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 executives on business goals, and working with internal teams to get customers where they need to go. Closing deals isn’t what gets you up in the morning. • You never solve problems alone. When an account shows signs of risk, you raise it early, pull in the right people, and keep the customer informed. • You’re not afraid of difficult conversations. You can handle tough renewal or recovery conversations with confidence and care. • You’re a strong cross-functional partner. You know how to work alongside Product, Support, and Sales, and you’ve handed off expansion opportunities to account executives or account managers before. • You thrive while things are still being built. You’re comfortable shaping processes as we go and don’t need a playbook for everything. • You’re excited about how AI can transform your work. You look for ways to reduce manual overhead and spend your time where it matters most. • Technical aptitude. You’re comfortable learning and navigating complex software, and you want to become an expert in our product. About the Process • Recruiter Chat – You’ll meet with Nahuel on the Recruiting team to chat through compensation, benefits, timeline, and company culture. • Value Add – You’ll meet with Annika, Customer Enablement Lead, to talk more about the role and your experience in more detail. • Project – We’ll give you a take-home project (we’ll pay for your time), then you’ll share it back to the team. • Team Chat – You’ll meet with two members of our Customer Success team to learn more about how we work and the customers we serve. • Final Chat – You’ll chat with our VP of Customers. • References – We’ll ask you for three references. Ideally, we’d like two of them to be managers, but we can be flexible. Compensation Each role at Help Scout has a pay range aligned to our salary formula and based on national market data. We take a competency-based approach and pay is based on the level and band of your role. We assess leveling during the hiring process for new teammates, during our bi-annual performance review cycles, and when a teammate’s role changes. OTE: $139K–$160K Company values Happy to Help Help is in our first name! We show up for each other — not out of obligation, but because we’re invested in the team’s collective success. We share knowledge freely, lead with generosity, and practice empathy with our teammates, customers, and community. Craft over Convention Our success relies on the quality and craft of the work we put into the world. The status quo simply won’t work. So we insist on narrow focus, sweating every detail, and relentless pursuit of customer delight. Progress not Perfection Achieving our true potential — collectively and individually — requires constant progress and forward momentum. By creating a culture of curiosity and openness, we aim to create a safe space for mistakes, the ability to identify them quickly, and use them to get better. Own the Outcome Own the outcome means taking full responsibility for the results of your work, decisions, and contributions. It reflects a mindset of accountability, proactiveness, and follow-through. If you “own the outcome,” you don’t just complete tasks, you ensure your work leads to meaningful results, and take initiative to solve problems rather than passing them along. Read more about how we define, share, and live these values here. Benefits And Perks • Competitive salary and an internal, transparent salary formula based on market data • Flexible time off – you choose the holidays and vacations that make sense for you • 12 weeks of fully paid parental leave for all new parents, including adoption and foster care • A home office stipend to help you get set up and productive • A co-working stipend up to $300 a month if you choose to work out of your house • A yearly professional development stipend of $1,800 to help you grow in your craft • If you’re in the U.S. or Canada, we offer top tier health insurance for you and your dependents. Hiring Guidelines: All roles at Help Scout are fully remote. Some positions have specific location requirements. For roles outside the U.S. and Canada, we work with teammates as independent contractors under country-specific agreements. We do not sponsor visas. Teammates must already be authorized to work from their home country. We are an equal opportunity employer and are committed to building a company that embraces and celebrates diversity and inclusion. We do not discriminate on the basis of race, religion, color, national origin, gender, gender identity or expression, sexual orientation, age, marital status, veteran status, or disability status. We have read the studies and understand that diverse teams build better products, bring more perspective to the table, contribute to a company’s financial success, and help foster a more inclusive environment for all employees, but the bottom line is that it’s the right thing to do. To provide you with the best experience, we can support you with accommodations or adjustments at any stage of the recruitment process. Simply inform our recruitment team during your conversation with them. A note on the use of AI in our interview process While we understand that AI is an important tool in a modern skillset, we ask that you do not utilize AI assistants live on our interviews. Of course, use any tools you need to prepare! But we’d like for you to have a real human-to-human conversation with our team. On our end, we utilize a platform called Brighthire as a notetaker and review tool to ensure a fair and transparent hiring process. Beware of scammers! All legitimate communication from Help Scout regarding your application will come directly from an @helpscout.com email address and through our applicant tracking system, Ashby. We will never ask for personal financial information or conduct interviews outside of these official channels.