Senior Implementation Delivery Lead

OpenKrill; United States; On-site; USD 115,000 - 170,000; Full time

Benefits offered by this job

Health benefits

Competitive compensation

Remote-first environment

Retirement savings plans

Job summary

bswift in Chicago, and remotely across the country, is seeking a Senior Implementation Delivery Lead to guide client implementations from start to finish, serving as a technical and functional SME for our clients.

You will own multiple workstreams, coach junior teammates, manage risks, and collaborate with product and development teams to deliver high-quality, client-centric solutions in a fast-paced environment.

Qualifications

• Bachelor’s degree in a related field.
• 5+ years of client relationship management, consulting, and implementation experience.
• Experience with benefits administration platforms and implementation processes.
• Proven ability managing complex client implementations.
• Strong relationships with clients and brokers.

Responsibilities

• Serve as SME during implementation status meetings and client-facing sessions.
• Manage client expectations and establish realistic delivery timelines.
• Consult clients on best practices and recommend system improvements.
• Build and maintain strong client relationships and ensure positive experiences.
• Research and recommend system enhancements with Product Managers and Developers.
• Own and manage multiple areas of client implementations (config, testing, data migration, payroll).
• Monitor progress to meet milestones and collaborate cross-functionally.

Skills

Communication

Customer service

Organizational skills

Team leadership

Excel proficiency

Problem solving

Travel willingness

Education

Bachelor’s degree in Business Administration / related field

Tools

Microsoft Excel

Microsoft Word

PowerPoint

Outlook

Teams

Job description

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 yo