[Hiring] Customer Success Advocate Team Lead @Contentstack

Role Description

We’re looking for a Team Lead, Customer Success Advocate to lead and scale our one-to-many Customer Success motion for long-tail customers. This is a player-coach role for a hands-on Customer Success leader who thrives at the intersection of customer engagement, commercial execution, and operational excellence.

In this role, you’ll manage your own portfolio of customers while also leading and developing a team of Associate Customer Success Advocates (CSAs). You’ll ensure our scaled programs run smoothly, customers stay engaged and on track, and renewal outcomes are predictable and data-driven. You’ll also act as a key connector between front-line execution and Customer Success leadership—bringing visibility, insights, and recommendations that help shape strategy at scale.

If you enjoy mentoring others, working across systems and teams, and using data to drive better customer and business outcomes, this role offers both leadership impact and hands-on ownership.

Responsibilities

• Lead, coach, and support a team, using AI-assisted insights to ensure consistent, high-quality execution across a large portfolio.
• Provide ongoing feedback and performance coaching, leveraging governed AI tools to analyze team interactions (calls, emails, outreach) and surface coaching insights and best practices at scale.
• Partner with Global Customer Success Leadership on hiring, onboarding, training programs, and performance evaluations.
• Act as “air traffic control” for the long-tail portfolio, balancing workloads and ensuring customers receive timely, effective engagement.
• Own a personal portfolio of customers, modeling best practices for scaled engagement and renewal readiness.
• Support the team in managing renewals, navigating commercial conversations, and identifying expansion or upsell opportunities.
• Maintain a strong understanding of subscription mechanics, renewal timelines, and risk signals.
• Identify early signs of churn or contraction and escalate risks with clear recommendations.
• Use data as the foundation for decision-making, applying governed AI to synthesize adoption trends, customer health signals, and team activity into actionable insights.
• Track and report on KPIs related to engagement, renewals, pipeline contribution, and program effectiveness.
• Provide data-backed recommendations to improve outreach strategies, workflows, and tooling.
• Set the standard for Salesforce and system hygiene, ensuring accurate, reliable reporting.
• Serve as a senior escalation point for internal teams including Technical Support, Solutions, and Product.
• Ensure customer feedback and trends from the long-tail segment are clearly communicated and prioritized.
• Balance internal leadership responsibilities with external customer needs in a fast-moving environment.

Qualifications

• 7+ years of experience in Customer Success, Account Management, or a related SaaS role, with prior leadership or team-lead experience preferred.
• Proven experience supporting renewals and commercial workflows in a subscription business.
• Strong analytical mindset—you’re comfortable using data to tell a story and influence behavior.
• Excellent organizational skills with the ability to juggle competing priorities across customers and team needs.
• Exceptional written and verbal communication skills, with confidence engaging both individual contributors and senior leaders.
• Familiarity with CS tooling such as Salesforce (SFDC), Gong, and reporting dashboards.
• Experience in SaaS, Martech, CMS, or digital experience platforms is a strong plus.

Requirements

• High-Performing Team: Associate CSAs consistently meet or exceed engagement, data quality, and pipeline KPIs.
• Revenue Protection: Strong renewal rates across the long-tail segment with clear identification of expansion opportunities.
• Operational Excellence: Scaled programs run smoothly, with improved processes, documentation, and training materials.
• Leadership Visibility: Customer Success leadership has a clear, AI-augmented and data-driven view into long-tail customer health, risks, and program impact.
• Experience: 6+ Years.
• Shift timing: 9PM to 6AM.
• Mode of work: Remote / Work from home.

Benefits

• Interesting Work: We hire curious trendspotters and brave trendsetters. This is NOT your boring, routine, cushy, rest-and-vest corporate job. This is the “challenge yourself” role where you learn something new every day, never stop growing, and have fun while you’re doing it.
• Tribe Vibe: We are more than colleagues, we are a tribe. We have a strict “no a**hole policy” and enforce it diligently. This means we spend time together - with spontaneous office happy hours, organized outings, and community volunteer opportunities. We are a diverse and distributed team, but we like to stay connected.
• Bragging Rights: We are dreamers and dream makers. Our efforts pay off and we work with the most prestigious brands, from big-name retailers to airlines, to professional sports teams. Your contribution will make an impact with many of the most recognizable names in almost every industry including AirFrance KLM, ASICS, Burberry, Mattel, Mitsubishi, Walmart, and many more!
• One Team One Dream: This is one of our values, and it shows. We don’t believe in artificial hierarchies. If you’re part of the tribe, you have an opportunity to contribute. Your voice will be heard and you will also receive regular updates about the business and its performance.