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Bradley Winges

President and Chief Executive Officer of Hilltop Securities at Hilltop HoldingsHilltop Holdings
Executive

About Bradley Winges

M. Bradley Winges is President and CEO of Hilltop Securities (a wholly owned subsidiary of Hilltop Holdings) since February 2019; age 57 as of April 28, 2025 . Prior to Hilltop, he spent nearly three decades at Piper Jaffray in senior leadership roles across fixed income trading, investment management, risk management, and municipal markets; he also serves on the Board of the Bond Dealers of America and is a committee member of Fixed Income Market Structure at the SEC . In 2024, Hilltop Securities delivered pre-tax income of $64 million (vs. $74 million in 2023), and Hilltop ranked in the 14th percentile of the KBW Regional Banking Index for 3-year total shareholder return through 12/31/2024, underscoring a mixed operating backdrop and market performance headwinds .

Past Roles

OrganizationRoleYearsStrategic Impact
Piper JaffraySenior Executive Managing Director; Head of Fixed Income Services and Firm Investments & Trading; President of Piper Jaffray Investment Management; firm risk management leadership; Co-Head Financial Products; Head of Municipal Sales & Trading; Institutional Municipal Sales1991–2019Led fixed income sales/trading and risk, built investment management and products; deep leadership experience in market structure and trading

External Roles

OrganizationRoleYearsStrategic Impact
Bond Dealers of AmericaBoard MemberNot disclosedIndustry advocacy and standards; network effects in fixed income markets
U.S. SEC (Fixed Income Market Structure)Committee MemberNot disclosedPolicy input on market structure; regulatory engagement

Fixed Compensation

MetricFY 2022FY 2023FY 2024
Base Salary ($)$500,000 $500,000 $500,000
Target Bonus (% of Salary)Not disclosedNot disclosed370% (set Feb 2024)
Target Bonus (% of Salary, forward)390% (set Feb 2025)
Annual Incentive Paid ($)$975,000 $2,386,328 $2,066,378
Perquisites ($)$20,176 $33,082 $5,822 (club)

Multi‑year compensation (as reported in Summary Compensation Table):

Component ($)FY 2022FY 2023FY 2024
Salary$500,000 $500,000 $500,000
Stock Awards$1,150,325 $912,230 $1,485,771
Non‑Equity Incentive Comp$975,000 $2,386,328 $2,066,378
All Other Compensation$20,176 $33,082 $20,246
Total$2,645,501 $3,831,640 $4,072,395

Performance Compensation

Annual Incentive structure and outcomes (2024):

  • Structure: At least 70% based on financial results (corporate and/or business unit earnings); 30% strategic/individual goals. Awards range from 50% (threshold) to 185% (maximum), subject to risk/compliance downward adjustments and clawback .
  • 2024 Results (relevant to Winges): Adjusted Hilltop Net Income target $108m vs. actual $120m (111% achievement); Hilltop Securities pre-tax target $58m vs. actual $63m (110% achievement). Winges’ annual incentive paid was $2,066,378, equating to 112% of his 2024 target .
MetricWeightingTargetActualAchievementPayout/Vesting
Financial Component (Corporate + Business Unit)≥70% of total See belowSee belowSee belowCash paid Feb 2025; subject to clawback
Adjusted Hilltop Net Income ($mm)Part of Financial$108 $120 111% Contributes to financial payout
Hilltop Securities Pre‑Tax Income ($mm)Part of Financial$58 $63 110% Contributes to financial payout
Strategic & Individual Goals30% of total Defined goals Achieved (effective leadership, risk mgmt, SBA launch, recruiting, culture) Committee assessment applied Cash; subject to clawback
Total Annual Incentive ($)Target per plan $2,066,378 112% of target Paid Feb 2025

Long‑Term Incentives (RSUs):

  • PRSUs: Earned over 3-year performance period (EPS goal with TSR modifier vs. KBW Regional Banks). Payout = EPS factor (50%–150%) × TSR modifier (80%–120%) = 40%–180% of target; 0% if EPS below threshold .
  • TRSUs: Time-based, cliff vest on the 3rd anniversary of grant; all RSUs require a 1‑year holding period post‑vesting; subject to double‑trigger CIC vesting and clawback .

Grants and vesting schedules:

AwardGrant DateShares (Target for PRSUs)Grant Date Value ($000s)Vesting
2024 PRSUsFeb 8, 202428,540 $875 Earn/vest after 3-year period (1/1/2024–12/31/2026) with TSR modifier
2024 TRSUsFeb 8, 202420,385 $625 Cliff vest on 3rd anniversary (Feb 8, 2027)
2025 PRSUsFeb 5, 202520,910 $675 Earn/vest after 3-year period (1/1/2025–12/31/2027) with TSR modifier
2025 TRSUsFeb 5, 202519,363 $625 Cliff vest on 3rd anniversary (Feb 5, 2028)

Historic PRSU performance (2012–2024 cycle awarded in 2022):

MetricThresholdTargetMaxActualPayout
3‑yr Cumulative EPS ($)5.63 7.50 9.38 5.04 0% (below threshold)
Relative TSR Percentile25th 50th 75th 14th 80% modifier (applied to EPS factor) → overall 0%

Equity Ownership & Alignment

Ownership ItemDetail
Beneficial Ownership38,296 common shares; excludes 115,506 RSUs not vesting within 60 days of April 28, 2025
Ownership as % of SOLess than 1%
Vested vs UnvestedUnvested RSUs excluded above; future vesting tied to performance/time schedules noted
Stock Ownership Guidelines3× salary for executive officers; all NEOs meet guidelines as of April 28, 2025; 1‑year post‑vesting holding period applies to equity
Hedging/PledgingExecutives prohibited from hedging, short sales, and derivatives; subject to restrictions on pledging; unvested RSUs cannot be hedged/pledged
Trading ControlsPre‑approval required; trading windows and 10b5‑1 plan requirements enforced

Upcoming potential supply (insider selling pressure mitigants):

  • Required 1‑year post‑vesting holding on RSUs dampens near-term sale pressure post vest .
  • 2024 TRSUs vest Feb 8, 2027 and 2024 PRSUs vest contingent on EPS/TSR through 12/31/2026; 2025 grants vest in 2028/earn through 2027 .

Employment Terms

TermKey Provisions
Agreement TermEffective 2/20/2019; amended 3/31/2022 (to 2/20/2025); further amended 4/25/2025 to extend to 2/29/2028 and update provisions
Base Salary$500,000
Annual/Long‑Term EligibilityEligible under company incentive plans; PRSU/TRSU mix; post‑vesting holding requirement
Severance (No CIC)If terminated without “cause”: Accrued amounts plus lump sum = base salary + average of last 3 annual incentive bonuses (subject to release)
Severance (CIC Double‑Trigger)If terminated without “cause” within 12 months after or 6 months before a change‑in‑control: 2× (base salary + average of last 3 annual incentive bonuses); unvested RSUs vest; amounts reduced to avoid “parachute payment” under 280G
Non‑Interference/Non‑Disparagement18‑month non‑interference obligation post termination or agreement termination
Retirement at Age 65Accrued amounts plus pro‑rata target incentive bonus (subject to release)
ClawbackIncentive Compensation Clawback Policy adopted Oct 19, 2023; amended Jan 2025 to expand triggers; RSUs subject to clawback
Trading/Hedging/PledgingPre‑approval, limited windows, 10b5‑1 restrictions; hedging/short sales prohibited; pledging restricted; unvested RSUs cannot be hedged/pledged

Investment Implications

  • Pay‑for‑performance alignment: High variable pay mix (370%→390% target bonus) and PRSU structures tie outcomes to multi‑year EPS and relative TSR; 2022–2024 PRSUs paid 0% due to under‑target EPS/TSR—evidence that equity awards are genuinely at risk .
  • Retention risk appears contained: Contract extended to Feb 2028; double‑trigger CIC protections; meaningful severance economics (2× base + average bonus under CIC termination) may stabilize leadership continuity .
  • Trading supply/selling pressure: Upcoming vesting cadence (2027/2028) and mandatory 1‑year holding period post‑vesting reduce immediate sell pressure; hedging/pledging restrictions further mitigate adverse alignment signals .
  • Execution track record: Hilltop Securities pre‑tax declined to $64m in 2024 vs $74m in 2023 amid market softness; annual bonus at 112% of target reflects strong strategic outcomes despite mixed financials (SBA launch, recruiting, risk management, culture) .
  • Governance signals: Robust clawback, ownership guidelines compliance, and prohibition of hedging/short sales underscore shareholder‑friendly alignment; say‑on‑pay support at 88% in 2024 indicates investor acceptance of the pay program .