Head of Sales Managed Services

Key Responsibilities

• Engage schools and MATs to understand current payments and income-management processes, volumes, controls and pain points
• Identify operational risk, control gaps, compliance/audit exposure, inefficiency and financial leakage
• Build a quantified case for change (time saved, risk reduction, improved collections), aligned to customer priorities
• Position the Managed Service as an outcome-led solution, tailoring the narrative for finance, operations and executive stakeholders

• Build and manage relationships across the buying group, including:
   
  • School Business Managers 
  • Finance Leads 
  • MAT CFOs and Operations Directors 
• Shared Services / central finance teams (where applicable)
• Lead commercially focused conversations and guide the customer through governance and procurement, including:
   
  • Stronger financial control and segregation of duties
  • Compliance, audit readiness and evidence trails
  • Income optimisation, debt reduction and improved reporting/forecasting

• Design customer-specific solutions using standard service components, balancing configuration with scalability
• Define scope, responsibilities, assumptions, SLAs and success measures; articulate outcomes and value
• Partner with Operations, Product, Finance and Legal to ensure proposals are deliverable, priced appropriately and contract-ready
• Present compelling, executive-ready proposals and business cases to senior stakeholders

• Build and manage a pipeline of qualified Managed Service opportunities, with clear next steps and decision criteria
• Work in partnership with Account Managers and Customer Success to identify target customers and run account plans
• Deliver new revenue in line with targets, maintaining accurate forecasting and CRM discipline

• Own the feedback loop into the business on:
   Evolving customer needs and buying drivers across schools and MATs; Objections, barriers and procurement constraints (including budget cycles); Competitive landscape and differentiation opportunities
• Collaborate with Product and Operations to formulate and evolve the proposition: service components, packaging, commercial model/pricing inputs, and sales enablement materials (playbooks, FAQs, value calculators and case studies)

• A strong pipeline of qualified Managed Service opportunities across priority segments (schools and MATs)
• Consistent conversion of opportunities into contracted, profitable recurring revenue
• High-quality, well-scoped deals that are deliverable, repeatable and scalable for operations
• Positive customer feedback on the relevance, impact and ease of adoption of the service
• Accurate forecasting and clear contribution to managed services growth, alongside measurable proposition improvements over time

Skills, Knowledge and Expertise

• Proven experience in consultative or solution-based sales 
• Experience selling services, managed services, or operational solutions (not just software) 
• Strong commercial acumen with the ability to articulate financial value and ROI 
• Excellent discovery and diagnostic skills 
• Ability to engage credibly with senior stakeholders (finance / operations) 
• Experience contributing to proposition development (packaging, value messaging, pricing inputs) and creating/reusing sales enablement assets
• Track record of building and closing complex deals 

• Experience in education, payments, or financial software 
• Understanding of financial processes, reconciliation, or income management 
• Experience working with Multi-Academy Trusts or public sector organisations 

• Curious and analytical style who seeks to understand before proposing solutions 
• Credible and trustworthy individual who can build confidence with customers quickly 
• Comfortable with ambiguity and able to operate in a developing proposition 
• Commercially driven, but not overly “salesy” in style 
• Resilient and self-sufficient, with a proactive mindset

About
At ParentPay Group, we believe that when schools run well, students thrive. That’s why we’ve spent decades building the operating system that supports well‑run schools – a seamless layer of tools, insights, and support that makes school life simpler for teachers, leaders, caterers, parents, and students alike.From cashless payments and parent engagement to catering management, library systems, and MIS platforms, we connect the everyday parts of education through simple, secure, and connected tools. What began as a way to make school payments easier has grown into Europe’s leading EdTech group – trusted by over 20,000 schools and 9 million users across the UK and Europe.Every day, our platforms process millions of payments, messages, and data points, quietly working in the background so schools can shine out front. Together, we’re helping schools save time, cut costs, and create more time for learning.ParentPay Group is more than a collection of brands. We are a group of people dedicated to supporting well‑run schools and giving time back to teachers, parents, caterers, admin staff – and most importantly, to students.