49 open positions

Underwriting Jobs with a Great Work-Life Balance

Browse 49+ underwriting jobs at companies offering unlimited PTO and best places to work—for a better work-life balance. 10 new this week. Hiring companies include Ledgebrook, Benefact Group, and Distinguished Programs.

Schedules on this page

4-day weeks 1
summer Fridays 3
unlimited PTO 20
best places to work 22
generous parental leave 2

Updated October 14, 2026

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Underwriter - Excess Casualty

Ledgebrook · Remote · USA

62 · GoodUnlimited PTO$75k – $150k

Cyber Underwriter

Ledgebrook · Remote · USA

62 · GoodUnlimited PTO$75k – $135k

Casualty Underwriter

Ledgebrook · Remote · USA

62 · GoodUnlimited PTO$75k – $150k

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New Business Commercial Underwriter - City Insurance

Distinguished Programs · Remote · USA

65 · GoodSummer Fridays$65k – $85k

Senior Product Manager - Consumer Credit Card

Mercury · Remote · Canada or USA

62 · GoodUnlimited PTO$201k – $251k

Underwriting Manager - Umbrella Program

1mo

Distinguished Programs · Remote · USA

65 · GoodSummer Fridays$120k – $165k

E&S Commercial Lines New Business Underwriter

1mo

Distinguished Programs · Remote · USA

65 · GoodSummer Fridays$70k – $85k

Senior Risk Associate

29d

Lithic · Remote · New York, NY, USA

62 · GoodUnlimited PTO$86k – $144k

Production Risk Engineer - MPL/Architects & Engineers

1mo

Counterpart · Remote · USA

62 · GoodUnlimited PTO

Senior Product Manager - Business Lending

3mo

Mercury · Remote · Canada or USA

62 · GoodUnlimited PTO$201k – $251k

Senior Technical Product Manager - Underwriting Platform

25d

Zip Co · Remote · USA

61 · GoodUnlimited PTO$133k – $165k

Underwriting/Credit Model Risk Senior Manager - Machine Learning

2mo

Affirm · Remote · USA

61 · GoodBest Place to Work$227k – $315k

Senior Product Engineer - Payments Risk

29d

WeTravel · Remote · Europe +2 more

60 · GoodUnlimited PTO

Senior Product Manager, PolicyCenter

20d

Guidewire · Remote · USA or Canada

58 · GoodBest Place to Work$148k – $254k

Pricing Sales Director

1mo

Guidewire · Remote · USA or Canada

58 · GoodBest Place to Work$136k – $204k

Underwriter

3mo

Hometap · Remote · Boston, MA, USA

58 · GoodBest Place to Work$75k

Senior Machine Learning Manager, Borrowing

3mo

Monzo · Remote · UK

56 · GoodGenerous Parental Leave£138k – £176k

Director of Program Operations

Ledgebrook · Remote · USA

62 · GoodUnlimited PTO$150k – $250k

Vice President, South Central Zone Leader - Underwriting

Ledgebrook · Remote · USA

62 · GoodUnlimited PTO$250k – $350k

Director of Program Operations

Ledgebrook · Remote · USA

62 · GoodUnlimited PTO$150k – $250k

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Frequently asked questions

Everything you need to know about 4-day week jobs

Employers hiring for Underwriting on this page include Ledgebrook, Benefact Group, and Distinguished Programs. Underwriting roles appear most frequently in engineering, data, and platform teams at companies that offer a 4-day week or another flexible schedule. Each listing indicates the seniority level and whether Underwriting is a primary requirement or one of several preferred skills — expand any role above to see the full stack and responsibilities.

Underwriting roles on this page span seniority levels, from entry-level and mid-level through senior, lead, and staff or principal positions. Filter by level in the sidebar to narrow the list above to the ones that fit you.

Lead with measurable outcomes over time spent — Underwriting hiring managers at companies that run 4-day weeks or flexible schedules care about delivered value, not hours worked. Highlight projects where you shipped at a steady cadence, collaborated asynchronously, or reduced engineering toil through automation or tooling. Include concrete metrics (latency improvements, adoption numbers, cost reductions) rather than vague duty descriptions. Expand listings above to see the exact framing each employer uses in their job descriptions.

Pay depends on the role, seniority, location, and employer — not on the schedule alone. Underwriting roles in tech and data typically command premium rates, and specific ranges depend on seniority and sub-specialty (e.g. backend vs frontend, infra vs ML). Individual listings above show exact bands where the employer publishes them.

Depends on the role, but Underwriting candidates who also demonstrate async communication, clean documentation, and cross-functional collaboration are typically strong fits for employers that run 4-day weeks or flexible schedules — those teams rely on written-first communication and high-context handoffs. Technical-adjacent skills vary by stack. Browse the top skills shown in the sidebar to see which tags co-occur most often with Underwriting on current listings.

Browse all 49 jobs

Underwriting Jobs with a Great Work-Life Balance

Browse 49+ underwriting jobs at companies offering unlimited PTO and best places to work—for a better work-life balance. 10 new this week. Hiring companies include Ledgebrook, Benefact Group, and Distinguished Programs.

Job listings

Frequently asked questions

Job listings

Frequently asked questions

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