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About the Role
Oakwell Private Wealth Management is seeking its first Portfolio and Trading Specialist to manage the implementation of investment strategies for households with significant taxable assets. This role is crucial for translating strategy into reality, focusing on individual tax lot management, transition execution, and ongoing portfolio oversight. You will work with experienced advisors, leveraging technology for systematic monitoring while applying critical judgment for exceptions and opportunities.
Responsibilities
- Own the implementation of investment strategies from transition through ongoing management.
- Manage individual tax lot level implementation for approximately fifty households.
- Review system-generated exceptions and opportunities, applying human judgment.
- Develop and execute complex position strategies, including multi-year diversification plans for concentrated and low-basis positions within capital gains budgets.
- Execute tax-aware implementation, including systematic tax loss harvesting, tax-aware rebalancing, asset location, and multi-year tax-budgeted allocation transitions.
- Prepare tax-aware transition plans and implementation plans for significant client life events.
- Oversee firmwide trading, including trade ticket review, reconciliation, error documentation, and provider coordination.
- Create implementation strategy documents and provide plain-language education support for qualifying households.
- Develop and maintain operating documentation, including procedures, household logs, and implementation records.
- Prioritize tasks under pressure, managing daily reconciliation deadlines and tax work.
Requirements
- 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 documented-process mindset prioritizing accuracy, fairness, and efficiency.
- Discipline to escalate rather than improvise.
- Employment is subject to the firm’s Code of Ethics, personal trading pre-clearance, outside business activity disclosure, and a background check.
- Experience hedging concentrated positions with covered calls, protective puts, or collars is valued.
Skills
- Portfolio implementation
- Trading
- Investment operations
- Rebalancing platforms
- Trading platforms
- Custodial platforms
- Tax lot accounting
- Wash sale rules
- Capital gains management
- Tax-aware trading
- Options trading (later-phase capability)
Location
- Permanently remote
Work Type
- Permanent
- Remote
Experience Level
- 7-10 years
Education Level
- Bachelor's degree in finance, economics, accounting, or a related field.
- Series 65 or investment adviser representative registration.
- CFA, CIMA, or CFP encouraged but not required.
Salary/Compensations
- $90K-120K base salary
- Quarterly bonus plan tied to implementation quality and firm performance
Benefits
- 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 for time away
About the Company
- Oakwell Private Wealth Management is a firm focused on providing investment strategies for households with significant taxable assets.
Equal Opportunity
- We are an equal opportunity employer.