CSM II

The Opportunity 🚀

Carrot is looking for a Customer Success Manager II to own the health, adoption, retention, and growth of a book of Small Business (SMB) accounts. Reporting to a Manager of Customer Success, you will serve as the primary point of contact and trusted advisor for HR benefits leaders across your portfolio, helping them communicate the value of the Carrot benefit, respond to their needs, and ensure Carrot remains a celebrated part of their benefits offering.

Your day-to-day will center on proactive account management: running regular check-ins and business reviews, monitoring success metrics like CSAT, utilization, and member engagement, and surfacing risks before they become churn drivers. You will support renewals across your book and identify expansion opportunities that contribute to ACV growth. This is an ideal role for a customer-centric CS professional who executes established playbooks with consistency and quality while building the foundation for growth into more complex account work at Carrot.

What You’ll Own 💼

In this role, you will:

Own the health, adoption, retention, and growth of a book of SMB accounts, serving as the primary point of contact for HR benefits leaders
Conduct regular check-ins and business reviews to align on goals, track program performance, and course-correct proactively
Monitor and act on success metrics including CSAT, utilization, and member engagement to identify risks and address churn drivers early
Support the renewal cycle across your book, partnering with Customer Success leadership to drive on-time close and strong retention outcomes
Identify and pursue expansion and upsell opportunities within your book, contributing to ACV growth
Partner with internal teams, including Product, Implementation, Member Support, and Operations, to ensure customers realize full value from their Carrot partnership
Maintain accurate account records and pipeline hygiene in Salesforce
Execute established SMB playbooks with consistency and surface feedback that helps the team improve and scale

What Success Looks Like 📈

In your first 12–18 months, you will have:

Built trusted relationships across your SMB book, reflected in strong CSAT scores and retention outcomes
Consistently met retention, engagement, and growth targets for your portfolio
Established a proactive account management rhythm, with risks surfaced and addressed before they escalate
Contributed expansion opportunities that grew ACV across your book
Earned a reputation as a reliable, collaborative teammate who operates established playbooks with quality and consistency

About You ✨

You likely have:

A bachelor’s degree
3+ years of experience in customer success, account management, or customer support in a high-growth technology environment
A track record of managing a book of business with strong retention and customer satisfaction outcomes
Comfort presenting to HR benefits leaders, with a clear, empathetic communication style that balances customer needs against internal priorities
Proficiency with Salesforce or another CRM
Strong organizational skills and a proactive, solutions-oriented mindset
Enthusiasm for Carrot’s mission and eagerness to be part of a collaborative, friendly, and dynamic team

Nice to Have ⭐

While not required, we would be especially excited if you bring:

Familiarity with Carrot’s buyers (HR benefits leaders) and the employee benefits landscape
Prior experience supporting renewal or expansion conversations with existing customers
Experience with tools beyond Salesforce, such as Gong, Airtable, or BI/reporting tools
Comfort working in an ambiguous, fast-scaling environment; organized, diligent, and self-motivated