Bridgeway Benefit Technologies

• Lead full-cycle data conversion across multiple customer projects (discovery → mapping → transformation → validation → go-live) • Act as the primary technical contact for customers, guiding data strategy, surfacing risks, and managing expectations • Collaborate with Business Analysts and other Professional Services teams to understand data requirements, provide data analyses to assist with the configuration of our software, and accurately map data to meet customer needs • Analyze and validate large, complex datasets using advanced SQL • Build and execute ETL/ELT processes (SSIS, Talend, Informatica, or similar) • Develop data mapping logic, transformation rules, and validation strategies • Identify and resolve data quality issues through profiling, cleansing, and root cause analysis • Work across file formats (CSV, Excel) to support data exchange • Plan and execute cutover activities, including go-live coordination and validation sign-off • Partner with internal teams to troubleshoot issues and ensure accurate data delivery • Mentor junior team members and contribute to improving migration processes and standards • Leverage generative AI tools such as Claude and Copilot to streamline workflows, enhance productivity, improve solution quality, and accelerate delivery of business outcomes.

• Work with Business Analysts to understand the customer’s request, including data mapping and process flows. • Create and configure customer documents such as Checks and Forms and automate workflow solutions using our proprietary software. • Collaborate with Business Analysts on business and technical requirements, to produce clearly defined document and workflow specifications. • Assist with translating requirements into documents, forms, letters, and other correspondences, to produce customer approved deliverables. • Create and revise complex batch, on-demand and interactive document templates, accurately mapping data fields, constructing grouping, repeating rows, headers, logos, pagination, etc., as applicable per the defined requirements. • Work with software developers to request data source changes and process modifications. • Work with customers and other stakeholders on the implementation, configuration, testing, and troubleshooting of our integrated document creation and management tool. • Utilize multiple tools and resources to resolve customer questions and issues in the areas of data, system configuration, setup, and product functionality. • Leverage generative AI tools such as Claude and Copilot to streamline workflows, enhance productivity, improve solution quality, and accelerate delivery of business outcomes.

Role Description Bridgeway Benefit Technologies is looking for a Systems Analyst to join our Professional Services team. In this role, you will be responsible for working with our data conversion team, as well as the customer, to convert customer data onto our basys software platform. You will test conversion programs, validate data, analyze for inconsistencies, and ensure accurate mapping into the basys platform, while collaborating with the Conversion Programming Team, Business Analysts, customers, and vendors. - Collaborate with Business Analysts and other Professional Services teams to understand data requirements and provide data analyses for software configuration. - Test conversion programs, validate data, analyze for inconsistencies, and ensure accurate mapping into the platform. - Work with customers to identify data requirements, map data, and consult on best practices for data conversion. - Coordinate with the Conversion Programming Team to provide instructions and feedback after data review and testing. - Communicate conversion status, research issues, and coordinate with vendors for data files. - Prepare system data files and run conversion programs on both internal and customer servers. - Coordinate data refresh efforts and final conversions at Go Live between customer, implementation team, and incumbent vendor. - Facilitate data and conversion validation efforts to verify that all data from customer legacy system confirms to Bridgeway Platform needs and meets customers business requirements. - Utilize SQL Server, MS Access, or similar tool to analyze data to evaluate data to verify thoroughness, accuracy and confirm all data has been loaded to the new system to meet historical and ongoing business needs. - Support internal and customer data validation testing. - Manage multiple conversion projects simultaneously and prioritize workload to meet deadlines. - Act as a subject matter expert on data domains and conversion processes. - Advocate for continuous improvement. Qualifications - 2-3 years of experience using Access and/or SQL. - Bachelor’s degree in computer science or similar technical discipline. - SQL programming skills are a plus. - Experience with data conversion/migration projects and data analysis. - Strong attention to detail and analytical skills. - Understanding data dictionaries, mapping documents, and relational database concepts. - Excellent communication, organizational skills, and time management. - Experience working with a variety of data file types is a plus. - Must be legally authorized to work in the US without sponsorship. Requirements - Bridgeway is an Equal Opportunity Employer. - Covid Message: We value the safety and well-being of our Bridgeway community, including our staff, customers, business partners, and beyond. This is why our team has required staff to be fully vaccinated for all in-person business activities, whether on-site at our corporate office or traveling for business. Candidates should consider this requirement before applying.

Role Description Bridgeway is looking for a Business Analyst who possesses an overall knowledge of benefits administration, to join our dynamic Professional Services team. In this role, you will have the opportunity to collaborate closely with our valued customers and internal teams to drive the successful delivery of multiple projects for our cutting-edge benefits administration solutions. Your main responsibilities will include: - Engage directly with customers to facilitate the implementation, configuration, testing, and training of Bridgeway’s software suite. - Effectively prioritize and execute multiple development projects, including eligibility files and module installations. - Translate business needs into well-defined and detailed requirements, user stories, and user-focused solutions and design documents. - Engage and positively influence stakeholders in requirements-gathering sessions and solution review meetings, demonstrating your ability to communicate with end users, executive sponsors, and IT resources. - Collaborate with cross-functional teams to ensure alignment with stakeholder needs and business objectives. - Utilize a variety of tools and resources to address customer application questions or issues related to database, system configurations/setup, product functionality, and business enhancements. - Develop and maintain a comprehensive understanding of our products, solutions, and capabilities. This is a remote position, with travel up to 30%, as needed. Qualifications - Possess 3+ years of experience as a Business Analyst or in software implementation, with experience working with external clients. - Knowledge of the benefits administration or Taft-Hartley industry is a plus. - Ability to manage multiple projects, prioritize tasks effectively, and meet deadlines. - Exceptional written and verbal communication skills, with an emphasis on clarity and conciseness. - Demonstrate strong initiative and a natural aptitude for learning in a complex and ever-evolving technology environment. - Advanced proficiency in Microsoft Office products, particularly Excel. - Bachelor’s degree in information systems, Computer Science, or a related field. Requirements - 3+ years of experience as a Business Analyst or in software implementation. - Experience working with external clients. - Knowledge of the benefits administration or Taft-Hartley industry is a plus. - Ability to manage multiple projects and prioritize tasks effectively. - Exceptional written and verbal communication skills. - Strong initiative and aptitude for learning. - Advanced proficiency in Microsoft Office products, particularly Excel. - Bachelor’s degree in information systems, Computer Science, or a related field. Company Description As the industry leader for innovative benefits administration solutions, we provide the Taft-Hartley community unmatched technology, capabilities, and industry expertise while maintaining the highest-level customer service and support. For over forty years and leveraging the power of our Basys and ISSI technology platforms, Bridgeway Benefit Technologies is the leader in our market, delivering reliable health and pension benefits processing, fund office administration, reporting, and member service on a platform built for data security, regulatory compliance, and a lower total cost of ownership.

• Iteratively design and develop scalable, resilient, and efficient platform solutions using cloud services and modern software design frameworks. • Create modular, reusable infrastructure using Terraform and related tools. • Partner interdepartmentally and cross-functionally to strengthen DevOps practices through automation. • Architect, develop, and maintain CI/CD pipelines for platform functions and customer needs at scale. • Deliver solutions based on event-driven, object-oriented, and functional design patterns. • Own the design and implementation of monitoring and logging solutions to ensure reliability and performance. • Support the definition and maintenance of a lifecycle process for platform systems to ensure updates, patches, and security compliance. • Apply deep expertise in platform engineering while leveraging cross-disciplinary knowledge to drive effective collaboration across development, operations, and security teams. • Resolve cloud infrastructure issues quickly, analyze performance, and implement improvements. • Analyze system performance and implement optimizations to improve speed, efficiency, and resource utilization. • Anticipate and plan infrastructure scaling to meet the growing needs of the business. • Apply a security-first approach, ensuring SOC, SOC2, HIPAA, NIST, and regulatory requirements are met. • Implement and manage IAM, firewalls, and SIEM solutions. • Integrate diverse and non-traditional systems to deliver practical, forward-thinking outcomes. • Navigate challenges creatively and find effective solutions when conventional approaches fall short. • Lead assigned projects, driving cross-team collaboration, execution delivery, and accountability. • Write clean, efficient, and well-documented code while following best practices and established development standards. • Take part in the on-call rotation to ensure the reliability and availability of platform services. • Use generative AI tools such as Claude, Copilot, or ChatGPT to improve productivity and deliver high-quality outcomes.

Director, Quality Assurance Remote Bridgeway is seeking a Director, Quality Assurance to join our Technology team. This leader will not only define and drive the QA strategy but will also actively engage in the design, development, and execution of testing solutions. The Director, QA will lead by example—remaining close to the code, automation frameworks, and testing practices—while building a high-performing team and ensuring delivery of high-quality software products that meet business, regulatory, and customer requirements. This role manages QA Engineers and QA Analysts, develops scalable testing strategies, and drives continuous improvement across processes, tools, and methodologies. The ideal candidate thrives in a player-coach capacity, balancing strategic leadership with direct technical contribution. This role will work closely with Product, Engineering, and Operations to embed quality throughout the software development lifecycle (SDLC). This is a remote position, with occasional travel. East Coast candidates preferred. Key Responsibilities: - Lead as a hands-on, player–coach QA leader, contributing directly to test automation design, framework development, code reviews, and the resolution of complex quality and production issues. - Define, implement, and evolve the overall QA strategy, standards, and best practices across manual and automated testing, ensuring alignment with business, regulatory, and customer requirements. - Architect and scale modern automation frameworks and CI/CD-integrated testing solutions, driving increased test coverage, reliability, execution speed, and long-term maintainability. - Own the end-to-end test lifecycle, including test planning, test case design, regression strategy, execution, defect management, and reporting, ensuring processes are repeatable, data-driven, and effective. - Ensure comprehensive quality coverage across all testing dimensions, including functional, regression, integration, performance, and security testing. - Embed quality deeply within Agile, Scrum, and DevOps workflows, promoting a shift-left testing culture focused on early validation, defect prevention, and continuous feedback throughout the SDLC. - Leverage metrics and insights to drive decisions, providing clear visibility into quality trends, release readiness, risks, and outcomes to technical and executive stakeholders. - Continuously improve QA processes, tooling, and execution, identifying bottlenecks and risks, piloting new technologies, prioritizing initiatives effectively, monitoring execution, and adjusting course as needed. - Build, lead, and mentor a high-performing QA team, fostering a culture of collaboration, accountability, and continuous improvement. This includes hiring, setting and monitoring individual performance objectives, career development, performance appraisals, and providing regular feedback and coaching. - Set clear expectations and create a positive work environment based on accountability, in collaboration with the engineering and management teams. - Build and maintain productive relationships across departments, navigating organizational complexity and silos.   - Lead and/or contribute to cross-functional initiatives and change efforts.   - Communicate clearly and persuasively, adapting messages for diverse technical and business stakeholders across levels and functions. Qualifications: - 7+ years of experience in software quality assurance, including 3+ years leading and managing QA teams delivering commercial software products (SaaS, on‑prem, and/or mobile). - Proven experience leading in a hands‑on technical leadership role, balancing people leadership with direct contribution to test automation, reviews, and complex quality issues. - Strong technical expertise in test automation, including designing, building, and maintaining scalable, maintainable automation frameworks and contributing production‑quality code. - Proficiency in Python and working knowledge of the .NET framework. - Deep experience with modern test automation tools and frameworks such as Playwright, Selenium WebDriver, TestNG, Cucumber, and SmartBear tools (TestComplete, ReadyAPI or similar). - Demonstrated experience integrating automated testing into CI/CD pipelines and DevOps toolchains (e.g., Azure DevOps or comparable platforms). - Hands‑on experience with test management and defect tracking tools, and ownership of test planning, execution, and reporting practices. - Strong analytical and problem‑solving skills, with experience using quality metrics and data to assess risk, inform release decisions, and drive continuous improvement. - Extensive experience delivering software in Agile/Scrum environments with frequent release cadences. - Passion for modernizing QA practices, including automation‑first strategies and movement toward cloud‑native (PaaS) architectures. - Bachelor's degree in Computer Science, Software Engineering or related discipline

• Own customer lifecycle from onboarding through expansion • Identify, shape, and close expansion opportunities in partnership with Sales • Proactively mitigate churn risk through data-driven engagement strategies • Maintain accurate forecasting for growth opportunities • Partner with customers to define clear, measurable success metrics aligned to their business goals • Develop and execute customer success plans tied to revenue growth or operational efficiency and aligned to the defined customer segmentation and engagement strategy • Drive product adoption as the foundation for value realization • Support new product, feature, and platform launches by driving customer awareness, readiness, and adoption within assigned accounts • Track and communicate progress against outcomes through QBRs and ongoing engagement • Leverage customer health, usage data, and engagement signals to identify risks and opportunities, prioritize actions and outreach, and inform account strategy • Monitor and act on customer health scoring and lifecycle milestones • Act as the internal orchestrator across Sales, Product, Engineering, Professional Services, and Support, including partnering with the assigned AE within a pod structure to align on account strategy and execution • Provide voice of the customer insights to influence product roadmap and GTM strategy • Partner cross-functionally to improve onboarding, adoption, and customer experience • Engage and influence senior stakeholders on business outcomes and strategy • Lead QBRs focused on value realization and commercial outcomes (not just activity reporting) • Navigate complex conversations, including billing and invoicing disputes, arrears, price increases, risk mitigation, and customer escalations requiring cross-functional coordination • Maintain accurate system documentation and effective pipeline visibility and management • Create, track, and report on customer-facing projects and initiatives across assigned accounts, ensuring scope, milestones, owners, and timelines are clearly documented and communicated in partnership with Professional Services • Monitor open support cases for assigned accounts, partnering with Support to drive resolution, surface trends, and keep customers informed • Synthesize project status and support activity into customer-ready reporting for QBRs, account reviews, and internal account health discussions • Follow and improve standardized processes (including execution against tier-based engagement models, customer onboarding and offboarding, QBRs, and reset plans for at-risk accounts) • Contribute to scalable CS practices, playbooks, and tooling improvements • Represent Bridgeway in customer-facing forums and community engagements (e.g., user groups, advisory boards, UGC conference) to deepen relationships and capture structured feedback • Maintain CRM hygiene and forecasting accuracy in HubSpot, expansion, terminations and customer health data are current and actionable • Use generative AI tools such as Claude, Copilot, or ChatGPT to improve productivity and deliver high-quality outcomes.

Role Description Bridgeway is seeking a Senior Data Engineer to design, develop, and maintain our data warehouse infrastructure. This role involves working closely with analysts, engineers, and other stakeholders to shape our data architecture, ensuring secure and efficient data pipelines, and enabling advanced analytics across the organization. The ideal candidate will have a strong background in data engineering, data warehousing, and ELT processes, along with a passion for optimizing data systems. This is a remote position, with preference given to East Coast candidates. - Design, develop, and maintain a scalable lakehouse architecture, including a medallion (bronze/silver/gold) data model optimized for analytics and AI/ML consumption. - Design, implement, and operate ELT pipelines, including workflow orchestration, scheduling, and monitoring, to ensure reliable and scalable execution. - Establish data quality, testing, and observability practices, and proactively monitor and resolve data and automation issues to ensure platform reliability and trust. - Ensure data security and compliance, including role-based access controls for security, encryption, masking, and governance best practices to ensure compliant handling of sensitive information. - Optimize performance of data workflows and storage for cost efficiency and speed. - Partner with engineers, analysts, and stakeholders to meet data needs; balance cost, performance, simplicity, and time-to-value while mentoring teams and documenting standards. - Provide technical leadership and mentorship to team members – guiding best practices, skill development, and collaboration cross-functionally. - Enable AI/ML use cases through well-structured data models, feature availability, and platform integrations using tools such as Databricks Vector Search and Model Serving. - Develop and maintain data pipelines using version control and CI/CD best practices in a collaborative engineering environment. - Collaborate within an Agile-Scrum framework and develop comprehensive technical design documentation to ensure efficient and successful delivery. - Serve as a trusted expert on organizational data domains, processes, and best practices. Qualifications - 5+ years of hands-on data engineering experience required. - 3+ years of experience building and operating data pipelines on a modern lakehouse platform (e.g., Databricks – Unity Catalog, Delta Live Tables, Asset Bundles), including data modeling, governance, and CI/CD deployment patterns. - 3+ years of experience with analytical SQL (ANSI SQL/T-SQL/Spark SQL) and Python for data engineering, including pipeline construction, transformation logic, and automation required. - Strong communication skills with the ability to collaborate and influence across engineering, analytics, and business stakeholders required. - Streaming and ingestion tools, such as Kafka, Kinesis, Event Hubs, Debezium, or Fivetran preferred. - DAX, LookML, dbt; Airflow/Dagster/Prefect, Terraform; Azure DevOps; Power BI/Looker/Tableau; GitHub CoPilot knowledge is a plus. - Bachelor’s degree in Computer Science, Information Technology, or a related field. Master’s degree preferred.

• Analyze and understand business, product, infrastructure, and technical requirements to ensure comprehensive test coverage. • Collaborate with cross-functional stakeholders to clarify requirements, identify risks, and ensure acceptance criteria are testable and automatable. • Define testing strategies and approaches that align with DevOps and CI/CD practices. • Identify testing scope, objectives, resources, timelines, and deliverables for automated and manual testing efforts. • Design, develop, and maintain well-structured, reusable, and maintainable automated test cases and frameworks. • Create and manage automated test scripts and test suites within Azure DevOps (ADO) or similar platforms. • Execute and maintain automated and manual tests, including functional, regression, performance, usability, and security testing. • Initiate and monitor automated test runs, analyze results, and validate test coverage for assigned scrum teams. • Identify, document, prioritize, and track defects and inconsistencies, partnering closely with developers to troubleshoot issues and validate fixes. • Develop a strong understanding of user story sizing, test planning, and test coverage within Agile and Scrum workflows. • Maintain clear and detailed documentation of test plans, test cases, automation frameworks, and regression testing results. • Prepare and communicate test results, regression reports, and quality metrics to technical and non-technical stakeholders. • Actively contribute to the automation roadmap by identifying opportunities to increase automation coverage and improve testing efficiency. • Recommend and implement process, tooling, and framework improvements to enhance the effectiveness, scalability, and reliability of the QA practice. • Stay current with industry trends, tools, and best practices in test automation, quality engineering, and secure software development.

• Lead as a hands-on, player–coach QA leader, contributing directly to test automation design, framework development, code reviews, and the resolution of complex quality and production issues. • Define, implement, and evolve the overall QA strategy, standards, and best practices across manual and automated testing, ensuring alignment with business, regulatory, and customer requirements. • Architect and scale modern automation frameworks and CI/CD-integrated testing solutions, driving increased test coverage, reliability, execution speed, and long-term maintainability. • Own the end-to-end test lifecycle, including test planning, test case design, regression strategy, execution, defect management, and reporting, ensuring processes are repeatable, data-driven, and effective. • Ensure comprehensive quality coverage across all testing dimensions, including functional, regression, integration, performance, and security testing. • Embed quality deeply within Agile, Scrum, and DevOps workflows, promoting a shift-left testing culture focused on early validation, defect prevention, and continuous feedback throughout the SDLC. • Leverage metrics and insights to drive decisions, providing clear visibility into quality trends, release readiness, risks, and outcomes to technical and executive stakeholders. • Continuously improve QA processes, tooling, and execution, identifying bottlenecks and risks, piloting new technologies, prioritizing initiatives effectively, monitoring execution, and adjusting course as needed. • Build, lead, and mentor a high-performing QA team, fostering a culture of collaboration, accountability, and continuous improvement. This includes hiring, setting and monitoring individual performance objectives, career development, performance appraisals, and providing regular feedback and coaching. • Set clear expectations and create a positive work environment based on accountability, in collaboration with the engineering and management teams. • Build and maintain productive relationships across departments, navigating organizational complexity and silos. • Lead and/or contribute to cross-functional initiatives and change efforts. • Communicate clearly and persuasively, adapting messages for diverse technical and business stakeholders across levels and functions.