Chief Technology Officer

Overview Dealership Accelerator is hiring a CTO / Founding Technical Leader

The CEO built the entire product with no prior technical experience. Scaled it to 8-figure revenue in 2 years. Bootstrapped, profitable, zero outside funding. Needless to say, we need the technical leader who turns it into a $100M platform.

Who are we?

Dealership Accelerator is a vertical AI company in the automotive industry. We built an autonomous sales engagement operating system that controls the entire lead lifecycle inside car dealerships, from first contact to closed deal, 24/7, across hundreds of clients.

Here\'s what makes this interesting from a technical perspective.

Because our system is the one doing the selling, not the reps, we own the data. Not just CRM data that\'s been polluted by inconsistent human behaviour. Clean, structured conversation data across hundreds of dealerships where we controlled the messaging, we controlled the follow-up cadence, we controlled the escalation logic, and we can see exactly which patterns led to a sale and which didn\'t. No other company in automotive has this. Most competitors are bolted onto CRMs where every rep does something different, so their data is noise. Ours is signal.

That data is the foundation for something much bigger. We\'re building toward proprietary AI models trained on real, outcome-labelled sales conversations at scale. Models that learn what works at a Ford dealership in Texas and apply it at a Toyota dealership in Florida. Every new client makes the system smarter for every other client. That\'s a genuine network effect, and it compounds the same way our product does.

The system already works. Leads enter, the AI engages them, reps get pulled in only when a human decision is needed, then the system takes back over. Nothing falls through the cracks. The pipeline doesn\'t reset monthly; it compounds. By month 6, a dealership isn\'t just working this month\'s leads; they\'re actively nurturing every lead from the previous 5 months without adding headcount.

The business model works too. 8-figure revenue, bootstrapped, profitable, no outside money. What doesn\'t exist yet is the proprietary platform this company deserves. That\'s the job.

What you\'ll be doing Designing and building a proprietary platform from the ground up. Greenfield architecture at a company that already has product-market fit and hundreds of paying clients. You\'ll lead the full platform migration, build the engineering team from small to 15+, architect the data layer for proprietary AI model training, and own the entire technical vision. This is not a maintenance role. This is building something from scratch at a company that\'s already winning.

This is also not a "sit in meetings and delegate" CTO role. Early on, you\'re writing code, reviewing pull requests, making architecture decisions in real time, and building alongside the team. You\'ll have your hands in the work every day until the team scales enough for you to shift into full-time leadership. If you want to manage from a distance, this isn\'t for you.

What is the pay $300,000 to $350,000 base + 3% equity (1-year cliff, 4-year vest). This is a profitable company with no outside investors. The equity is priced at today\'s valuation. If we execute, the upside is significant.

What we\'re looking for Must-haves:

Built and shipped multi-tenant SaaS platforms at scale (hundreds to thousands of clients, not hobby projects)

Led a platform rebuild or major migration while keeping a live production system running. You\'ve done the strangler pattern, parallel builds, and zero-downtime cutovers before

Built and scaled engineering teams from a small founding group (3-5) to meaningful size (10-20+), including hiring, establishing culture, and managing performance

Established engineering practices at a company that didn\'t have them. CI/CD pipelines, automated testing, code review processes, infrastructure-as-code, monitoring and alerting

Managed production systems handling high-volume real-time workloads. Messaging at scale, event-driven architectures, or AI inference in production

Architected data layers and pipelines. You understand how to structure data collection today for model training and analytics tomorrow

Fluent in modern backend and infrastructure. TypeScript/Node.js, PostgreSQL, Redis, message queues, cloud infrastructure (AWS preferred)

Willing and able to be hands-on. You\'ll be writing code and shipping features alongside the team in the early months, not just drawing diagrams

Strong advantages:

Experience with event-driven architectures and state machine design patterns

AI/ML depth. Fine-tuning LLMs, building evaluation frameworks, designing training data pipelines, or deploying models to production

Been through Series A, growth-stage fundraising, or acquisition due diligence on the technical side. You know what evaluators look for and how to present a technical story

Vertical SaaS experience, especially in industries with legacy CRM ecosystems and relationship-driven sales cycles (automotive, real estate, insurance, etc.)

Experience building real-time dashboards, analytics products, or internal tooling that drives behavioral change in end users

The intangibles that actually decide this hire :

You see a product first and technology second. You understand the business problem before you think about the architecture.

You respect what\'s been built. A non-technical founder who scaled a product to 8-figure revenue didn\'t get lucky. They understood the customer better than anyone. You want to partner with that person, not replace their judgment.

You communicate in outcomes, not jargon. You can explain technical progress to a CEO who doesn\'t code without dumbing it down or drowning them in implementation details.

You're a builder, not a maintainer. You\'ve been at companies where the interesting problems were already solved, and you\'re done with that. You want a blank canvas.

You thrive in ambiguity. This isn\'t a Series C company with playbooks and processes. You\'re writing the playbooks.

You're hungry. Not for a CTO title. For the chance to build something from the foundation up at a company that\'s already proven the hardest part.

What are the logistics Remote, North America. Profitable, high-growth company. No VC pressure, no runway clock, no board telling you what to build. Revenue funds the build directly.

What are the next steps If this resonates, do the following -

Connect with the CEO

(linkedin.com/in/keenangennrich)

DM the CEO , letting him know you\'re interested.

He will share a detailed breakdown of the product, current technical landscape, and what we\'re building toward.

Serious candidates will have the opportunity to do a paid deep-dive project to show us how they think.

If this isn\'t for you, but you know someone it\'s perfect for,

tag them.

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