Sr. Customer Success Manager - Help Scout

Who we are

Help Scout started in 2011 with a simple premise: support software should treat customers like people, not tickets. 3+ billion conversations later, more than 10,000 companies use Help Scout to grow relationships with customers of all types, from clients to patients and beyond.

Now we’re in a new chapter: not only building AI that gives teams more space to focus on the customer experience, but also reimagining how we operate in an AI-native world. That means shipping and learning faster, without compromising on craft. Great work here carries a strong opinion and sweats the details, regardless of the tools we use to drive it.

We’ve been a fully remote team since day one, with 120+ teammates now all over the world. It’s a culture where you’ll be trusted to take ownership, stay curious, and raise the quality of work around you. It comes with clear expectations and a team that will push you to do some of the best work of your career.

The Opportunity

As a Senior Customer Success Manager at Help Scout, you’ll own a named book of 80–100 accounts, representing around $4M in recurring revenue. You’ll be the trusted partner for the people who rely on Help Scout every day, from day-to-day users to the executives who sponsor the relationship.

Your first priority is building a strong relationship rhythm across your book: regular check-ins, executive business reviews, and a clear understanding of what each customer is trying to achieve. You’ll connect those goals to the best of what Help Scout offers, and you’ll be the first to notice when something starts to slip.

You won’t carry an expansion quota. When you spot an opportunity to grow an account, you’ll partner with our expansion team and hand it off warm, so you can stay focused on retention and long-term value. You’ll also be the customer’s voice inside Help Scout, bringing what you learn to Product, onboarding, and the rest of the team.

Key Responsibilities

• Own a book of 80–100 accounts end-to-end. From onboarding handoff through adoption and renewal, you’re accountable for the health and retention of every account.
• Build multi-threaded relationships. Work across levels in each customer, including executives and decision makers, and align on business outcomes.
• Catch risk early. Watch for signals like dropping usage or slowing communication, escalate early, and bring in internal partners to resolve issues.
• Lead executive business reviews and regular check-ins that drive adoption, surface underused features, and strengthen product alignment.
• Own renewals and retention. Drive success measured by net dollar retention (NDR) for your book.
• Surface expansion opportunities and partner with our expansion team to close them.
• Bring the voice of the customer inside. Share customer feedback with Product and cross-functional teams to shape the roadmap and onboarding.
• Design your own workflows. Leverage AI tools to stay organized and ensure seamless account management.
• Raise the bar for the team. Share best practices, document learnings, and help shape Customer Success at Help Scout.

About You

• 5+ years of Customer Success experience in SaaS, with experience in SMB, mid-market, strategic, or enterprise segments.
• Track record managing a large book of business, including experience managing 50+ accounts with a consistent cadence.
• Strong retention metrics. Proven ability to maintain and speak to high renewal rates, retention, or NDR.
• Relationship-driven. Passion for serving as a strategic advisor, aligning with executives, and guiding customer outcomes.
• Collaborative problem solver. Proactive in raising risks early and bringing in cross-functional partners.
• Confident communicator. Comfortable managing difficult renewal or account recovery conversations.
• Cross-functional partner. Experienced working alongside Product, Support, and Sales teams.
• Adaptable. Comfortable navigating evolving processes and shaping playbooks.
• AI-forward. Excited to utilize AI tools to reduce manual overhead and improve workflows.
• Technical aptitude. Quick learner capable of becoming an expert in Help Scout's software.

Interview Process

1. Recruiter Chat with Recruiting team
2. Value Add with Customer Enablement Lead
3. Paid Project (take-home assignment presented to the team)
4. Team Chat with two Customer Success team members
5. Final Chat with the VP of Customers
6. Reference Checks

Benefits & Perks

• Competitive salary based on transparent market formula
• Flexible time off
• 12 weeks of fully paid parental leave for all new parents
• Home office setup stipend
• Co-working stipend up to $300/month
• Yearly professional development stipend of $1,800
• Top-tier health insurance for US/Canada employees and dependents