Sr. Customer Success Manager

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. If that kind of challenge gives you energy, we’d love to meet you. 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. • 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. You’ll work across levels in each customer, including executives and decision makers, and align on the business outcomes that matter to them. • Catch risk early. You’ll watch for signals like dropping usage or slowing communication, escalate early, and bring in the right internal partners to turn things around. • Lead executive business reviews and regular check-ins that drive adoption, surface underused features, and strengthen product alignment. • Own renewals and retention. Your success is measured on net dollar retention for your book. • Surface expansion opportunities and partner with our expansion team to close them. • Bring the voice of the customer inside. Share what you learn with Product and cross-functional teams to help shape the roadmap, onboarding, and how we work. • Design your own workflows. You’ll have freedom to use AI tools to stay organized and make sure nothing falls through the cracks across a large book. • Raise the bar for the team. You’ll share what works, document your learnings, and help shape how Customer Success grows at Help Scout. About You • You have 5+ years of Customer Success experience in SaaS , with time spent in SMB, mid-market, strategic, or enterprise segments. • You’ve owned a large book of business. At some point in your career, you’ve managed 50+ accounts and kept a consistent cadence with all of them. • Retention is your track record. You can talk about your renewal rates, retention, or NDR, and what you did to move them. • You love the relationship side of the work. You enjoy being a strategic advisor, aligning with e