Head of Customer Success

Shape the Future of AI-Powered Workforce Learning & Customer Success

Cloud Assess is a leading SaaS platform designed to power competency-based training, assessment and workforce development. We help organisations deliver scalable, compliant, and engaging learning experiences.

As we continue to grow, we are looking for a commercially minded and technically adept Head of Customer Success to lead and scale our customer success function. This is a high-impact leadership role suited for someone who thrives in fast-paced SaaS environments, bridging pre-sales technical architecture with long-term post-sale account retention and expansion.

The Role

The Head of Customer Success is a critical leadership role responsible for the long-term commercial health, adoption and retention of our global customer base.

In this role, your primary role will be to lead the Customer Success team to drive Net Revenue Retention (NRR). Secondarily you will also assist the pre-sales function and partner directly with Sales during the deal cycle to help scope technical integrations and compliance requirements (e.g., APIs, webhooks, data schema mapping, and NAT file extractions).

This position is ideal for a hands-on leader who combines technical acumen with a data-driven approach to account management and revenue growth.

Key Responsibilities & Core Pillars

1. Customer Success Management & Commercial Growth

• Drive Net Revenue Retention (NRR): Own the net retention metric across all customer tiers, mitigating churn through proactive account health monitoring and identifying expansion/upsell opportunities.
• Account Multi-Threading: Equip and guide the CS team with strategic frameworks to multi-thread client relationships, building deep executive ties across compliance, operations, and leadership levels.
• Retention & Health Frameworks: Design data-driven "health check" frameworks and early warning systems to identify at-risk accounts early and execute targeted intervention playbooks.
• Commercial Account Strategy: Partner with sales leadership on renewal strategies and expansion playbooks, ensuring smooth commercial continuity across the customer journey.

2. Pre-Sales Solution Scoping

• Technical Deal Partnering: Partner closely with the Sales team during pre-sales cycles to evaluate, scope, and validate complex client technical requirements, API integration capabilities, webhooks, and custom data workflows.
• Compliance & Migration Scoping: Architect and oversee the technical viability of mission-critical compliance migrations such as standard data schema mapping and NAT file extractions before contracts are signed.
• Frictionless Handovers: Set accurate expectations, eliminating scope creep and establishing clear baselines for long-term customer success from Day 1.

Key Performance Indicators (KPIs)

• Net Revenue Retention (NRR): Achieving a target of >100% through churn reduction, high renewal rates, and account expansion.
• Gross Retention Rate (GRR): Minimising account churn and contraction across mid-market and enterprise customer segments.
• Pre-Sales Scoping Accuracy: Ensuring seamless post-sale transitions with minimal technical friction or scope creep stemming from pre-sale architecture.

Qualifications & Experience

• SaaS Leadership: 2+ years of leadership experience within Customer Success, Solutions Engineering, or Technical Account Management in a B2B SaaS environment.
• Technical Scoping & Governance: Hands-on experience with pre-sales solution architecture, API/webhook integration scoping, and complex data/compliance migration workflows (e.g., NAT file extractions or schema mapping).
• Commercial & Growth Mindset: Track record of driving NRR (>100%), managing renewals, and scaling expansion strategies within existing accounts.
• Process Architecture: Proven ability to translate complex technical and commercial processes into scalable, repeatable corporate playbooks.
• Data-Driven Approach: Strategic, analytical mindset comfortable leveraging data and account health metrics to drive proactive customer outcomes.
• Global Scale: Experience managing remote teams and supporting a globally distributed customer base.
• Cultural Alignment: A baseline requirement of simply being a great human being!

Our Values

• Integrity: Acting with honesty, doing right by customers and team members, and maintaining high ethical standards.
• Inclusion: Valuing diverse perspectives and fostering a culture where everyone feels supported and empowered.
• Growth: Embracing continuous improvement, innovation, and development in our product, our people, and our impact.
• Challenge: Being ambitious, solving complex problems, and striving to deliver exceptional outcomes for our customers.

If you're a customer-centric leader who thrives on driving retention, growth, and exceptional customer experiences, we'd love to hear from you. Apply today and help shape the future of customer success at Cloud Assess.