Crumdale Specialty

• Drive regional revenue growth by developing and executing a strategic sales plan focused on TPA solutions within the broader health plan ecosystem • Cultivate and expand relationships within the limited distribution network of brokers, consultants, and agents • Identify, develop, and close new business opportunities while strengthening existing partner relationships • Educate broker partners on the full suite of health plan solutions, with an emphasis on TPA-led plan design and administration strategy • Serve as a trusted advisor to brokers and consultants by delivering data-driven insights and strategic plan design recommendations • Collaborate cross-functionally with underwriting, actuarial, operations, and leadership teams to deliver competitive, customized proposals • Lead finalist presentations, strategy meetings, and executive-level discussions with brokers and employer groups • Maintain a disciplined pipeline management process, providing accurate forecasting and sales reporting • Monitor regional market trends and competitor activity to proactively position solutions • Achieve and exceed assigned sales targets, growth metrics, and profitability goals • Ensure alignment with underwriting discipline and long-term profitability strategy • Represent Crumdale at industry events and broker functions to expand market presence • Uphold culture of alignment, innovation, and integrity

Role Description As a Regional Sales Director, you will be a cornerstone of our growth strategy. This role demands a highly driven, organized, and strategic professional with a passion for sales, broker development, and consultative solution selling. You will be responsible for building strong broker relationships, managing a robust sales pipeline, and closing high-quality business aligned with our integrated health platform. We’re looking for a driven, broker-focused sales leader who knows how to win in the self-funded health plan space, with a focus on positioning and growing our Third Party Administration (TPA) platform. Key Responsibilities - Drive regional revenue growth by developing and executing a strategic sales plan focused on TPA solutions within the broader health plan ecosystem. - Cultivate and expand relationships within the limited distribution network of brokers, consultants, and agents. - Identify, develop, and close new business opportunities while strengthening existing partner relationships. - Educate broker partners on the full suite of health plan solutions, with an emphasis on TPA-led plan design and administration strategy. - Serve as a trusted advisor to brokers and consultants by delivering data-driven insights and strategic plan design recommendations. - Collaborate cross-functionally with underwriting, actuarial, operations, and leadership teams to deliver competitive, customized proposals. - Lead finalist presentations, strategy meetings, and executive-level discussions with brokers and employer groups. - Maintain a disciplined pipeline management process, providing accurate forecasting and sales reporting. - Monitor regional market trends and competitor activity to proactively position solutions. - Achieve and exceed assigned sales targets, growth metrics, and profitability goals. - Ensure alignment with underwriting discipline and long-term profitability strategy. - Represent Crumdale at industry events and broker functions to expand market presence. - Uphold culture of alignment, innovation, and integrity. Qualifications - 5+ years of successful sales experience in self-funded health plans, TPA platforms, stop-loss, or employee benefits markets. - Demonstrated success building and managing broker/consultant relationships. - Proven track record of meeting or exceeding revenue and growth targets. - Strong understanding of alternative funding, captives, cost-containment strategies, and TPA operations. - Ability to articulate complex solutions in a consultative, value-driven manner. - Experience navigating multi-stakeholder sales cycles and leading executive presentations. - Strong pipeline management and CRM proficiency. - Financial acumen with focus on profitability. - Entrepreneurial mindset and ability to operate independently. - Willingness to travel within assigned region. Benefits - Medical - Telemedicine - Dental - Vision - Life, AD&D, Disability - 401(k) - Flexible Time-off

• 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