Technical Support Engineer (Weekend Lead)

PayNearMe, Inc.; United States; On-site; USD 80,000 - 120,000; Full time

Benefits offered by this job

Stock options

Premium medical benefits

WFH setup stipend

Equipment stipend

Job summary

PayNearMe, Inc. is seeking a curious investigator to connect the dots across payments, systems, and business processes, owning customer outcomes. The role blends financial, payment, product, and integration investigations with AI-assisted problem solving, requiring exceptional communication and cross-functional collaboration.

We value professionalism, empathy, and clear client communication. The position includes weekend support leadership, escalation management, and opportunities to improve

Qualifications

• Excellent written and verbal communication with clients and colleagues.
• 7+ years in technical product support, payments operations, or related customer-facing work.
• Curiosity and independent judgment: follow evidence and elevate when needed.
• Strong investigative skills across software, APIs, data interfaces, and business processes.
• Aptitude to learn and apply AI to investigations and process design.
• Experience managing complex cases and coordinating incidents with cross-functional teams.

Responsibilities

• Investigate and resolve financial, payment, product, integration, and operational issues.
• Use Datadog, Looker, transaction data, logs, and configuration to trace behavior and test hypotheses.
• Apply AI tools to investigate and propose changes for Product and Engineering.
• Own cases in Zendesk and coordinate with Jira or FireHub for handoffs.
• Lead weekend Support, providing guidance and coaching to teams.
• Partner with cross-functional teams to resolve issues and implement improvements.

Skills

Communication

Tech support experience

Curiosity

Investigation

AI for investigations

Case management

Tools

Datadog

Looker

Zendesk

Atlassian

Job description

Company Description

At PayNearMe, we’re on a mission to make paying and getting paid as simple as possible. We build innovative technology that transforms the way businesses and their customers experience payments. Our industry-leading platform, PayXM™, is the first of its kind—designed to manage the entire payment experience from start to finish. Every click, swipe or tap is seamless, fast and secure, helping non-commerce businesses boost customer satisfaction, accelerate payments, and reduce costs.

Company Description

At PayNearMe, we’re on a mission to make paying and getting paid as simple as possible. We build innovative technology that transforms the way businesses and their customers experience payments. Our industry-leading platform, PayXM™, is the first of its kind—designed to manage the entire payment experience from start to finish. Every click, swipe or tap is seamless, fast and secure, helping non-commerce businesses boost customer satisfaction, accelerate payments, and reduce costs. Our single platform handles it all: cards, ACH, digital wallets such as PayPal, Venmo, Cash App Pay, Apple Pay and Google Pay, and even cash at more than 62,000 retail locations nationwide. Today, thousands of businesses across consumer lending, iGaming and online sports betting, property management, and tolling trust PayNearMe to deliver a payment experience that drives real results. In September 2025, we raised a $50 million Series E funding round to accelerate our growth. We’re a team of 300+ employees across 41 states, headquartered in Silicon Valley with satellite offices in Dallas, TX and Holmdel, NJ. Join us and be part of a team that’s shaping the future of payments—one experience at a time. At PayNearMe, we manage the product and customer experience through the lens of Support. We want a curious investigator who connects the dots across payments, systems, and business processes and owns the customer outcome. Support is primarily email, with limited phone handoffs and internal or client conference calls. This support role combines financial, payment, product, and integration investigations with AI-assisted problem solving. It is not a software development role. Professionalism, empathy, and clear communication with clients and colleagues are essential. Cross-functional work offers opportunities to broaden your skills and grow internally.

Schedule and Coverage

• A five-day schedule including Saturday and Sunday is required. Example: Friday through Monday plus one weekday, 8:00 AM to 5:00 PT.
• Holiday schedules, alternate days off, and weekends off are coordinated with management.
• Weekend coverage is an ongoing requirement; future schedule changes depend on business needs and available opportunities.
• Participate in the paid on-call rotation, providing after-hours support for incidents and escalations.

Responsibilities

• Investigate and resolve financial, payment, product, integration, and operational issues, including settlement, reconciliation, payment status, reporting, business rules, APIs/callbacks, bulk files, and portal behavior.
• Use Datadog, Looker, transaction data, logs, and configuration to trace behavior, test hypotheses, and distinguish defects from configuration, integration, or process issues.
• Apply approved AI tools such as Claude, Cursor, ChatGPT / Codex to investigate, including authorized code-level analysis. Validate findings and propose changes for Product and Engineering to evaluate.
• Own cases in Zendesk through resolution or a clear handoff, prioritize customer and business impact, and elevate promptly through Jira or FireHydrant. Communicate professionally with IT and finance leaders, executives, payment agents, and individual consumers.
• Lead weekend Support, owning queue priorities, escalations, and frontline handoffs. Provide real-time technical guidance and coaching to internal and outsourced teammates; improve documentation and runbooks.
• Partner with Account Management, Professional Services, Product, Engineering, SysOps, Finance, Security, Compliance, Legal, and external partners to resolve issues.
• Make authorized production configuration and operational changes through supported interfaces and established controls. Engineering owns production code changes.
• Serve as lead customer liaison during daytime weekend incidents and escalations. Coordinate impact assessment, mitigation, calls, updates, and handoffs with on-call backup and management as severity warrants.
• Turn recurring issues into product and process improvements. Help design and implement AI-assisted workflows and automation, and assess their impact on the customer experience.

Qualifications

• Excellent written and verbal communication, empathy, discretion, and composure with clients and colleagues at all levels, including expectation setting and difficult conversations.
• 7+ years in technical product support, payments operations, implementation, or related customer-facing work, or equivalent education and experience.
• Curiosity and independent judgment: follow evidence, test assumptions, persist through ambiguity, and know when to elevate.
• Strong investigative skills across software, APIs, data interfaces, financial questions, and business processes using logs, transaction data, reports, and configuration.
• Aptitude and willingness to learn and apply AI to investigations and business-process design.
• Experience managing complex cases, coordinating client-facing incidents, and coaching teammates across technical and nontechnical teams, with sound judgment, clear documentation, and follow-through.

Preferred Qualifications

• Payments or banking operations: settlement, reconciliation, payment files/NACHA, chargebacks, disputes, disbursements, or ACH.
• Datadog, Looker, Zendesk, Atlassian, or comparable logging, reporting, and support tools.
• SaaS services and partner integrations, APIs/webhooks, JSON/XML, SFTP, and batch processing.
• Workflow, knowledge-base, or business-process improvement using data, automation, or AI.
• Digital wallets, card processing, cash-at-retail/POS, payment processors, or gift card networks.
• Online gaming, including sports betting, casino/poker, fantasy sports, and sweepstakes gaming.
• Payments compliance concepts such as BSA, AML, OFAC, and UDAAP.

Annual Salary Range

$80,000 - $120,000 USD

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

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/