Head of Customer Success (US)

Department: Customer Success

Employment Type: Full Time

Location: United States

Reporting To: Chief Executive Officer

Description

Hi 👋 I’m Tom, CEO at Pinpoint.

We’re a high-growth, bootstrapped HR tech startup building and selling software that helps in-house recruitment teams attract, hire, and onboard the right talent. Today, we have a strong foundation in place, with a mature product, rapid growth, strong product-market fit, and happy customers.

As our U.S. customer base grows rapidly, managing a diverse portfolio of accounts with varied needs and workflows requires focused leadership. Our talented Customer Success team is doing great work (just look at our G2 and Capterra reviews), but we need a dedicated U.S.-based leader to provide focused management, drive consistent execution, and deliver strong commercial outcomes through retention, renewals, and expansion.

To that end, we’re hiring a Head of Customer Success, US to oversee our U.S.-based CSM team (currently 4 members), support 500+ customers, and deliver an excellent experience at scale. The strategy and systems are in place — we’re looking for someone to run the function day to day, coach the team, and drive retention, renewals, and expansion.

This role is ideal for a Customer Success leader ready to own and scale a growing, complex customer base. Whether you’re managing a small team and looking for your next step or have led a larger org but want to return to a hands-on, execution-focused role, this is a leadership position for someone who takes full ownership of results, loves working directly with customers and teams, and is driven by impact.
The fine print (but way more exciting):

• 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
• This role involves occasional travel: expect 1–2 trips per year to the UK (to collaborate with our broader team), 3–4 U.S. meetups with the CSM team, and occasional visits to key enterprise customers as needed
• 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

You’ll be responsible for leading our U.S. Customer Success team and ensuring our customers stay successful, satisfied, and engaged. Your impact will be measured by how well you drive customer retention (GRR), revenue growth and account expansion (NRR), product adoption and onboarding effectiveness (Customer time-to-value), team performance and engagement, and overall customer health.

This is an execution-focused role: you’ll drive performance, reinforce playbooks, and hold the team accountable for results. Your day-to-day responsibilities include:

• 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, the 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