---
id: brief-sasha-orloff
title: "Networking Brief — Sasha Orloff (Puzzle CEO, Sponsor)"
type: brief
status: final
owner: ivan
created: 2026-02-21
updated: 2026-02-21
tags: [hackathon, networking, sponsor]
---
# Sasha Orloff — Networking Brief
**Role:** CEO & Co-Founder, Puzzle (Hackathon Sponsor)
**Twitter:** [@saborloff](https://x.com/saborloff) | **LinkedIn:** [sashaorloff](https://www.linkedin.com/in/sashaorloff/)
**Company:** [puzzle.io](https://puzzle.io)
---
## Background
- **Repeat founder** — 3 companies, all in fintech
- **LendUp** — Co-founded. Alternative lending platform for underbanked consumers. Grew significantly before regulatory challenges
- **Mission Lane** — Spun out of LendUp. Credit card company for underserved consumers
- **Puzzle** — Current company. Real-time accounting platform for startups. $66.5M+ raised ($17.5M Series A + $31M Series B)
- ~85 employees, San Francisco
## Puzzle's Product & Framework
- **"Autonomous Accounting"** — Sasha's framework with Levels 0-5 (like self-driving car levels):
- Level 0: Manual bookkeeping
- Level 1: Basic automation (bank feeds)
- Level 2: Smart categorization
- Level 3: Real-time financial intelligence
- Level 4: Predictive anomaly detection
- Level 5: Fully autonomous accounting
- **Key metrics/terminology** in their API:
- `available_cash_balance`
- `burn_multiple`
- `spotlight_anomalies`
- Revenue recognition, runway calculations
## Why He Matters To Us
**We built our financial modeling around Puzzle's exact terminology.** Our demo's deal impact dashboard uses:
- `available_cash_balance` for cash position
- `burn_multiple` for efficiency metrics
- `spotlight_anomalies` for financial alerts
When Puzzle's API is available, it's a **direct swap** from our configured baseline to live sync.
## Quick Opener
> "Sasha, I'm Ivan from Markster. We built our financial modeling layer using your exact Puzzle terminology — available_cash_balance, burn_multiple, spotlight_anomalies. When your API is ready, we're a direct swap from configured to live. Want to see it?"
## What To Show Him
- **Step 3 of the demo** — "What does a $50K deal mean?" → Financial dashboard with his metrics
- **Step 4** — Pricing simulator → Real margin/runway impact calculations
- Emphasize we chose Puzzle's framework deliberately, not as a hackathon afterthought
## What NOT To Say
- Don't ask about LendUp's regulatory issues
- Don't position as a competitor to any accounting tool
- Don't suggest we built "accounting" — we built financial intelligence for revenue operations
## Partnership Angle
- Puzzle → financial data source
- Markster → financial intelligence layer in AI conversations
- Together: founders get real-time financial context inside their AI workspace
- We could be an early API integration partner
---
_Priority: HIGH — Sponsor. Show him we built around his framework. Potential partnership._
