Benefits Advising (Renewals) Manager

Gusto, Inc.•Quinte West, ON

8d•$86,530 - $113,000•Hybrid

About The Position

Gusto is seeking a leader for our Benefits Advising team who is passionate about providing small business owners and their employees with the best customer experience and expert benefits advice. You will lead a licensed benefits advisor organization by empowering and enabling your individual contributors to deliver a best in class customer experience effectively in a fast paced environment. You’ll be a great fit if you also have experience in effectively managing OKR/team initiatives while also leading a high performing team. The Benefits Advising team at Gusto is focused on understanding the health insurance needs of small businesses, and consulting on solutions to help their employees thrive. The Benefits Advising leader will empower a team in Gusto’s licensed advising renewal organization, ensuring our customers offer the best health insurance and benefits offerings for their employees. This role will balance both customer impact and operational excellence: you’ll be responsible for driving customer retention, expansion, and exceptional customer experience at scale. Your team will support small business owners in accessing the best health insurance and holistic benefits offerings - including ancillary coverage, tax-advantaged accounts, and retirement plans like 401(k). Much of this work is centered around small group health insurance, including fully insured and level-funded plans, where tailored guidance is essential for customer success. You’ll directly empower a team of 10-15 licensed advisors and specialists, guiding them through renewal cycles and enabling them to serve as trusted advisors to our customers.

Requirements

4-6 years of formal leadership experience in benefits advisory, customer success or renewals, or a similar field
Direct experience with small group health insurance (fully insured, level-funded or PEO models) is required.
Proven ability to drive revenue growth, customer retention, and expansion through consultative renewal and upsell strategies
Analytic and strategic thinker with the ability to translate data into insights and actions
Strong operational skills, proactive approach to process improvement, and previous experience driving initiatives and best practices that improve customer experience
Ability to evaluate and adopt AI tools strategically to measurably improve advisor productivity, customer retention, and operational efficiency—while balancing innovation with risk management, compliance requirements, and maintaining customer trust in a licensed advisory context
Experience with technology/automation solutions such as Salesforce, APIs, and benefits administration platforms
Executive presence with the ability to align leaders across CX, Sales, and Product, to lead high-impact initiatives
Customer-first mentality with a first-principles-thinking approach
Thrives in and can lead a team through a fast-paced environment with constant change and rapid growth
Able to make measured, objective, data-driven decisions on a daily basis
Holds (or will be expected to hold) a Life & Health insurance license

Responsibilities

Provide regular coaching and performance management (via 1:1s and monthly reviews) focused on technical mastery, customer-centricity, and hitting KPIs.
Deliver on retention targets by ensuring tailored, high-quality renewal experiences through a customer’s renewal and ongoing benefits experience.
Use customer feedback and data to identify and drive improved processes and deliver more holistic, outcomes-focused advising. Act as project manager for large-scale, cross-functional initiatives that result in better outcomes for our customers.
Guide organization-wide improvements, enabling advisors and managers to adapt and thrive in a dynamic environment.
Build a culture rooted in Gusto’s values, creating an environment of trust, feedback, and continuous learning.
Partner with Product, Carrier Ops, Sales, and other CX teams to act as the voice of the Advisor by surfacing feedback to improve tooling, training, workflows, and the overall customer experience.
Identify high-impact opportunities, coach your team to build critical AI fluency, and shape the future of our customer journey by leveraging new tools for smarter, more proactive customer engagement.