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Insurtech Chicago Jobs (NOW HIRING)

Honeycomb Insurance

VP of Legal

New York, NY · On-site

Dual-headquartered in Chicago and Tel Aviv (R&D center), and with 5 offices across the U.S., we are ... Anticipate regulatory shifts in insurance, insurtech, and data/privacy and convert them into ...

Obie

Client Manager

Chicago, IL

Experience in InsurTech, PropTech, or real estate-adjacent industries * Chicago-based or able to come into the Chicago office as needed Interview Process At Obie, transparency is core to our ...

Obie

Client Manager

Chicago, IL · On-site +1

$50K - $70K/yr

Experience in InsurTech, PropTech, or real estate-adjacent industries * Chicago-based or able to come into the Chicago office as needed Interview Process At Obie, transparency is core to our ...

Obie

Business Development Specialist

Chicago, IL · On-site +1

$60K - $100K/yr

Experience in InsurTech, PropTech, or real estate-adjacent industries * Chicago-based or able to come into the Chicago office as needed Interview Process At Obie, transparency is core to our ...

Kin Insurance, Inc.

Finance Manager

$120K - $140K/yr

Built In Chicago's Best Places to Work, Midsize Companies (2021-2026) * Forbes' America's Best ... scaling insurtech. You'll work alongside leadership across the business, translating complex ...

Liberate

Enterprise Account Executive

Boston, MA · Hybrid

$140K - $175K/yr

Columbus, Chicago, Dallas, Atlanta, Miami, Los Angeles, San Francisco, or Boston hybrid role (2 day ... Familiarity with insurtech disruptors and incumbent vendors (e.g., Guidewire, Duck Creek, Majesco)

Liberate

Enterprise Account Executive

San Francisco, CA · On-site

$140K - $175K/yr

Columbus, Chicago, Dallas, Atlanta, Miami, Los Angeles, San Francisco, or Boston hybrid role (2 day ... Familiarity with insurtech disruptors and incumbent vendors (e.g., Guidewire, Duck Creek, Majesco)

Liberate

Enterprise Account Executive

Columbus, OH · Hybrid

$140K - $175K/yr

Columbus, Chicago, Dallas, Atlanta, Miami, Los Angeles, San Francisco, or Boston hybrid role (2 day ... Familiarity with insurtech disruptors and incumbent vendors (e.g., Guidewire, Duck Creek, Majesco)

Liberate

Enterprise Account Executive

Chicago, IL · On-site

$140K - $175K/yr

Columbus, Chicago, Dallas, Atlanta, Miami, Los Angeles, San Francisco, or Boston hybrid role (2 day ... Familiarity with insurtech disruptors and incumbent vendors (e.g., Guidewire, Duck Creek, Majesco)

Liberate

Enterprise Account Executive

San Francisco, CA · Hybrid

$140K - $175K/yr

Columbus, Chicago, Dallas, Atlanta, Miami, Los Angeles, San Francisco, or Boston hybrid role (2 day ... Familiarity with insurtech disruptors and incumbent vendors (e.g., Guidewire, Duck Creek, Majesco)

Liberate

Enterprise Account Executive

Boston, MA · On-site

$140K - $175K/yr

Columbus, Chicago, Dallas, Atlanta, Miami, Los Angeles, San Francisco, or Boston hybrid role (2 day ... Familiarity with insurtech disruptors and incumbent vendors (e.g., Guidewire, Duck Creek, Majesco)

Liberate

Enterprise Account Executive

Dallas, TX · On-site

$140K - $175K/yr

Columbus, Chicago, Dallas, Atlanta, Miami, Los Angeles, San Francisco, or Boston hybrid role (2 day ... Familiarity with insurtech disruptors and incumbent vendors (e.g., Guidewire, Duck Creek, Majesco)

Liberate

Enterprise Account Executive

San Francisco, CA · Hybrid

$140K - $175K/yr

Columbus, Chicago, Dallas, Atlanta, Miami, Los Angeles, San Francisco, or Boston hybrid role (2 day ... Familiarity with insurtech disruptors and incumbent vendors (e.g., Guidewire, Duck Creek, Majesco)

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All JobsInsurtech Chicago Jobs

Insurtech Chicago information

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$10

$67

$125

How much do insurtech chicago jobs pay per hour?

As of Jun 9, 2026, the average hourly pay for insurtech chicago in the United States is $67.68, according to ZipRecruiter salary data. Most workers in this role earn between $23.32 and $92.31 per hour, depending on experience, location, and employer.

What types of projects do professionals typically work on in Insurtech roles based in Chicago?

In Insurtech roles in Chicago, professionals often collaborate on innovative projects such as developing digital insurance platforms, implementing data analytics for risk assessment, and creating customer-centric mobile applications. Teams are usually cross-functional, bringing together software developers, data scientists, product managers, and insurance experts to address industry challenges. The dynamic environment encourages continuous learning and adaptation to new technologies, offering plenty of opportunities for professional growth and advancement within both startups and established insurance companies.

What are the key skills and qualifications needed to thrive in an Insurtech role in Chicago, and why are they important?

To thrive in an Insurtech role in Chicago, you need a solid understanding of insurance fundamentals, data analytics, and technology integration, often backed by a degree in business, finance, or computer science. Familiarity with insurtech platforms, digital claims processing systems, and data analysis tools like SQL or Python is typically required. Strong problem-solving, adaptability, and communication skills help professionals navigate a rapidly evolving industry and collaborate with cross-functional teams. These competencies are crucial for driving innovation and efficiency in Chicago’s competitive insurance technology market.

What is Insurtech Chicago?

Insurtech Chicago refers to the community and ecosystem of insurance technology (insurtech) companies, startups, investors, and professionals based in Chicago. This group focuses on leveraging technology to innovate and improve the insurance industry, from customer experience to underwriting and claims management. Insurtech Chicago often hosts networking events, conferences, and educational sessions to connect industry leaders and foster collaboration. The city is becoming a hub for insurtech due to its strong financial sector, talent pool, and supportive business environment.

What is the difference between Insurtech Chicago vs Insurance Underwriter?

AspectInsurtech ChicagoInsurance Underwriter
CredentialsTypically requires a bachelor’s degree in business, finance, or related fieldsRequires a bachelor’s degree; certifications like CPCU or ARM are common
Work EnvironmentTech-driven startups, insurance technology companies, innovation hubsInsurance companies, underwriting departments, corporate offices
Industry UsageFocuses on insurance technology solutions, digital platforms, and innovationFocuses on evaluating risks, pricing policies, and approving coverage

Insurtech Chicago involves working within technology-focused insurance companies or startups, emphasizing innovation and digital solutions. In contrast, Insurance Underwriters primarily assess risks and determine policy terms within traditional insurance firms. Both roles require similar educational backgrounds and industry knowledge but differ in work environment and focus areas.

What cities are hiring for Insurtech Chicago jobs? Cities with the most Insurtech Chicago job openings:
What states have the most Insurtech Chicago jobs? States with the most job openings for Insurtech Chicago jobs include:
What job categories do people searching Insurtech Chicago jobs look for? The top searched job categories for Insurtech Chicago jobs are:
Insurtech Chicago jobs near you
Infographic showing various Insurtech Chicago job openings in the United States as of June 2026, with employment types broken down into 100% Full Time. Highlights an 50% In-person, and 50% Remote job distribution, with an average salary of $140,766 per year, or $67.7 per hour.

VP of Legal

Honeycomb Insurance

New York, NY • On-site

Full-time

Medical, Dental, Vision, Retirement, PTO

Posted 15 days ago

Job description

Honeycomb
At Honeycomb, we're not just building technology, we're reshaping the future of insurance.
In 2025, Honeycomb was recognized by Dun & Bradstreet as "Top 10 Best Start Up Companies to Work For" in Israel and named by LinkedIn as "Top 10 Startups in Chicago".
How did we earn these honors?
Honeycomb is a rapidly growing global startup, generously backed by top-tier investors and powered by an exceptional team of thinkers, builders, and problem-solvers. Dual-headquartered in Chicago and Tel Aviv (R&D center), and with 5 offices across the U.S., we are reinventing the commercial real estate insurance industry, an industry long overdue for disruption. Just as importantly, we ensure every employee feels deeply connected to our mission and one another.
With over $55B in insured assets, Honeycomb operates across 20+ major states, covering 60% of the U.S. population and increasing its coverage.
If you're looking for a place where innovation is celebrated, culture actually means something, and smart people challenge you to be better every day - Honeycomb might be exactly what you've been looking for.
VP of Legal
Role Title: VP of Legal
Location: NYC (hybrid - 3 days from the office)
Reports to: COO
Position Summary
As VP of Legal, you will own Honeycomb's legal strategy and lead the legal function end-to-end. You will be the principal legal advisor to the CEO, COO, and Senior Leadership Team (SLT) on governance, risk, and strategic transactions.
Key Responsibilities:
  • Strategic legal leadership: Serve as principal legal advisor to the CEO, COO, and SLT, on enterprise strategy, business initiatives, product launches, partnerships, regulatory/licensing matters, fundraising, fronting carrier and reinsurance arrangements, corporate governance, contracts, and material risk.
  • Develop and lead the legal function: Structure and manage external counsel relationships; own the legal budget and ensure cost-effective, high-quality outcomes across commercial contracts, licensing, regulatory filings, corporate governance, IP, data privacy and security, employment law, and litigation management.
  • Board & governance: Act as corporate secretary for the company; prepare Board and committee materials, manage minutes and resolutions, and advise on directors' duties, equity administration, and entity governance across the corporate structure.
  • Insurance & regulatory strategy: Own the regulatory strategy across all jurisdictions in which Honeycomb operates - state DOI relationships, multi-state licensing, MGA/agency model integrity, P&C filings, market conduct, and surplus lines compliance. Anticipate regulatory shifts in insurance, insurtech, and data/privacy and convert them into operating decisions.
  • Growth enablement: Drive the legal workstream behind growth - entering new states, new product lines, and new jurisdictions; ensure legal readiness, sequencing, and enablement so the business can ship on time.
  • Carrier, reinsurer & partner negotiations: Lead the legal posture in negotiations with carriers, reinsurers, MGAs, wholesalers, agencies, and distribution partners, resolve red lines pragmatically, and protect Honeycomb's long-term economics.
  • Strategic transactions: Lead legal execution on fundraising rounds (equity and debt facilities), M&A, strategic partnerships, and capital structure work; manage diligence, deal documentation, and post-close integration.
  • Legal operating system: Build, scale, and mature Honeycomb's legal infrastructure - playbooks, standard contract templates, approval workflows, KPI dashboards, and stakeholder service-level expectations - so the function compounds as the company scales.
  • Risk & cross-functional partnership: Partner with the CISO, CFO, and CUO to ensure legal support for insurance-related programs and operations, cyber, privacy, and data-governance risks; partner with Finance on enterprise risk and insurance program design.
  • Trusted advisor: Translate complex legal and regulatory issues into clear, business-friendly recommendations - enabling the business to move fast without compromising quality.
  • Regulatory & legal horizon scanning: Monitor relevant regulatory and legal developments (insurance law, P&C regulations, insurtech legislation, data/privacy, AI) and proactively advise the business on emerging risks and opportunities.
Qualifications & Experience
  • J.D. from a prestigious law school; admitted to practice in relevant U.S. jurisdiction(s) and in good standing.
  • 10+ years of legal experience, including 3+ years leading an in-house legal function or a major sub-function at a regulated company; insurance or insurtech experience strongly preferred.
  • Deep familiarity with U.S. insurance regulation - state licensing, MGA/agency models, P&C underwriting, fronting carrier and reinsurance arrangements, distribution and agent relationships - plus working knowledge of technology, data, privacy, and AI regulatory matters.
  • Demonstrated experience advising a Board of Directors, serving as (or partnering with) the corporate secretary, and supporting fundraising rounds, M&A, or other strategic transactions.
  • Track record of building and scaling a legal function and operating system at a growth-stage company - hiring, structuring external counsel, and embedding playbooks, templates, and approval workflows.
  • Strong commercial mindset: thrives by partnering with business stakeholders (product, underwriting, marketing, operations, sales, partnerships, human resources) to enable growth while protecting the company.
  • Excellent communicator (written and verbal); able to simplify legal risk into actionable business recommendations for executive and Board audiences.
  • High integrity, strong sense of ownership, and the executive judgment to make timely, high-stakes decisions in a fast-paced, scaling environment.
  • Comfortable operating globally (US + Israel base/resourcing) and cross-functionally across operations, marketing, HR, finance, and risk.
  • Preferred: Prior experience as a General Counsel, Deputy General Counsel, or Head of Legal at a startup/tech-enabled insurer or insurtech; multi-state licensing experience; reinsurance treaty negotiation; and experience standing up legal operations tooling.
Culture Fit / Behaviours
  • Embraces our culture: takes full ownership, challenges the status quo, readily adapts (Flexibility), stays focused on what matters, prioritizes "we" over "I," and acts with urgency.
  • Executive presence: credible with the CEO, COO, SLT, regulators, carriers, and reinsurers; calm and decisive in high-stakes moments.
  • Comfortable in a start-up/scale-up environment with ambiguity and rapid change.
  • Collaborative; builds strong relationships across functions and geographies.
  • Continuous improvement mindset: always looking to refine legal processes, enhance operational efficiency, and embed craftsmanship.
  • Maintains the highest ethical standards - as an insurance business with regulatory/regime risk, trust and integrity are non-negotiable.
  • Hybrid availability: Must be located in and able to work from our NYC office three days per week (Tuesday through Thursday).
Benefits
  • Salary: $270,000 - $290,000 + 20% Bonus
  • ISO stock options
  • Medical, dental, and vision coverage for you and your dependents
  • HSA with company contributions
  • 401(k) with employer match
  • Flexible time off
  • 10 company-paid holidays
  • Paid family leave

Honeycomb is committed to fair and equitable compensation practices. The base salary range listed in each job posting represents our good faith estimate of what we expect to pay for the role. Actual compensation may vary based on skills, experience, education, and location, as well as internal alignment and market factors.

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