About this role.
Carrot is hiring a Customer Success Manager II to manage the health, adoption, retention, and expansion of an SMB customer portfolio. The role serves as the primary advisor to HR benefits leaders, using regular check-ins, business reviews, and engagement metrics to demonstrate value and proactively mitigate churn risk. The CSM will support renewals, identify upsell opportunities, maintain Salesforce records, and coordinate with Product, Implementation, Member Support, and Operations. Success depends on consistent execution of SMB playbooks, strong customer relationships, and achievement of retention, satisfaction, engagement, and ACV-growth goals.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
3/5Pace & Pressure
4/5Autonomy Level
4/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
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Sample interview questions
I would establish a regular review cadence using health indicators such as utilization, member engagement, CSAT, stakeholder participation, support trends, and renewal timing. When I identify a risk signal, I would validate the underlying cause with the customer, build a documented action plan with owners and dates, involve the appropriate internal teams, and monitor progress through resolution.
I would tailor the review to the customer’s original goals and present a concise story using adoption, utilization, member engagement, satisfaction, and program-impact data. I would connect the results to their benefits priorities, discuss obstacles and upcoming milestones, confirm action items, and identify opportunities to deepen value before the next review.
I listen carefully to understand the customer’s desired outcome rather than immediately committing to a specific solution. I communicate transparently about current capabilities and constraints, bring well-documented feedback to internal teams, and offer practical alternatives or workarounds that protect trust while remaining aligned with company priorities.
I would look for expansion opportunities through account goals, engagement patterns, stakeholder feedback, organizational changes, and demonstrated program value. I would qualify the need, quantify the potential impact where possible, align with the customer’s renewal or planning cycle, and partner with leadership or sales resources to present a relevant recommendation rather than a generic upsell.
I use consistent operating routines: logging meaningful interactions immediately, maintaining next steps and renewal dates, updating health status after key meetings, and reviewing my pipeline weekly. Standardized templates, task reminders, and a clear prioritization framework help ensure data accuracy without taking focus away from high-impact customer work.
About Carrot:
Carrot is the leading global fertility and family care platform, built on intelligent care orchestration: the right clinical guidance, at the right moment, in the context of each member’s life. More than a thousand multinational employers, health plans, and health systems trust Carrot to support millions of members across 195 countries – from pre-pregnancy through menopause and major life moments in between. Carrot’s comprehensive clinical program delivers industry-leading cost savings for plan sponsors and award-winning experiences and improved outcomes for millions of people worldwide.
Carrot is widely regarded as a defining force in healthcare innovation as a recipient of several top-tier awards, including Fast Company’s ‘Most Innovative Companies’ and CNBC’s ‘100 Barrier Breaking Startups’. The company is regularly cited by leading global outlets — including The Economist, Bloomberg, The Wall Street Journal, NPR, ABC News, and Harvard Business Review — as a leading voice on digital health, the future of work, and family health. Learn more at get-carrot.com.
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
Why This Role Matters 🧡
SMB customers make up a large share of Carrot’s customer base, and the CSM II role is the front line of how those customers experience Carrot. Strong account management at this level directly protects retention, drives member engagement, and creates the expansion pipeline that fuels segment growth.
Every renewed account and every engaged member means more people accessing fertility and family-building care through their benefits. This role turns Carrot’s mission into a lived experience for thousands of members, one well-managed account at a time.
Interview Process 🤝
We believe in a thoughtful and transparent interview process designed to create alignment for both candidates and our team.
For this role, candidates can expect:
- Recruiter Screen — 30 minutes
- Hiring Manager Interview — 30–45 minutes
- Presentation Interviews — 45 minutes
- Executive Leadership Conversation — 30 minutes
- Hiring Manager Wrap-Up — 15 minutes
Throughout the process, we will share additional context about the team, business priorities, customer landscape, and what success looks like in this role.
Why Candidates Join Carrot 🌍
Carrot offers the opportunity to do meaningful work in service of a deeply human mission.
Highlights include:
- A mission-driven company focused on expanding access to fertility and family-forming care globally.
- A high-growth environment where leaders are empowered to shape strategy and drive impact.
- Competitive compensation, equity, and comprehensive benefits.
- Flexible Time Off and a culture that actively encourages employees to recharge.
- Comprehensive parental leave and family-forming benefits.
- A collaborative, inclusive, and values-driven culture.
- The opportunity to work alongside passionate, thoughtful teammates committed to improving healthcare outcomes worldwide.
Compensation 💰
Carrot offers a holistic Total Rewards package designed to support our employees in all aspects of their life inside and outside of work, including health and wellness benefits, retirement savings plans, short- and long-term incentives, parental leave, family-forming assistance, and a competitive compensation package. The starting base salary for this position will range from $70,000.00 $82,000.00. Actual compensation may vary from posted base salary depending on your confirmed job-related skills and experience.
Fraud and Security Notice: Please note that all communication regarding job opportunities at Carrot will come exclusively from an @get-carrot.com email address. If you receive messages from any other domain, please disregard them and report the incident to: securityreporting@get-carrot.com
A Note on AI
At Carrot, we believe AI can help us work smarter, move faster, and create more meaningful experiences for our members, customers, and each other. While not every role requires deep technical AI expertise, we value people who are curious, eager to learn, and excited to thoughtfully incorporate AI into their day-to-day work.
For some roles, AI fluency is a core requirement—and we’ll call that out clearly in the qualifications. For everyone else, we’re looking for people who embrace new ways of working, use AI responsibly to improve quality and efficiency, and continue to learn as the technology evolves.
Why Carrot?
Carrot has received national and international recognition for its pioneering work, including Fast Company’s Most Innovative Companies and World Changing Ideas, Inc. Power Partners, and Modern Healthcare’s Innovators. Carrot’s global workforce has been acknowledged with several accolades, including Fortune’s Best Workplaces in Healthcare, Great Place to Work, and Age-Friendly Employer certifications. Carrot is regularly featured in media reporting on issues related to the future of work, women in leadership, and healthcare innovation, including MSNBC, The Economist, Bloomberg, The Wall Street Journal, CNBC, National Public Radio, Harvard Business Review, and more. Learn more at carrotfertility.com.
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