Randy Carlson
About Randy Carlson
Randy Carlson is PSQ Holdings’ Chief Technology Officer (CTO), appointed in August 2024 after serving as Senior Vice President of Engineering since January 2023 . He is 50 and holds a Bachelor’s in Computer Science (Metropolitan State University) and a Bachelor’s in Graphic Design (Bemidji State University) . His credentials include deep software engineering, product development, and cloud infrastructure expertise, leading engineering and technology strategy across PSQ’s marketplace, brand, and fintech divisions . PSQ does not disclose executive-specific TSR or revenue/EBITDA growth metrics for Carlson; company-level performance disclosures show continued net losses and material share-based compensation expense in 2025 .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| PSQ Holdings, Inc. | Chief Technology Officer | Aug 2024–present | Leads engineering and technology strategy across marketplace, brand, and fintech divisions; focused on scalable, high-performing tech solutions to drive growth . |
| PSQ Holdings, Inc. | SVP of Engineering | Jan 2023–Aug 2024 | Senior engineering leadership during post-Business Combination scaling . |
| Target Corporation | Director of Engineering | 2014–2022 | Directed teams for omnichannel retail fulfillment, mapping, and location-based services; oversaw critical cloud-based systems and enterprise engineering best practices . |
External Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| — | — | — | Not disclosed in PSQ’s proxy/filings for Carlson . |
Fixed Compensation
| Component | 2024 | Notes |
|---|---|---|
| Base Salary ($) | Not disclosed | Carlson was not a 2024 named executive officer (NEO), and PSQ’s summary compensation table only covers Seifert, Searle, and Weisbecker . |
| Target Bonus (%) | Not disclosed | Not in NEO disclosure; bonus targets for CTO not provided . |
| Actual Bonus Paid ($) | Not disclosed | Not in NEO disclosure . |
PSQ’s compensation philosophy emphasizes equity as the primary motivator, with competitive base and bonus levels; specifics for non-NEO executives are not reported .
Performance Compensation
| Metric | Weighting | Target | Actual | Payout | Vesting |
|---|---|---|---|---|---|
| Annual bonus metrics (CTO) | Not disclosed | Not disclosed | Not disclosed | Not disclosed | Not disclosed . |
| RSUs (CTO-specific grants) | Not disclosed | Not disclosed | Not disclosed | Not disclosed | Company-wide RSUs typically vest over three years, one-third on each anniversary for many executive grants (illustrated for NEOs granted 9/25/2023) . |
| PSUs/options | Not disclosed | Not disclosed | Not disclosed | Not disclosed | Not disclosed . |
- Company RSU mechanics: RSUs are valued at grant-date stock price and expensed ratably over the vesting period . As of 9/30/2025, unrecognized RSU expense was ~$8.7M; unvested outstanding RSUs had a weighted average remaining vesting period of 1.59 years .
- Vested-but-unsettled RSUs and sell-to-cover: 838,393 RSUs were vested but unsettled at 9/30/2025; PSQ historically facilitates “sell-to-cover” for withholding taxes upon vesting, implying routine insider sales near vest dates for tax coverage (general practice, not person-specific) .
Equity Ownership & Alignment
| Item | Detail |
|---|---|
| Total beneficial ownership | Not disclosed for Carlson in the beneficial ownership table (table highlights certain executives/directors; Carlson not enumerated) . |
| Ownership % of SO | Not disclosed . |
| Vested vs. unvested shares | Not disclosed for Carlson; company-wide RSU activity disclosed in aggregate . |
| Options (exercisable/unexercisable) | Not disclosed for Carlson . |
| Shares pledged as collateral | Company policy prohibits pledging and hedging; exceptions only in extraordinary situations with demonstrated capacity to repay without resorting to pledged shares . No pledges by Carlson disclosed . |
| Hedging | Prohibited for employees, officers, directors, and consultants . |
| 10b5-1 plans | Executives are authorized to enter 10b5-1 plans; as of proxy record date none of the directors had plans in effect; executive-specific adoption not disclosed . |
| Ownership guidelines | Company does not have formal stock ownership guidelines for executive officers; compensation committee believes existing stock/option holdings provide alignment . |
Employment Terms
- Employment agreement: No CTO-specific employment agreement terms (salary multiples, bonus multiples, or change-of-control provisions) were disclosed for Carlson. NEO employment agreements contain severance, COBRA, and accelerated time-based equity vesting under change-of-control for certain executives, but CTO terms are not provided .
- Restrictive covenants: NEO agreements include confidentiality, non-compete, non-solicitation of employees/customers, and non-disparagement; CTO-specific covenant disclosure not provided .
- Indemnification: PSQ entered into indemnification agreements with each director and executive officer, providing advancement and indemnification to the fullest extent permitted by Delaware law .
- Controlled company governance: Founder/CEO controls majority voting power via dual-class structure; PSQ has elected certain NYSE controlled company exemptions (e.g., majority-independent board not required), with intent to keep a fully independent compensation committee .
Performance & Track Record
| Indicator | Detail |
|---|---|
| Company net loss trend | Net loss for Q3 2025 was $(11,982,888); YTD and prior quarter losses were also disclosed, indicating ongoing investment stage losses . |
| Share-based compensation | Total share-based compensation expense was $4.42M for Q3 2025 and $7.98M for the first nine months of 2025; earn-out share expense of $0.9M (Q3) and $2.7M (YTD), with ~$9.5M unrecognized earn-out compensation cost outstanding . |
| RSU program scale | Unvested RSUs increased to 3,845,653 by 9/30/2025, with 838,393 vested-but-unsettled RSUs pending settlement post-10-Q filing . |
Compensation Committee Analysis
- Composition: Blake Masters (Chair), James Rinn, and Willie Langston; all independent under NYSE standards; two meetings held in 2024 .
- Mandate: Oversees executive/director compensation, administers the 2023 Stock Incentive Plan and ESPP, retains advisors, and sets/approves salaries, bonuses, and equity awards; CEO makes recommendations for the team (other than himself) .
- Philosophy: Emphasizes equity-based compensation as key motivator; competitive cash comp with performance linked to stockholder value creation .
- Ownership/Trading Policy: Prohibits hedging and pledging; permits 10b5-1 plans; no formal executive ownership guidelines .
Risk Indicators & Red Flags (as relevant to Carlson)
- Hedging/pledging risk: Mitigated by company-wide prohibitions; extraordinary pledge exceptions possible but none disclosed for Carlson .
- Insider selling pressure: Routine “sell-to-cover” mechanics on RSU vesting can create predictable sale flows near vest dates across executives, not specifically tied to Carlson unless disclosed .
- Related party transactions: Extensive related party section covers others; no transactions tied to Carlson disclosed .
- Section 16 compliance: Delinquency disclosures list several executives/directors; Carlson is not mentioned among late filers for 2024 events .
Investment Implications
- Alignment: Absence of formal ownership guidelines and lack of CTO-specific compensation metrics reduces transparency on pay-for-performance alignment, though hedging/pledging prohibitions and potential 10b5-1 plans support disciplined trading .
- Selling pressure: Company’s sell-to-cover practice around RSU vesting implies periodic insider sales; monitoring Form 4s and vest schedules is prudent for short-term trading signals, though Carlson-specific grants are not disclosed .
- Retention/CoC economics: Without a disclosed CTO employment agreement, severance and change-of-control protections are unknown—raising uncertainty on retention leverage compared to NEOs with defined multiples and accelerated vesting .
- Execution risk: Carlson’s large-enterprise cloud and omnichannel background aligns with PSQ’s scaling needs; however, company-level losses and material share-based comp indicate ongoing investment and dilution pressures, necessitating delivery of product/infra milestones to justify equity-heavy comp structures .