Head of Customer Success

Job Description

Overview 

We are hiring a hands-on Head of Customer Success to own and run the entire post-sales function across Customer Success, Professional Services (implementation & project management), and Customer Support. 

Flexigrant is on a mission to become an AI-first company. We sit on one of the richest data sets in the grants management sector; years of application, review, and funding outcome data across hundreds of customers, and we are building the capabilities to help our customers unlock powerful insights from that data. This role is central to that transformation: you will be the bridge between our AI and data ambitions and the customers who stand to benefit most. 

You will lead a small, lean team and be expected to personally drive execution, especially across project delivery, onboarding, and customer escalations. 

This role combines delivery ownership, customer management, and commercial responsibility, including pricing and packaging decisions. 

This is not a purely strategic role, you will be directly involved in the day-to-day running of customer accounts and projects. Your initial focus will be on strengthening the Customer Success function to ensure customers are deriving maximum value and ROI from the Flexigrant platform, while laying the groundwork for AI-powered automation and data insights that will become a core part of the customer proposition. 

We are looking for someone who is AI-native in how they work and thinks boldly about what AI can do, not just to improve internal efficiency, but to transform the value we deliver to customers. You will help shape how Flexigrant leverages its unique data position to offer AI-powered insights, benchmarking, and decision support that no competitor can match. 

Key Responsibilities 

1. Own the Customer Lifecycle (Directly) 

• Manage a few key customer relationships personally, including exec sponsorship, adoption, renewals, and expansion  

• Act as the primary escalation point for at-risk or high-value accounts  

• Run QBRs and customer check-ins where needed (not fully delegated)  

• Track and act on churn, NRR, and customer health score. Use platform usage data and AI-driven analytics to identify at-risk accounts early and surface expansion opportunities  

2. Lead & Execute Implementations (Professional Services Focus) 

• Overall responsibility for all implementations and onboarding projects end-to-end  

• Act as lead project manager on complex or high-risk deployments  

• Define and manage scope, timelines, and delivery expectations  

• Create just enough structure (templates, plans) to ensure consistency  

• Balance speed vs. quality vs. customization in delivery  

3. Run Customer Support (Lean & Practical) 

• Oversee daily support operations across a small team  

• Step into tickets escalations directly when needed  

• Ensure SLAs, response times, and customer satisfaction are met  

• Analyse and identify root causes of recurring issues, and secure fixes by the R&D team 

• Drive improvements that reduce support volume over time, including the adoption of AI tools  

4. Commercial Value 

• Define and evolve pricing, packaging, and discounting together with the Pricing Committee working with the Product Manager 

• Support renewals, upsells, and deal structuring alongside Sales and the Customer Success Manager 

• Ensure services and custom work are scoped and priced profitably  

• Use real delivery data to improve margins and efficiency  

• Leverage customer insights to develop new services and expand the service catalogue over time 

• Champion the commercial potential of Flexigrant’s data assets and help customers understand and adopt AI-powered automation, analytics and insights services built on the platform’s rich grants data 

• Influence pricing strategy using real customer insights in collaboration with the Pricing Committee  

5. Lead a Small Team  

• Manage a small team across CS (x1), PS (x2), and Support (x1)  

• Set clear priorities and step in where capacity or capability is lacking  

• Hire carefully and maintain a high bar with minimal layers  

• Build simple processes that enable execution without bureaucracy  

6. Drive the AI-First Agenda - Internally and for Customers 

• Identify and implement opportunities to use AI to streamline workflows, including:  

• Customer onboarding and communication  

• Support ticket handling and knowledge management  

• Customer Success adoption of contracted product features and modules 

• Internal reporting and analysis  

• Customer-facing data insights, benchmarking, and AI-powered reporting drawn from Flexigrant’s grants data 

• Reduce manual work and improve scalability through automation and tooling  

• Act as a champion of practical AI adoption, embedding it into daily team operations  

• Continuously evaluate new tools and approaches to improve team productivity and customer experience  

• Be the voice of the customer in shaping Flexigrant’s AI automation and data insights product roadmap, feeding back what customers need and validating new AI features before launch 

7. Make the Function Work End-to-End 

• Ensure smooth handoff from Sales → Implementation → Live → Support  

• Work closely with Product/R&D to resolve issues quickly  

• Prioritise what matters most each week in a resource-constrained environment  

• Focus on highest-impact improvements rather than trying to optimise everything at once  

Requirements 

• Strong experience in Customer Success and/or Professional Services in SaaS  

• Proven track record in a hands-on role managing implementations or projects  

• Experience leading small teams while remaining highly operational  

• Commercial acumen, including pricing, scoping, or deal support  

• Demonstrated ability to use AI tools to improve productivity or workflows  

• Data-literate and excited about helping customers extract insights from their data. You don’t need to be a data scientist, but you should understand the value of data-driven decision-making and be able to articulate it to customers 

• Comfortable working in a lean environment with limited resources  

• Willingness to personally handle projects, customers, and escalations  

What Success Looks Like 

• Implementations run smoothly with minimal delays and escalations  

• Customers go live on-time and achieve clear, measurable value  

• Support is responsive, efficient, and improving over time  

• Churn is low and expansion revenue is growing  

• Pricing and services delivery are aligned with customer value and profitability  

• The team operates more efficiently over time through practical use of AI and automation  

• Focus remains on high-impact improvements rather than over-engineering processes  

• Over time the team creates and sells new services driving additional revenue streams 

• Customers are actively engaging with Flexigrant’s AI capabilities and leveraging the data insights and data services, seeing the platform as indispensable to their grant-making decisions 

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