Head of Product & Engineering

Role title: Head of Product & Engineering - Agencify

Reporting and working relationships

Reports to: Head of Growth & Operations, Agencify

Works closely with: GM Agencify, Group CTO, Product Lead, Engineering Lead(s), QA, Support, Sales Operations, Customer Success, AI & Workflow Automation, and experienced Agencify/Caava advisors

Scope: Agencify product and engineering execution - delivery discipline, production stability, partner integration reliability, roadmap execution and team maturity

Role type: Hands-on, high-potential operational leadership role

Growth path: Opportunity to grow into broader Product & Platform leadership as Agencify scales

 

Why this role exists

Agencify is entering an important stabilisation and scaling phase. The platform has strong strategic value to Caava Group: it supports independent insurance agents, connects insurers and agents, generates valuable market data, and creates a testbed for AI and workflow automation.

The Head of Product & Engineering will work with the Head of Growth & Operations, GM Agencify, Group CTO, Product and Engineering leads, Support, Commercial teams, and experienced Agencify/Caava colleagues. But they will be expected to take day-to-day ownership, bring order to execution, and grow quickly into a stronger leadership role.

Role purpose

The Head of Product & Engineering will lead the day-to-day product and engineering execution rhythm for Agencify.

• Improve production stability.
• Restore delivery predictability.
• Strengthen release discipline.
• Reduce repeat escalations.
• Improve partner integration reliability.
• Translate business priorities into executable product and engineering plans.
• Support the Head of Growth & Operations in scaling WAT, GWP, agent activation and customer confidence.
• Mature a young product and engineering team into a more disciplined execution unit.

Core responsibilities

1. Stabilise production and reduce repeat issues

• Track recurring product, platform, integration and support issues.
• Identify the top production trust-breakers affecting agents, insurers and internal teams.
• Work with Engineering, Product, Support and Operations to reduce repeated incidents.
• Ensure production issues are logged, owned, prioritised and closed.
• Improve incident response, escalation and post-incident learning.
• Build a simple weekly production health view for Agencify leadership.

2. Drive product and engineering execution

• Maintain a clear product-engineering workplan.
• Translate business priorities into sprint, release and delivery plans.
• Improve sprint discipline, delivery visibility and accountability.
• Remove blockers across Product, Engineering, QA, Support and Operations.
• Keep roadmap commitments realistic and current.
• Assess urgent requests against stability, capacity and business value.

3. Improve release discipline

• Establish release checklists and release readiness discipline.
• Ensure releases have QA review, rollback thinking, basic monitoring and support readiness.
• Work with the Group CTO team on release gates, architecture expectations and platform standards.
• Reduce surprise failures after release.
• Create a culture where speed and stability are balanced properly.

4. Improve partner integration reliability

• Track transaction success and failure patterns by insurer, product and workflow.
• Work with Engineering and Support to identify root causes.
• Separate Agencify issues from insurer-side, payment-side or third-party issues.
• Improve monitoring and escalation paths.
• Support clear communication to Commercial and Customer Success teams when issues arise.

5. Build team maturity

• Clarify ownership across Product, Engineering, QA and Support coordination.
• Coach team members on execution discipline and follow-through.
• Build a no-blame but high-accountability culture.
• Support better planning, estimation, review and retrospectives.
• Identify emerging internal leads and help them grow.

Success profile: first 6 months

• Product and engineering execution is visibly more organised.
• Agencify has a clear weekly product-engineering rhythm.
• The top recurring production issues are known, owned and being reduced.
• Release readiness has improved.
• Partner integration failures are more visible and better managed.
• Support and Commercial teams have clearer answers on product and engineering issues.
• The Head of Growth & Operations can run growth campaigns with fewer hidden platform surprises.
• The Group CTO has better visibility into Agencify technical risk.
• The team is more accountable and less dependent on ad hoc intervention.
• At least one to two internal team members are emerging as stronger product/engineering leads.

Key KPIs

Category                        Metric                                   First 6-month expectation

Production stability   Critical incidents No repeat Sev-1 from known unresolved issues.

Incident response     MTTR Baseline established in first 30 days; improving trend by month 3.

Partner reliability       Transaction success by insurer/product   Baseline established; top failure points reduced.

Delivery discipline     Sprint predictability       Improving trend toward 80-85%.

Release discipline      Release readiness   Release checklist operating consistently.

Escalations                 Repeat customer/product escalations  Material reduction in repeat issues.

Team maturity            Weekly product-engineering cadence Operating consistently within 60 days.

Leadership depth       Emerging internal leads   One to two potential leads identified and being coached.

 

Required profile

• 5+ years in product, engineering, delivery, technical operations or platform execution roles.
• Has led people, squads, workstreams or delivery teams, even if not yet at large-company head-of-function level.
• Experience working in a live customer-facing platform environment.
• Experience working closely with engineering teams and business/commercial teams.
• Experience with SaaS, fintech, InsurTech, marketplace, payments, lending, agency banking, platform operations or integration-heavy environments.

Technical and delivery capability

• Understands APIs, integrations and basic distributed-system issues.
• Can read system diagrams and integration flows.
• Understands release management, QA, rollback, monitoring and incident response.
• Can ask engineers practical questions and challenge respectfully.
• Can distinguish between product issues, engineering issues, support issues, user-training issues and partner-side issues.
• Can communicate technical issues clearly to non-technical teams.

Leadership attributes

• High ownership.
• Learns fast.
• Stays calm under pressure.
• Direct and clear communicator.
• Comfortable with ambiguity.
• Can bring order without creating bureaucracy.
• Comfortable being coached.
• Can challenge respectfully.
• Can work with senior leaders without becoming passive.
• Can grow quickly as the business grows.

Why join Agencify

Agencify is building the operating platform for independent insurance agents. The business already has strong insurer relationships and a clear revenue model. The 2026 challenge is to make the model repeatable, reliable and scalable.

This role gives the right person a rare opportunity to step into a visible leadership position, work closely with senior operators and technical leaders, stabilise a real platform, and grow quickly with the business. The person will be supported, but they will also be trusted with real responsibility.

Interested and qualified candidates are encouraged to apply by 27th May 2026.