Senior Implementation Delivery Lead

Want to be a bswifter? At bswift we’ve been transforming benefits administration since 1996, making it simpler, smarter, and more human. Our state-of-the-art, cloud-based technology and services empower employees to understand, manage, and love their benefits. From downtown Chicago, and remotely across the country, we serve thousands of companies and millions of people nationwide, reducing administrative burdens and freeing HR teams to focus on creating thriving, people-first workplaces. We’re looking for motivated and goal-driven individuals who share our passion for delivering excellence and creating solutions that make a difference. The reward is a fun, flexible and creative environment with ample opportunity for professional and personal growth. If you love the bswift values of pursue excellence, embrace accountability, deliver superior service, and be a great place to work, we want to hear from you! ABOUT US bswift is a leading benefits administration company that specializes in providing tailored solutions for our clients. Our mission is to simplify the complex world of employee benefits and deliver exceptional service to our clients. We are seeking a highly motivated and experienced Senior Implementation Delivery Lead to join our growing team and help deliver best-in-class benefits administration software and services to our clients. WHAT YOU’LL DO The Senior Implementation Delivery Lead is responsible for helping bswift meet and exceed client expectations throughout the implementation lifecycle. This role serves as a technical and functional subject matter expert, partnering with clients, internal stakeholders, and implementation teams to deliver successful implementations while ensuring a high level of client satisfaction. This position requires strong consulting, project management, client relationship, and leadership skills. The Senior Implementation Delivery Lead proactively identifies risks, drives solutions, manages multiple implementation workstreams, and coaches team members while maintaining excellence in delivery and client service. WHAT YOU WILL BE RESPONSIBLE FOR (Essential Functions) Reasonable accommodations may be made to enable individuals with disabilities to perform these essential functions. Implementation Leadership & Client Management Serve as the bswift technical and subject matter expert during implementation status meetings and other client-facing meetings throughout the implementation process. Manage client expectations by proactively anticipating challenges, communicating project status, and establishing realistic delivery timelines. Consult clients on industry best practices and recommend system and process improvements to support business objectives. Build and maintain strong client relationships while ensuring a positive implementation experience. Research and recommend system enhancements based on client needs and collaborate with Product Managers and Developers on enhancement specifications. Implementation Delivery & Project Execution Own and manage multiple areas of client implementations, including but not limited to: System configuration, testing, and auditing COBRA and Direct Bill setup management Employee communications Vendor integrations Data conversion and migration activities Payroll configuration and implementation activities Monitor project progress to ensure milestones, deliverables, and deadlines are achieved. Collaborate cross-functionally with internal teams to ensure services are delivered accurately, efficiently, and on schedule. Identify project risks proactively and communicate concerns and mitigation strategies to the Implementation Delivery Manager. Research, troubleshoot, and resolve client inquiries related to system functionality, configuration, and process gaps. Consulting & Continuous Improvement Stay current on benefits administration industry trends, emerging technologies, and implementation best practices. Recommend improvements to client delivery processes, implementation methodologies, and service models. Support process improvement initiatives that drive operational efficiency and enhanced client outcomes. Contribute to the continuous improvement of implementation tools, documentation, and standards. Team Leadership & Development Coach and mentor Implementation Analysts to support successful project delivery and professional development. Provide guidance on implementation best practices, issue resolution, and client communication. Foster collaboration, accountability, and knowledge sharing across the implementation team. Assist in developing team capabilities and promoting high-quality service delivery standards. WHAT YOU NEED TO SUCCEED (Required Education and Experience) Bachelor’s degree in Business Administration, Human Resources, Information Systems, or a related field. 5+ years of client relationship management, consulting, and implementation experience. Current or previous experience with benefits administration platforms, implementation processes, and methodologies. Proven experience managing complex client implementations and multiple concurrent projects. Demonstrated success developing and maintaining strong relationships with clients and brokers. Skills & Abilities Excellent verbal and written communication skills with the ability to effectively engage technical and non-technical audiences. Strong customer service orientation with a commitment to delivering exceptional client experiences. Strong organizational skills with exceptional attention to detail and accuracy. Ability to work independently and collaboratively in a team environment. Ability to navigate ambiguity and make sound decisions in a fast-paced environment. Strong analytical and problem-solving skills with the ability to guide others in resolving complex issues. Ability to take initiative, demonstrate resourcefulness, and implement innovative solutions while maintaining quality standards. Advanced Microsoft Excel skills, including VLOOKUPs, Pivot Tables, data analysis, and reporting. Proficiency in Microsoft Office applications, including Word, PowerPoint, Outlook, and Teams. Strong leadership, coaching, and mentoring capabilities. NICE TO HAVE (Preferred Education and Experience) Experience with benefits administration platforms and HR technology solutions. Prior experience leading implementation teams or mentoring junior team members. Knowledge of COBRA, Direct Bill administration, payroll integrations, and vendor connectivity processes. Experience working in a client-facing consulting or professional services environment. Project management experience and familiarity with implementation methodologies. OTHER DUTIES Willingness and ability to travel as business needs require. Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities required of the employee for this job. Duties, responsibilities, and activities may change at any time with or without notice. Why Join bswift? At bswift, we empower our employees to make a meaningful impact, innovate, and grow. Joining our team means stepping into a collaborative and dynamic environment that values creativity, initiative, and a passion for client success. We are dedicated to fostering an inclusive workplace that celebrates diversity and values each team member’s unique contributions. Benefits of Working at bswift: Comprehensive Health Benefits : Access to health, dental, and vision plans to support your wellness and that of your family. Competitive Compensation : A compensation package that recognizes your skills, experience, and contributions, including performance-based incentives for most roles. Remote first, Office friendly environment! No time to commute? No problem! Retirement Savings Plans : Options to help you plan for a secure financial future with employer-sponsored retirement savings programs. Professional Development : Opportunities for career growth, including training and access to resources to support your career progression. Supportive Culture : A work environment that encourages collaboration, open communication, and creative problem-solving, where your voice and ideas are valued. Employee Wellbeing Initiatives : Programs focused on mental health, financial planning, and wellness resources to help you thrive inside and outside of work. Make an Impact : At bswift, your work directly contributes to transforming how organizations approach benefits administration and client engagement. Join us to be part of an organization that is making a meaningful difference in the lives of our clients and their employees. Specific benefit offerings vary by position and may be subject to change. Standard working hours are 8am-5pm Central Time, unless otherwise stated in the Job Description. In the spirit of pay transparency, we are excited to share the base salary range for this position is $80,000-$100,000, exclusive of fringe benefits or potential bonuses. If you are hired at bswift, your final base salary compensation will be determined based on factors such as geographic location, skills, education, and/or experience. In addition to those factors – we believe in the importance of pay equity and consider internal equity of our current team members as a part of any final offer. Please keep in mind that the range mentioned above is the full base salary range for the role. Hiring at the maximum of the range would not be typical in order to allow for future & continued salary growth. We also offer a generous compensation and benefits package! At bswift, our mission is clear: Become the preeminent benefits administrator through exceptional people, innovative technology, and delighted customers. And our values are at the heart of everything we do to accomplish that mission. We Pursue Excellence, Embrace Accountability, Deliver Superior Service, and strive to Be A Great Place To Work . We take pride in having an engaged, collaborative team that goes the extra mile to get the job done right. bswift has been regularly named one of Chicago’s Best and Brightest Companies to Work For®, as well as one of the Nation’s Best and Brightest Companies to Work For® year after year. We offer a fun, flexible, and creative environment where you can grow both professionally and personally. If you have what it takes to join our award-winning culture, we’d love to hear from you!