Senior Insurance Broker II

Wrapbook
2dRemote

About The Position

This role is for an accomplished broker who excels in both revenue generation and complex risk placement. As part of a rapidly scaling insurance solutions group inside a technology company, this position blends traditional brokerage expertise with the advantages of modern infrastructure, and warm distribution. The Senior Insurance Broker II generates new revenue, architects complex commercial production risks, executes submission and negotiation strategies, and participates directly in the Placement function. The role partners closely with Wrapbook’s cross functional Sales and Customer Success teams across business lines, including Payroll Sales and Payroll Customer Success, to coordinate opportunities and amplify revenue impact. This is a strong fit for a broker who works with independence, sound judgment, commercial instinct, and a forward looking approach to where insurance and technology intersect. What Makes This Opportunity Unique This is not a traditional agency seat. The Senior Insurance Broker II benefits from: A built in pipeline of warm leads from Wrapbook’s payroll and accounting platform Access to clients already engaging with Wrapbook for financial services Emerging bespoke insurance products designed to integrate with production workflows A technology forward environment where quoting, placement, servicing, and data handling are evolving rapidly Significant cross sell opportunities between insurance, payroll, and accounting Opportunities to contribute directly to technology development, workflow design, and new insurance product capabilities A modern technology ecosystem supporting both company employees and customers At the same time, the role requires an established network, independent pipeline development, and strong carrier relationships.

Requirements

  • 6+ years in entertainment focused commercial P and C insurance with deep production risk expertise
  • Clear track record of winning new business and managing complex placements
  • Senior level carrier negotiation experience
  • Experience in both client facing and technical placement responsibilities
  • Property and Casualty license required
  • Deep command of production coverages and risk structures
  • Ability to independently architect and negotiate complex submissions
  • Strong written and verbal communication with polished client presence
  • High proficiency with Salesforce or similar systems preferred
  • Ability to operate effectively in a fast moving, fluid environment

Nice To Haves

  • Experience at a tech enabled brokerage, MGA, or carrier
  • Established network within production carriers and wholesalers
  • Ability to think commercially about how insurance, payroll, and operational data intersect
  • Interest in supporting innovation, technology design, or emerging insurance programs

Responsibilities

  • Drive new new and new on existing revenue using a blend of warm platform leads and personal network development
  • Convert existing Wrapbook users and adjacent verticals into long term insurance clients
  • Lead client conversations with both technical fluency and commercial clarity
  • Partner with Business Development and Payroll Sales to coordinate outreach and opportunity routing
  • Own the architecture, strategy, and negotiation of complex production insurance submissions
  • Participate directly in the Placement discipline to shape carrier engagement and market strategy
  • Lead high complexity underwriting conversations with senior carrier partners
  • Maintain accuracy, clarity, and E and O discipline across all submission and binding workflows
  • Contribute to continuous updates on carrier appetite and market intelligence
  • Work with Payroll Sales and Payroll Customer Success to identify insurance opportunities and deepen revenue tie ins
  • Partner with Customer Success on mid market or technically complex renewals that require senior expertise
  • Coordinate with Insurance Operations on workflow integrity, documentation, and system consistency
  • Collaborate with Platform, Product, and Data teams to inform technology requirements, automation, and insurance roadmap needs
  • Support the Placement function in developing playbooks, appetite guides, and carrier strategies
  • Provide mentorship to brokers, CSRs, and cross functional partners
  • Model high standards of technical accuracy and operational maturity
  • Offer calm leadership in ambiguous or high stakes underwriting and client situations
  • Contribute to a culture grounded in learning, quality, and scalable execution

Benefits

  • Unlimited Paid Time Off
  • Work from anywhere in Canada and USA
  • Health and Dental benefits
  • Up to $1,500 USD/ $2,025 CAD towards IT set up for your home
  • Up to 2% matching RRSP / 401K
  • Learning and Development opportunities
  • Up to $50 USD/ $67.50 CAD towards Internet/Cell phone service

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What This Job Offers

Job Type

Full-time

Career Level

Mid Level

Education Level

No Education Listed

Number of Employees

101-250 employees

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