Director, DevOps at Happy Money

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Happy Money is a financial technology company on a mission to develop and deliver affordable and accessible financial tools and services that empower people to use money as a tool for their happiness. Members benefit from loans funded by a national network of customer-focused lending partners and designed to help them accomplish their goals. 

Backed by leading investors including Anthemis Group, FirstMark Capital, and CMFG Ventures, Happy Money has helped over 208,000 members since inception – working with lending partners to fund over $3.7 billion in loans*. Founded in 2009, Happy Money has a passionate and purpose-driven employee base of over 400 people across the United States. For more information, please visit 

*As of 12/31/2021


The Director of DevOps will be responsible for ensuring defect-free, quality and real-time performance of all applications and platforms. Working closely with engineering leadership, this leader will lead all activities related to Continuous Integration and Deployment (CI/CD) Automation and production deployments. The successful candidate will combine passion for quality and automation with the ability to build a reliable process and automation frameworks as well as excellent cross-functional collaboration, leadership skills.

In This Role...

  • Lead and manage a team responsible for the design, deployment, and maintenance of Happy Money’s infrastructure in the AWS cloud
  • Identify and execute on opportunities for increased, improved automation, monitoring and security
  • Lead projects, anticipating/identifying issues that inhibit the attainment of project goals and implementing corrective actions. 
  • Foster and maintain good relationships with customers and Engineering teams to meet expected customer service levels
  • Design optimizations to meet the scalability and performance needs of the organization and actively and continually optimize cloud resources to ensure lowest cost while ensuring security, scalability, and high availability
  • Perform hands-on activities involved in creating cloud infrastructure components, migrating from, or integrating with on-premises services, and developing self-service tooling and metrics to empower delivery teams’ autonomy
  • Responsible for the overall health, performance, and capacity of the Production Environment
  • Support the DevOps organization in an advisory role to shepherd our development teams towards adoption of Operations infrastructure, tools, services and standards
  • Design, build, and maintain the CI/CD infrastructure
  • Architect, design and oversee the implementation of enterprise monitoring across the full stack, including infrastructure and lead efforts to enhance existing monitoring and reliability metrics across our platform
  • Mentor/coach engineers to facilitate their development and provide technical leadership to them
  • Lead design and implementation efforts for Disaster recovery tasks in collaboration with Engineering teams for each application
  • Participate in the Architecture committee and advise on AWS architecture and offer solutions
  • Document system designs and application operation procedures, host and deliver operations’ and participate in Developer design reviews
  • Serve in an on-call team and as an escalation contact for service trouble incident
  • Help identifying, troubleshooting, and resolving defects encountered during various stages of project delivery, including deployment and implementation of the solution in production environments


  • 10+ years in DevOps and minimum of 5+ years in DevOps leadership role for large scale projects
  • 15+ years experience of Linux and/or Unix administration, configuration, and in-depth troubleshooting
  • 10+ years administering mission-critical and large-scale web application
  • 7+ years with “cloud” IaaS provider with at least 5 years of expertise with various AWS technologies (e.g. EC2, S3, RDS, ELB, IAM, ECS, CloudWatch) to develop and maintain an Amazon AWS based cloud solution, with an emphasis on best practice cloud security
  • Track record of successful implementation experience with AWS or other public cloud platforms using infrastructure-as-code tools like Terraform
  • Strong experience with CI/CD processes preferably AWS CodeBuild/CodeDeploy or similar tools
  • Strong system monitoring using AWS CloudWatch and DataDog or similar tools such as New Relic etc.Relational and non-relational clustered DB experience (PostgreSQL, MySQL, Kafka, Spark, Hadoop, Mongo)
  • Expert in configuration tooling (Chef, Puppet, Ansible, SaltStack, etc) and orchestration automation (Terraform, CloudFormation, etc)
  • Strong programming ability in at least one scripting or shell language, such as Python, Ruby, Perl, and/or the Bourne Again shell
  • Thorough understanding of all aspects of software development life cycle and quality control practices.
  • Strong experience with Agile, Lean, and/or test-driven software development environments
  • Hands-on experience with networking for a cloud-based Internet application (load balancing, reverse proxies, DNS, CDN’s, firewalls, security applications)
  • Possess a systematic problem-solving approach, with strong communication skills and a sense of ownership and drive
  • Excellent cross-functional collaborative skills working with multiple development teams and ability to build relationships
  • Highly collaborative with an ability to influence and reach consensus
  • Ability to influence development teams in adopting cloud technologies, processes, and best practices
  • Ability to define and solve logical problems for highly technical applications
  • Have a great attitude and be ready to hustle


  • Experience with Information Security compliance, including SOC-2 or PCI compliance preparation
  • Experience with financial systems or loan origination systems

Here at Happy Money, we live by our core values of Love, Trust, and Hustle and welcome all. Love is shown in how we develop meaningful relationships with everyone we interact with; whether it’s a member or your manager. Trust is shown through how we empower each other to come to work as our true selves and embrace our differences. Hustle is shown through how we fail fast and learn from our mistakes. No one is perfect, we’re all human; if this job description doesn’t exactly match your background, we encourage you to apply anyway!

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