Overview
Insurance Implementation Specialist (Eight by Zero) Jobs in Remote at Diagram Ventures
Eight by Zero (a Diagram startup) is building the next generation of absence management automation — a platform that intelligently connects employer HR systems to insurance carriers, eliminating the manual, fragmented, and error-prone workflows that slow down implementations today.
As we scale, we are looking for a Carrier Implementation Advisor who has lived the API implementation process from the carrier side. This role will help us build a product that reflects how carriers work and may evolve into a full-time leadership position as we grow.
The Opportunity
Group benefits implementation is broken. When an employer wants to connect their HR system to a carrier’s absence management platform, they face a process that is slow, manual, and heavily dependent on tribal knowledge. Employer data is inconsistent. Questionnaires are exchanged over email. API implementation timelines drag on for months.
At Eight by Zero, we are building a platform that:
- Automates employer onboarding — discovery, questionnaires, system configuration
- Orchestrates data between employer HR systems (Workday, Dayforce, ADP) and carrier platforms
- Reduces implementation timelines from months to days, for carriers and TPAs alike
Backed by Diagram Ventures and working directly alongside leading insurance carriers as co-design partners, we are developing the next generation of AI-powered absence management tooling. This is an opportunity to join early and shape the product from the inside.
What You’ll Do
- Serve as Eight by Zero’s carrier-side implementation expert — the voice of the carrier operations team in everything we build
- Review and validate our product UX and employer onboarding workflows — flag what would and wouldn’t work in a real carrier implementation
- Advise on the employer questionnaire process: what carriers need to know from employers, in what format, and at what stage of onboarding
- Share domain knowledge on carrier-to-employer data connections: how plans are structured, what metadata matters, how systems are configured
- Provide input on carrier onboarding workflows — how carriers set up new employer groups, manage plan specifications, and handle integration edge cases
- Guide our product roadmap to reflect real-world carrier priorities and pain points
- Optionally participate in carrier conversations as a subject matter expert as we deepen partnerships with carriers.
- What We’re Looking For
- 3+ years of experience in group benefits implementation, with direct exposure to the carrier side of employer connections
- Hands-on background in carrier implementation operations: onboarding employer groups, managing data intake, build API integrations with HR systems, configuring absence management plans
- Deep familiarity with employer HR systems (Workday, ADP, Dayforce, UKG) from a carrier integration standpoint, including API integrations.
- Strong understanding of employer questionnaire and discovery processes — you know what questions matter and why
- Experience at an insurance carrier, TPA, or benefits technology company in an implementation, client onboarding, or employer connections role
- Entrepreneurial mindset — excited to translate hard-won operational knowledge into a product that scales
Why Join Us
- Be part of an early-stage venture solving one of the most frustrating problems in group benefits — a space you know better than anyone
- Work directly with the founding team and Diagram Ventures to shape the product and go-to-market from day one
- Flexible part-time advisory engagement — designed to fit around your current commitments, with the option to grow into a full-time role
- Compensation options include cash, equity, or a mix
If you’ve spent years on the carrier side wondering why implementation is still so manual — and you want to help fix it — we’d love to talk.
About Diagram Ventures
Diagram is a venture builder that conceives and launches technology companies in the financial, insurance, and climate industries. We’ve designed a unique platform for entrepreneurs who have a proven track record or domain expertise to start their next business by combining access to venture capital investment, hands-on support, and a vast network of partners and incumbents. Since 2016, Diagram has raised over $400M and launched 30+ new companies across North America. Our ecosystem is home to 200+ angel investors, including 60+ entrepreneurs with >$15B in exits and an extended global network of corporate partners, investors, and builders. Notable Diagram portfolio companies include Synctera (Series A), Nesto (Series C), and Dialogue (IPO).
Applying for this position
Diagram and its portfolio companies are equal opportunity employers. We appreciate your interest in working with us; however, only those applicants selected for interviews will be contacted. Diagram may contact you about other possible opportunities you may be a fit for. We launch five new ventures each year and are continually excited to talk to founders and top talent who want to join us.
Title: Insurance Implementation Specialist (Eight by Zero)
Company: Diagram Ventures
Location: Remote
