About PointFive
PointFive is the AI Efficiency OS. From the cloud to the coding agent, we're the only platform that manages AI spend everywhere it happens.
Engineering and FinOps teams use PointFive to make their organizations more efficient and their cloud and AI more effective. We don't just show what you spend. We show what you're wasting, and we fix it autonomously. NuBank saw ROI in 10 days. Customers average 1,200%+ ROI and a 4.9 rating on G2.
Founded by the team behind IntSights (acquired by Rapid7), PointFive recently closed a $60M Series B led by Accel, with participation from Entrée Capital and Salesforce Ventures.
What you'll do
We are seeking a visionary and execution-oriented Head of Customers to lead our post-sales organization, encompassing Customer Success, Technical Support, and Professional Services. In this critical leadership role, you will design and execute the overarching strategy to maximize customer retention, accelerate product adoption, and deliver world-class support for our enterprise clients. As a strategic partner to the executive team, you will build a scalable operational framework that transforms customer satisfaction into measurable business growth and continuous cloud optimization.
Architect the Unified Customer Experience: Build, scale, and align the Customer Success, Technical Support, and Professional Services functions into a cohesive ecosystem focused on delivering rapid time-to-value and high net retention.
Drive Retention and Expansion: Establish robust methodologies for tracking health scores, proactive risk mitigation, and continuous value realization to secure renewals and uncover expansion opportunities.
Standardize Customer Success & Support Delivery: Evolve and scale our onboarding, adoption, support, and escalation frameworks to deliver consistent, enterprise-grade customer experiences. Establish the processes, metrics, and operating rhythms required to improve efficiency, accelerate time-to-value, and drive customer satisfaction.
Build and Scale Professional Services: Build PointFive’s Professional Services offering from the ground up, defining the service strategy, packaging, delivery model, and operating framework. Partner closely with customers to shape and validate the offering, then build the processes, automation, and team required to scale delivery while continuously incorporating customer feedback.
Champion the Voice of the Customer: Serve as the internal advocate for our enterprise users, partnering closely with Product, Engineering, and FinOps teams to translate customer feedback and cloud utilization insights into high-impact roadmap innovations.
Scale and Mentor the Team: Build and develop a world-class customer organization through thoughtful hiring, leadership development, and scalable operating practices. Establish the team structure, processes, and performance frameworks needed to support growth while fostering a culture of technical excellence, customer empathy, and accountability.
Requirements
Proven B2B SaaS Leadership: 7+ years of progressive leadership experience managing multi-disciplinary customer-facing organizations (Success, Support, Services) within a fast-growing tech startup environment.
Deep Cloud & Infrastructure Domain Expertise: Comprehensive understanding of public cloud environments (AWS, Azure, GCP), cloud billing mechanisms, FinOps methodologies, or infrastructure management platforms.
Strategic & Analytical Mindset: Demonstrated ability to build data-driven retention models, design customer journeys, and manage operational budgets and capacity planning.
Executive Communication: Outstanding cross-functional orchestration capabilities, with a track record of building trusted advisor relationships with enterprise technology executives and internal engineering stakeholders.
Nice to have
Direct familiarity with modern Customer Success platforms and advanced ticketing systems.
Experience scaling teams through hyper-growth phases (e.g., from Series A to Series B and beyond).
Compensation & Benefits
Salary Range: $240,000 - $285,000
Health, dental, vision (yes, all three!), equity in something early-stage and exciting, generous PTO, 401K, meal & commuter benefits, and a team that will actually challenge you.
Why PointFive
Founders with a track record — Built and sold IntSights to Rapid7. Backed by top-tier investors with deep conviction in this category.
Category-defining product — DeepWaste detection and agentic remediation with clear, measurable ROI for both engineering and finance teams.
Early-stage leverage — Your work directly shapes the product, the culture, and the go-to-market playbook.
A true builder's seat — as one of the first AEs on the US team, you'll shape the territory playbook and GTM motion that the next wave of hires will follow.
Equal Opportunity Statement
PointFive is proud to be an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We welcome candidates from all backgrounds, experiences, and perspectives to apply.