Obsidian Systems Logo

Obsidian Systems

Head of Engineering

Posted 4 Days Ago
Be an Early Applicant
In-Office or Remote
Hiring Remotely in Puerto Rico
Expert/Leader
In-Office or Remote
Hiring Remotely in Puerto Rico
Expert/Leader
Develop and lead a scaling engineering team, focusing on performance management, cultural development, and operational accountability to enhance engineering delivery in a fast-growing software company.
The summary above was generated by AI

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

  • 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.

Similar Jobs

12 Hours Ago
Remote
Mid level
Mid level
Information Technology • Software
The Electric Technician conducts corrective and preventive electrical activities, inspects utility equipment, assists with maintenance tasks, and provides technical support within commercial properties.
Top Skills: Building Automation SystemsElectrical SystemsHvacPredictive Maintenance
12 Hours Ago
Remote or Hybrid
65K-65K Annually
Mid level
65K-65K Annually
Mid level
Other
Responsible for outside sales of NRS products, managing a distributor network, and increasing market reach through customer engagement and training.
Top Skills: Crm SoftwareSalesforce
12 Hours Ago
Remote
Senior level
Senior level
Food
The Senior Account Executive will drive sales in logistics services, develop customer relationships, and support team development in the Puerto Rico market.
Top Skills: CRMMS Office

What you need to know about the Boston Tech Scene

Boston is a powerhouse for technology innovation thanks to world-class research universities like MIT and Harvard and a robust pipeline of venture capital investment. Host to the first telephone call and one of the first general-purpose computers ever put into use, Boston is now a hub for biotechnology, robotics and artificial intelligence — though it’s also home to several B2B software giants. So it’s no surprise that the city consistently ranks among the greatest startup ecosystems in the world.

Key Facts About Boston Tech

  • Number of Tech Workers: 269,000; 9.4% of overall workforce (2024 CompTIA survey)
  • Major Tech Employers: Thermo Fisher Scientific, Toast, Klaviyo, HubSpot, DraftKings
  • Key Industries: Artificial intelligence, biotechnology, robotics, software, aerospace
  • Funding Landscape: $15.7 billion in venture capital funding in 2024 (Pitchbook)
  • Notable Investors: Summit Partners, Volition Capital, Bain Capital Ventures, MassVentures, Highland Capital Partners
  • Research Centers and Universities: MIT, Harvard University, Boston College, Tufts University, Boston University, Northeastern University, Smithsonian Astrophysical Observatory, National Bureau of Economic Research, Broad Institute, Lowell Center for Space Science & Technology, National Emerging Infectious Diseases Laboratories

Sign up now Access later

Create Free Account

Please log in or sign up to report this job.

Create Free Account