A use case map identifying where DcisionAI's decision intelligence creates immediate, measurable value across CastleOak's trading, capital markets, and advisory businesses.
Prepared for CastleOak Meeting · May 2026
Boutique investment bank and broker-dealer, founded 2006 in New York City. 100% independently owned, 92% minority-owned. ~75 professionals across 5 regional offices.
Offices: NYC · ATL · CHI · SF · LA · PDX
Leadership: David R. Jones (CEO), Patrick de Catalogne (EVP, Fixed Income), Robert Bacon (EVP, Capital Markets)
Total assisted across equity and fixed income markets
Fixed income trading across all product types
Tier I–IV counterparties across the platform
Middle-market advisory transactions closed
30+ professionals. Corporate, MBS, ABS, GSE, hybrid, CP. $4.3B average daily volume.
Proprietary electronic fixed income trading platform with Bloomberg BOLT integration. Institutional liquidity pool.
Underwriting, distribution, and structuring across fixed income products for institutional issuers.
60+ global markets. Algorithmic strategies. ~$10B notional share repurchase execution per year.
Middle-market M&A under $1B. Fortune 500 divestitures. $79B+ in completed transactions.
Secondaries advisory, LP/GP liquidity solutions, fund management, and capital raising for alt asset managers.
When CastleOak co-manages or underwrites a bond offering, it must allocate bonds across 670+ institutional accounts — simultaneously balancing underwriter economics, relationship fairness, regulatory concentration limits, and syndicate desk preferences. Today, this is done in spreadsheets, introducing both errors and opportunity cost.
Allocation amount per account per tranche — a classic multi-objective linear/mixed-integer program with hundreds of decision variables and hard constraints on diversification, fill rate, and revenue-weighted priority.
Higher-revenue accounts receive preferential allocation
Minimize dissatisfaction from unfilled institutional orders
No single account exceeds defined % of deal size
Syndicate and regulatory rules enforced as hard constraints
CastleOak executed ~$10B in notional share repurchases last year for 25+ corporate clients. Each program requires multi-period scheduling to minimize market impact while remaining inside SEC Rule 10b-18 safe harbor provisions — exactly the problem structure DcisionAI has already proven.
≤25% of ADTV per day, excluding block trades
Not in last 10 minutes for active NMS stocks
No bid above highest independent bid in the market
One broker per day for open-market purchases
Client savings from 2–5 bps execution improvement on $10B notional
Multi-period optimization already demonstrated: 7-year Roth conversion, 14 variables, solved optimally
"Mathematically optimal execution" — a compelling story for winning corporate mandates
CastleOak's Private Capital Advisory (PCA) practice, launched March 2025, advises LPs on secondary market sales of fund interests. Each mandate requires selecting the optimal subset of a client's portfolio to sell — maximizing proceeds while maintaining diversification, respecting NAV discount tolerance, buyer capacity limits, and GP consent requirements.
Binary sell/hold decision per fund interest — a classic mixed-integer program. DcisionAI finds the mathematically optimal subset, with full constraint transparency for LP clients who want to see the reasoning behind every recommendation.
PCA launched March 2025. No legacy tools, no system to displace.
Sell/hold per fund interest is the exact structure DcisionAI's PE models solve.
"Mathematically optimal, not judgment-based" — a transparency story that resonates with institutional LPs.
DcisionAI makes each PCA engagement faster and more rigorous.
CastleOak Shares (COSXX, CASXX) are branded money market products that must construct portfolios maximizing yield while maintaining full SEC Rule 2a-7 compliance. DcisionAI solves this as a constrained security selection problem — automatically enforcing all regulatory parameters as hard constraints while optimizing for yield.
Weighted average maturity limit enforced at every rebalance
Weighted average life constraint across the full portfolio
Minimum daily liquid asset percentage maintained
No single issuer exceeds defined % of fund NAV
COSXX and CASXX — any yield improvement is directly attributable to CastleOak
Eliminates manual 2a-7 checking; enables dynamic rebalancing as rates shift
DcisionAI optimizes the portfolio that trades on State Street Fund Connect
DcisionAI's architecture was built for exactly the problems CastleOak faces every day — constrained optimization at speed, with regulatory hard constraints that can never be violated.
Solver runs in <100ms for inventory-size problems. $4.3B/day of trading decisions demand real-time answers, not overnight batch runs.
Domain cards with cited regulatory references — SEC 15c3-1, 10b-18, Rule 2a-7. Hard constraints are never relaxed, never violated.
Boutique firms can't hire quant optimization teams. DcisionAI's natural language interface lets traders describe problems — the engine formulates and solves them.
7-year Roth conversion with 14 variables solved optimally — the same architecture handles 30-day repurchase schedules with 10b-18 compliance windows.
"Our execution is mathematically optimal, not rule-of-thumb." — The story CastleOak tells institutional clients with DcisionAI powering the desk.
40+ new issues in the last 6 months — CastleOak can run a retroactive test against real allocations immediately.
No allocation optimization tool in place. Zero incumbent to displace.
Revenue-weighted priority, fill rate, diversification, and regulatory constraints — a textbook LP/MILP problem.
Wrong allocation doesn't lose money — it just leaves relationship value on the table. Safe to test.
Run DcisionAI against CastleOak's last 3 actual new issue allocations — same orders, same account tiers, same constraints.
Fill rate improvement · account satisfaction delta · relationship value left on the table
2–3 weeks to model + results presentation