Crumdale Specialty

• Own all inbound and outbound file processes across vendors (PBM, networks, medical management, etc.). • Monitor, validate, and reconcile daily file activity (eligibility, claims, accumulators, EOBs, etc.). • Ensure proper file formatting, delivery, acknowledgments, and error resolution. • Troubleshoot and resolve file failures across SFTP connections, vendors, and internal systems. • Maintain and optimize file workflows to support scalability and automation. • Serve as the primary technical contact for vendor file integrations. • Manage connectivity across SFTP platforms, APIs (where applicable), and vendor data exchanges. • Build, maintain, and enhance operational and client-facing reports using SQL. • Perform cross-system data audits between claims system, vendor outputs, and internal reporting. • Support new client implementations from a file and reporting readiness perspective. • Identify opportunities for automation, efficiency improvements, and standardization.

Role Description We are hiring a Technical Operations Analyst to own inbound and outbound file operations, vendor data integrations, and reporting across our growing TPA environment. This role will serve as the central hub for file management, data movement, and operational reporting; ensuring accurate, timely, and scalable data exchange across all partners including networks, PBMs, and other vendors. This position is highly technical and data-focused, requiring strong SQL skills, deep understanding of TPA workflows, and the ability to translate business needs into reliable reporting and file solutions. Key Responsibilities - File Operations & Data Exchange Management - Own all inbound and outbound file processes across vendors (PBM, networks, medical management, etc.). - Monitor, validate, and reconcile daily file activity (eligibility, claims, accumulators, EOBs, etc.). - Ensure proper file formatting, delivery, acknowledgments, and error resolution. - Troubleshoot and resolve file failures across SFTP connections, vendors, and internal systems. - Maintain and optimize file workflows to support scalability and automation. - Vendor Integration Oversight - Serve as the primary technical contact for vendor file integrations. - Manage connectivity across SFTP platforms, APIs (where applicable), and vendor data exchanges. - Coordinate with vendors and claims system to resolve discrepancies, mapping issues, and data inconsistencies. - Ensure alignment between vendor requirements and internal system capabilities. - Reporting & Data Analytics - Build, maintain, and enhance operational and client-facing reports using SQL. - Translate business and client reporting needs into scalable data solutions. - Support reporting across eligibility, claims, accumulators, and vendor data. - Partner with internal teams (Account Management, Claims, Finance) to deliver accurate reporting insights. - Data Quality & Reconciliation - Perform cross-system data audits between claims system, vendor outputs, and internal reporting. - Identify and resolve root causes of data discrepancies (eligibility, claims, accumulators). - Ensure consistency of data across all downstream systems and vendor partners. - Develop processes to proactively monitor and improve data quality. - Implementation & Go-Live Support - Support new client implementations from a file and reporting readiness perspective. - Ensure all vendor file connections are tested, validated, and operational prior to go-live. - Partner with implementation and TechOps leadership to meet critical deadlines and dependencies. - Assist in defining file requirements, layouts, and reporting needs for new clients. - Operational Process Improvement - Develop and maintain SOPs for file management, error handling, and reporting processes. - Identify opportunities for automation, efficiency improvements, and standardization. - Support the evolution of a scalable TPA operating model as client and vendor volume grows. Qualifications - 5+ years of experience in TPA operations, healthcare data operations, EDI, or technical operations. - Strong experience managing inbound/outbound file processing across multiple vendors. - Advanced SQL skills required (data extraction, transformation, reconciliation, reporting). - Experience with file formats such as 834, 835, 837, CSV, flat files, JSON. - Hands-on experience with SFTP platforms and file automation workflows. - Strong understanding of TPA ecosystem (eligibility, claims, accumulators, PBM, network integrations). - Proven ability to troubleshoot complex data and file issues across systems and partners. - Strong analytical mindset with attention to detail and data accuracy. - Excellent communication skills with both technical and non-technical stakeholders. Benefits - Medical - Telemedicine - Dental - Vision - Life, AD&D, Disability - 401(k) - Flexible Time-off Company Description Crumdale Specialty is a diversified insurance firm providing custom, self-funded healthcare solutions to a limited distribution network of brokers, consultants, and agents nationwide. Ranked on the Inc. 5000 Fastest Growing Companies and Best Workplaces, we leverage industry expertise, superior talent, data analytics, and a disruptive mindset to manufacture, underwrite, and administer agile, transparent, and cost-saving solutions. At Crumdale, people come first. Our culture is rooted in alignment, innovation, accountability, and integrity.

• Develop strong stop loss carrier partnerships with Crumdale’s existing stop loss partners as well as identify and cultivate new stop loss carrier partnerships. • Implement new, and enhance existing, processes to improve efficiency and speed to quote while driving competitive performance from Crumdale’s stop loss partners. • Mastery of Crumdale’s cost containment programs, how they impact plan pricing and their application to stop loss insurance. • Work closely with the Pricing, Quoting, & Center of Excellence teams to develop proper quote requests and process to maximize impact to the organization. • Negotiate proposals with and without direction to secure the best possible quotes prior to releasing to the sales team. • Help the team drive more stop loss proposals to go firm and final and ultimately close as new sold business. • Leverage technology and artificial intelligence to amplify the expertise of the team and Crumdale’s carrier partners, and accelerate quote throughput thus reducing time to quote at all stages of the process.

Crumdale Specialty is seeking a Captive Sales Advisor to partner with Regional Sales Directors to win alternative funding opportunities specifically by turning “captive” from a conceptual idea into a clear, finance‑ready decision for employers. This role elevates the effectiveness of our field teams by simplifying technical components of self-funding, captives, stop‑loss strategy, and cost-containment solutions. The Captive SME plays a critical part in shaping deal strategy, enabling producers, and ensuring that opportunities move efficiently from discovery to close. **Key Responsibilities:** - Serve as the subject matter expert on complex captive and alternative funding cases. - Equip producers with concise talk tracks, discovery paths, and executive-friendly explanations of risk, funding mechanics, governance, and key tradeoffs. - Support regional sales leaders in positioning Crumdale’s captive solutions competitively and effectively. - Build, activate, and maintain referral networks across brokers and consultants. - Make it simple for external partners to introduce captive strategies. - Deliver training, tools, and confidence-building resources that expand captive pipeline opportunities. - Coordinate with underwriting, operations, account management, and solution partners to ensure cohesive deal execution. - Translate discovery findings into credible proposals and ensure readiness for financial and operational evaluation. - Maintain disciplined timelines and ensure seamless handoffs into onboarding. - Bring structure to the alternative funding sales motion with clear KPIs, next steps, and progress tracking. - Help internal teams prioritize support based on probability to close. - Ensure opportunities do not stall in “maybe” by driving accountability and clarity throughout the process. - Develop field-ready materials that increase speed-to-proposal and close rates. - Contribute to internal training, content creation, and tools that simplify complexity for both buyers and brokers. - Represent Crumdale’s captive capabilities with clarity and authority in the market.

• Responsible for the customer’s total service experience with Crumdale • Acts as a trusted advisor while managing ongoing client relationships (brokers, TPAs & employers) and ensuring service delivery with a focus on the pharmacy benefit • Represents clients internally as advocate and coordinates with other functional areas within the company to implement client benefits, complete projects, and address service needs • Building strong relationships with our client groups • Implementing benefit communication programs with the client’s organization • Helping the client interpret data to guide decision making • Troubleshooting any issues that may arise to ensure client satisfaction with Crumdale

Crumdale Specialty is a diversified insurance firm providing custom, self-funded healthcare solutions to a limited distribution network of brokers, consultants, and agents nationwide. Ranked on the Inc. 5000 Fastest Growing Companies and Best Workplaces, we leverage industry expertise, superior talent, data analytics, and a disruptive mindset to manufacture, underwrite, and administer agile, transparent, and cost-saving solutions. We optimize the fragmented health benefits supply chain to reduce health benefit costs and create better outcomes for employers and employees. At Crumdale, people come first. We strive to make a positive impact on the people we serve. We believe this starts with the passion and purpose of our team. Our company culture is rooted in alignment, innovation, and integrity. About the Role: The Senior Account Executive (SAE) within the PBM/Pharmacy Division is responsible for the customer’s total service experience with Crumdale. The Senior Account Executive acts as a trusted advisor while managing ongoing client relationships (brokers, TPAs & employers) and ensuring service delivery with a focus on the pharmacy benefit. Acts as the client centric, client facing resource for assigned clients. Represents clients internally as advocate and coordinates with other functional areas within the company to implement client benefits, complete projects, and address service needs.  This includes serving as the key liaison between the customer and Crumdale, building strong relationships with our client groups, implementing benefit communication programs with the client’s organization, helping the client interpret data to guide decision making, and troubleshooting any issues that may arise to ensure client satisfaction with Crumdale. The commitment and dedication required of the Senior Account Executive is critical to the growth and success of the company.

• Recommend new clinical strategies to improve the health of our groups, lower trend and promote savings by analyzing and interpreting prescription claims data • Provide oversight of clinical programs • Will be accountable for developing and presenting strategies to enhance pharmacy benefit savings for employers • Clinical liaison for internal Specialty including account management, sales, underwriting, pricing, finance, and leadership • Develops clinical materials and presentations for sales and marketing • Provide clinical support to Specialty Solutions team including directly interacting with brokers, clients, patients, providers, and manufacturers • Client-facing and direct interaction with PBM leadership teams, RX vendor Specialty, brokers and clients • Meet with brokers and clients to discuss clinical trends, review relevant pharmacy data, and provide recommendations/supportive rationale for clinical management strategies • Support the VP of Clinical Strategies & Solution in the development of new offerings for employer groups • Support growth of pharmacy products, as well as assist in developing a robust clinical management playbook for client management • Translate and decipher how current pharmacy/healthcare trends will affect our group’s clinical strategies • Provide drug information and act as the clinical consultant/subject management expert on the account management team • Proactively make recommendations for clients to stay ahead of the curve regarding drug pipeline activity (new generics, new brands, new clinical rules and specialty)

• Handle day-to-day relationships with clients • Troubleshoot and respond to different types of requests • Work with multiple partners to find client solutions • Handle communications, project management, reporting, analyzing trends, solving member issues • Address emergent needs for clients

Crumdale Specialty is a diversified insurance firm providing custom, self-funded healthcare solutions to a limited distribution network of brokers, consultants, and agents nationwide. Ranked on the Inc. 5000 Fastest Growing Companies and Best Workplaces, we leverage industry expertise, superior talent, data analytics, and a disruptive mindset to manufacture, underwrite, and administer agile, transparent, and cost-saving solutions. We optimize the fragmented health benefits supply chain to reduce health benefit costs and create better outcomes for employers and employees.   At Crumdale, people come first. We strive to make a positive impact on the people we serve. We believe this starts with the passion and purpose of our team. Our company culture is rooted in alignment, innovation, and integrity. About the role: The PBM/Pharmacy focused Account Manager will handle day-to-day relationships with their clients, working to troubleshoot and respond to different types of requests. This role is a cross-functional opportunity where you will work with multiple partners to find client solutions. You will be handling communications, project management, reporting, analyzing trends, solving member issues, and addressing emergent needs for your clients.

Title: VP of Sales Location: Paoli, Pennsylvania, United States Type: Full-time Workplace: Fully remote Job Description: RemoteSalesFull time Description Crumdale Specialty is seeking a dynamic and strategic Vice President of Sales to accelerate growth across our Health Plan Service Solutions portfolio. This executive will be responsible for building and executing a high‑performance sales strategy, strengthening broker and consultant partnerships, expanding distribution channels, and driving sustainable revenue growth in a rapidly evolving healthcare and risk‑financing market. The VP of Sales will help shape Crumdale’s national go‑to‑market strategy, lead and develop a high‑impact sales team, and collaborate cross‑functionally to enhance our market presence, value proposition, and client experience. Key Responsibilities 1. Sales Leadership & Strategy - Build, execute, and continuously refine Crumdale’s national sales strategy across Stop‑Loss, Captive, TPA, and Specialty Benefits solutions - Set clear sales goals, performance targets, compensation strategies, and forecasting dashboards - Develop a disciplined pipeline management approach with strong accountability and transparency - Identify new market opportunities, competitive advantages, and strategic partnerships 2. Team Development & Performance Management - Recruit, lead, mentor, and scale high‑performing Regional Sales Directors within assigned territories - Establish training programs, playbooks, and repeatable processes for sales excellence - Foster a culture of collaboration, motivation, and results, grounded in Crumdale’s values and client‑centric mindset 3. Broker, Consultant & Partner Relationships - Serve as a senior‑level relationship lead with key national and regional brokers, consultants and distribution partners - Drive engagement, education, and alignment across the broker ecosystem to deepen channel partnerships - Represent Crumdale at industry events, conferences, and partner meetings 4. Revenue Growth & Market Expansion - Deliver consistent year‑over‑year revenue and margin growth - Lead initiatives to expand into new regions, verticals, and product lines - Collaborate cross functionally with Sales, Stop-Loss, Underwriting, Pharmacy, TPA, Compliance and operations teams to enhance value propositions and win new business 5. Collaboration & Cross‑Functional Alignment - Partner with Marketing to develop strong campaigns, branded materials, sales enablement tools, and market positioning - Work closely with Operations, Client Success, and Implementation to ensure seamless onboarding and exceptional client outcomes - Provide ongoing market feedback to Product, Underwriting, and Executive Leadership 6. Executive Leadership & Reporting - Own sales forecasting, performance analytics, market intelligence, and board‑level reporting - Serve as a key member of the sales leadership team, contributing to Crumdale’s strategic planning and growth initiatives - Ensure alignment between sales, underwriting, product, and operational roadmaps Requirements - 7+ years of progressive sales leadership experience in Stop‑Loss, Captives, Self‑Funded Benefits, PBM, TPA services, or related healthcare/insurance verticals - Proven success leading a national or regional sales team with measurable revenue growth results - Strong existing relationships with brokers, consultants, and distribution partners - Deep understanding of self‑funded health plans, risk financing, Stop‑Loss underwriting, and employer benefits - Exceptional communication, presentation, and influencing skills - Highly strategic thinker with strong operational discipline and an execution‑driven mindset - Ability to thrive in a fast‑paced, entrepreneurial, scaling environment - Willing to travel nationally (40–60%) Location Remote or hybrid; travel required for training, broker meetings, team events, and industry conferences Benefits At Crumdale, we strive to provide a comprehensive and supportive benefits package to ensure the well-being of our employees. Our benefits include: - Medical - Telemedicine - Dental - Vision - Life, AD&D, Disability - 401(k) - Flexible Time-off Please note: Crumdale Specialty is not engaging with external recruitment agencies; please refrain from contacting us regarding this position.