Portfolio and Trading Specialist

Windward Recruiting

. Own implementation of investment strategies for households with significant taxable assets, concentrated and legacy positions, embedded gains, trusts, executive compensation, and customized Investment Policy Statement requirements .

Posted 11/5/2026full-timeRemote • Texas • United StatesSeniorLead💰 $90,000 - $120,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in portfolio implementation and tax-aware trading strategies, with a strong focus on capital gains management and tax lot accounting. Proficient in developing and executing customized investment strategies while maintaining compliance with regulatory standards.

Highest-signal resume keywords

Portfolio ImplementationTax Lot AccountingRebalancing and Trading PlatformsSeries 65 RegistrationCapital Gains Management

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Tax-Aware Trading MechanicsLoss HarvestingInvestment Policy Statement DevelopmentTrade Ticket ReconciliationDiversification PlanningWash Sale TrackingHedging Concentrated PositionsDocumented-Process MindsetTransition PlanningDaily Reconciliation Management

Soft Skills

Judgment ApplicationProactive CommunicationDiscipline to EscalateAttention to DetailPrioritization Under Pressure

Tools & Technologies

Orion EclipseTamaracIRebalSchwabFidelity

Certifications & Qualifications

Series 65CFACIMACFP

Industry Keywords

Registered Investment AdvisorWealth ManagementTrust CompanyAsset ManagementInvestment Operations

About the role

Key responsibilities & impact

Own implementation of investment strategies for households with significant taxable assets, concentrated and legacy positions, embedded gains, trusts, executive compensation, and customized Investment Policy Statement requirements
Build and execute household implementation strategies from transition through ongoing management at the individual tax lot level
Review portfolio monitoring exceptions and opportunities and apply judgment to household-specific circumstances
Develop written, multi-year diversification plans for concentrated and low-basis positions within each client’s capital gains budget, paired with loss harvesting
Perform systematic tax-loss harvesting with household-wide wash sale tracking
Conduct tax-aware rebalancing within defined bands and asset location across taxable, tax-deferred, and Roth accounts
Prepare tax-aware transition plans before assets move
Implement plans for business sales, inheritances, retirement income, and large withdrawals
Review and reconcile trade tickets across the firm’s accounts
Document and escalate errors and coordinate with providers
Prepare implementation strategy documents and plain-language education support for qualifying households
Provide proactive advisor briefings on milestones, risks, and opportunities
Maintain procedures, household logs, and implementation records
Manage daily reconciliation deadlines and prioritize work under volume spikes
Report to the Financial Planning Manager, with investment oversight from the Investment Committee

Requirements

What you’ll need

Seven to ten years in portfolio implementation, trading, or investment operations at a registered investment advisor, wealth manager, trust company, or asset manager
Hands-on experience with rebalancing and trading platforms (Orion Eclipse, Tamarac, iRebal, or similar) and major custodial platforms
Schwab and Fidelity strongly preferred
Working fluency in tax lot accounting, wash sale rules, capital gains management, and tax-aware trading mechanics
A bachelor’s degree in finance, economics, accounting, or a related field
Documented-process mindset prioritizing accuracy, fairness, and efficiency over speed
Discipline to escalate rather than improvise
Series 65 or investment adviser representative registration
CFA, CIMA, or CFP not required but encouraged to apply
Experience hedging concentrated positions with covered calls, protective puts, or collars is valued
Employment subject to the firm’s Code of Ethics, personal trading pre-clearance, outside business activity disclosure, and a background check

Benefits

Comp & perks

Quarterly bonus plan tied to implementation quality and firm performance
Firm pays 75 percent of health care cost for the employee
401(k) with company match
Twenty days of paid time off
Additional firm holidays
Cross-trained backup coverage
Permanently remote position