--- title: 'Sr. Observability Engineer at FreedomPay' canonical: 'https://feeny.ai/job/sr-observability-engineer-freedompay-united-states-0st8srd45men' type: 'job' last_seen: '2026-09-08' --- # Sr. Observability Engineer at FreedomPay - **Company:** FreedomPay - **Location:** United States - **Employment:** full-time - **Work type:** hybrid - **Posted:** 2026-07-27 - **Last confirmed live:** 2026-09-08 - **Apply:** https://jobs.lever.co/freedompay/640f44ef-6a03-4cf7-981d-407d4ea0ecab ## Job description The Senior Observability Engineer is responsible for defining, leading, and advancing enterprise observability strategy, architecture, and implementation across applications, platforms, infrastructure, and operational services. This role requires deep hands-on expertise with Dynatrace SaaS and recent Dynatrace platform capabilities and innovations, as well as strong experience with OpenTelemetry, cloud-native observability, AIOps, and agentic operations. This individual will serve as a principal-level technical leader, applying strategic thinking, systems architecture expertise, and sound decision-making to establish modern observability standards and scalable telemetry practices. Working in a fast-paced, highly collaborative technology environment, this role partners closely with engineering, site reliability, platform, security, infrastructure, operations, and architecture teams to guide the organization beyond traditional monitoring toward more intelligent and adaptive operational models. Essential Duties & Responsibilities: - Define and evolve our enterprise observability vision, standards, principles, and roadmap, using strategic thinking and sound judgment to align technical direction with business needs. - Lead the implementation, optimization, and adoption of Dynatrace SaaS and its latest platform capabilities across the enterprise. - Establish scalable telemetry architecture and OpenTelemetry standards that improve consistency, interoperability, and long-term flexibility. - Design observability solutions for Kubernetes, containers, microservices, distributed applications, and public cloud environments. - Apply AIOps and agentic operations capabilities to strengthen detection, event correlation, diagnosis, automation, operational response, and continuous improvement. - Develop and maintain service health models, SLOs, dashboards, alerting strategies, telemetry governance, and observability best practices that support operational excellence and service reliability. - Collaborate across engineering, site reliability, platform, security, infrastructure, operations, and architecture functions to expand observability adoption and maturity. - Guide the transition from legacy monitoring practices to modern, adaptive, and outcome-focused observability models, including initiatives involving production systems and enterprise platform transformation. - Mentor engineers, influence technical direction, solve complex problems, and help shape enterprise architecture and engineering standards. Required Qualifications : - Master’s degree from an accredited college or university in Computer Science, Information Systems, Engineering, or a related technical field. - 8+ years of experience in observability, monitoring, site reliability engineering, platform engineering, infrastructure engineering, or related technical disciplines. - Deep hands-on experience with Dynatrace SaaS and recent Dynatrace platform capabilities and innovations. - Strong experience with OpenTelemetry and telemetry instrumentation, collection, and architecture practices. - Experience designing and implementing observability solutions for cloud-native infrastructure, distributed systems, and modern application environments. - Hands-on experience implementing AIOps and/or agentic operations capabilities. - Strong understanding of metrics, logs, traces, event correlation, service health, alerting models, and operational intelligence. - Demonstrated ability to apply lessons from traditional monitoring approaches to modern observability strategy and technical design. - Proven ability to lead technical initiatives, influence architectural decisions, and drive adoption across multiple teams and stakeholders. - Strong verbal and written communication skills, with the ability to collaborate across functions and influence technical and non-technical stakeholders. Preferred Qualifications: - Experience leading enterprise-scale observability transformation initiatives. - Experience with AWS, Azure, and/or Google Cloud Platform. - Strong knowledge of site reliability engineering principles, including SLIs, SLOs, incident response, and operational resilience. - Experience with automation, orchestration, and remediation workflows. - Familiarity with additional observability platforms, frameworks, or ecosystems beyond Dynatrace. - Experience with scripting or programming languages such as Python, Go, Bash, or JavaScript. ## About FreedomPay ## Company Overview - **One-liner**: FreedomPay provides a flexible, agnostic payment orchestration platform that connects commerce systems (POS, e-commerce, mobile) with 1,500+ third-party solutions to enable secure, omnichannel transactions. - **Entity Type**: Private (funding stage not publicly disclosed) - **Headquarters**: Philadelphia, Pennsylvania, USA (with a UK/Europe headquarters in London, England) - **Founded**: Not publicly disclosed (company has over 20 years of history) - **Founders**: Not publicly available ## Core Business - Primary industry: Payment Technology / Commerce Platform - Target customers: B2B, primarily mid-market and enterprise merchants across multiple verticals (retail, food service, hospitality, etc.) - Mission or purpose statement: "We exist to help forward thinkers, fast movers, and next-level achievers unleash the power of pay to sell, manage, and grow like never before." [corporate.freedompay.com] ## Products & Services - **FreedomPay Payment Orchestration Platform**: A SaaS-based platform that unifies POS, e-commerce, mobile payments, loyalty programs, and more into a single integration. Features include advanced security (PCI-validated P2PE, encryption, fraud prevention), real-time transaction processing (<600ms), and data-driven analytics. [corporate.freedompay.com] ## Market Standing - **Valuation/Market Cap**: Not disclosed (private company) - **Key Metric**: Over "billions of transactions managed annually" and 100% client retention at the enterprise level [corporate.freedompay.com] - **Notable Investors/Partners**: Shake Shack, Klarna, Microsoft, JP Morgan, Foot Locker, Amazon, Citi, Worldpay, Lloyds Bank, Toast, Visa, and many more [corporate.freedompay.com/about-us/our-story] - **Growth Signals**: Rapid expansion across 88 countries; announced global expansion to Europe and Asia; launched a rebrand to "Next Level Commerce™"; maintains a start-up mentality despite 20+ years of history. [corporate.freedompay.com/about-us/our-story] ## Competitive Advantages - **Independent and agnostic**: FreedomPay is not tied to any single processor or payment method, giving merchants flexibility and freedom to adapt to new trends. - **1,500+ integrations**: The platform connects to a vast ecosystem of POS, PMS, kiosk, web, and mobile solutions – a strong network effect. - **Industry‑leading security**: Pioneered one of the first PCI‑validated P2PE solutions in North America, including EMV and NFC support. - **Proven enterprise retention**: 100% client retention at the enterprise level demonstrates deep customer loyalty and value. ## Strategic Focus - Continued global expansion (Europe, Asia) and deepening partnerships with major processors and merchants. - Innovation in payment security, compliance, speed of integrations, business intelligence, and loyalty. - Maintaining an open, agnostic platform that allows merchants to avoid vendor lock‑in and easily adapt to new payment trends. ## Why Work Here - **Culture**: Described as a diverse, inclusive environment with a "start-up mentality" where everyone is all‑hands‑on‑deck. Employees are empowered to be their best selves. [corporate.freedompay.com/resources/blogs/life-at-freedompay] - **Workplace Flexibility**: Flexible working environment offering remote and hybrid options depending on role (e.g., Select USA Remote Locations, London hybrid). [jobs.lever.co/freedompay] - **Benefits**: Above‑market and comprehensive healthcare, company‑wide bonus plan based on shared performance, above‑market compensation, and strong emphasis on training and advancement. [corporate.freedompay.com/about-us/careers] - **Growth Environment**: A rapidly growing company that attracts top talent – "talent attracts talent." Employees work with thought leaders and have the opportunity to grow into new roles as the company scales. ## Sources 1. [corporate.freedompay.com/about-us/careers](https://corporate.freedompay.com/about-us/careers) 2. [jobs.lever.co/freedompay](https://jobs.lever.co/freedompay) 3. [corporate.freedompay.com](https://corporate.freedompay.com/) 4. [corporate.freedompay.com/about-us/our-story](https://corporate.freedompay.com/about-us/our-story) 5. [corporate.freedompay.com/resources/blogs/life-at-freedompay](https://corporate.freedompay.com/resources/blogs/life-at-freedompay) ## Other roles at FreedomPay - [Associate Site Reliability Engineer](https://feeny.ai/job/associate-site-reliability-engineer-freedompay-united-states-a73709kqc8ph) — United States - [Enterprise Customer Success Manager](https://feeny.ai/job/enterprise-customer-success-manager-freedompay-united-states-8vwy6x1kkx73) — United States - [Enterprise Customer Success Manager (English/Spanish Speaking)](https://feeny.ai/job/enterprise-customer-success-manager-english-spanish-speaking-freedompay-london-k3xj68zxjcm8) — London, United Kingdom - [Director, Global Brand Design](https://feeny.ai/job/director-global-brand-design-freedompay-philadelphia-mkze1tky2wxc) — Philadelphia, PA - [Snowflake Data Engineer](https://feeny.ai/job/snowflake-data-engineer-freedompay-united-states-wh0yd8bq0k03) — United States - [Platform Operations Engineer](https://feeny.ai/job/platform-operations-engineer-freedompay-philadelphia-9xbtr556zwgx) — Philadelphia, PA - [Install Support Analyst](https://feeny.ai/job/install-support-analyst-freedompay-dublin-accrea4kwrpx) — Dublin, Ireland - [Sales Development Representative](https://feeny.ai/job/sales-development-representative-freedompay-philadelphia-xzn8d9t2mckq) — Philadelphia, PA - [Sr. Systems Engineer - Load Balancing](https://feeny.ai/job/sr-systems-engineer-load-balancing-freedompay-philadelphia-w5n9gdayj7s1) — Philadelphia, PA - [HR Business Partner, Technology](https://feeny.ai/job/hr-business-partner-technology-freedompay-philadelphia-5dw7k9p4aqr2) — Philadelphia, PA