Technical Director

Company & Product Profile

Pleased.com provides customer service software (SaaS) to clients all over the world. The company has been live with paying customers for years, and is currently used by around 5 million end users each month (our clients’ customers). Pleased has a remote development team in Europe with around 30 people, and due to the success of the product is seeking to hire around 100 more people in the Philippines to further develop and scale. Pleased’s goal is to capture a larger portion of the US market.

We have a >1,000 sqm office space in BGC that we’re moving into at the end of July. It’s an open-office layout, with several breakout areas and lots of meeting rooms. All technical staff are equipped with the best technology to perform their duties (high-spec MacBook Pros, multiple monitors, noise cancelling headphones, and more). We have several AI subscriptions to aid with coding in order to maximally leverage your skills. With that said, everyone is expected to have a strong programming foundation so they can ensure any generated code is suitable for production, and ultimate responsibility falls on each individual. In our tech department, you will never have anyone in your managerial chain that doesn’t know how to code. Everyone, from the most junior developer all the way up to our CEO, is a programmer and we are “dev first”.

As for how we operate, we’re divided into product teams that work on specific areas of the product. Each product team has 2-3 BE, 1-2 FE, 1-2 QA, 1 Product Manager, and 0.5 Project Managers. Separate to this, we have a Business Intelligence team for wrangling data into easily-used, useful formats, a DevOps and DBA team for managing infrastructure, a UXUI team for making beautiful user journeys and designs, and a dedicated AI team.

Our work environment is that of a fast-moving startup, not a large, slow enterprise. We value focusing on our users, taking ownership, and getting things done. In order to create a collaborative, high-energy environment, all of our team in the Philippines works on site. This is not for everyone, but if it sounds like a good fit for you, we look forward to hearing from you!

Company Description

PLEASED Technologies specializes in customer support software. We are establishing a tech and product office in the Philippines, aiming to hire 100 staff in the next 6-12 months. Our software has existed for about 5 years, and we are planning to expand our client base with a focus on the US market. We have a brand new office, modern equipment, and a startup culture.

Job Overview

We are seeking an experienced Technical Director with strong programming and systems architecture expertise to lead our engineering organization and drive technical strategy focused on rapid delivery, clean code, and scalability. You will oversee product development, architecture, and infrastructure while scaling our SaaS platform for enterprise customers globally.

Key Responsibilities:

Leadership & Strategy

• Define and execute the technical vision and roadmap aligned with business objectives

• Build and mentor high-performing engineering teams across backend, full-stack, DevOps, and QA

• Establish coding standards, development processes, and DevOps best practices

• Lead technical hiring and talent development

• Collaborate with executive and product leadership on strategic planning

• Promote automation, monitoring, and operational excellence

Programming & Architecture

• Lead by example. All our technical managers spend at least 20% of their time hands-on, writing code.

• Design scalable, secure, and maintainable multi-region architectures

• Evaluate and recommend cloud-native technologies and tools

• Ensure code quality through reviews and testing standards

• Lead technical debt management and system optimization

DevOps & Infrastructure

• Lead AWS infrastructure strategy across EC2, EKS, S3, IAM, RDS, VPC, Lambda, and EBS

• Manage Kubernetes and Rancher deployments, including service mesh implementation

• Drive Infrastructure as Code practices using Terraform

• Implement monitoring and observability solutions using Grafana, Prometheus, Loki, Tempo, and CloudWatch

• Oversee centralized logging using ELK stack, Rsyslog, and Log4j2

• Manage Nginx configurations and Cloudflare CDN strategy

• Optimize MySQL, Oracle, MyBatis, and Druid configurations

• Implement caching solutions using Redis, Redisson, and ElastiCache

• Lead Apache RocketMQ deployment and configuration

• Support rapid infrastructure deployment across new regions and countries

• Improve infrastructure efficiency and optimize AWS costs

• Implement disaster recovery, backups, and multi-region failover strategies

• Ensure security and compliance standards including SOC 2 and GDPR

Operations & Reliability

• Ensure system reliability, security, and compliance

• Maintain automated alerts, dashboards, and monitoring systems

• Define and monitor SLAs and performance metrics

• Lead incident response and post-mortem reviews

• Drive preventative infrastructure improvements

• Maintain 24/7 operational readiness and on-call processes

Cross-Functional Collaboration

• Partner with Product, Design, and Sales teams on technical planning

• Communicate technical decisions to non-technical stakeholders

• Support customer success through reliable infrastructure

• Collaborate with international teams on global infrastructure initiatives

Required Qualifications:

• 10+ years of software engineering experience

• 5+ years in technical leadership roles

• 5+ years of hands-on DevOps and infrastructure experience

• Proven experience scaling SaaS platforms with high availability requirements

• Strong AWS and distributed systems expertise

• Deep knowledge of Kubernetes and container technologies

• Experience building and mentoring engineering teams

• Knowledge of SOC 2, GDPR, and security best practices

• Experience with Agile/Scrum methodologies

Preferred Qualifications:

• Startup or high-growth company experience

• Enterprise-scale AWS production experience

• Expertise in Terraform and Infrastructure as Code

• Experience with service mesh technologies such as Kuma or Istio

• Familiarity with observability platforms and LGTM stack

• Database optimization and sharding experience

• Open-source contributions in DevOps or cloud-native ecosystems

• Multi-region deployment and disaster recovery experience

Our Tech Stack:

Cloud & Infrastructure

• AWS: EC2, VPC, ECS, EKS, Lambda, RDS, S3, IAM, CloudWatch

• Kubernetes, Rancher, and service mesh technologies

• Terraform and CloudFormation

• Nginx and Cloudflare CDN

Monitoring & Observability

• Prometheus, Grafana, Loki, Tempo

• AWS CloudWatch

• ELK stack, Rsyslog, Log4j2

Database & Data

• MySQL

• MyBatis, Druid, ShardingSphere

• Redis, Redisson, ElastiCache

Message Queues & Scheduling

• Apache RocketMQ

• Elastic Job

• Event-driven architecture

Programming & Scripting

• Java 21 and Spring Boot

• TypeScript and JavaScript

• Python automation scripting

• Bash/Shell scripting

Required Qualifications

Preferred Qualifications

Technical Skills

Core Competencies