Vice President, Cloud - Remote

Were investing heavily to harden reliability modernize our stack and accelerate product velocity. Today we operate two worlds:

1. A missioncritical Rails monolith on AWS EC2 that runs 247365.
2. A modern services stack (Go on Kubernetes) were rapidly scaling.

We need a handson VP of Cloud to own both worlds: driving proactive reliability transforming infrastructure as code and making it fast and safe for product teams to ship. Youll lead the program that turns reliability into a competitive advantage and lays the runway for the next stage of growth.

What youll do & own

• Reliability & SLOs: Define and enforce SLOs (target 99.95% for core services). Lead incident management and the shift from reactive to proactive reliability (redundancy failure testing chaos/DR exercises error budgets).
• AWS at Scale: Own our AWS environment (EC2/EKS VPC ALB/NLB Route 53 S3 RDS/Aurora IAM/KMS). Drive cost/performance tradeoffs and manage a sevenfigure AWS budget with clear FinOps guardrails.
• Two Stacks One Standard: Operate and evolve the Rails monolith (EC2 today; containerized & Terraformmanaged going forward). Standardize the Go/Kubernetes services stack (EKS Helm) with pavedroad templates service bootstrapping and zerotoil deploys.
• Infrastructure as Code & CI/CD: Make infrastructure repeatable and reviewable using Terraform (authoring and review) Helm and GitLab CI/CD. Reduce manual work to near zero.
• Networking & Service Mesh: Own ingress/egress (NGINX) and service mesh (Linkerd). Establish golden patterns for traffic management authn/z and resiliency.
• Observability: Ensure endtoend visibility (DataDog CloudWatch logs/traces). Set highsignal alerting and dashboards tied to user outcomes.
• Security & Compliance Partnering: Work handinhand with Security to meet/beat PCI SOC 2 and related audits; build controls into the platform by default.
• Data Layer Alignment: Partner with Data/DBA teams (Aurora MySQL & Postgres). Advise on reliability strategies to support horizontal scaling of relational databases (examples under evaluation include TiDB and Vitess) backups/restore and multiAZ/region patterns. Scope may expand to include DB Engineering over time.
• People & Org: Lead 1012 engineers/contractors initially (growing to 15). Uplevel talent hire barraisers and coach legacy sysops profiles toward DevOps/SRE. Clarify roles oncall and ownership to reduce bottlenecks.

Qualifications :

Must-Have Experience:

• 10-12 years in engineering with 5 leading Infra/Platform/DevOps/SRE teams.
• Deep AWS experience operating 247 highvolume systems.
• Rails at scale: Youve operated a Ruby on Rails application in production on AWS (EC2/containers) and understand its deployment/runtime characteristics.
• Kubernetes expert: Designed/operated EKS (or equivalent) for missioncritical services; multiAZ patterns autoscaling rollout strategies.
• Terraform author: Youve written and reviewed Terraform in anger; you enforce code review testing and module standards.
• CI/CD & automation: GitLab pipelines Helm container build/publish progressive delivery.
• Observability & incident leadership: You set SLOs build usable dashboards and run worldclass oncall.
• Security & audits: Comfortable building for PCI/SOC 2 controls in regulated environments.
• Pragmatic technologist: Preference for boring battletested tech over novelty; bias to shipping.

Nice-to-Haves 

• Payments/fintech or other highly regulated domains (banking healthcare insurance).
• Sharding/partitioning at scale (Aurora MySQL/Postgres; Vitess/TiDB exposure).
• Go and Ruby proficiency (enough to review and challenge design/operational choices).
• Experience leading/absorbing DBA teams into a cloud/reliability org.

What Success Looks Like in 12 Months

• Boringly reliable core: We cant remember the last time a core service failed for infrastructure reasons; SLOs are met or exceeded quarter after quarter.
• Monolith modernized: The Rails monolith is on its way to be described in Terraform with containerized runtime and automated change management; manual oneoffs are eliminated.
• Services at the push of a button: Two additional production services launched using a pavedroad template; new service infra bootstraps in hours not weeks.
• Faster incident loop: MTTR materially reduced; blameless postmortems produce guardrails and automation not tickets.
• Efficient at scale: Cost per payment trending down; AWS spend within plan with realtime visibility and enforceable budgets.
• Auditready by default: PCI/SOC 2 controls automated in pipelines and infrastructure; zero critical findings.

What youll do in your first 90180 days

• 90 days: Reliability & risk assessment across EC2/EKS; publish SLOs and error budgets; map single points of failure; perform a review and update of the roadmap to reach infrastructure-as-code for the monolith.
• 120 days: Ship pavedroad v1 (service template CI/CD IaC). Begin Terraform coverage of monolith infrastructure. Establish oncall rotations with clear runbooks.
• 180 days: Complete containerization/Terraform plan for monolith; launch second production service on the paved road; land initial cost optimizations and gameday DR.

Current Data Stack:

• Key AWS services: EC2 ELB EKS Elasticache Aurora/RDS
• Puppet (project underway to replace it with Ansible)
• nginx Passenger
• Hashicorp Vault
• NATS
• Terraform FluxCD Helm

Additional Information :

Why Join Us:

• Competitive salary and benefits with growth-company options grant
• Fast- paced and professional work culture
• Stock options with standard startup vesting - 1 year cliff; 4 years total
• $50 monthly communication expense stipend to go towards your phone/internet bill
• $250 stipend to enhance your WFH setup
• Reimbursement for peripheral equipment: monitor (up to $400) keyboard and mouse (up to $200)
• Premium medical benefits including vision and dental (100% coverage for employees)
• Company-sponsored life and disability insurance
• Paid parental bonding leave
• Paid sick leave jury duty bereavement
• 401k plan
• Flexible Time Off (our team members typically take off 3-4 weeks per year)
• Volunteer Time Off
• 13 scheduled holidays

Salary Range: $260000 - $300000

PayNearMe strives to create a workplace where all employees thrive. Our core values represent who we are today and we take pride in the way we work with each other as well as with our stakeholders.

Were in this together to do the right thing. We deliver real results we are proud of while remaining respectful transparent and flexible.

PayNearMe is an equal opportunity employer. We are diligently and thoughtfully working towards cultivating a diverse workforce which in turn enhances our products and services for the communities we serve. Applicants who represent all backgrounds are strongly encouraged to apply.

CALIFORNIA CONSUMER PRIVACY ACT: APPLICANT NOTICE

Effective Date: January 1 2020

Last Reviewed on: December 23 2019

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2. the purposes for which the Company uses that Personal Information.

For purposes of this Notice Personal Information means information that identifies relates to describes is capable of being associated with or could reasonably be linked directly or indirectly with a natural person that the Company may collect in connection with screening applicants for job openings at the Company.

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Remote Work :

Yes

Employment Type :

Full-time