalsite

Chief Compliance Officer

Glastonbury, CT · On-site +1

LOCATION 100% Remote - Anywhere within the US RESPONSIBILITIES • Owns and leads Finalsite ... and underwriting, KYC/KYB, AML, sanctions screening, transaction monitoring, fraud controls ...

Finalsite

Chief Compliance Officer

Glastonbury, CT · Remote

LOCATION 100% Remote - Anywhere within the US RESPONSIBILITIES ● Owns and leads Finalsite ... and underwriting, KYC/KYB, AML, sanctions screening, transaction monitoring, fraud controls ...

New

Phsorg

Remote: Open to applicants in the United States, excluding CA, IL, ND, NY, OH, WA, and WY. Hybrid ... C. Product Development, Underwriting and pricing Partner with product, underwriting, and finance ...

Tihinsurance

Chief Title Officer

Phoenix, AZ · On-site +1

Work closely with counsel and agency underwriting personnel on complex underwriting matters ... Any KV office Nationwide or Remote Benefits: * Health insurance * Dental insurance * Vision ...

Tucker's Farm

Be Seen First

CEO of ~$40M Equity PE-backed Commercial Services Roll Up

New York, NY · Remote

$300K - $350K/yr

Remote initially, Hybrid TBD Start date: Immediately Annual Compensation: details included below ... At least 4+ years of Investing experience including sourcing, underwriting, deal execution, and ...

New

Tucker's Farm

Be Seen First

CEO of ~$40M Equity PE-backed Commercial Services Roll Up

New York, NY · Remote

$300K - $350K/yr

Remote initially, Hybrid TBD Start date: Immediately Annual Compensation: details included below ... At least 4+ years of Investing experience including sourcing, underwriting, deal execution, and ...

New

AIG

Global Technical Engineering Specialist - Property

$150K - $190K/yr

... Chief Underwriting Office, and Risk Engineering Leadership to determine AIG's stance on the topic ... S. locations, including Remote, along with Toronto, Canada. The base salary range for this position ...

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As of Aug 18, 2026, the average yearly pay for remote chief underwriter in the United States is $192,837.00, according to ZipRecruiter salary data. Most workers in this role earn between $132,500.00 and $257,000.00 per year, depending on experience, location, and employer.
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Infographic showing various Remote Chief Underwriter job openings in the United States as of August 2026, with employment types broken down into 1% As Needed, 92% Full Time, 6% Part Time, and 1% Contract. Highlights an 91% Physical, 3% Hybrid, and 6% Remote job distribution, with an average salary of $192,837 per year, or $92.7 per hour.

Senior Underwriter - Medical Stop Loss - Remote

Jencap

Phoenix, AZ • On-site, Remote

$97K - $115K/yr

Full-time

Re-posted 4 days ago

Job description

Why Jencap? We are one of the largest wholesale insurance intermediaries in the United States with expertise in wholesale brokerage, binding authority, and program management. The common thread woven throughout our success story is our collaborative and driven team of people. Our teams are empowered and work together to find solutions. We have a passion culture – with teamwork, collaboration and a focus on growing individuals and giving them the tools & development opportunities to have a successful career.

About the Company:

Jencap A&H is a leading provider of innovative insurance solutions for self-funded employers and their partners. We are committed to delivering exceptional value, service, and expertise to our clients. As part of our ongoing growth, we are seeking a highly experienced Senior Underwriter specializing in stop loss insurance to join our dynamic team.

The Senior Underwriter – Medical Stop Loss is responsible for the evaluation, risk assessment, pricing, and underwriting of stop loss insurance for self‑funded employer groups. The ideal candidate brings strong stop loss market expertise, sound analytical judgment, and the ability to develop trusted relationships with brokers, consultants, TPAs, and internal stakeholders.

This role is ideally suited for candidates located in the Phoenix, AZ area working remotely; however, highly qualified candidates located elsewhere in the U.S. will be considered for a fully remote arrangement.

Key Responsibilities:

  • Underwrite new and renewal stop loss business in accordance with underwriting guidelines, risk appetite, and profitability targets
  • Analyze complex self‑funded employer group data, including claims experience, demographics, plan design, and funding structures
  • Partner closely with the Chief Underwriting Officer to develop customized underwriting and pricing solutions
  • Establish and maintain strong relationships with brokers, consultants, TPAs, and clients; participate in finalist presentations and renewal discussions as needed
  • Monitor portfolio performance and support profitable growth initiatives
  • Contribute to underwriting process improvements, product enhancements, and best‑practice initiatives

Qualifications:

  • Bachelor's degree in business, finance, actuarial science, or a related field required; advanced degree or professional designations (e.g., CEBS, FLMI, ASA) preferred
  • 5–10 years of experience underwriting stop loss insurance for self‑funded employer groups
  • Strong knowledge of stop loss insurance products, market dynamics, and regulatory requirements
  • Proven ability to make sound risk decisions and contribute to profitable portfolio performance
  • Excellent analytical, quantitative, and problem‑solving skills
  • Strong relationship‑building, negotiation, and communication abilities
  • Proficiency in underwriting systems, analytics tools, and Microsoft Office Suite
  • Ability to work independently while collaborating effectively in a fast‑paced, growth‑oriented environment

The base salary offered for the successful candidate will be based on compensable factors such as job-relevant education, job-relevant experience, training, licensure, demonstrated competencies, geographic location, and other factors. Discretionary incentive compensation may be awarded. Jencap also offers a range of benefits and programs, based on eligibility, which currently include but are not limited to; comprehensive health care coverage, a 401k plan, and tuition reimbursement. Jencap is an emerging and rapidly growing leader in the industry and as such, we approach talent acquisition as an opportunity to identify the best talent. Therefore, the level of the role and compensation may vary depending upon the best available candidate.

Want the opportunity to build something new? Expand your knowledge and stretch your experience through new and emerging risks? Have your voice heard, your skills properly applied, and to add tangible value to an organization? You're in the right place.

Jencap is dynamic, bold, tenacious, and trusted in the industry. Here, you are not just one of the many, you are one of us. We truly are better together.

Jencap is an Equal Opportunity Employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin or citizenship status, sexual orientation, gender identity or expression, pregnancy, marital or familial status, disability status, medical condition, genetic information, military or veteran status, political affiliation, or any other characteristic protected by law. We are committed to fostering a work community where every colleague feels welcomed, valued, respected and heard, as we believe that that creating an environment where every employee feels included and empowered, helps us to deliver the best outcome to our clients.