Head of AI Strategy & Enablement

About Waverock Software

Waverock Software is a long-term SaaS holding company that acquires and partners with high-potential software businesses. Built and run by entrepreneurs and operators, we take a patient, hands-on approach to growth—preserving the legacy and culture of the businesses we partner with while investing in the people, processes, and infrastructure needed to thrive. Our portfolio includes Grasp Technologies, PlanIt Geo, and WorthPoint. As a company, we're committed to building a long-term home where employees, customers, and founders all win.

The Role

This is one of the most important hires we will make. The Head of AI Strategy & Enablement is the person who teaches our Operating Companies (OpCos) to use AI well, builds the AI agents that run the holding company, and ships custom AI solutions where they unlock real productivity gains.

You'll regularly join executive leadership meetings at Waverock and work directly with C-level and VP leaders at our operating companies. You will be the one who knows AI cold and can help us come up with solutions to challenges and needs across Waverock and the portfolio. You will be the one who shows people what's possible.

We care more about AI fluency, creativity, and follow-through than about years of experience. If you've vibe-coded solutions for friends, family, an internship, or a side hustle; if you geek out on the latest models, agent frameworks, and prompt techniques; if your default reaction to any problem is "how do we solve this with AI?" keep reading.

What You'll Do

Your work splits across three areas. The first two are where you'll spend most of your time. The third is for high-leverage quick wins.

1. Coaching & Enablement Across the Operating Companies

Make every employee at every OpCo fluent in AI. Not just "can write a prompt" fluent — fluent enough to build their own skills, set up their own agents, and (for the more technical ones) vibe-code their own tools.

• Build and run AI training programs in Rippling, tailored by role and function. Roll them out across all OpCos.
• Spot the best AI practices already happening inside individual OpCos and turn them into shared playbooks the whole portfolio can use.
• Run 1:1 coaching, AI office hours, internal show-and-tells, and a cross-OpCo community where builders share what they're working on.
• Coach C-level and VP leaders directly. Help them identify where AI should change how their teams operate, and hold them accountable to adoption goals.
• Stay one step ahead. New models, tools, and techniques drop constantly — your job is to evaluate them, separate the real from the hype, and get the useful ones into people's hands fast.

Success here: high AI fluency across the portfolio. Employees aren't just prompt engineers — they're building skills and agents on their own, and a meaningful subset of power users are vibe-coding their own solutions.

2. Building the Agent-Powered Holding Company

Waverock is building shared services for our portfolio in a non-traditional way. Instead of hiring a typical back-office, we're building a team of agents. You will be central to making that real.

• Replicate ops roles with agents. Build agents that manage systems, pull and reconcile data, generate reporting across OpCos, and flag anomalies for human review.
• Automate the recruiter role with agents. Build agents that source candidates, screen resumes, draft outreach, and manage early-stage pipelines.
• Build coach agents. Train agents on the best practices we collect across the portfolio (sales, customer success, finance, ops, etc.) so OpCo leaders can get high-quality coaching from an agent on demand.
• Build the systems that make the above scale: skills, RAG knowledge bases, evals, guardrails, and a clean way for OpCo teams to use what you've built.

Success here: roles we'd otherwise have hired humans for at Waverock are run by agents you've built and maintained.

3. Custom AI Solutions for the Operating Companies (quick wins)

Long term, we want each OpCo to own its own AI solutions. Short term, you'll execute on a handful of high-leverage quick wins to demonstrate what's possible, and then transfer ownership.

• Identify 2–3 places per OpCo where a custom agent or vibe-coded tool would noticeably improve productivity or quality of work product.
• Build the MVP. Ship it. Iterate.
• Train the OpCo team to own and extend it once it's working.

Who You Are

Required

• You've built real things with AI. A friend's problem, an internship project, a side hustle, a small business, it doesn't matter. What matters is that you shipped something that solved an actual problem for actual people.
• You think AI-first and follow through. Your first instinct when a problem shows up is "how do we use AI here?" You're flexible about what that means: vibe-coding a tool, setting up an agent, building a RAG knowledge base, training a skill. You ship MVPs, iterate, and don't wait for perfection.
• You stay ahead of the curve. You follow AI news, tools, and trends because you're genuinely interested, not because it's your job. You experiment for fun. You know what dropped last week.
• You've operated in the real world. You have worked with teams in a professional environment: Internships, a first job, a business you launched, all count. You've worked alongside other people, hit deadlines, and gotten things done.
• You're entrepreneurially curious. You like big, messy challenges. You want to understand how businesses grow, scale, and break. You don't need an M&A background, but you have to find this stuff genuinely interesting and be able to point to something that shows it.
• You build capability, not dependency. You're skilled, and you know it. But your goal is never to be the only one who can do something. You get energy from teaching, explaining, and making AI accessible to people who don't speak the language yet. You can sit across from a VP who has never touched an agent and leave them excited and capable, not impressed and reliant on you. We're scaling this across a portfolio of companies, and that only works if you distribute the knowledge.

Education

A degree is preferred but not required. Tech or AI-focused degrees are ideal. Business degrees are great if paired with internships or projects where you delivered AI work like what's described above. If you don't have a degree, that's fine — but you'll need a track record we can verify and references we can call who can speak to your skills.

Bonus (none of these are required)

• You've launched a business or product on your own, even a small one.
• You've built and shipped agents using third-party platforms.
• You can hold your own with a software engineer in a code review of a vibe-coded tool.
• You've worked in or around a startup, a small business, or a holdco/PE-backed environment.

Why This Role Is Worth Taking

• You'll have a real seat at the table. You'll be in executive leadership meetings at a holding company. That's exposure that usually takes a decade to earn.
• You'll work across a portfolio of real software businesses — not one company. The variety of problems will allow you to gain real experience quickly.
• You'll get to actually build. This is not a present and consult role. You need to be hands-on and ship impactful AI products across the OpCos .
• You'll help rewrite what a work looks like in an AI-native world. If we get this right, this role becomes a template.
• Equity in Waverock means you participate in what you help build — not just one OpCo, but the holding company itself.
• We’re not the highest-paying option on the market. What we offer instead: real access to executive leadership, a portfolio of companies to learn across, the chance to build things that matter. If you’re optimizing for learning speed and long-term upside this is the role for you.

Compensation

• Base salary: $60,000–$80,000
• Performance bonus: $20,000–$30,000
• Equity in Waverock Software — not just one OpCo, but the holding company you’re helping build
• Fully remote, US-based
• Competitive benefits package

Waverock Software is an equal opportunity employer.