Senior Benefits Operations Manager

About the Opportunity

This dynamic role is responsible for the vision, strategy, selection, and implementation of Cribl’s benefits programs, including both the technical stack and overall program design. As a remote-first company, Cribl delivers People programs through technology, making seamless solutions critical to a positive employee experience. We’re looking for someone who is passionate and tech-forward, with an operational mindset, attention to detail, excellent vendor management skills, and sophisticated creative problem-solving abilities. Benefits and time-away programs are a significant reason people come to and stay at Cribl; this role is key to making the experience exceptional for our employees (our "goats") and their families.  

In our hyper-growth stage, this role will be instrumental in maturing Cribl’s Benefits experience. Responsibilities include enhancing systems architecture, improving automations and integrations, and delivering human-centric processes to create a frictionless employee experience while driving excellence with our outsourced vendors and partners. This role requires in-depth expertise in Benefits, as well as experience leading large-scale transformations, including implementing new systems and vendors, and consolidating or deprecating existing ones.  

Beyond technical and operational knowledge, this role requires the ability to communicate and influence a wide range of audiences, including internal and external stakeholders, both technical and non-technical. The transformational work ahead also demands strong project management skills, as this role will oversee multiple initiatives across the Benefits portfolio. Responsibilities include building business cases, articulating the financial impact of decisions, and guiding executive leadership on Benefits and Total Rewards strategies.  

Day-to-day responsibilities may include running RFPs for new carriers or benefits, managing annual renewals and open enrollment, troubleshooting technical issues, or designing and launching new employee experiences.  

This role collaborates closely with Cribl’s US-based benefits broker team, carriers, contingent workforce, and various internal teams, including People Operations, People Business Partners, Compensation, Talent Acquisition, Talent Success, and Finance (Payroll, FP&A, and Procurement). It reports to the Director of People Operations within the People Team.  

What You’ll Accomplish

• Through a series of transformational, benefits-related projects, scale our Benefits programs from a 750-person to 1500+ benefits experience.
• Lead the transition of new benefits administration technology; we are moving to Workday HCM & Workday Ben Admin in June of 2025.
• Provide thought leadership for our globalized People strategy; evaluate, recommend, build a roadmap for Benefits-related policies, technology, services and new programs.
  Deep analysis of existing processes and integrations; through this develop a roadmap of repairs and enhancements and execute against the roadmap.
• Lead RFPs, selection and implementation of any new or changing carriers and partners
• Use data to make decisions and drive strategy; develop and administer a US benefits survey, obtain and analyze benchmarking data
• Lead troubleshooting activities when technical or employee issues arise (e.g. integration errors, incorrect deductions); design and implement durable solutions to ensure issues won’t occur again. 
• Interpret statutory and Cribl policies related to time away programs (leave of absence, annual leaves, medical leaves) and design process and systems configurations to support administration.
• Drive excellence in performance and hold vendors accountable; lead through QBRs and post-mortems to ensure our employees are receiving high quality benefits and time away experiences.
• Interpret compliance-related requirements and translate them into processes or systems design to maintain compliance. Maintain a pulse on changes in US benefits and time away policies and laws, anticipating changes that may impact program or systems designs.
• Participate as a key member in a transition to Workday; provide requirements, design process, partner with carriers to ensure new integrations/feeds/automations are built and implemented, test and fully migrate to new Ben Admin tool.

What You’ll Bring

• Extensive subject matter expertise and leadership in US Benefits policy, technology, administration, compliance and process; experience preferred at a multinational, high growth start up. 
• Business process excellence, highly detailed and passion for creating seamless and frictionless employee experience.
• Confidence with data and analytics; this role will generate, engage and/or analyze data in Google Sheets, Excel, and Looker as well as pull reports and data from various benefits-platforms.
• Excellent communication (verbal and written) and influencing skills; strong presentation, organization, time management, problem solving and follow-up skills. 
• The ability to build consensus and drive alignment and clarity across many internal and external stakeholders, teams, and vendors.
• Strong Project and portfolio management experience; ability to track and report against multiple projects simultaneously and communicate frequent updates, roadblocks, and risks.
• Comfort  in a remote environment, self motivated to work asynchronously and independently.
• Ability to work with a sense of urgency, collaboratively in a team-focused environment.
• Curiosity, creativity and willing to take risks or experiment with new ideas