Vice President, Cloud - Remote

Company Description PayNearMe develops technology to facilitate the end-to-end customer payment experience, making it easy for businesses to accept, disburse and manage payments. Our modern and reliable platform lowers the total cost of payments by increasing acceptance rates, driving self-service and simplifying exceptions. We future-proof our clients’ payments roadmap by including all payment types and channels through a single contract and integration. With PayNearMe, businesses can focus on acquiring new customers while we make accepting payments a modern and seamless experience. PayNearMe has over 240 employees and is processing over $40B in payments annually. We are a fully-funded private company headquartered in Silicon Valley with our employees distributed across the U.S. This is an opportunity to join a high-growth, private, venture-backed company during its critical growth phase. Come help us solve our clients’ biggest payment problems. Job Description

We’re investing heavily to harden reliability, modernize our stack, and accelerate product velocity. Today, we operate two worlds:

A mission‑critical Rails monolith on AWS EC2 that runs 24×7×365 A modern services stack (Go on Kubernetes) we’re rapidly scaling We need a hands‑on 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. You’ll lead the program that turns reliability into a competitive advantage and lays the runway for the next stage of growth. Responsibilities 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 seven‑figure AWS budget with clear FinOps guardrails Two Stacks, One Standard: Operate and evolve the Rails monolith (EC2 today; containerized & Terraform‑managed going forward). Standardize the Go/Kubernetes services stack (EKS, Helm) with paved‑road templates, service bootstrapping, and zero‑toil 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 end‑to‑end visibility (DataDog, CloudWatch, logs/traces). Set high‑signal alerting and dashboards tied to user outcomes Security & Compliance Partnering: Work hand‑in‑hand 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 multi‑AZ/region patterns. Scope may expand to include DB Engineering over time People & Org: Lead ~10–12 engineers/contractors initially (growing to ~15). Uplevel talent, hire bar‑raisers, and coach legacy sysops profiles toward DevOps/SRE. Clarify roles, on‑call, and ownership to reduce bottlenecks Qualifications 10-12+ years in engineering with 5+ leading Infra/Platform/DevOps/SRE teams Deep AWS experience operating 24×7, high‑volume systems Rails at scale: You’ve 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 mission‑critical services; multi‑AZ patterns, autoscaling, rollout strategies Terraform author: You’ve 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 world‑class on‑call Security & audits: Comfortable building for PCI/SOC 2 controls in regulated environments Pragmatic technologist: Preference for boring, battle‑tested tech over novelty; bias to shipping Preferred Qualifications 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 can’t 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 one‑offs are eliminated Services at the push of a button: Two additional production services launched using a paved‑road 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 real‑time visibility and enforceable budgets Audit‑ready by default: PCI/SOC 2 controls automated in pipelines and infrastructure; zero critical findings What you’ll do in your first 90–180 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 paved‑road v1 (service template + CI/CD + IaC). Begin Terraform coverage of monolith infrastructure. Establish on‑call 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 game‑day 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 Location: Flexible/Remote (within the US)

Great compensation package plus extensive benefits, including:

100% Remote (must be in US) Base salary per year (paid semi-monthly) 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 2x / year in-person team meet-ups (2-3 days, company paid) Salary Range: $260,000 - $300,000

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. We’re 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. — Candidate information will be treated in accordance with our job applicant privacy notice found at: https://home.paynearme.com/ccpa-privacy-notice-jobs-employees/ Assistance for Disabled Applicants Alternative formats of this Notice are available to individuals with a disability. Please let us know if you need assistance. All your information will be kept confidential according to EEO guidelines.