Greg Smitherman
About Greg Smitherman
Greg Smitherman, 61, has served as Chief Financial Officer of Cloudastructure, Inc. since October 2021, bringing 20+ years in M&A and venture capital and 10 years of operating experience; he holds a BS in Aerospace Engineering from the University of Michigan and an MBA from the University of Chicago . Under his tenure, the company’s reported revenues increased from $0.489M in 2022 to $1.364M in 2024, while EBITDA losses narrowed from -$11.429M to -$6.054M, indicating improving operating leverage as the business scaled; total shareholder return (TSR) was not disclosed in filings reviewed (financials below) . Values retrieved from S&P Global.
| Metric (USD) | FY 2022 | FY 2023 | FY 2024 |
|---|---|---|---|
| Revenues | $489,000* | $607,000* | $1,364,000* |
| EBITDA | -$11,429,000* | -$8,503,000* | -$6,054,000* |
Values retrieved from S&P Global.
Past Roles
| Organization | Role | Years | Strategic impact |
|---|---|---|---|
| Accelergy Corporation | Chief Financial Officer | Feb 2013 – Oct 2021 | Managed financials; led fundraising and JV negotiations; oversaw closing of $20M+ in funding |
External Roles
| Organization | Role | Years | Notes |
|---|---|---|---|
| — | — | — | No public external directorships disclosed in the 2025 proxy |
Fixed Compensation
| Component | 2023 | 2024 | Notes |
|---|---|---|---|
| Base Salary | $262,500 | $161,667 | 2024 salary reflects wage reduction agreement effective Sep 1, 2024 to conserve cash during direct listing; temporary reduction to $35,000 annualized until equity financing thresholds met |
| Target Bonus % | 25% of base salary | 25% of base salary | As per employment agreement; committee retains discretion |
| Actual Bonus Paid | — | $60,000 (awarded Mar 2025; paid biweekly through Dec 31, 2025) | Committee awarded 2024 bonuses in Mar 2025, with payout schedule specified |
| Other Cash/Perqs | — | $125/month cell phone stipend | Company-wide benefit; also 401(k) with no match |
Wage Reduction Agreement details: From Sep 1, 2024, NEO salaries were reduced to $2,916.67/month ($35,000/year) until $2.0M of new equity financing was raised; if $4.0M was raised, a stay bonus equals the foregone salary during the deferral period × 1.5 . The Series 1 equity financing closed Jan 29, 2025 .
Performance Compensation
- Annual Cash Bonus Framework
- Structure: Bonuses historically based on corporate and individual goals; committee retains discretion and may deviate from formulaic payouts .
- 2024 Outcome: $60,000 bonus, awarded Mar 2025; paid in equal biweekly installments through Dec 31, 2025 .
| Metric | Weighting | Target | Actual | Payout | Vesting/Timing |
|---|---|---|---|---|---|
| Annual Cash Bonus (2024) | Discretionary; based on corporate and individual goals | 25% of base salary | Not itemized (committee discretion) | $60,000 | Biweekly installments through Dec 31, 2025 |
- Equity Awards (Options)
- Equity mix and practices: Prior to Dec 31, 2024, equity was granted as stock options into Class B shares; company may introduce RSUs going forward . Options generally vest over 4 years with a 1-year cliff and expire 10 years from vesting date .
- 2024 Grant Value: $506,001 (grant-date fair value, ASC 718) .
| Award Type | Period | Grant-date Fair Value | Strike Price(s) | Vesting | Expiration |
|---|---|---|---|---|---|
| Stock Options (Class B) | FY 2024 | $506,001 | Range: $0.024 – $2.70 | 4 years; 1-year cliff | 10 years from vest; existing awards expire Apr 2029 – Jun 2034 |
Clawback: All awards subject to company clawback policy .
Equity Ownership & Alignment
- Beneficial Ownership and Lock-up
- Beneficial ownership (within 60 days of July 9, 2025): 2,502 Class A shares and 924,999 Class B shares issuable upon exercise of options; Class B represents 86.3% of Class B outstanding on that basis; Class A ownership is <1% .
- Lock-up: Company and Mr. Smitherman entered a Lock-Up Agreement prohibiting transfers of Class A shares and related securities until August 18, 2025 .
- Hedging/Pledging: Board policy prohibits hedging and pledging of company stock by executives and directors .
| Ownership Detail | Value |
|---|---|
| Class A shares beneficially owned | 2,502 (<1%) |
| Class B shares beneficially owned (issuable within 60 days) | 924,999 (86.3%) |
| Lock-up expiry | Aug 18, 2025 |
| Hedging/Pledging policy | Hedging and pledging prohibited |
- Vested vs. Unvested, and Option Profile (Dec 31, 2024)
- Options exercisable: 1,179,418; unexercisable: 633,335; strike price range: $0.024 – $2.70; expirations: Apr 2029 – Jun 2034 .
| Options (Dec 31, 2024) | Count | Exercise Price | Expiration Window |
|---|---|---|---|
| Exercisable | 1,179,418 | $0.024 – $2.70 | Apr 2029 – Jun 2034 |
| Unexercisable | 633,335 | $0.024 – $2.70 | Apr 2029 – Jun 2034 |
Employment Terms
| Term | Detail |
|---|---|
| Agreement & Role | At-will employment; CFO since Oct 7, 2021 |
| Base Salary History | Initially $300,000; reduced to $225,000 in 2023 |
| Annual Bonus Eligibility | 25% of base salary; terms negotiated; committee discretion |
| Equity Eligibility | Eligible for equity compensation of approximately 2.5% of the company |
| Severance | 3 months’ salary if terminated without cause |
| Change-in-Control (CIC) | If awards are not assumed/continued in a sale event, time-based awards accelerate at close; performance awards may vest at administrator discretion or as specified in award agreements |
| Clawback | Awards subject to the company’s clawback policy |
| Hedging/Pledging | Prohibited for executives and directors |
| 401(k) | Available; no company match |
| Perquisites | $125 monthly cell phone stipend |
Additional Governance and Process Notes
- Compensation Committee: Comprised of Qashu (Chair), Johnson, and Kirby; met five times in 2024; approves equity awards and evaluates CEO/exec compensation against goals, budgets, and market trends; CEO sets base pay for other executive officers .
- Equity Plan Design: 2024 Amended & Restated Equity Incentive Plan includes minimum 1-year vesting (limited exceptions), anti-dilution adjustments, and CIC acceleration if awards are not assumed; RSUs and other award types newly available under the plan .
Performance & Track Record Under Tenure
- Financial progress since 2022 shows revenue scaling and EBITDA loss compression (see “About” table above). Values retrieved from S&P Global.
- CFO leadership evidenced by required SOX certifications on Q3 2025 10-Q and execution of earnings/8-K filings as principal financial officer, indicating accountability for disclosure controls and financial reporting .
Insider Activity and Selling Pressure
- Form 4 filings: No Form 4 transactions found in the period searched, limiting visibility into open-market selling or option exercises to date [ListDocuments: Form 4 search returned none].
- Lock-up expiration (Aug 18, 2025) is a potential catalyst for incremental supply from eligible shares/options, subject to window and policy constraints .
Compensation Structure Analysis
- Mix shift: 2024 compensation for Smitherman skewed toward equity, with option grant value ($506,001) exceeding cash salary ($161,667) and bonus ($60,000), aligning incentives to long-term value creation during a capital-constrained period .
- Discretionary bonuses: Committee retains discretion on payout determination rather than strict formula; 2024 bonuses were awarded post-year end with staged payouts through 2025 .
- Equity design: Option-heavy program pre-2025 with standard 4-year vest/1-year cliff; plan now allows RSUs/other awards, which may lower risk for executives versus options if implemented .
- CIC terms: Single-trigger acceleration if awards are not assumed/continued in a sale event could create retention risk mitigation but also potential windfalls in a change-of-control scenario .
Related Party Transactions
- The proxy discloses a related-party aircraft lease involving the founder and another company; no related-party transactions are disclosed as involving Smitherman personally .
Investment Implications
- Pay-for-performance alignment: 2024 pay leaned into equity while cash compensation was temporarily reduced, aligning CFO incentives with long-term outcomes amid financing constraints .
- Retention and overhang: Significant outstanding options (1.81M total; 1.18M exercisable) with multi-year vesting and an anti-hedging/pledging policy support retention and alignment; lock-up expiry on Aug 18, 2025 could introduce near-term selling pressure if windows permit .
- Governance risk flags: CIC acceleration for unassumed awards is shareholder-sensitive and should be monitored; bonus discretion without detailed metric disclosure reduces transparency of pay-performance link .
- Execution track record: Financial trajectory under his tenure shows revenue growth and improving EBITDA losses, but absolute losses persist; further scaling and cash discipline remain key to sustaining momentum. Values retrieved from S&P Global.