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About this role
As the Head of Enterprise Application Engineering you will be part of the CIO Technology Engineering senior leadership team. You will lead the engineering, integration, configuration and continuous improvement of enterprise applications currently spanning Modern Workplace, , and HR & Finance platforms.
Head of Enterprise Application Engineering | JobCheckPoint
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You will be acting as the technology lead maintaining the guardrails for safe and secure development and deployment, working closely with relevant stakeholders including CIO Group Architecture, CIO leadership, business stakeholders and suppliers to improve adoption, productivity, resilience service performance and commercial outcomes in line with Hastings’ strategy.
This is a senior leadership role requiring strong technical judgement, stakeholder influence and people leadership. You will help shape application roadmaps, drive high-quality outcomes, and champion continuous improvement in customer and colleague experience.
Job details:
Define and enforce engineering standards and governance, including configuration and integration standards and controls for integrity, availability, supportability, compliance and resilience.
Drive service quality through prevention, automation and continuous improvement, including monitoring, root cause analysis and action to keep technical debt low.
Lead application strategy, guardrails and roadmap alignment, working with CIO Group Architecture to maintain design principles and cohesive delivery across teams.
Build capability across Modern Workplace, Telephony, and HR & Finance.
Provide technical leadership, stakeholder engagement and supplier management.
Develop high-performing teams through coaching, recruitment and succession planning.
Champion innovation, best practices and emerging technologies.
Use Management Information and agreed KPIs to track progress, improve service performance and recommend continuous improvements.
Contribute to enterprise-wide priorities through strategic alignment, cross-functional collaboration, change leadership and governance oversight.
Skills we would love you to have:
Proven leadership experience in enterprise application engineering, driving productivity, service quality and operational efficiency within a fast-paced, enterprise-scale technology environment.
Strong knowledge of Microsoft 365, Modern Workplace, Contact Centre, and HR & Finance platforms, with the judgement to balance integration, security, supportability, resilience and business value.
Experience with engineering methodologies, tools and best practices with the ability to set a pragmatic engineering culture that improves quality, pace and consistency.
Excellent analytical, troubleshooting and problem-solving capabilities.
Strong strategic and commercial awareness, with the ability to translate business strategy into technology priorities, trade-offs and measurable outcomes.
Enterprise leadership capability, including cross-functional collaboration, change leadership, risk-aware decision-making and the ability to lead through ambiguity.
A collaborative, organised and adaptable leadership style, with a focus on quality, customer outcomes and developing people.
Regrettably we are unable to offer sponsorship for this role
Benefits: competitive salary and £6k car allowance
Flexible working – we champion a flexible hybrid working approach – please speak to your recruiter to discuss in more detail
Competitive bonus scheme - all colleagues are eligible for our annual 4Cs performance bonus
Physical wellbeing – as a Band 5 colleague, Hastings pay for you to receive private medical Insurance (also known as PMI). This gives you flexibility and convenience to see a specialist or consultant and allows you to decide when and where you will be seen
Financial wellbeing – as well as providing you with 4x your salary with our life assurance cover, income protection at no extra cost, and matched pension contributions up to 10%, we are proud to provide you with an award winning package which includes – discounts, cashback, free independent mortgage advice and free access to financial wellbeing support
Mental wellbeing programme – we have the thrive mental health app, our colleague assistance programme available 24/7, our own in-house mental health first aiders, support groups and a dedicated team to make sure we are covering your needs
There's more! – 27 days annual leave + bank holidays, with the option to buy or sell one of your weeks, access to our health care cash back plans, dental plans, discounted health assessments, Cycle to work and tech schemes, discounted and free onsite facilities, social events throughout the year and much more ….
Hastings Group is an equal opportunities employer which means we treat people fairly. We welcome applications from all suitably skilled persons regardless of their gender, age, race, disability, ethnic background, religion/belief, sexual orientation, gender reassignment or marital/family status. Please also note that we have a thorough referencing process, which includes credit and criminal record checks.
At Hastings Direct, we’re committed to creating an inclusive environment where everyone has the opportunity to succeed. If you require any reasonable adjustments during the recruitment process, we encourage you to be open with us. Our recruitment team is here to provide the support you need to ensure a fair and accessible experience for all.
Job posting end date:
30/11/2026
Would you like to learn more about how we value diversity and inclusion at Hastings Direct and what our rewards and benefits package looks like? Are you interested in how we engage with and support our local communities and the wonderful wellbeing programme you will have access to? Click [here](https://www.hastingsdirectcareers.com) and check out the what we offer tab to learn more.
Hastings Direct is a fast growing, agile, digitally focused general insurance provider of products and services to over 4 million customers in the UK, employing over 4,600 colleagues. Our vision – to be the best and biggest digital insurance provider in the market.
It's our attitude and the way we run our business that makes us different. We focus on getting it right for our colleagues, customers, company and community. It's a dynamic, flexible, fun and constantly changing environment. You'll enjoy the scope to make a real difference for our customers, influence our company, benefit the communities we work in and have fun along the way.
If you enjoyed the video and would like to learn more about #LifatHD, check out our colleague [stories](https://www.hastingsdirectcareers.com/inside-hastings)
Strategy
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Pension
Private healthcare
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