AI Strategist

We’re an AI services firm that helps companies figure out where and how to use AI. We’ve built Casper Studios to roughly 45 people, worked with 30+ clients, and done deals with some of the largest companies, PE funds, and model providers.

It all comes down to how we work with clients. Before we build anything, we listen, understand the business, and help them figure out the highest-leverage way to get started on their AI journey.

We're hiring an AI Strategist to be the first person in with our clients. You'll partner with executives and their teams to understand how the business actually runs today, identify where AI can make the biggest difference, prioritize what matters most, and work with our engineers to design solutions that actually get built.

This is the work that sets up everything else. Done well, it turns into long-term partnerships where we deliver real outcomes alongside our clients' teams. Done poorly, nothing that comes after matters. You'll own that.

The best background for this is someone who's spent 4–7 years at a top strategy firm (McKinsey, Bain, BCG, PwC, Deloitte, or similar) and has since gone deep on AI. We're also open to strong candidates from product, strategy, or operations roles at AI-forward companies. What matters most is that you think about problems through the lens of what AI makes newly possible — and that you're hungry to build, not just execute a playbook.

• Partner with client executives and operators to map the current state of the business — how things run today, where the friction is, and what's most worth changing

• Identify and prioritize the highest-leverage AI opportunities and frame the ROI in a way that drives decisions

• Translate messy qualitative input into clear narratives, plans, and prioritized roadmaps

• Work alongside our engineers to shape solutions — scoping what to build, informing architecture choices, and making sure execution stays tied to business outcomes

• Present recommendations to C-suite stakeholders and keep business and technical stakeholders aligned throughout the engagement

• Own the handoff to implementation so nothing gets lost in translation

• 4–7 years of experience; strong preference for top-tier strategy consulting, though we're open to product, strategy, or ops backgrounds at AI-forward companies

• AI-native mindset — you use AI tools daily and think from first principles about what AI changes

• Strong discovery and diagnostic instincts — you know how to ask the right questions and figure out what matters

• Comfortable in the executive room and able to hold your own with C-suite stakeholders

• Strong synthesis — you can take messy input and produce clear, actionable plans

• Comfort working with technical partners — you don't need to write production code, but you can shape a solution alongside engineers and translate in both directions

• Self-directed, thrives in ambiguity, and excited by the pace of an early-stage, fast-growing firm

• Fully remote, US/Canada based, with occasional client travel. We have team members across North America and internationally, mostly overlapping North American time zones.

• Compensation calibrated to your location and seniority - we'll talk comp and align on specifics early.

• 🏥 Medical, Dental, and Vision Coverage: Comprehensive health benefits to keep you and your family healthy.

• 🌴 Flexible PTO: Take the time you need to relax and rejuvenate.

• 🚑 Health FSA/HSA: Manage out-of-pocket health expenses effectively.

• 🏥 Life Insurance: Providing peace of mind for you and your loved ones.