Bryan Freeman
About Bryan Freeman
Bryan Freeman, age 55, is Executive Vice President, Operations at Prairie Operating Co. (PROP). He joined the company in October 2022 and has served as EVP, Operations since May 2023; he holds a B.S. and M.S. in Engineering from the University of Texas and has 35+ years of industry experience across operations, drilling and completions at Rosehill, SM Energy, Hess, Chevron, Schlumberger and Weatherford . During his tenure, PROP’s disclosed pay-versus-performance metrics show a cumulative TSR value of $11.10 in 2023 and $8.07 in 2024 on a $100 base, alongside net losses, indicating a rebuilding phase post-merger and asset acquisitions .
Company performance metrics (context for pay-for-performance)
| Metric | FY 2022 | FY 2023 | FY 2024 |
|---|---|---|---|
| TSR value of $100 investment ($) | $1.81 | $11.10 | $8.07 |
| Net Income (Loss) ($) | $(13,418,814) | $(79,080,800) | $(40,912,000) |
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Rosehill Resources | SVP, Drilling & Completions | Apr 2017–Mar 2020 | Led drilling/completions; multi-basin experience and cost optimization |
| Capstone Energy Management | Employee | Aug 2020–Oct 2022 | Operational support leading into PROP tenure |
| Tema Oil & Gas | Drilling & Operations Manager | Jul 2016–Apr 2017 | Managed drilling/ops for private E&P |
| SM Energy | Production & Operations Engineering Manager | Jul 2013–Jul 2016 | Hydrocarbon exploration operations and production engineering |
| Hess Corporation | Senior Production Engineer | 2012–2013 | Production engineering in large-cap E&P |
| Chevron | Engineering roles | 2006–2012 | Integrated energy operations exposure |
| Schlumberger | Service sector roles | 2004–2006 | Service-side drilling/completions expertise |
| Weatherford | Service sector roles | 2001–2004 | Oilfield services know-how |
External Roles
No public company board roles disclosed for Freeman in the proxy; management slides highlight operations leadership rather than external directorships .
Fixed Compensation
- Freeman is a non-director executive officer but not a Named Executive Officer (NEO); as a smaller reporting company, PROP discloses compensation detail only for NEOs (CEO, President, former CFO), so Freeman’s base salary, target bonus, and bonuses were not itemized in the DEF 14A .
- The proxy indicates ongoing use of base salary and annual bonus constructs for executive officers under employment agreements, but individual figures for Freeman are not provided .
Performance Compensation
Long-Term Incentive Plan (LTIP) architecture applicable to executives
| Incentive Type | Metric | Weighting | Target Design | Payout Scale | Vesting | Settlement | Notes |
|---|---|---|---|---|---|---|---|
| PSUs | Relative Total Shareholder Return vs peer group | Not disclosed | 3-year performance period; market condition via Monte Carlo valuation | 0%–200% of target PSUs | Earned at end of 3 years (e.g., grants in 2024/2025 vest at period end) | Stock unless Committee determines otherwise | Classified as equity; service requirement through performance period |
| RSUs (employees) | Service-based | Not disclosed | Ratable vesting over 3 years | N/A | 3-year ratable schedule | Stock; standard tax withholding | Accelerated vesting on death, disability, retirement; change-in-control provisions below |
Change-of-control and termination mechanics for RSUs/PSUs (employees)
- Change-of-control: If awards are not assumed/substituted, RSUs become 100% vested; PSUs vest based on actual performance through the CoC date, settled immediately prior to the CoC .
- Double-trigger: If assumed/substituted and termination occurs without “cause” or for “good reason” within 24 months following CoC, RSUs/PSUs vest fully (PSUs vest at greater of target or actual-to-date) .
- Non-CoC termination: Pro-rata vesting of RSUs/PSUs based on months elapsed from grant (36-month denominator) for terminations without cause or for good reason; full vesting upon death/disability; retirement earns full RSUs and performance-through-period PSUs .
Equity Ownership & Alignment
| Attribute | Detail |
|---|---|
| Total beneficial ownership (group) | Directors and executive officers as a group owned 15.44% of common stock as of April 8, 2025; individual holdings for Freeman not separately disclosed |
| Ownership guidelines | Not disclosed in proxy |
| Hedging/Pledging | Insider Trading Policy prohibits hedging transactions and pledging securities by directors and officers |
| RSU/PSU settlement | Employee RSUs settle in stock; PSUs settle primarily in stock unless Committee decides otherwise |
| Vested vs unvested | Company-level RSU/PSU activity disclosed; individual breakdown for Freeman not disclosed |
| Lock-up history | Freeman was a lock-up party in the March 2025 offering; standard underwriter lock-up applied (offering price $4.50; date after which new company issuance allowed: June 22, 2025) |
Employment Terms
| Term | Detail |
|---|---|
| Employment start | October 2022 |
| Current role start | EVP, Operations since May 2023 |
| Contract term/expiration | Not disclosed for Freeman (employment agreements detailed for CEO, President, CFO only) |
| Non-compete / Non-solicit | Not disclosed for Freeman |
| Garden leave | Not disclosed |
| Post-termination equity | RSU/PSU award agreements provide pro-rata or full vesting under specified conditions (death, disability, retirement; pro-rata for terminations without cause/for good reason) |
| Change-of-control equity | If awards not assumed/substituted, 100% vesting (RSUs) and performance-based vesting (PSUs); double-trigger full vesting if assumed and terminated within 24 months |
| Clawback | Company LTIP subject to clawback policy; aligns with SEC and exchange standards |
Additional operating context tied to execution
- Freeman is credited by management for cost unbundling and efficiency programs; team targets disciplined capital, leverage ~1x, and ~80% hedged 2025 production post Bayswater acquisition, supporting cash flow stability for drilling plans .
- Management presentations note Freeman has drilled over 2,000 wells across multiple basins, underpinning execution capability in DJ Basin operations .
Compensation Structure Notes (company-level context)
- The Compensation Committee and Board discussed Special Retention Awards for executive officers, including Freeman, to recognize execution of the Bayswater acquisition and to enhance market competitiveness; contemplated form is time-based RSUs vesting over ≤3 years (amounts not disclosed) .
- LTIP pool increased from 7.5M to 15.0M shares pending shareholder approval in 2025, with expected dilution of ~11.1% on a fully diluted basis (excluding Series F instruments) to support retention and pay-for-performance awards .
Investment Implications
- Alignment: PSUs tied to relative TSR (0–200% payout) and double-trigger vesting on CoC create high equity-at-risk, aligning Freeman’s incentives with shareholder returns, though individual grant sizes are undisclosed .
- Retention risk: Board’s consideration of Special Retention Awards suggests proactive retention strategy amid transformative acquisitions; absence of disclosed personal grant detail limits precision on Freeman’s retention runway .
- Selling pressure: Three-year RSU schedules and potential accelerated vesting on CoC can create event-driven supply; lock-up participation in March 2025 limits near-term selling, but future vesting cycles warrant monitoring .
- Governance safeguards: Prohibition on hedging and pledging reduces misalignment risk; clawback policy provides recourse on restatements or misconduct .
- Execution: Freeman’s extensive operations background and cost programs are positives for value creation in DJ Basin exploitation strategy; company TSR and net losses indicate early-stage scaling post-merger, so performance convergence with incentive metrics should be tracked over the 2024–2027 PSU cycles .