Head of Engineering

Obsidian Systems is the premier software development consulting solution for institutional clients building next-generation technology. We are currently scaling from sixty to over one hundred people and need a Head of Engineering to lead this expansion.

Our growth comes from the trust our clients place in us to deliver best-in-class software through a novel approach that builds it right the first time. We specialize in high-security and high-functionality systems that demand rigorous engineering for consequential projects. As the de facto Canton development shop, we handle ledger systems and complex quantitative problems that are difficult for other firms to conceptualize. This leadership role focuses on managing our technical talent and maintaining our culture of quality and accountability.

This is a leadership-first role for someone who builds great teams, creates clarity, holds people well, and can scale a culture.

What We Are Looking For

• Proven experience leading and scaling engineering teams in a high-growth environment; you have managed senior individual contributors and technical leaders at scale

• A genuine appreciation for functional programming principles. You do not need to write Haskell, but you need to understand why the philosophy matters and be prepared to advocate for it

• A track record of building engineering culture. You know how to help a team internalize values and ways of working, resulting in a best-in-class engineering culture.

• Strong instincts around coaching, performance, developing leaders who are new to management, and knowing when to push and when to listen

• Experience in a consulting or services-plus-product environment, or comfort operating across more than one business model

• Demonstrated ability to partner with deep technical experts. You know how to work alongside strong technical leaders without overstepping or underdelivering

• Comfortable operating in a remote-first, global, low-ego environment where directness and trust are the currency

• Comfortable with ambiguity and building structure as you go

Key Responsibilities

People Leadership and Team Management

• Own engineer accountability on delivery, partnering closely with the Head of Consulting Operations, so engineers have a clear, consistent manager, and the Project Management team can focus on what they do best

• Lead, coach, and develop our engineering team, including our Tech Leads who are strong technically and growing in their influence

• Own performance management, feedback cycles, and career development for all engineers

• Own hiring and onboarding for all engineering roles, building the team, and raising the bar as we scale

• Build and manage a rotation assignment program, ensuring engineers grow across projects, teams, and lines of business

Engineering Operations and Culture

• Champion our engineering methodology and cultural values, and help the next generation of engineers internalize them

• Own AI usage policy and guardrails for the engineering team

• Own internal security practices and compliance accountability

• Serve as the primary point of cross-departmental engagement and escalation for engineering

Engineering Delivery Accountability

• Oversee incident management and change management processes

• Own technical risk mitigation at the team and delivery level

• Support sales engineering efforts and research and development as needed

• Guide business analysis capability within the engineering team

Who Should Apply?

Our engineering culture is rooted in functional programming principles. We do not mandate FP, but the philosophy of composability, clarity of reasoning, and building systems that are easy to understand shapes how we think and how we build. If that excites you, you will fit right in.