Head of Engineering - Stackpoint Ventures

About Stackpoint

Stackpoint is a venture studio that conceives, builds, launches, and scales AI-native companies in high-barrier verticals like real estate, construction, hospitality and financial services. Led by co-founders who have both built unicorn real estate tech companies from scratch, we're a tight team of engineers, product managers, designers, and operators with decades of experience building products, teams, and businesses from startup to scale.

We focus all of our energy on discovering and solving customer and business problems, designing financially strong and defensible business models, activating growth engines, hiring world-class founding teams, and helping them thrive (and none of our energy on big-company b.s.). Our dedicated capital, experienced team, proven process, and deep strategic network supercharge founders and accelerate growth. We're based in Boston but have a distributed team, work remotely and come together every quarter for in-person team building.

We're now evolving our engineering function from pod-embedded roles to a pooled, Studio-wide model — and we're looking for the person to lead it.

The Role

Context - How the Studio operates: We launch one new company per quarter. For each, we embed a pod — a dedicated PM, Designer, and (in the model we're moving toward) one or more Studio Engineers — for ~6 months alongside a founding CEO we recruit and back. The first three months focus on discovery: identifying the wedge product, assessing technical feasibility, and accumulating design partners. The second three months shift to building the wedge while hiring the company's founding technical team (Head of Engineering, sometimes 1-2 IC engineers or contractors) in parallel. Because launches are staggered quarterly, at any given time the Studio is hands-on in ~2 companies at different stages. Shared resources across Marketing, Sales, Finance, Ops, and Recruiting flex across companies during the first 6-12 months based on what's needed to hit key milestones.

As Head of Engineering, you will own the technical direction of Stackpoint's Studio engineering function. This is not a role embedded inside a single portfolio company. You will operate across all active builds — making the highest-leverage architectural decisions, driving R&D, and building the systems and team that compound across everything we do.

You'll build a small, high-caliber engineering team (3 IC engineers) with support from our in-house Head of Talent, and flex that team across companies and internal Studio product based on where demand is highest. You'll also oversee the hiring and technical evaluation of portfolio company Heads of Engineering and key contractors as companies graduate from Studio-led prototyping to company-owned execution.

What You'll Do

Technical Leadership Across the Portfolio Lead major architectural and feasibility decisions at the moments that matter most — wedge definition, MVP architecture, infrastructure choices, and build-vs-buy calls. You'll context-switch across multiple companies and domains, and your judgment will directly shape what gets built and how.

R&D and Technical Frontier Keep Stackpoint on the cutting edge of AI-native development. Evaluate emerging tools, frameworks, and models. Run experiments. Make pragmatic adoption decisions that give our portfolio companies a technical edge from day one.

Studio Tooling and Reusable Systems Build internal tools and frameworks that create compounding leverage across company builds — from shared infrastructure patterns to AI-powered internal capabilities that make the Studio operate faster and smarter.

Team Leadership and Engineering Culture Build, lead, and develop the pooled engineering team. Set the bar for technical excellence, pragmatism, and speed. Create a working environment where strong engineers want to stay and grow.

Hiring and Technical Evaluation Own the technical hiring process for portfolio company engineering leaders (Heads of Engineering, senior ICs). Evaluate candidates, design technical assessments, and ensure smooth transitions from Studio-led builds to company-owned teams.

Cross-Functional Collaboration Partner closely with PMs, designers, and founding CEOs across pods. Translate technical constraints into business language. Contribute to feasibility assessments and help teams understand what's buildable, what's risky, and what's worth a bet.

What We're Looking For

Experience and Background

• 10+ years of software engineering experience, with significant time in leadership roles (Staff+, Engineering Manager, VP Eng, CTO, or equivalent)
• Multiple 0-to-1 builds — not just features at established companies, but products built from nothing to launch in startup or early-stage environments
• Experience leading and scaling small, high-performing engineering teams (3-10 people)
• Track record of making high-quality architectural decisions across diverse domains and tech stacks
• Hands-on experience with AI/ML integration in production systems — prompt engineering, structured outputs, RAG patterns, model evaluation, cost/performance tradeoffs

Technical Breadth

• Full-stack proficiency: strong across frontend (React, Vue, etc.) and backend (Python, Node.js, Go, etc.)
• Cloud infrastructure: hands-on with AWS, GCP, or Azure — can stand up environments, make platform decisions, and operate without a dedicated DevOps team
• Database design: SQL and NoSQL, with sound judgment on data modeling and platform selection
• DevOps and CI/CD: Docker, GitHub Actions or equivalent, infrastructure-as-code (CDK, Terraform)
• AI tooling fluency: actively uses AI-powered dev tools (Cursor, Claude Code, Copilot) and stays current on the rapidly evolving landscape

Working Style

• Context-switching is a feature, not a bug. You find variety energizing and ramp fast into new domains and codebases
• Speed and pragmatism define your output. You know the difference between "build to learn" and "build to scale" and make that call explicitly
• You're a strong cross-functional collaborator who translates technical complexity into clear language for non-engineers
• You lead by example — writing code, reviewing PRs, and staying close to the work while also thinking strategically about systems and people
• You're low-ego, generous with knowledge, and someone other engineers want to work with

Why This Role Is Different

• Breadth over depth: You'll touch more industries, domains, and technical challenges in a year than most engineering leaders see in five. Real estate, insurance, construction, finance — each portfolio company is a new problem space.
• Leverage over headcount: You're not managing a 50-person org. You're leading a small, elite team where every person and every decision compounds across the entire portfolio.
• Building the machine that builds the companies: Your tooling, systems, and R&D work don't just serve one product — they accelerate every future company Stackpoint creates.
• Direct impact: You'll work directly with founders, the full Stackpoint Studio team, and portfolio company customers. No layers. No politics. Just building.

Logistics

• Compensation: Competitive base, comprehensive health benefits + equity participation in every company we launch during your time here.
• Location: Flexible within U.S. - we operate remotely
• Reports to: Matt Zisow (our Partner & Head of Platform)