Staff Software Engineer

ROLE / DEPARTMENT OVERVIEW

Pathstream is seeking a Staff Software Engineer to lead large, cross-team technical work on our platform. This is a senior individual contributor role on one of our engineering pods. Our pods are small, fast-moving teams that own their area end to end and ship to production often. You will report to your pod's engineering lead and have no direct reports.

You will be an expert in the systems your team owns, and you will understand how data moves through the rest of Pathstream's platform. You will lead multi-person projects from design to production, set the technical bar for your pod, and help the engineers around you grow.

A core expectation of this role is the ability to advance Pathstream's AI-native engineering practices. AI adoption is already deeply embedded in how we build software at Pathstream. We are looking for a technical leader who not only embraces this approach but actively pushes the organization forward in building, evaluating, and deploying AI-enabled development tools and agentic engineering workflows. Both as a hands-on practitioner and as a force-multiplier for engineers across the org.

WHAT WE DO

Pathstream was founded on the premise that substantial unrealized economic and human potential exists within each organization's frontline workforce. We are reshaping the way employees and managers on the frontlines excel in their careers. In this age of rapid tech evolution, our enterprise partnerships transform frontline teams from transactional to relational, and from task-oriented to strategic.

We impact companies' bottom lines with improved productivity, increased retention, and differentiated quality of customer experience, while employees experience greater success in their current roles and unlock future professional growth.

We're a tight-knit, hardworking, mission-driven team of ~60 employees eager to scale our solution and transform the careers of our customers.

THE ROLE

AI-NATIVE ENGINEERING

• Own how your team delivers with AI, in addition to your own output. Reshape how projects are scoped, sequenced, and staffed now that implementation is cheaper, so the team's throughput goes up.
• Own the team's shared AI patterns as a set: context files, skills, conventions, and workflows, including ones others wrote. Keep them maintained, and retire the ones that no longer help.
• Lead adoption of new AI tools and methods in your area. Our current toolset includes Claude Code, Claude skills, MCP servers, and AI code review.
• Notice when the team's verification practices fall behind how fast code is now produced, and drive the fix end to end. Test strategy, staged rollout, and observability are part of that work.
• Make room for the team to experiment, and keep it safe to report that something did not work. Tell an experiment worth running from a distraction, and say no to distractions without killing the team's appetite to try new things.

TECHNICAL OWNERSHIP & DELIVERY

• Lead large feature releases end to end. These are usually multi-person projects that cross team boundaries.
• Take on significant, unique engineering problems where the data is incomplete and the trade-offs include intangibles. Diagnose root causes quickly and guide others through the trade-offs.
• Break complex initiatives into clear, maintainable pieces that less experienced teammates can own.
• Know when to focus on stability and quality, and when to ship quickly and iterate.
• Write architecture documents that show how systems work together and where they are weak. Review other teams' technical documents with clear, timely feedback.

QUALITY, SECURITY & OPERATIONS

• Recognize when systems or workflows need reinforcement to protect quality, and drive the solution end to end.
• Apply strong security practice in your domain. Partner with engineering leadership on SOC2, vulnerability management, and the controls that protect our enterprise customers and learners.
• Give code review that others seek out because it is thorough, helpful, and kind.
• Jump into incidents outside your normal scope in an emergency. Improve how the team detects, prevents, and responds to incidents.

COLLABORATION & MENTORSHIP

• Grow other engineers over an extended period. Tailor feedback to each person's skills, background, and working style.
• Build strong relationships with product, design, and cross-functional partners. Represent your team's technical view in conversations about scope, sequencing, and trade-offs.
• Write clear narratives that create understanding and help decisions get made. Adapt how you communicate to your audience.
• Influence hiring and help develop strong engineering talent.

ABOUT YOU

AI PRACTICE

• AI is a core part of how you work today. You can describe, with examples, how it changed the way you scope, build, and review software.
• You have built AI tooling for yourself and for others: skills, MCP servers, context files, evaluation harnesses, or multi-step agentic workflows. Other engineers adopted and kept using at least one of them.
• You have shipped AI features in production systems where an LLM is a first-class component. You have dealt with evaluation, observability, and cost.
• You verify AI output with rigor. You can name the failure modes you watch for and the checks you added to catch them.
• You keep up with the tools because you want to, not because someone asked you to. You run your own experiments, you have opinions about what works, and you share what failed as readily as what worked.

EXPERIENCE

• You bring 7+ years of professional software engineering experience, with a strong track record as a senior engineer.
• You are an expert in one or more technical areas and proficient across a broad range of others.
• You have led projects that crossed team boundaries, and you have shipped systems that other engineers depend on.
• You bring deep familiarity with modern web application stacks similar to ours: Ruby on Rails, React, JavaScript/TypeScript, Python, Docker, PostgreSQL, and AWS.
• You have practical experience operating production systems that hold customer data, including security and compliance work in a SaaS environment.

HOW YOU WORK

• You lead through influence. Other engineers seek you out for technical feedback because your advice is thorough, helpful, and kind.
• You are comfortable with ambiguity and shifting priorities. You make data-informed decisions when perfect information is not available.
• You stay calm under pressure and help your team through change.
• You ask for feedback and act on it. You celebrate the work of others, and you treat disagreement as a way to reach a better answer.

WHAT WE OFFER

• Transparent and social culture, challenging work, fast learning cycles, practical training, and meaningful feedback
• Strong sense of ownership and strategic work that impacts our product, users, colleagues, business, and world
• Salary and total compensation offerings are contingent upon the candidate's level of expertise and geographic location, ensuring equitable remuneration.
• Tier 1: San Francisco Bay Area and New York City: $190,000 to $220,000 
• Tier 2 metropolitan markets: $171,000 to $198,000
• Tier 3 regional markets: $152,000 to $176,000

Comprehensive benefits package:

• 100% employer-paid medical, dental, and vision for you; 50% for partner/spouse and dependents
• Health, commuter, and parking flexible spending accounts
• Employee Assistance Program (mental health, financial health, legal support)
• Free access to wellbeing apps (Ginger, Headspace)
• Flexible paid time off and paid holidays
• Generous paid parental leave
• Short and long-term disability insurance
• Annual professional development budget
• Company-provided laptop
• Remote-first culture
• Life insurance (100% company paid)
• 401(k)

COMMITMENT TO DIVERSITY AND INCLUSION

Our company values diversity and believes diverse teams make innovation possible. We work on complex, difficult problems with no linear or clear solutions. We need a diverse team that can bring different perspectives and approaches, and whose experiences reflect the full set of stakeholders we seek to serve. Pathstream is an equal opportunity employer. We encourage all qualified applicants from any race, color, religion, sex, gender identity, sexual orientation, national origin, disability status, protected veteran status, or other characteristics to apply.

WORK AUTHORIZATION

Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment Visa at this time.

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