Insurance Customer Success Manager

Feathery•Toronto, ON

44d•Onsite

About The Position

Feathery automates data intake workflows for insurance companies. Industry leaders rely on Feathery to power mission-critical workflows like underwriting, client onboarding, policy servicing, and automated account openings. With rapid revenue growth and expanding enterprise demand, we’re scaling our customer success function to support increasingly complex implementations across the insurance ecosystem. This role is ideal for someone who understands the insurance landscape and thrives in building processes, owning customer relationships, and driving long-term success. You’ll act as a strategic partner to customers while ensuring successful implementations, strong adoption, and expansion across accounts. This is a high-ownership role that blends end-to-end customer lifecycle ownership (post-sale through renewal), implementation and workflow design for insurance use cases, strategic account management across brokers and carriers, and building processes, playbooks, and the foundation of a CS function. You’ll own the full post-sale journey — partnering with sales during handoff, working closely with solutions engineering during implementation, and driving long-term success across enterprise insurance accounts.

Requirements

3–4+ years of experience in Customer Success, Implementation, Solutions, or Account Management in B2B SaaS
Experience working with insurance brokers, carriers, or within the insurance ecosystem
Strong understanding of insurance workflows (e.g., underwriting, onboarding, policy management)
Experience managing enterprise, multi-stakeholder accounts
Strong ability to translate technical products into clear business outcomes
Highly organized and comfortable managing multiple implementations
Excellent communication skills and executive presence
Comfortable operating in fast-moving, early-stage environments
Strong cross-functional collaborator with a high-ownership mindset

Nice To Haves

Experience working with workflow automation, integrations, APIs, or data platforms
Experience supporting regulated industries and compliance-heavy environments
Experience helping build or scale a Customer Success function from scratch
Background in high-growth B2B SaaS companies

Responsibilities

Own onboarding and implementation for insurance brokers and carriers
Partner with customers to design and optimize workflows such as underwriting, onboarding, and policy servicing
Ensure successful deployment of complex, regulated insurance workflows
Collaborate with Solutions Engineering on technical implementations
Act as the primary point of contact and trusted advisor for insurance customers
Build relationships with stakeholders across operations, underwriting, and leadership teams
Drive product adoption, retention, and expansion across accounts
Own renewals and partner with sales on upsell opportunities
Support executive-level conversations for strategic accounts
Represent the voice of insurance customers internally
Work closely with Product and Engineering to surface feedback and influence roadmap priorities
Help resolve customer challenges and ensure a high-quality experience
Define and track customer success metrics (adoption, usage, health scores, retention)
Build scalable CS processes, documentation, and playbooks tailored to insurance customers
Proactively identify risks and address them early
Lay the foundation for the CS function, including workflows, standards, and future team structure
Contribute to hiring and mentoring as the team grows