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Remote Chief Operating Officer Insurance Jobs in Boston, MA

Miratech

Executive Assistant to CRO

Boston, MA · Hybrid

Manage professional and personal scheduling for the Chief Revenue Officer, including agendas, email ... Ability to work effectively in a remote environment and coordinate across multiple time zones.

Kodex, Inc

Strategic Account Executive

Boston, MA · On-site +1

$200K - $300K/yr

Deal strategy with the CEO - Work directly with leadership on the biggest deals. Bring account ... Benefits * Remote-first within the U.S. * Offsites in exciting locations. Past trips include ...

Robert Half

Senior Manager of FP&A - SaaS

Kingston, MA · Remote

$111K - $152K/yr

My client, a private 100% REMOTE SaaS company is hiring for a Senior Manager of FP& A to join the team. The Senior Manager of FP& A will report directly to the CFO and handle all things FP& A related ...

Condor Agency

Senior Account Executive

Boston, MA · Remote

$60K - $90K/yr (+ commission)

Fully remote * Work directly with the CEO * Significant influence over the company's growth strategy * High-autonomy environment * Flexible work environment * PTO and holidays Company Description ...

Priority1

Territory Manager-Remote

Norwood, MA · On-site +1

... CFO, President, and Vice President. This outside sales position is focused on new business ... operating cost. This Territory Manager position is the start of a career path that creates ...

Priority1

Territory Manager-Remote

Norwood, MA · On-site +1

... CFO, President, and Vice President. This outside sales position is focused on new business ... operating cost. This Territory Manager position is the start of a career path that creates ...

Cognito Therapeutics

Project Manager

Cambridge, MA · On-site +1

Project Manager, Office of the CEO, Cognito Therapeutics, Inc. Location: Boston, or Remote USA ... operating rhythm on track. This role is an excellent opportunity for a detail-oriented, highly ...

PaxeraHealth

Vice President of Finance

Newton, MA · On-site +1

Remote (U.S.) or Hybrid Job Type: Full-Time | Exempt About PaxeraHealth PaxeraHealth is a leading ... Partner with the CEO and executive leadership team to develop and execute the company's long-term ...

PaxeraHealth

Vice President of Finance

Newton, MA · Remote

Remote (U.S.) or Hybrid Job Type: Full-Time | ExemptAbout PaxeraHealth PaxeraHealth is a leading ... Partner with the CEO and executive leadership team to develop and execute the company's long-term ...

Liberty Mutual Insurance

Environmental Claims Officer

MA · On-site +1

$94K/yr

We will also consider highly qualified remote candidates who do not reside near a hub location ... Functional knowledge of law and insurance regulations in various jurisdictions * Demonstrated ...

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All JobsChief Operating Officer Insurance JobsRemote Chief Operating Officer Insurance JobsRemote Chief Operating Officer Insurance Jobs in Boston, MA

Remote Chief Operating Officer Insurance information

See Boston, MA salary details

$45.1K

$164.3K

$292.8K

How much do remote chief operating officer insurance jobs pay per year?

As of Sep 2, 2026, the average yearly pay for remote chief operating officer insurance in Boston, MA is $164,267.00, according to ZipRecruiter salary data. Most workers in this role earn between $121,100.00 and $201,000.00 per year, depending on experience, location, and employer.

What is the difference between Remote Chief Operating Officer Insurance vs Remote Insurance Underwriter?

AspectRemote Chief Operating Officer InsuranceRemote Insurance Underwriter
Required CredentialsLeadership experience, industry knowledge, often MBA or similarLicenses, underwriting certifications, industry knowledge
Work EnvironmentExecutive leadership, strategic planning, cross-departmental oversightAnalyzing applications, assessing risk, decision-making within underwriting guidelines
Employer & Industry UsageInsurance companies, large brokerages, industry leadership rolesInsurance carriers, underwriting firms, risk assessment departments

The Remote Chief Operating Officer Insurance focuses on strategic leadership and overall operations management within insurance organizations, requiring executive experience. In contrast, the Remote Insurance Underwriter specializes in evaluating insurance applications and assessing risks, typically requiring underwriting-specific certifications. Both roles are vital in the insurance industry but differ significantly in responsibilities and required credentials.

What are popular job titles related to Remote Chief Operating Officer Insurance jobs in Boston, MA?

For Remote Chief Operating Officer Insurance jobs in Boston, MA, the most frequently searched job titles are:

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Cities near Boston, MA with the most Remote Chief Operating Officer Insurance job openings:

Remote Chief Operating Officer Insurance jobs near you

Technical Co-founder (CTO) - AI Collections Agent

FutureSight

Boston, MA • On-site, Remote

Full-time

This job post has expired today. Applications are no longer accepted.

Job description

The Opportunity
Finance teams at B2B companies lose cash the same way every month: an invoice ages past 45 days, someone sends an email, no reply, someone calls, voicemail, they call again next week, still nothing. AR teams spend 60-70% of their week on manual follow-up instead of posting cash, closing disputes, or analyzing aging. Adding headcount doesn't fix it; manual follow-up simply doesn't scale, and every ERP hits the same wall.
Problem and solution validation are complete. Live pilots are running with early design partners and entering production evaluation. The next phase is proving in-production reliability, delivery economics, and scalability. The teams that ship credible AI workers into finance-sensitive functions in the next 18 months will define the category. We intend to be one of them.
The Venture
Argentl delivers an AI collections agent that handles outbound debtor follow-up automatically - trained, monitored, and continuously improved by our team. Rather than another self-serve SaaS tool, Argentl is evaluated on outcomes: DSO reduction, hours returned to the AR team, and cash commitments captured - not configuration effort.
Give us a list of overdue accounts and our voice agent calls each debtor, confirms invoice awareness, and captures exactly what they say - a payment commitment, a dispute, a request to split, or silence. The AR team gets a clean morning report: who's committed, who's disputing, who's gone silent, and what to do next. No ERP migration, no system credentials, no workflow overhaul - we're calling within a week of receiving the data. The roadmap expands from collections follow-up into adjacent AI finance-ops roles, all delivered through the same managed model.
The Partnership
The CEO co-founder is in place. The customer thesis is validated, design partners are engaged, and live pilots are running. What remains is to bring on the technical co-founder - a partner who will own product and engineering with the same conviction, urgency, and ownership stake.
This is a co-founder role, not a CTO hire. In return for that level of commitment, you receive founder-level equity, founder-level authority with co-decision rights on product, technology, hiring, fundraising, and strategy, and a genuine partnership with the CEO on every material decision.
What you'll own
As Co-Founder & CTO, you will take over the production code and continue building the product (the first lines of production code), set the technical direction, and lead execution end-to-end.
  • Architecture & Reliability - Harden the voice and workflow systems for in-production reliability. Establish core architecture, observability, and audit-trail standards for a product that speaks to customers' debtors on their behalf.
  • Delivery Layer - Build the internal infrastructure that lets the team configure, monitor, and optimize agent performance without scaling engineering headcount. Mature the workflow engine so every call, intent classification, and next-action flows through reliably.
  • Integrations & Distribution - Own the accounting and ERP integration layer (QuickBooks, Xero, and beyond) that turns Argentl from a CSV upload into an embedded part of the finance stack - the primary distribution unlock.
  • Unit Economics - Own the trade-offs between AI quality and cost-per-call, and lock in unit economics within a productized monthly pricing model.
  • Customer & Market - Represent the company in front of finance leaders, partners, and investors as the technical voice of the venture.
  • Roadmap - Convert pilots into paying customers, expand the AI staff beyond collections, and begin a path toward custom and self-hosted models where data-privacy and financial-compliance requirements demand it.
  • Team - Recruit and lead the founding engineering team, and establish the cultural foundation of the company
Co-Founder Profile
Must Have:
  • Shipped LLM-powered and voice systems into production environments where incorrect outputs carried real consequences
  • Full-stack confidence across applied LLMs, real-time voice and conversational AI, telephony, human-in-the-loop workflows, observability, and secure multi-tenant SaaS
  • Well-formed convictions about reliability engineering, edge-case management, and the trade-offs between AI quality and cost-per-call
  • Experience building managed and service-heavy platforms, with the discipline to scale delivery without scaling engineering headcount
  • Prepared to operate as a principal - including saying "this won't scale" or "this isn't ready" when the integrity of the product requires it
  • A hands-on builder - you still write code and ship, and you're happiest close to the product

Great to Have:
  • Finance, accounting, or FinOps background - you understand AR, DSO, aging, disputes, and how finance teams actually work
  • Based in Los Angeles or the San Francisco Bay Area (or ready to be)
  • Pragmatic and creative - a solution finder who gets to "working" fast and iterates from there
  • Co-operative, strategic, and hands-on in equal measure
  • Capable and willing to help in finding and closing early customer partnerships
  • An active social media presence you can put to work for founder-led distribution
How to Apply
Please submit your resume, LinkedIn profile, and a brief note on why this venture aligns with your goals as a founder. We will move quickly for the right candidate.
FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.

Apply