Director of AI and Automation

Orion Group is a holding company dedicated to building the highest-quality, highest-throughput investing business in the world — and we believe AI is a core part of how we get there.

This role’s mission is to optimize how we invest, hire, and scale. Orion backs exceptional service businesses and gives them the tools, talent, and capital to thrive. We’re operators at heart, focused on what works in the real world — and now we’re ready to put AI at the center of how we execute that mission.

We’re not chasing vanity metrics, academic papers, or one-off prototypes. We’re building applied systems that drive measurable ROI across investing, talent acquisition, and finance. If you're a hands-on builder who thrives at the intersection of AI and business, we want to talk to you.

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As the Director of AI and Automation, you’ll act as Orion’s internal founder for AI — identifying high-impact use cases, building and deploying solutions, and transforming how our teams work.

This is not a strategy or advisory role — it’s an execution-heavy leadership position where you’ll:

· Build AI tools that double the throughput of our deal and recruiting teams

· Design systems that improve conversion and retention rates across functions

· Develop a repeatable playbook for AI ideation and deployment

· Launch products that are adopted, trusted, and relied on by our team

· Prototype quickly, iterate based on feedback, and deliver measurable business impact

You'll collaborate closely with stakeholders across Orion — from recruiters to investors — and serve as a force multiplier for their work.

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· 2x more deals closed per deal execution professional

· 50% increase in hires per recruiter

· 50% increase in qualified deals sourced

· 10%+ improvement in deal conversion metrics

· 50% reduction in two-year turnover of key hires

· AI ROI dashboard built and used across the business

· AI systems fully integrated into day-to-day workflows

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We’re looking for a high-agency, high-output builder who gets energy from solving hard problems and delivering results. You likely have:

· 7+ years of experience

· Background in AI engineering, product, or as an early-stage founder

· Experience building production-ready AI or automation tools

· Fluency with modern AI tools (LLMs, APIs, low-code platforms)

· Strong product instincts and the ability to turn vague problems into elegant systems

· A bias toward lightweight MVPs and rapid iteration

· Business judgment to prioritize what’s valuable over what’s novel

You thrive in ambiguity, move fast, and know how to get things done without a roadmap or large team.

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· Growth: Growth creates opportunity for our people

· Partnership: Growth creates opportunity for our people

· Empowerment: Our people move fast and act as owners.

· All-In: We find fulfillment in the hard work excellence demands.

· Win the Right Way: We never shortcut integrity.

· Pursuit of Quality: We take pride in doing things well and pursuing excellence.

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· You need a large team or mature infrastructure to get started

· You prefer theoretical exploration over practical results

· You aren’t comfortable getting your hands dirty with code or workflows

· You need a clearly defined scope to make progress

· You struggle to influence non-technical stakeholders

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We’re looking for builders who want to make a real-world impact — not just design strategy. If that sounds like you, let’s talk.