Double Down Group · 16 hours ago
Head of AI Deployments - Investment Technology
New York, NY
Full-time
Hybrid
Director/Executive
$200K/yr - $250K/yr
10+ years expDouble Down Group is a startup focused on AI technology for financial institutions, seeking a Head of AI Deployments to lead their Outcome Engineering function. This role involves building and scaling a team to deliver world-class workflow automation and ensure that AI agents produce reliable outputs for clients.
Staffing & Recruiting
Hiring Manager
John Dolan
Responsibilities
Hire the first cohort of Senior OEs and establish the core operating model of the team
Design and run the OE Academy: a structured program to train high-potential talent from finance or AI backgrounds into workflow engineers
Define the OE career ladder, operating principles, technical standards, and delivery playbooks
You will ensure that AI agents deliver correct, reliable outputs across credit, investment, monitoring, and ESG workflows
You will guide OEs as they:
Shadow analysts and map messy workflows
Design multi-step agent logic (prompts, chaining, evals, error paths)
Ship production-grade workflows in weeks, not months
Ensure every workflow includes evals, audit trails, and logic transparency
Build the mechanisms that turn client-specific workflows into reusable primitives, components, and SKUs in the core platform
Establish standards for what becomes “product,” what stays “configuration,” and what is never built as bespoke
Drive a predictable feedback loop with Product & Engineering to accelerate roadmap development
Build central libraries for reusable modules (e.g., covenant analysis, EBITDA adjustments, risk signals)
Ensure OEs aren’t rebuilding the wheel for each client
Co-own account expansion outcomes: identifying adjacent teams, new workflows, and new regions where agents can deliver value
Reduce time-to-value for new deployments and accelerate commercial adoption
Build trusted relationships with senior client stakeholders (MDs, Heads of Credit, CIOs, COOs)
Drive OE-touched accounts toward 140–150%+ NRR
Maintain strong delivery economics, balancing speed, quality, and reusability
Ensure the OE function grows in leverage, not one-to-one with revenue
Create capacity planning, utilization models, and repeatable delivery frameworks that support high-growth enterprise scale
Knowing when to say “no” or re-scope overpromised work
Qualification
Required
10+ years in a hybrid role across finance, AI, product, or forward-deployed/solutions teams
Prior experience in private credit, PE, asset management, investment research, portfolio monitoring, or credit analytics
Ability to understand and validate logic in credit memos, IC decks, monitoring packs, risk frameworks, KPIs, and underwriting models
Experience designing or supervising multi-step LLM workflows, prompt chains, eval design, error-handling strategies, and structured output pipelines
Comfortable guiding non-engineers to build high-quality prototypes in Python, SQL, or low-code platforms
Led teams delivering complex, cross-functional deployments at financial institutions or highly regulated enterprises
Skilled in stakeholder management, discovery, requirements shaping, success metrics, and escalations
Able to mentor OEs on financial logic, AI workflow design, and structured evaluation
Balances 'client value tomorrow' with 'platform scalability next quarter.'
Comfortable being a player-coach early, then scaling into organizational design and leadership
Naturally sees expansion pathways and understands the economic drivers of high-NRR enterprise SaaS
Strong instincts for process, repeatability, and margin discipline — but only when the time is right
Credible with Heads of Credit, Partners, CIOs, and CTOs; trusted as a thought partner
Company
Double Down Group
Double Down Group (DDG) is an extremely unique executive search and advisory firm that brings a fresh perspective to placing highly qualified talent at premier firms within the financial technology and financial services industries.
2-10 employees
Funding
Current Stage
Early StageLeadership Team
John Dolan
Founder
Company data provided by crunchbase