Head of Customer Success (US)

Department: Customer Success

Employment Type: Full Time

Location: United States

Reporting To: Chief Executive Officer

Description

• This is a remote role based in the U.S., with a few in-person team meetups each year. Our HQ is in Jersey, UK, and our 80-person team is spread across the U.K. and U.S.
• Our product is deep, flexible, and genuinely complex. At the same time, we serve a wide variety of customers across many different industries and sizes.
• Our average contract values are relatively low given the depth and complexity of our product, which means each CSM manages around 50 accounts with an average book size of $2 million ARR. Driving efficient, high-quality execution at scale is essential.
• Pinpoint isn’t for everyone. We’re still in startup mode. Things move fast, some processes are still evolving, and you’ll need to be proactive, adaptable, and hands-on.
• Our values shape how we work. We’re looking for people who embody these values in everything they do.

About the Role

• Managing and coaching a team of 4 Customer Success professionals to achieve implementation, retention, renewal, and upsell goals
• Building the muscle for renewals and upsells—ensuring each team member understands how to spot, shape, and close expansion opportunities
• Overseeing the customer experience for 500+ U.S. accounts, including managing a small book of strategic accounts
• Monitoring customer health and usage metrics to proactively address risks and drive account success
• Serving as an escalation point for high-impact customer issues
• Partnering with RevOps, UK Head of CS, Sales, Product, and Marketing to implement playbooks, share customer insights, and support expansion
• Leading hiring and onboarding efforts as the team grows

About You

• Proven track record leading Customer Success teams in B2B SaaS, with experience managing CSMs focused on implementation, adoption, renewals, and expansion.
• Comfortable supporting a technically complex product with diverse customer workflows
• Strong people manager — you lead with empathy, structure, and accountability
• Proven track record of driving retention and expansion with a strong commercial mindset that understands how Customer Success impacts revenue
• Hands-on and high-agency — you’re happy rolling up your sleeves
• Excellent communicator who can influence across functions
• Deep understanding of customer value drivers and post-sale customer journeys
• Experience in a high-growth or startup environment
• Based in the U.S. (EST or CST preferred) with valid work authorization
• Proven track record of acting on and making decisions that align with our core values

What We Offer

• 🩺 Gold-plated healthcare – The best medical, dental, and optical coverage money can buy. We’ve got you (and your family) covered
• 🏝️ Unlimited holidays – Work-life balance matters. Take the time you need to rest, recharge, and enjoy life
• 🧠 Mental health support – Unlimited, immediate access to professional counseling through Spill—because your well-being comes first
• 💰 Retirement matching – A competitive plan to help you hit your long-term financial goals
• 🌍 Remote-first culture – Work where you're most productive. As a remote-first team, we prioritize flexibility and trust
• 📈 Meaningful equity – You’re helping build something special, and you should share in its success
• 👶 Generous parental leave – Up to 16 weeks of fully paid leave to support new parents
• 📚 Learning budget – Annual funds for courses, books, or anything else that fuels your personal and professional growth
• 💻 Top-of-the-line equipment – MacBook Pro, 4K monitors, and all the right tools to do your best work
• 🤝 A team that’s got your back – Smart, driven, kind people who want you to succeed, our clients to be wowed, and our business to grow