Gregory Rayzman
About Gregory Rayzman
Gregory Rayzman, age 62, is Chief Technology Officer (CTO) of Cloudastructure, Inc. (CSAI), serving as CTO since 2015 and originally joining the company in 2004; he holds Bachelor’s and Master’s degrees in Computer Science (Moscow University) and completed postdoctoral education in Applied Mathematics at the Academy of Science . He is a seasoned Silicon Valley technologist with deep Big Data and database architecture expertise, including pivotal leadership designing massively scalable, database-backed infrastructures for Apple (2013–2015) and building relevance/popularity algorithms at TheFind (acquired by Facebook in 2015) . Company- or executive-specific TSR, revenue growth, and EBITDA performance metrics tied to his tenure are not disclosed in CSAI’s proxy or 10-K.
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Apple | Architecting massively scalable, database-backed infrastructures | 2013–2015 | Led pivotal design and development of scalable infrastructure underpinning large-scale systems |
| TheFind | Engineering; shopping search engine relevance/popularity | 2010–2015 | Built search/algorithm engines; company acquired by Facebook in 2015 |
| NebuAd | Chief Data Architect | 2006–2009 | Developed behavior-targeted advertising based on aggregate data |
| ITM Software | Founding engineer; Chief Architect | Prior to 2006 | Enterprise IT financial mgmt; acquired by BMC (alignment with enterprise buyers) |
| Claridyne Inc. | CTO | Prior to 2006 | IT infrastructure/integration; technical leadership |
| Annuncio Inc. | Founding engineer; Director of Software Engineering | Prior to 2006 | Marketing automation; acquired by PeopleSoft (now Oracle) |
External Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| SteppeChange | CTO and Chief Data Architect | 2015–present | Leads telecom, finance, and security projects; external platform for advanced data architecture |
Fixed Compensation
| Item | 2023 | 2024 |
|---|---|---|
| Base Salary ($) | $235,000 | $158,333 (reflects 9/1/24 wage reduction to $35,000 annual until financing) |
| Bonus ($) | — (not disclosed) | — (no bonus awarded for Rayzman for FY2024) |
| Perquisites | — | $125 monthly cell phone stipend (company-wide policy) |
| Employment Agreement | At-will; base began $250,000, decreased to $230,000 in 2023; eligible for benefits and expense reimbursement | At-will; wage reduction agreement from 9/1/24 to conserve cash pre-listing; restoration tied to equity financing thresholds |
Notes:
- Wage Reduction Agreement: salaries temporarily reduced to $35,000 annual until CSAI raised $2,000,000; a stay bonus formula applied if $4,000,000 was raised (committee discretion; Rayzman not listed with a 2024 cash bonus) .
Performance Compensation
| Award Type | Grant/Period | Grant Date Fair Value ($) | Vesting | Strike/Conversion | Expiration |
|---|---|---|---|---|---|
| Stock Options (Class B) | FY2024 | $616,000 (ASC 718 grant-date fair value) | Generally 4-year vest, 1-year cliff per plan; time-based (no specific PSU metrics disclosed) | $0.024–$2.70 (range of strikes) | April 2029 – June 2034 |
- CSAI historically granted stock options into Class B common; the Amended & Restated 2024 Equity Incentive Plan allows RSUs/PSUs and cash-based awards, with minimum 1-year vesting and clawback applicability, but no Rayzman-specific PSU/metric disclosures were provided for 2024 .
Equity Ownership & Alignment
| Ownership Snapshot (Record Date: July 9, 2025) | Amount | % of Class |
|---|---|---|
| Class A Common – shares owned | 2,500 | <1% |
| Class B Common – options exercisable within 60 days | 1,433,238 | 90.7% (beneficial ownership of class, including 60-day exercisables) |
| Series 1 Preferred | — | — |
| Series 2 Preferred | — | — |
Vested vs Unvested Options (as of Dec 31, 2024):
- Exercisable options: 4,382,299
- Unexercisable options: 2,057,120
- Strike range: $0.024–$2.70; expirations Apr 2029–Jun 2034
Alignment Policies and Restrictions:
- Anti-hedging and anti-pledging policy restricts hedging and pledging of company stock by officers/directors .
- Lock-Up Agreement: prohibits transferring/disposal of Class A shares or related securities until August 18, 2025 .
- Standstill Agreement: irrevocably restricts Rayzman from acquiring common stock that would result in >49% of CSAI’s voting power .
- Stock ownership guidelines (salary multiple): not disclosed; no pledging reported (policy prohibits) .
Employment Terms
- At-will employment; initial base salary $250,000, reduced to $230,000 in 2023; benefits eligibility and reimbursement of ordinary-course business expenses .
- Severance, non-compete, non-solicit, and change-of-control economics: not disclosed for Rayzman in proxy/10-K .
- Clawback: Plan awards subject to CSAI’s clawback policy; Plan imposes minimum 1-year vesting with limited exceptions .
- Governance/compensation oversight: Compensation Committee (Qashu—Chair; Johnson; Kirby) met 5 times in 2024; authority to engage independent consultants; CEO sets base salaries for non-CEO executives .
Related Signals: Vesting & Insider Selling Pressure
- Lock-up ended August 18, 2025 for Rayzman, removing near-term transfer restrictions on Class A-related securities; combined with substantial exercisable options, watch for potential liquidity events/selling pressure around vest dates and post-lockup windows .
- Anti-hedging/anti-pledging constraints limit aggressive risk management trades; Standstill caps voting control growth above 49% .
Compensation Structure Analysis
- Heavy equity tilt via long-dated options; RSUs/PSUs available under the 2025 Plan but 2024 awards for Rayzman were options with time-based vesting, indicating at-risk pay tied to long-term value creation rather than near-term cash .
- Cash compensation was temporarily curtailed under the 2024 Wage Reduction Agreement, aligning liquidity conservation with equity financing milestones; Rayzman did not receive a 2024 bonus, reducing guaranteed pay .
- No evidence of option repricing, tax gross-ups, or guaranteed/discretionary bonuses for Rayzman despite missed targets; performance metric targets/weights for executives not disclosed .
Performance & Track Record
- Major achievements: Apple-scale infrastructure leadership; TheFind algorithmic search; founding roles and exits (Annuncio → PeopleSoft; ITM → BMC); extensive Big Data architecture across telecom/finance/security via SteppeChange .
- Controversies/legal proceedings for Rayzman: none disclosed in proxy/10-K .
- Company financing backdrop: significant Streeterville capital transactions, conversion mechanics and potential dilution risk at CSAI level (contextual for execution risk but not individualized to Rayzman) .
Equity Incentive Plan Mechanics (Context)
- Amended & Restated 2024 Equity Incentive Plan: 19.5 million shares authorized; minimum 1-year vesting; permits options, RSUs, PSUs, SARs, cash-based awards; director annual total comp cap ($500k, first-year $1M) .
- Options generally at ≥FMV on grant; 10-year term; 4-year vest/1-year cliff standard; clawback applies .
Investment Implications
- Alignment: Very large option overhang and 90.7% beneficial ownership of Class B (including 60-day exercisables) provides strong equity exposure, but the Standstill caps voting power at 49%, mitigating absolute control risk; anti-hedging/pledging enhances alignment with shareholders .
- Retention: Significant unvested options (2,057,120) and long-dated expirations support retention; absence of severance/change-of-control benefits reduces exit incentives, though market alternatives for a senior data architect remain robust .
- Trading signals: Post-lockup freedom as of August 18, 2025 combined with a deep pool of exercisable options may increase selling pressure around vest dates; monitor Form 4 activity and option exercises for timing/scale of disposals (policy constraints apply) .
- Pay-for-performance transparency: No disclosed PSU metric framework (revenue/EBITDA/TSR) for Rayzman; equity is primarily time-vested options. Analysts should supplement with company-level KPIs and product execution milestones to infer pay-performance linkage .
Key watch items: (1) any transition from options to RSUs/PSUs with explicit KPIs under the 2025 Plan, (2) Form 4s post-lockup for selling pressure signals, (3) compliance with anti-hedging/pledging and clawback policies in practice, (4) evolving role scope tied to AI/data architecture commercialization.