Senior Staff Software Engineer, Pathstream
$163-226k
Salary varies depending on location
React
AWS
Docker
TypeScript
JavaScript
Python
Postgres
Ruby on Rails
Expert level
Remote from US
More information about location
Web-based platform for teaching tech skills
Be an early applicant
Web-based platform for teaching tech skills
101-200 employees
B2CEducationTraining
Be an early applicant
$163-226k
Salary varies depending on location
React
AWS
Docker
TypeScript
JavaScript
Python
Postgres
Ruby on Rails
Expert level
Remote from US
More information about location
101-200 employees
B2CEducationTraining
Company mission
To change the future of careers.
Role
Who you are
- We are looking for someone who has already built a strong foundation as a senior engineer in one or more critical domains, and who now brings the maturity, range, and ambition to set technical direction across teams — shaping architecture, raising the bar on quality and security, and accelerating the engineers around them, including those they directly manage
- 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
- You bring 10+ years of professional software engineering experience, with a strong track record at the senior IC level — typically 3+ years as a Staff or equivalent senior IC, or a Senior IC ready to step into broader scope
- You have built and shipped systems that other engineers depend on at scale, and you have been the technical owner for a major service, platform area, or greenfield initiative end-to-end
- You have a proven track record of driving multi-team technical initiatives. Setting architectural direction, unblocking cross-team dependencies, and influencing decisions beyond your immediate team
- You bring deep familiarity with modern web application stacks similar to ours: Ruby on Rails, React, JavaScript/TypeScript, Python, Docker, PostgreSQL, and AWS
- You bring practical experience with security and compliance work in a SaaS environment including SOC2, vulnerability management, authentication systems, and the day-to-day discipline of operating production systems that hold customer data
- You have experience mentoring or leading engineers as a tech lead, a senior IC running a working group, or in a formal management capacity. Direct people-management experience is a plus but not required; what is required is genuine interest in growing engineers and the maturity to take on direct reports with thoughtful coaching support from your manager
- You are genuinely hands-on with modern AI-enabled development tools and agentic engineering approaches. We are looking for someone who has already integrated AI deeply into their engineering workflow and can speak from practical experience about what works, what doesn't, and why
- You have built or meaningfully contributed to agentic workflows: MCP servers, skills, evaluation harnesses, multi-step automations, or AI-assisted development pipelines where AI orchestrates work rather than just assisting with individual tasks
- You can architect and ship AI features in production systems, designing systems where AI is a first-class component (LLM orchestration, evaluation, observability, cost management)
- You have a strong understanding of scalability and system design, with experience building or guiding systems through significant growth in scale, complexity, or scope of ownership
- You lead through influence rather than authority. You are sought out for technical feedback because of your thorough, helpful advice and your kind, respectful communication
- You communicate complex technical ideas in ways that are accessible to a wide range of stakeholders. You write crisp narratives that create understanding, influence decisions, and unblock teams
- You are comfortable operating in environments with ambiguity and shifting priorities, and you bring a proactive, data-informed approach to decision-making even when perfect information is unavailable
- You bring curiosity, humanity, and generosity to your work. You invest deeply in the engineers around you, celebrate the wins of others, and treat disagreement as a collaboration tool rather than a contest to win
- You are excited by the hybrid nature of this role. You want to stay deep in the technical work while taking on direct people responsibility, and you see managing two engineers as a way to multiply your impact
What the job involves
- Pathstream is seeking an experienced Sr Staff Software Engineer to operate as a senior technical leader on the engineering team, accountable for the most ambiguous, highest-leverage technical work across our platform. This is a hybrid role reporting to the SVP of Engineering: you will operate as a hands-on Sr Staff engineer and as the direct manager of two mid-level engineers
- Set technical direction across multiple domains of Pathstream's platform and shape architecture decisions that span service and team boundaries. Produce the technical documentation that lets your team learn from and execute
- Own the most complex, ambiguous, and consequential technical work in your domain end-to-end: greenfield service design, large refactors, new platform capabilities, and unprecedented problems with no clear playbook
- Anticipate systemic risks across the platform before they surface, scalability ceilings, data-flow brittleness, security posture, cross-service contracts and drive resolution
- Operate as a credible voice at the engineering org level. Lead roadmap conversations that cross team boundaries, identify and drive resolution of org-level technical risks, and influence how Pathstream's engineering teams build collective technical capability
- Set and evolve the bar for quality versus speed in your domain, ensuring alignment with strategic goals and coaching others on making pragmatic trade-offs. Fostering a culture that values effective execution without unnecessary complexity
- Act as a senior technical authority for security and compliance in your domain. Partner with engineering leadership on SOC2, vulnerability management, threat modeling, and the controls that protect Pathstream's enterprise customers and learners
- Be deeply involved in code reviews of significant scope and impact. Provide thorough, constructive feedback that raises the quality bar and that helps less experienced engineers grow
- Be willing and able to jump into incidents well outside your normal scope of work in an emergency. Translate on-call insights and operational pain into new technical priorities and architectural opportunities
- Be a hands-on practitioner and force-multiplier for AI-native engineering at Pathstream. You are not just adopting AI-enabled development tools (Claude Code) you are pushing the frontier of how Pathstream uses them
- Lead the design and adoption of agentic engineering workflows in your domain where AI systems assist with or automate multi-step engineering tasks. Build internal frameworks, skills, MCP servers, evaluation harnesses, and reusable patterns that let engineers leverage AI safely and effectively
- Partner with engineering leadership to shape Pathstream's evolving AI engineering strategy: evaluate emerging tools, define where AI creates the most leverage, and ensure responsible adoption aligned with internal AI guardrails
- Coach engineers across the organization on how to collaborate effectively with AI systems. Define what good context engineering looks like, when to use which tool, how to evaluate AI-generated output, and how to know when not to trust it
- Directly manage two mid-level engineers. Own their growth and performance end-to-end, regular 1:1s, growth plans, performance reviews, compensation recommendations, and timely candid feedback
- Your reports should grow faster because they work with you, through pairing, design feedback, code review, and exposure to the technical decisions you are leading. People management is a force-multiplier on your technical leadership, not a separate track
- Develop engineers beyond your direct reports. Invest in coaching teammates across the engineering org, through pairing, code review, design feedback, and thoughtful technical critique
- Build strong relationships with product managers, designers, and cross-functional partners. Represent your team's and your domain's technical perspective clearly in conversations about scope, sequencing, and trade-offs
Our take
Applicant Tracking Systems are frequently used by companies to filter out resumes that do not include essential skills. However, University degrees often focus on generalized skill sets as opposed to career-critical skills, resulting in many strong candidates slipping through the cracks.
Pathstream builds optimized digital skill programs for job seekers by partnering with companies and educational institutions, with programs designed in collaboration with companies including Salesforce, Facebook and Tableau. The startup's aim is to deliver courses in career-critical skill sets to ensure applicants have all the necessary skills relevant to their career path.
Pathstream believes that degrees in the US still focus too much on qualifications in antiquated skill sets. It does not want to replace educational institutes, but partner with them to teach platform-centric and industry-critical skill sets. Strong funding and a good initial reach will support this aim moving forward.
Freddie
Company Specialist at Welcome to the Jungle
Insights
Led by a woman
Top investors
-9% employee growth in 12 months
Company
Funding (last 2 of 3 rounds)
Jun 2023
$38.8m
LATE VC
Aug 2019
$12m
SERIES A
Total funding: $51.8m
Company benefits
- Disability, life insurance
- Flexible spending accounts
- Flexible vacation
- Commuter benefits
- 401(k)
- Team Activities
- Work from home opportunities
- Health insurance
Company HQ
Union Square, San Francisco, CA
Leadership
Eleanor Cooper
(Co-Founder & CEO)Worked at Morgan Stanley as an Investment Banking Analyst. Was a Private Equity Investment Associate at Energy Capital Partner, and New Venture Lead at Entangled Ventures.
Lauren Pizer
(Co-Founder & SVP of Learning Experience)Was a Special Projects Associate at Explore Schools, Teaching Team Member at Hasso Plattner Institute of Design, and Director of Student Experience at MissionU. Was also Case Team Leader at Entangled Ventures.
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