Technical Director
About the job
- At least 10 years of software engineering experience.
- At least 5 years in technical leadership roles.
- At least 5 years of hands-on DevOps and infrastructure experience.
- Proven experience scaling SaaS platforms with high-availability requirements.
- Strong expertise in AWS and distributed systems.
- 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.
- 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.
- Spend at least 20% of working time writing code and lead by example.
- 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.
- 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 the 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.
- 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.
- 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.
- 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 the LGTM stack.
- Database optimization and sharding experience.
- Open-source contributions in DevOps or cloud-native ecosystems.
- Multi-region deployment and disaster recovery experience.
About the company
Pleased is a software company providing multichannel customer-service tools. The company offers help-desk ticketing, live chat, knowledge bases, workflow automation, assignments, analytics, and customer context. It serves growing businesses and support teams managing customer conversations across channels. Its operating model centers on a subscription platform designed for quick setup and progressively more sophisticated support operations. Teams work across product, engineering, design, support operations, sales, marketing, and customer success. The business combines technical knowledge, practical execution, and ongoing support across the markets it serves.
Company Size
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Company Stage
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Total Funding
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Headquarters
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Founded
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Simplify's Take
What believers are saying
- Pleased opened its BGC headquarters on September 8, 2026, signaling committed expansion.
- It plans 100 to 110 Philippine hires over twelve months, mostly product and engineering roles.
- Enterprise AI chat, voice agents, and omnichannel support improve upsell potential for larger customers.
What critics are saying
- Zendesk, Intercom, and Freshdesk crush crowded support-software pricing and feature parity.
- Pleased lacks disclosed funding, leaving expansion dependent on customer revenue and founder capital.
- Philippines hiring plans expose execution risk if it misses 50 engineers by December 2026.
What makes Pleased unique
- Pleased sells multi-channel support software spanning chat, voice, email, WhatsApp, and Telegram.
- Its pricing tiers scale from $15 to $150, with enterprise AI and dedicated infrastructure.
- The company is opening a BGC headquarters to build a Philippines engineering hub.
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Benefits
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Company News
New PH jobs could give skilled OFWs another option back home. Pleased.com is expanding in the Philippines and plans around 100 to 110 hires. The company says it wants Filipino professionals to access competitive salaries without leaving the country, potentially giving skilled OFWs another career option if they decide to return home. New job contracts By Staff Writer September 21, 2026 2:41 PM Discover more Digital work permits MANILA: Skilled overseas Filipino workers who are thinking about returning to the Philippines may soon have more local job options as international software company Pleased.com expands its operations in the country. Philippines news updates The company has opened its Philippine headquarters in Bonifacio Global City and reportedly plans to hire around 100 to 110 workers over the next 12 months. Most of the planned positions are expected to be in technology and product development. Company wants Filipinos to earn more without leaving home. Pleased.com founder and CEO Jonathan Sterling said one reason for expanding in the Philippines is to give Filipino professionals access to competitive salaries while allowing them to stay close to their families and communities. Access Online Encyclopedias Sterling noted that many Filipinos working overseas are highly skilled professionals. These include workers in fields such as engineering, medicine and law who may leave the country partly because of better-paying opportunities abroad. The company believes better local compensation could give more Filipino professionals a reason to build their careers in the Philippines. Some tech roles offer six-figure monthly pay. Pleased.com has already started recruiting in the Philippines. One recent job posting for a backend developer in Taguig listed monthly pay of around ₱95,000 to ₱140,000. Discover more UAE residency info Dubai attraction tickets investment Another posting for a technical director offered around ₱150,000 to more than ₱300,000 per month, depending on experience and qualifications. New job contracts These salary ranges apply only to specific jobs and should not be taken as the expected pay for every position the company will open. Why this could matter to returning OFWs. Salary is often one of the biggest concerns for OFWs considering permanent return to the Philippines. Returning workers may need to balance being closer to family with the possibility of earning less than they received abroad. Companies offering globally competitive jobs from the Philippines could help narrow that gap, especially for OFWs with experience in software, engineering, technology and other specialized fields. However, the current Pleased.com expansion is not an OFW-only hiring program. Interested workers would still need to meet the qualifications listed for each available position. Philippines news updates More hiring expected as PH team grows. Pleased.com reportedly already has around 10 engineers working locally and aims to grow this number to about 50 by the end of 2026. The wider Philippine workforce could eventually reach around 100 to 110 employees as the company continues expanding. For OFWs planning to return home, the development is worth watching as more international companies build teams in the Philippines. It may not replace overseas employment for everyone, but it could provide another path for skilled Filipinos who want to continue earning competitive salaries while living closer to their families.