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 int