Toolmill Briefswhat companies are building, read from their hiring

Company brief · updated 2026-10-18

Jerry

jerry.ai · Fintech · Jerry is a licensed insurance broker and app built to make owning things easier. Since 2017, we’ve helped simplify car and home ownership. Discover our story, mission and team

36open roles
36new in 30 days
45closed in 30 days
36remote-eligible
acceleratinghiring velocity

What they're building

Remote insurance sales and policyholder service team; sales paid hourly plus uncapped commissions, service paid hourly strong signal

Today: Jerry is a licensed insurance broker and app built to make owning things easier

Roles: Remote Sales Agent (Insurtech Startup) · Remote Sales Representative - Fintech · Customer Experience Advocate (Remote, Insurance Tech Startup) · Insurance Sales Agent (Remote) · Inbound Insurance Sales Representative (Remote) · Licensed Insurance Sales Agent | 100% Remote · Remote Call Center Agent · Customer Service Agent (Remote) · Remote Customer Support Agent (P&C)

Requirements mention: consultative account management · high-touch service · P&C license · call center environment · process service requests

Inference: Jerry is staffing a remote sales and service team across several US states to sell and service insurance policies through its app. Insurance is the largest department, with 16 of 37 open roles.

Product expansion beyond car into home, motorcycle, RV and boat strong signal

Today: Licensed insurance broker and app, starting with car insurance

Roles: Product Manager (2x YC founder mentorship) · Product Manager-in-Training (YC cofounder/CEO-led) · GM-in-Training (YC cofounder/CEO-led) · Senior Product Manager, Emerging Products (0-1) · Founder's Associate Program (2x YC founder)

Requirements mention: home insurance · motorcycle insurance · property tax · roadside assistance · 0-to-1 scope

Inference: these hires are meant to build new product lines beyond car. Home and motorcycle insurance are named most often in the requirements.

Analytics and experimentation team strong signal

Today: Licensed insurance broker and app for car and home ownership

Roles: Senior Associate, Business Operations & Analytics · Associate, Business Operations & Analytics · Data Scientist · Associate Data Scientist

Requirements mention: SQL · Python · design experiments · Define metrics

Inference: metrics and experiment capacity is being added on a shared stack (Clickhouse, Metabase, Jupyter Hub, GitHub). The roles are listed in New York and marked remote.

Car insurance sign-up and purchase funnel moderate signal

Today: Car insurance marketplace

Roles: Product Manager, Growth (10-to-100) · Senior Product Manager, Growth (10-to-100)

Requirements mention: signup funnels · quote shopping · app download pages · landing pages

Inference: Growth PM hiring targets the existing car insurance sign-up and purchase funnel.

Reddit and community content marketing moderate signal

Today: Jerry is a licensed insurance broker and app built to make owning things easier

Roles: Comedian + Copywriter · Community Manager · Copywriter, Reddit · Social Media Manager, Reddit

Requirements mention: Reddit · LLM citation · share of voice · referral traffic

Inference: Jerry is staffing a Reddit and search content channel. Four of the five open Marketing roles are in it.

Partnerships behind repair, diagnostics and loan refinancing features moderate signal

Today: NOW, WE HANDLE EVERYTHING THAT COMES WITH OWNERSHIP

Roles: Director, Business Development & Partnerships (Remote) · Manager, Business Development and Partnerships

Requirements mention: partner ecosystem · repair marketplace · car diagnostics · loan refinancing

Inference: BD hires will manage and grow the partners behind existing repair, diagnostics and refinancing features.

Where the headcount is going

DepartmentOpen
Insurance9
Business Development5
Growth & Marketing5
Data Analytics & Strategy4
Product4
Finance3
Legal3
People Team2
Leadership1

Of 37 open roles, 16 are in Insurance, 7 in Product, 5 in Marketing, 4 in Data, 2 each in People Team and Business Development, and 1 in Finance, with 34 opened in the last 30 days.

Who they need

Seniority: Mostly junior (13) and mid-level (15) roles, with 5 senior, 2 manager, 1 director and 1 unspecified.

Skills named most: sales, consultative account management, high-touch service, customer service, P&C license, SQL, Python, Clickhouse, Metabase, Jupyter Hub, GitHub, product building

Locations: 36 of 37 roles are marked remote. New York, New York has 7 roles, Palo Alto, California has 5 (including the non-remote Founder's Associate Program), and the San Francisco Bay Area has 3. Remote postings do not name a country.

How to use this

If you're applying: Most roles are remote. Before applying, check your background against the P&C license, SQL and Python, or call center requirements. Product roles tied to home, motorcycle and other new lines ask for consulting, VC or PE backgrounds. The Founder's Associate Program in Palo Alto is not remote.

If you're selling or recruiting: Insurance is the largest department, with 16 roles. Sales postings pay $19.00 - $21.00 hourly plus uncapped commissions; service and call center postings pay $19.00 - 21.00 hourly. Product is second, with 7 roles, five of them tied to new lines beyond car. Reach out with P&C-licensed sales candidates, service candidates with call center experience, or product candidates from consulting, VC or PE.

Get told when Jerry opens new roles.

Weekly, only when something changed. One click to stop.

Open roles (36)

TitleDepartmentLocationPosted
Director of Strategic Partnerships, New BusinessBusiness DevelopmentNew York, New York (remote)2026-10-23
Finance ManagerFinanceRemote (remote)2026-10-23
Manager, Strategic Finance FinanceRemote (remote)2026-10-23
Operations Associate (Legal & Compliance)LegalToronto, Ontario (remote)2026-10-23
Comedian + CopywriterGrowth & MarketingRemote (remote)2026-10-23
Community Manager Growth & MarketingPalo Alto, California (remote)2026-10-23
Copywriter, RedditGrowth & MarketingRemote (remote)2026-10-23
Social Media Manager, RedditGrowth & MarketingRemote (remote)2026-10-23
Associate Data ScientistData Analytics & StrategyNew York, New York (remote)2026-10-23
Data ScientistData Analytics & StrategyNew York, New York (remote)2026-10-23
Senior Associate, Business Operations & AnalyticsData Analytics & StrategyNew York, New York (remote)2026-10-23
GM, Emerging Products (0-1)LeadershipPalo Alto, California (remote)2026-10-23
Senior Product Manager, Emerging Products (0-1)ProductRemote (remote)2026-10-23
Product Manager (2x YC founder mentorship)ProductPalo Alto, California (remote)2026-10-23
GM-in-Training (YC cofounder/CEO-led)ProductPalo Alto, California (remote)2026-10-23
Product Manager-in-Training (YC cofounder/CEO-led)ProductPalo Alto, California (remote)2026-10-23
Associate, Business Operations & AnalyticsData Analytics & StrategyNew York, New York (remote)2026-10-23
Legal Researcher (Remote)LegalToronto, Ontario (remote)2026-10-23
Legal Operations Associate (Remote)LegalToronto, Ontario (remote)2026-10-22
Customer Service Agent (Remote, Tech Startup)InsuranceTucson, Arizona (remote)2026-10-22
Customer Experience Advocate (Remote, Insurance Tech Startup)InsuranceSan Antonio, Texas (remote)2026-10-20
Customer Care Associate - Retail & Hospitality Backgrounds Welcome (Remote)InsuranceOrlando, Florida (remote)2026-10-20
Strategic Finance ManagerFinanceRemote (remote)2026-10-20
Senior Creative Strategist, GrowthGrowth & MarketingNew York, New York (remote)2026-10-20
HR GeneralistPeople TeamRemote (remote)2026-10-20
People Operations GeneralistPeople TeamRemote (remote)2026-10-20
Insurance Compliance & Regulatory Senior Lead InsuranceDallas, Texas (remote)2026-10-20
Manager, Business Development and PartnershipsBusiness DevelopmentSan Francisco Bay Area (remote)2026-10-20
Director, Business Operations (Business Development)Business DevelopmentNew York, New York (remote)2026-10-14
Manager, Business Operations (Business Development)Business DevelopmentSan Francisco Bay Area (remote)2026-10-14
Director, Business Development & Partnerships (Remote)Business DevelopmentNew York, New York (remote)2026-10-12
Remote Sales Agent (Insurtech Startup)InsuranceLas Vegas, Nevada (remote)2026-10-09
Remote Sales Associate - Retail/Service Backgrounds Welcome!InsuranceNew York, New York (remote)2026-10-08
Insurance Sales Agent (Remote)InsuranceHouston, Texas (remote)2026-10-07
Remote Inside Sales Associate (Insurance Tech Startup)InsuranceRaleigh, North Carolina (remote)2026-10-02
Remote Inbound Sales Agent (Fintech)InsuranceNashville, Tennessee (remote)2026-10-02