Sentry

Analyst

• Act as the primary point of contact for lienholders
• Validate conditional payment notices against medical records
• Identify unrelated charges
• Maintain accurate system data and ICD codes
• Proactively negotiate Medicare, Medicaid, and MAP liens
• Dispute inaccurate charges
• Present evidence to secure compromise offers
• Partner with claim representatives to integrate lien resolution into overall case strategy
• Ensure all resolutions adhere to the Medicare Secondary Payer (MSP) statute
• Maintain comprehensive, audit-ready files

Senior Lien Resolution Analyst – Secondary Payer

Risk

• Conduct onsite facility evaluations to determine if operational exposures are being adequately controlled to prevent building losses.
• Determine scope and schedule of preventative maintenance programs on key mechanical equipment within the facility (electrical systems, HVAC, machinery in use, and roof condition).
• Assist in determining if facility protections (fire suppression systems, alarm systems, etc.) are acceptable for the building occupancy, exposures, and special hazards.
• Complete detailed reports for each covered line of business – Property, General Liability, Auto, & Workers Compensation, etc. – to assist our underwriting groups with account acceptability and insurability.
• Assist customers with development and implementation of safety polices, programs, and procedures specific to each account & loss exposure.
• Provide advanced risk management and consultative services to assigned clients.
• Conduct Job-site safety inspections and OSHA 10-hour seminars for our Regional construction line of business.
• Maintain and demonstrate safety management and expertise in areas such as commercial property protection, general liability, product liability, fleet safety, and employee safety.
• Develop, coordinate, and conduct safety/risk management seminars and training programs for accounts to promote awareness and reduce claim frequency and severity.
• Develop and execute service proposals and plans to qualified accounts.

Risk Control Consultant

Account Specialist

• Serve as primary point of contact and resource for designated producer(s), customers, and/or agents within the territory.
• Act as a relationship builder by using a combination of soft skills to connect with internal teams, customers and agents
• Partner with producers to service existing book and identify opportunities for partner placement agency (Parker Stevens Agency or Hortica Brokerage)
• Make detailed decisions and understand business risks and consequences of them
• Serve as primary point of contact and owner of all service-related items, such as incoming customer calls, emails, and faxes regarding service needs, changes, questions, and problems
• Provide proactive service needs to ensure completion, including quotes, renewals, policy changes, urgent recommendations, billing, and audits
• Create new and renewal applications to smaller businesses
• Act as a relationship builder and liaison between sales producer, underwriting, other internal departments, and/or customers or agents in gathering of underwriting requirements and customer documents/signatures

Client Services Representative

• Monitor and maintain workflow tasks for assigned clients to ensure requests and services are completed within the required deadlines
• Monitor incoming email and voice messages while corresponding with clients to provide accurate information regarding employer contributions, payroll, and plan information
• Collect, verify, and update required customer information accurately within Sentry systems
• Develop and maintain an understanding of Sentry’s plan documents, contracts, systems, and compliance requirements
• Perform other job-related duties as assigned

Associate Client Service Specialist

Customer Support

• Ensure quality customer service by interpreting phone calls for personal and commercial lines insureds and claimants.
• Translate and transcribe documents and recordings accurately.
• Translate verbally phone conversations and rewrite documents in both English and Spanish.
• Participate on phone calls between Sentry and Claimants.
• Interpret various dialect meanings while translating verbally or in written form.
• Provide translation services to all Sentry offices.
• Translate a high volume of calls daily.
• Provide a high quality of customer service for internal and external customers.

Customer Service Representative, Translator

Manager

• Own end-to-end processing of deals — including quote creation, discount review, order form generation, and approval routing — with minimal escalation and fast turnaround.
• Partner with our Senior Deal Desk Manager to ensure coverage across the full deal portfolio so no single point of failure exists on the team.
• Become an expert in our CPQ system and Salesforce integration– not just as a user, but as a critical voice for what should change. Document pain points, propose solutions, and work alongside our GTM Tech team to drive improvements.
• Help design and implement self-service guardrails and automation that reduce the volume of deals requiring manual Deal Desk intervention, working toward a future where reps can handle standard deals entirely on their own.
• Build and maintain deal desk playbooks, approval matrices, and process documentation that create consistency and reduce re-review.
• Support pricing updates by ensuring that changes are reflected accurately and promptly in CPQ, and flagging downstream impacts before they become problems for sales.
• Identify patterns across deal data — approval rates, exception types, deal velocity — and surface insights that inform policy and pricing decisions.

Deal Desk Manager

Engineer

• Lead daily jobsite kickoffs covering scope, sequencing, safety, and schedule
• Coordinate crew start times, locations, and daily expectations
• Ensure crews have proper tools, materials, and training to perform safely and efficiently
• Supervise erection of PEMB systems, including structural steel, insulation, and exterior steel
• Maintain high-quality standards while prioritizing jobsite safety
• Manage equipment, machinery, and crane coordination
• Approve timecards and track labor productivity
• Complete required documentation including timesheets, work orders, and incident reports
• Train, mentor, and evaluate crew members
• Participate in hiring, performance reviews, and disciplinary actions as needed
• Communicate job completion status for invoicing and operations coordination

Steel Erection Supervisor – Pre-Engineered Metal Buildings

Support Engineer

• Master the Sentry Ecosystem & Support Elite Developers
• Deep-Dive Debugging: Perform root-cause analysis on complex issues and distributed tracing gaps across polyglot environments.
• Support the Great Minds: Act as a strategic consultant for senior engineers at our largest enterprise customers, solving high-stakes architectural challenges that push the boundaries of observability.
• Troubleshoot SDK Implementations: Go deep into the source code of Sentry’s SDKs to help developers instrument complex frameworks and custom environments.
• Engineer Agentic Operations: Engineer the logic that powers our support agents, moving beyond probabilistic guesses to high-fidelity, autonomous resolutions.
• Knowledge Engineering: Build the right context into our systems so they can resolve issues consistently and indefinitely.
• Agentic Tooling Development: Use MCP (Model Context Protocol) and Sentry’s internal APIs to build "skills" for our agents, allowing them to perform complex lookups or state-checks autonomously.

Technical Support Engineer

Appraiser

• Lead efficient claim decisions by assessing losses and securing fair settlements
• Conduct inspections on auto damage to prepare and review repair estimates
• Virtually inspect damaged vehicles for structural, body, mechanical, and interior damage
• Prepare detailed damage reports and repair estimates using specialized software
• Maintain records of appraisals, photographs, and communications related to each claim
• Review insurance policies to determine coverage and liability
• Negotiate settlements with repair facilities and clients
• Communicate effectively with clients, repair shops, and insurance adjusters
• Provide exceptional customer service, addressing client concerns promptly
• Stay updated on industry trends and repair techniques
• Obtain and maintain state adjuster/appraiser licenses as required

Auto Claims Appraiser

Account Executive

• Selling Dairyland, Harley Davidson, and The General products
• Promote Dairyland, Harley Davidson, and The General Insurance Services
• Understanding of specific company products
• Answer inbound customer inquiries on coverage limits, deductibles, etc.
• Provide quotes and bind coverage for customers in a timely fashion

Licensed Direct Sales Representative – P&C

Marketing

• As the Powersports Marketing Manager, you will prospect, develop and maintain motorcycle focused accounts for new business production.
• Manage the assigned US territory and/or have areas of responsibility assigned that are countrywide such as new business development of dealership, affinity accounts, and/or motorcycle agents.
• Deliver new business sales through the use of all applicable distribution channels via implementation of an effective strategy for distribution of products.
• Oversee operation and effectiveness of marketing and sales activities in area of responsibility.
• Work closely with Product Management in the development and design of motorcycle and power sports insurance products to increase production; this may include recommending specific product changes, process improvements, and workflows along with geographical locations and agency/account management to maximize growth opportunities.
• Maintain an awareness of industry trends, determines competitiveness of current products.
• Recommend and collaborate with corporate marketing in the creation and implementation of promotional, marketing, branding, and content activities for the motorcycle niche.
• Assist in measuring the effectiveness of these activities.
• Research, recommend and establish marketing niches for motorcycle and powersports products.
• Ensure systems, processes, technology and service methods support the marketing efforts.

Powersports Marketing Manager

General Counsel

• Represent the interest of the insured and Sentry in defending claims
• Ensure there is no conflict of interest between the policyholder and Sentry
• Handle a full caseload of minimally to moderately complex matters representing insureds up to, and including, through trial
• Communicate and report to policyholders and claims associates on the progress of litigation, strategy, and evolution of matters
• Assist in preparing forms for use throughout the department including pleadings, discovery, jury instructions, dispositive motions, and correspondence

Trial Attorney – In-House Counsel

General

• Lead day-to-day field operations from project startup through project completion
• Coordinate subcontractors, vendors, suppliers, and self-perform crews
• Maintain project schedules and ensure key milestones are achieved
• Conduct site safety meetings and enforce company safety standards
• Review construction drawings, specifications, and project documents
• Identify and resolve field issues before they impact schedule or productivity
• Maintain quality standards and ensure work is completed correctly
• Communicate project progress with project managers, owners, engineers, and other stakeholders
• Manage manpower, equipment, materials, and daily jobsite activities

Construction Superintendent

Platform Engineer

• Architect and scale the core systems that power Sentry's billing infrastructure.
• Collaborate on building the next generation of Sentry’s usage tracking pipeline.
• Help design flexible pricing primitives that support various billing models.
• Contribute to technical decisions on data consistency challenges unique to billing.

Senior Software Engineer, Billing Platform

Engineering Manager

• Lead a team of engineers owning critical workflows such as checkout and invoicing.
• Define and drive the team's roadmap and align team goals with organizational objectives.
• Provide technical leadership and guidance on complex distributed systems and design.
• Partner closely with business and technical teams to translate business goals into actionable objectives and scalable solutions.
• Lead, mentor, and grow a team of talented engineers, including Staff-level engineers.
• Effectively communicate team progress, challenges, and strategic direction to senior leadership, stakeholders, and the wider organization.