Head of Engineering

May 27, 2026

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Obsidian Systems is a fast-growing, founder-led software company with a global remote team. We have grown from 20 to 60 people in the past year, and we are not slowing down. The Head of Engineering is a newly created role designed to scale engineering from 60 to 100+ across our consulting business. You will take ownership of people leadership, engineer development, and team accountability as we enter our next stage of growth.This is a leadership-first role. What we need is someone who builds great teams, creates clarity, holds people well, and can scale a culture.What We Are Looking For<ul style="min-height:1.5em"><li>Proven experience leading and scaling engineering teams in a high-growth environment, you have managed senior individual contributors and technical leaders at scale</li><li>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</li><li>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.</li><li>Strong instincts around coaching, performance, developing leaders who are new to management, and knowing when to push and when to listen</li><li>Experience in a consulting or services-plus-product environment, or comfort operating across more than one business model</li><li>Demonstrated ability to partner with deep technical experts. You know how to work alongside strong technical leaders without overstepping or underdelivering</li><li>Comfortable operating in a remote-first, global, low-ego environment where directness and trust are the currency</li><li>Comfortable with ambiguity and building structure as you go</li></ul>Key ResponsibilitiesPeople Leadership and Team Management<ul style="min-height:1.5em"><li>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</li><li>Lead, coach, and develop our engineering team, including our Tech Leads who are strong technically and growing in their influence</li><li>Own performance management, feedback cycles, and career development for all engineers</li></ul><ul style="min-height:1.5em"><li>Own hiring and onboarding for all engineering roles, building the team, and raising the bar as we scale</li><li>Build and manage a rotation assignment program, ensuring engineers grow across projects, teams, and lines of business</li></ul>Engineering Operations and Culture<ul style="min-height:1.5em"><li>Champion our engineering methodology and cultural values, and help the next generation of engineers internalize them</li><li>Own AI usage policy and guardrails for the engineering team</li><li>Own internal security practices and compliance accountability</li><li>Serve as the primary point of cross-departmental engagement and escalation for engineering</li></ul>Engineering Delivery Accountability<ul style="min-height:1.5em"><li>Oversee incident management and change management processes</li><li>Own technical risk mitigation at the team and delivery level</li><li>Support sales engineering efforts and research and development as needed</li><li>Guide business analysis capability within the engineering team</li></ul>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.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

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With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

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Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

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The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

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10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...

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