Head of DevOps & AI Enablement (Remote-First)

Point Digital Finance, Inc. Canada; San Francisco (CA); Hybrid; USD 270,000 - 298,000; Full time

Benefits offered by this job

Generous health benefits

Unlimited paid time off

Flexible remote and onsite work

Fully paid parental leave

Equity

Financial wellness

Extra work/life benefits

Job summary

Point is building a new AI Enablement function and seeks an experienced leader to run reliability, delivery, and cloud foundations for a lending business. You will partner with HR, Legal, Compliance, Accounting, Finance, and Operations to automate and augment workflows with AI, while coordinating with IT and Security for safe adoption.

Join Point’s growing Engineering team in a pivotal role. This senior role requires depth in DevOps, SRE, and platform engineering with a track record of shipping

Qualifications

• 10+ years in DevOps, platform, SRE, or infrastructure engineering.
• 3+ years leading and growing engineering teams, including hiring and performance management.
• Proven experience shipping AI automations to production (LLM agents, tool calling, RAG).
• Automation work tied to measurable business outcomes.
• IaC, CI/CD, containers, and at least one cloud (AWS, GCP, or Azure).
• Strong observability and incident-management practices.
• Fluency with Python or equivalent for engineering guidance.
• Excellent cross-functional communication with non-engineering stakeholders.

Responsibilities

• Lead the infrastructure platform and shared-services organization across SRE and infra functions.
• Own reliability, CI/CD, IaC, cloud platforms, containers, release tooling, and observability including SOC 2 compliance.
• Stand up and run AI Enablement as the central hub with sanctioned components.
• Partner with corporate functions and Operations to design AI-enabled workflows and integrations.
• Collaborate with IT and Security to keep enablement safe and compliant.
• Define success metrics and drive adoption of shipped solutions.
• Define multi-quarter roadmaps tied to business outcomes.
• Stay current on AI and automation advances and adjust the roadmap.
• Set technical and quality standards through architecture guidance.

Skills

DevOps leadership

SRE leadership

Engineering team leadership

AI automation shipping

Automation to business outcomes

IaC Terraform

CI/CD

Docker

Kubernetes

Cloud platforms (AWS/GCP/Azure)

Observability

Incident management

Python or similar

Cross-functional communication

Tools

Terraform

Docker

Kubernetes

AWS

GCP

Azure

Job description

Point is building a new AI Enablement function and seeks an experienced leader to run reliability, delivery, and cloud foundations for a lending business. You will partner with HR, Legal, Compliance, Accounting, Finance, and Operations to automate and augment workflows with AI, while coordinating with IT and Security for safe adoption.

Join Point’s growing Engineering team in a pivotal role. This senior role requires depth in DevOps, SRE, and platform engineering with a track record of shipping