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VP of Engineering



Software Engineering
San Francisco, CA, USA · Remote · United States
Posted on Friday, January 19, 2024

VP of Engineering

Pathstream | Engineering | Remote


This is a full-time exempt position based out of our HQ in San Francisco, CA -OR- remote and based out of your home location and reports to the CEO.

Are you a dynamic and visionary engineering leader ready to make a profound impact on the lives of individuals seeking career mobility? Pathstream is actively seeking a passionate VP of Engineering to play a pivotal role in transforming how people navigate and elevate their careers. As the driving force behind our technical strategy, you'll have the opportunity to lead a high-performance engineering team dedicated to creating pathways for professional growth and success.

You are customer-focused. You have a track record of deeply understanding your customers, partners, and stakeholders. You have a passion for building products, services, and platforms that enable your customers and stakeholders to succeed. You’re empathetic to the expectations of our customers and students, as well as the needs of our developers.

You understand how the platform enables product development. You’ve driven the complex and challenging tradeoffs between speed, cost, and functionality when building a platform while supporting product development in one or more fast-moving companies. You have deep experience in managing complex projects with a variety of Agile tools in your toolbelt.

You can create, evangelize and execute your vision of product engineering. You can arrive at a vision that enables customers and internal developers, and communicate that vision to your team and stakeholders throughout engineering and the broader organization. You can drive the implementation of the vision and get results. You learn from others and continuously adapt the engineering vision to match the needs of the company.

You are a skilled mentor and coach. You have a passion and a track record of mentoring engineers and leaders while at the same time growing your own skills. You realize the best way to grow a team is by helping them to grow themselves. You're able to effectively share your experience and provide a clear framework for growth.

You're a skilled communicator. Pathstream is a mostly remote team and writing is our primary means of communication, but you recognize when other mediums may be more effective. Your communication capabilities will be essential to share vision, strategy, plans, findings, and results to the engineering and full Pathstream team.

You're a champion for doing things efficiently. At Pathstream, the work you do will have a disproportionate impact on the business. We believe in systems and processes that let us scale our impact to be larger than ourselves.


Company leadership & cross-functional partnership:

  • Be a trusted partner to our executive team and leaders across other departments, as the leader driving the overall technology strategy for Pathstream & ensure our technology strategy is represented in company level decisions.
  • Collaborate with Product to develop and execute a roadmap of product features, bug fixes, technology, tech debt, and tooling aligned to build delightful products that achieve business goals.
  • Communicate effectively with your team members, your peers, and your internal and external customers

Engineering team & technical leadership:

  • Lead and manage the technical team (both product and website), fostering a culture of accountability, collaboration, quality, and delivery.
  • Establish a sense of urgency and direction, setting clear expectations with teams and individuals in alignment to business goals.
  • Measure, manage and optimize key metrics such as velocity, estimation accuracy and defect counts
  • Make architecture, infrastructure, and technology partner decisions, maximizing business and customer value. Help solve complex software engineering tasks, while maintaining high engineering standards and practices
  • Ensure the security and compliance of our software and processes (including SOC 2) and engage with customer prospects on security.
  • Lead resource planning & budgeting for engineering team & tooling
  • Recruit world-class engineering talent and participate in the process including attracting, screening, and closing high caliber candidates.


  • Inspirational. The ideal candidate will earn the respect of the technical team and inspire the delivery of world-class software.
  • Business-driven pragmatic leader. You will help us strategically invest our technical resources against competing business priorities, including keeping an eye on our existing systems.
  • Communicator. You possess a talent for communicating highly technical things to non-technical people.
  • Remote-ready. You are comfortable managing a fully remote team.


  • Direct experience scaling an engineering organization from 10 to 100 engineers
  • Has experience managing engineering managers and owning the delivery of a rapidly improving and expanding product.
  • Proven experience in building and optimizing geographically dispersed teams
  • A track record of creating innovative solutions to challenging problems. A willingness to challenge assumptions and negotiate solutions.
  • Has excellent product skills both in instincts for what makes a product great, and using data to develop the right products.
  • Is an excellent communicator: much of the work you do will involves writing documentation that explains and justifies how the engineering organization can function better, and talking to engineers and business/strategy stakeholders to get buy-in for your ideas.
  • Experience with some or all of our tech stack - we primarily run Ruby on Rails services with React SPA frontends and AWS


  • 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.
  • Comprehensive benefits package
    • 100% employer-paid medical, dental, and vision insurance coverage for you and 50% for your partner/spouse and dependents
    • Health, commuter, and parking flexible spending accounts
    • Employee Assistance Program (mental health, financial health, legal support, and more)
    • Free access to wellbeing apps like Ginger and 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)


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. As such, 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.


Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.