Founding Head of Engineering - Abstract

Stackpoint Ventures; United States; Remote; USD 180,000 - 320,000; Full time

Benefits offered by this job

Comprehensive health benefits

Job summary

Abstract is seeking an engineering leader to guide the AI operating layer for real estate title and settlement. You will lead three engineers with a hands-on, player-coach approach, shaping architecture, data models, and the technical culture from day one.

You'll own the platform's evolution, ensuring reliable, scalable AI that handles real transactions, integrates with legacy systems, and supports both internal operators and client workflows.

Qualifications

• 10+ years of software engineering experience in product-focused roles.
• Proven leadership delivering shipped products in fast-paced environments.
• Experience building AI-powered workflows with evals, prompts, and cost tradeoffs.

Responsibilities

• Lead architecture, data models, and platform direction with the team.
• Ship AI features for real-world transactions with human-in-the-loop safeguards.
• Build internal tools and client-facing experiences for high-volume operations.
• Translate discovery into scoped engineering work with product/ops.
• Hire, mentor, and grow a hands-on engineering team.

Skills

Engineering leadership

Full-stack development

AI/ML systems

Product thinking

Systems architecture

Tools

Python

TypeScript/React

AWS/GCP

Data modeling

Job description

Lead the team building the AI operating layer for real estate title and settlement. Remote, U.S.

About Abstract

Title and settlement is a $17B-a-year industry, and $3.5–5.0B of it is back-office spend that runs on fixed, manual labor. Across roughly 20,000 independent title and settlement service providers processing 5.5M+ real estate transactions a year, back-office teams do overwhelmingly rules-based work: extracting data from contracts, classifying documents, ordering vendor services, tracking exceptions, and recording files post-closing. This workforce is retiring, and we are building the national platform that converts its fixed-cost labor into a variable, AI-powered cost structure: faster closings, fewer errors, lower cost per file.

The prize is bigger than the spend we replace. The company that absorbs this work doesn't sell software to the title industry, it becomes the operating layer the industry runs on, with the margin structure of software and the revenue of the services it replaced. We are building this operating layer from inside the industry. Our CEO runs one of the largest independent title operations companies in the country and has opened its workflows, team, data, and hundreds of customers to us, accelerating and derisking our build from day one.

Why Abstract

• Demand is already flowing. Our CEO is an industry pioneer who operates a major title agency network with existing assets, relationships, customers and revenues. Your work is to rebuild an AI-native system and absorb existing volume and scale, not to find the first customers.
• Studio backing. Stackpoint, the venture studio behind a portfolio of vertical AI real estate companies, is our first investor and operating partner: founded by repeat entrepreneurs who have built unicorn tech companies, Stackpoint provides capital, engineering support, and a deep network of real estate operators and executives.
• Multiple growth levers. New states, adjacent services on the same rails, and partnership models that let established operators run their volume through our platform. Each lever compounds the others.
• True influence from day one. Youʼll shape strategy, product, culture, and execution from the beginning.

The Role

You'll be Abstract's technical leader. You'll lead three engineers at mixed levels, from early-career to principal, and shape how the team grows from there.

This is a hands-on, player-coach seat that spans architecture, code, evals, and how the team operates. You'll take the first version of the platform, built with Stackpoint's studio team, and extend it to new lines of business and new agencies. Together with the founding engineers, you'll set the technical foundation every future engineer builds on.

You'll report to our Head of Product & Operations and work closely with our CEO.

What You'll Drive

1. Own the architecture and the technical bar

• Lead system architecture, data models, and platform direction with the engineering team, and make the call when the team doesn't converge.
• Decide what to build, buy, or integrate, and when a prototype has earned the investment to scale.
• Keep the platform reliable and cost-efficient as volume grows and we expand to new agencies and states.
• Set the engineering standards the team works to: code review, testing, and deployment.

2. Ship agentic AI that holds up on real transactions

• Lead how the team builds extraction, classification, and retrieval over messy title and settlement documents, including integrations with the legacy software, portals, and email- and file-based workflows the industry still runs on.
• Own the evaluation system and guardrails: measure accuracy and confidence before anything ships, and decide what work goes to human review.

3. Build the human-in-the-loop product

• Lead the build of the internal operations console where title staff review, correct, and approve AI output all day, with their corrections feeding back into evaluation.
• Shape the client-facing experience agencies use to submit work, track status, and act on results.
• Make PII and sensitive transaction data a design constraint across both, with access control, audit trails, and tenant isolation.

4. Turn discovery into what gets built

• Partner with the Head of Product & Operations to translate operator and customer discovery into scoped, sequenced engineering work.
• Join operator and customer discovery so engineering decisions start from how the work gets done today.

5. Build and lead the engineering team

• Hire and grow the engineering team, and shape how it's organized and how it works as Abstract scales.
• Mentor early-career engineers and give senior engineers real ownership.
• Lead how the team uses AI to plan, build, review, and ship, and keep refining it as the tools change.

What Success Looks Like

• Onboarding the next agency or workflow is configuration, not a project.
• Automation and cost per file improve release over release, and the team can prove it in production data.
• Operators trust the review console, and correction time keeps falling.
• The team ships on a steady cadence without you as the bottleneck.

What You Bring

An engineering leader who still builds. You've led and grown engineers at different levels while staying hands-on in architecture and code, including meaningful production code in the last two years. AI coding agents and tools are core to how you work.

Production agentic AI. You've shipped LLM-powered workflows that real users depended on, and you know how to make them reliable: evals, structured outputs, retrieval, prompt design, and model and cost tradeoffs.

Full-stack and data range. You work across a Python or Node backend, a TypeScript/React frontend, relational and vector databases, and AWS or GCP. You've built pipelines that turn unstructured documents into structured data, integrated with legacy systems that lack clean APIs, and handled PII in a regulated setting.

Product sense for operational users. You've built internal or operator-facing tools for high-volume work, and improved them based on real usage.

A clear communicator across technical and non-technical teams. You've worked alongside product or operations leaders to turn discovery into plans engineers could execute, and explained technical risk and tradeoffs to non-technical leadership in plain terms.

Startup DNA. You've worked in ambiguous, resource-constrained environments, shipped quickly without lowering the quality bar, and moved between strategy and execution as the week required.

Experience

• 10+ years of software engineering experience, particularly in product-focused, full-stack roles.
• Demonstrated success as an engineering leader in a fast-paced startup or high-growth environment.
• At least one product taken from a blank page to production and scaled past its first customers.

This role is designed for a builder. If your recent experience is mostly managing managers, leading large-org transformation, or advising rather than shipping, it's unlikely to be the fit.

What Makes This Role Unique

• Ground truth from day one. Live orders, real volume, and operator corrections that become your evaluation set. Most AI startups spend their first year trying to get data like this.
• Founder-level scope. Real ownership and influence over the product, the platform, and the team you build.

An Ecosystem of Exceptional Builders

Joining Abstract also means joining Stackpoint's tight-knit ecosystem of founders, product leaders, and operators building alongside you. Engineering leaders across the portfolio are peers, not silos:

• Regular cross-portfolio sessions with founders and product and engineering leaders
• Shared learning on AI, GTM, hiring, and scaling challenges
• Direct access to other builders solving similar 0→1 problems in parallel, and pattern recognition across multiple early-stage companies

We value judgment, speed, and substance over process theater.

Compensation

• Competitive salary calibrated for founding team members
• Significant equity with asymmetric upside if we execute
• Comprehensive health benefits