Head of Engineering

Cumulus Digital Systems, Inc.

Boston (MA)

Hybrid

USD 200,000 - 230,000

Full time

14 days+

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Benefits offered by this job

Equity incentives

Unlimited PTO

Commuter benefits

Health and dental insurance

Flexible Spending Account

Retirement plan with company match

Job summary

Cumulus Digital Systems, Inc. in the Boston area seeks a Head of Engineering to grow and run high-performing engineering squads that ship the product roadmap with craft and sustainable pace.

You will partner with Product, Platform, and Architecture to translate strategy into deliverable sprint work, while maintaining a culture of psychological safety and continuous improvement.

Qualifications

12+ years of software development experience, with at least 5 years leading engineering teams.
Experience scaling teams in startup or high-growth environments is strongly preferred.
Hands-on leader who can mentor while building sustainable processes.

Responsibilities

Grow and run high-performing engineering squads that ship the product roadmap.
Set operating rhythm, hiring plans, and leadership bench for growth.
Collaborate with Scrum Masters, Product, and Platform to translate roadmaps into deliverable work.
Maintain engineering standards and judge technical trade-offs without owning architecture decisions.
Partner with Product Owners to align scope, sequencing, and trade-offs for high-value work.
Scale teams and manage contractor surges as business needs evolve.

Skills

Leadership

Mentoring

Hiring

Performance management

People development

Strategic leadership

Education

Bachelor's or Master's degree in CS/Software Engineering

Tools

React

React Native

AWS

CI/CD

DevOps

Job description

About Cumulus

Cumulus is a Quality Management System (QMS) that ensures critical construction and maintenance activities are done right the first time, every time. By integrating AI-powered workflows and connected IoT devices, the Cumulus QMS improves the productivity and quality of critical work, such as bolt tightening, welding, and pressure testing.

To date, Cumulus has been used to manage over 15,000,000 work completions across industries such as energy, construction, manufacturing, semiconductors, data centers, transportation, chemicals, renewables, and more. In addition to improving safety and sustainability, our technology also has been proven to reduce costs for quality control and data review by over 60%.

Cumulus’s transformative technology has been widely recognized in the industry, including the following awards and honors:

2023 BuiltWorlds Americas Summit Demo Day Winner for Cumulus AI
2022 BuiltWorlds Maverick Awards winner for Cumulus CEO Matthew Kleiman
2021 BuiltWorlds Smart Jobsites 50 Leader List
2020 IoT Breakthrough “IoT Startup of the Year” award
2019 CNBC Upstart 100 list

Role Overview

The Head of Engineering reports directly to the CTO and operates alongside peer leaders, including the Architect and the Head of Platform, each of whom also reports to the CTO. Each peer role carries a clearly defined scope and sphere of authority. This structure is designed to give the CTO leverage across the organization by ensuring that technical strategy, engineering execution, and platform reliability are each owned by a dedicated leader with full accountability in their domain.

The Head of Engineering owns execution. Where the Architect defines what Cumulus is building toward technically, and the Head of Platform owns how it is delivered and operated, the Head of Engineering owns how the teams build: the people, the process, and the pace. You are responsible for growing and running high-performing engineering squads that ship the product roadmap predictably, sustainably, and with craft.

This is a builder's role. You will grow the team, set the operating rhythm, and make sure great work ships without burning people out. You will work closely with Scrum Masters to eliminate execution blockers, partner with Product to translate the roadmap into deliverable sprint work, and build the leadership bench that allows the engineering organization to scale. You do not own architecture decisions, but you bring technical judgment to execution decisions and hold the team to high engineering standards.

Responsibilities

Team Building and People Leadership

Run full hiring, onboarding, mentoring, and performance cycles across the engineering organization.
Build a leadership bench of squad leads and senior engineers who can run their own teams.
Create and protect a culture that ships great work without burning out: psychological safety, clear expectations, sustainable pace, and room to grow.
Set high standards for delivery and professional growth, and hold the team to them with fairness and consistency.
Own career development conversations and performance management for all direct reports.

Delivery Execution and Operating Rhythm

Own the delivery cadence across squads: sprint planning, demand-versus-capacity planning, predictable execution, and transparent status to the CTO and leadership.
Work with Scrum Masters to identify and eliminate execution blockers: process, dependencies, resourcing, and coordination friction that slow the team down.
Balance roadmap commitments against reactive work (customer tickets, live incidents, technical debt) so planned initiatives are not repeatedly crowded out.
Run an agile environment with tight feedback loops, iterative delivery, and continuous improvement.
Own delivery metrics: completion rate, throughput, carry-over rate, and the sprint health signals that indicate systemic risk.

Hands-on Engineering Judgment

Stay close to the work: participate in code reviews, help unblock hard problems, and bring practical technical judgment to delivery decisions.
Bring depth in mobile and web delivery (React Native and React) and the judgment to know when to dive in versus delegate.
You do not own architecture decisions, but you engage meaningfully in design reviews and ensure your teams do the same.

Partnership with Product

Work closely with Product Owners and the Product function to align on scope, sequencing, and trade-offs so the team delivers the highest-value work first.
Translate the product roadmap into executable sprint plans, making capacity and sequencing trade-offs visible and explicit.
Communicate proactively when delivery risk surfaces, and come to those conversations with options, not just problems.

Partnership with Platform and Architect

Partner as a co-equal peer with the Head of Platform: engage squads early in architecture design reviews, honor Definition-of-Done gates for observability and test automation, and guarantee squad capacity for platform work.
Partner with the Architect to ensure teams understand and apply technical standards; elevate systemic standards gaps rather than patching them sprint by sprint.
Keep Software Quality Engineers embedded and effective in the squads day-to-day.

Scaling the Organization

Grow the engineering organization to meet the company's scaling needs, phasing hires thoughtfully as the business evolves and new delivery demands emerge.
Spin a contractor surge team up and down with demand, keeping commitments flexible and cost-aware.
Work with the Architect and Head of Platform to ensure new teams are onboarded into a coherent technical and operational context.

You are an experienced engineering leader who has spent many years building software and leading the teams that ship it. You lead from the front — you have run full hiring, mentoring, and performance cycles, you still care about the craft, and you build teams that do great work without burning out. Specifically, you should:

Have led iOS, mobile, platform, and/or web engineering teams through real growth, ideally in a startup or high-growth environment.
Be a mentor and coach who sets high standards for quality, delivery, and professional development while keeping the team healthy and motivated.
Be hands-on enough to earn the team's technical respect, and strategic enough to build an organization that runs without you in the room.
Thrive in a fast-paced, resource-conscious environment and pivot quickly as priorities evolve.

Qualifications

Education

Bachelor's or Master's degree in Computer Science, Software Engineering, or a related field.

Experience

Minimum of 12 years of software development experience, with at least 5 years leading engineering teams, including direct responsibility for hiring, mentoring, and performance management. Experience scaling teams and standing up new squads in a startup or high-growth setting is strongly preferred.

Technical Expertise

Strong background in web and mobile development, especially using React and React Native.
Working knowledge of cloud services (particularly AWS), distributed systems, and modern DevOps and CI/CD practices.
A solid grasp of platform, reliability, and quality-engineering concerns, and how to partner with an architecture leader to serve them.

Leadership

A proven track record of building high-performing, sustainable engineering teams and delivering complex product roadmaps.

Location

This role is based in the Greater Boston area (Newton / Waltham / I-95 corridor). On-site presence is expected on a hybrid schedule; this position is not remote.

Benefits