Outcome Strategist

Trust is everything for financial institutions, but it gets harder to earn as customer expectations rise and fraud keeps evolving. At Casap, we’re on a mission to deliver outcomes that were once out of reach, building a future where fraud is rare and trust is a given.

We started with disputes, some of the highest-stakes work financial institutions can’t afford to get wrong, and have expanded the same approach across fraud, collections, claims and more. Today, more than 100 banks, credit unions, fintechs and processors trust our AI agents to make decisions, take actions, move money and file chargebacks, from first signal to final outcome.

Founded by product leaders from Robinhood and Chime, Casap has raised $90M, including a $56M Series B led by Base10 Partners with continued investment from Lightspeed and Emergence. We were named Tearsheet’s 2026 AI Company of the Year, and our CEO, Shanthi, was named to Inc.’s 2026 Female Founders 500. We have an exceptionally ambitious and kind culture, and we’re just getting started.

The role

As one of our first Outcome Strategists, you'll start from first principles and ask: with no constraints, what's the best possible result for a financial institution and the people it serves? Then you'll help build it. You'll partner with leaders at banks, credit unions and fintechs to find where AI can make the biggest difference, prove it on their own data, and work directly with our founders, engineers and product team to turn that vision into reality, delivering real outcomes in weeks.

Location

This is a remote role open to candidates anywhere in the US. Expect to travel to customer sites about 25 to 50% of the time.

What you'll do

• Find where AI will change outcomes most. Embed with operations, fraud and executive teams. Shadow the work, dig into the data, and map how disputes, fraud, collections, claims and onboarding really run today.
• Build the case. Size each opportunity in dollars, hours and risk, and bring a clear recommendation to everyone from frontline managers to the C-suite.
• Prove it on their data. Design pilots with clear success metrics and show results on the customer's own cases before scaling.
• Put it into production. Configure agents, decide what runs on Autopilot and what stays with the customer's people based on their policies and risk tolerance, launch, and keep tuning until the results show up: lower losses, faster resolutions, and staff who get their time back.
• Build trust through governance. Make sure every deployment meets the bar for compliance, model governance and auditability, and help customers explain AI decisions to examiners and regulators.
• Grow the partnership. Turn one successful deployment into the next, and partner with Sales on expansion.
• Shape the product. Bring what you learn in the field back to Product and Engineering, and turn one-off wins into repeatable playbooks every Casap customer can use.

What we're looking for

• 5+ years of experience in a client-facing deployment, consulting or product role, where you worked directly with enterprise customers to understand their operations and deliver solutions that changed how they work.
• A track record of owning measurable outcomes, not just delivering projects.
• Comfort in regulated, high-stakes environments where accuracy, compliance and auditability matter as much as speed.
• The ability to break an ambiguous operational problem into clear, prioritized steps.
• Strong analytical skills. You're comfortable working in data (SQL or advanced spreadsheets) to size an opportunity or prove impact.
• Technical fluency. You can read API docs, follow data models and system architecture, and keep up in engineering tradeoff discussions. You don't need to write production code.
• Executive presence. You build trust quickly with anyone from an operations analyst to a CEO, and you write and present with clarity.
• High agency. You see around corners, run several engagements at once, and do what it takes to get customers live.

Nice to have

• Experience at a forward-deployed company like Palantir, Sierra or Scale AI, or at a top-tier consulting firm like McKinsey, BCG, Bain or Oliver Wyman.
• Hands-on experience deploying AI or LLM agents in production, such as designing evals, writing prompts or defining quality bars.
• Experience as a founder, early employee or operator who has balanced craft, ownership and speed.
• Light scripting in Python or SQL for analysis and prototyping.

Compensation

The base pay range for this role is $175,000 – $250,000 per year.

Casap's compensation package includes a competitive base salary benchmarked against real-time market data, as well as equity for all full-time roles. We also offer exceptional benefits, as well as bonuses and commission plans for applicable roles. The listed US-based compensation range is a guideline and may be modified. Final compensation will vary based on market conditions, geographic location, and candidate qualifications, including relevant knowledge, skills, and experience assessed during the interview process.

• 📈 Start-up equity
• 🦷 Full health, vision & dental coverage
• 🏦 401K with match
• 🩺 One Medical membership
• 🍽️ Stocked kitchens + lunches
• 🚍 Commuter benefit
• 🚠 Team building events & happy hours
• 🌴 Flexible PTO
• 💻 Apple equipment + annual home office budget

Casap is an equal opportunity employer that supports workplace diversity and does not discriminate on the basis of race, color, religion, gender identity/expression, national origin, age, military service eligibility, veteran status, sexual orientation, marital status, physical or mental disability, or any other protected class. Casap is committed to working with and providing reasonable accommodation to applicants with physical and mental disabilities.