Portfolio and Trading Specialist

Hiring Firm: Oakwell Private Wealth Management
Hiring Manager: Brian Luper - Brian@RIArecruiting.com

Oakwell Private Wealth Management is hiring its first Portfolio and Trading Specialist. This position will be PERMANENTLY REMOTE. The firm’s investment strategy is institutionalized through its Investment Committee and professionally managed models; your job is the layer where strategy becomes reality for households with significant taxable assets, concentrated and legacy positions, embedded gains, trusts, executive compensation, and customized Investment Policy Statement requirements. The models and the investment strategy belong to the Investment Committee, and the firm’s outsourced Chief Investment Officer. This role owns their implementation, not their selection. Roughly fifty households are expected to qualify.

You will work at the individual tax lot level, alongside experienced advisors who own the client relationship, building and executing each household’s implementation strategy from transition through ongoing management. Technology does the broad watching: systems monitor portfolios systematically, and you review the exceptions and opportunities they surface, applying the judgment an algorithm cannot, such as an upcoming withdrawal, a charitable intention, or a family’s intention for a legacy holding. One person is accountable for implementation from beginning to end. That person is you. The week is weighted toward household implementation, with a defined block reserved for firmwide trade quality.

Salary and Benefits

• Base salary of $90K-120K, plus a quarterly bonus plan tied to implementation quality: plans completed and kept on schedule, error and exception rates, and documentation completeness, alongside firm performance.
• Firm pays 75 percent of health care cost for the employee, with a 401(k) and company match.
• Twenty days of paid time off plus additional firm holidays.
• Cross-trained backup coverage, so that time away is real and the firm’s two-week continuity standard is met.
• 401(k) with company match
• Permanently remote position

What You Will Own

• Complex position strategies. Written, multi-year diversification plans for concentrated and low-basis positions, executed within each client’s capital gains budget, paired with loss harvesting. Conservative hedging under a dedicated options procedure is a later-phase capability of the Portfolio Strategist rather than a first-year responsibility.
• Tax-aware implementation. Systematic tax loss harvesting with household-wide wash sale tracking, tax-aware rebalancing within defined bands, asset location across taxable, tax-deferred, and Roth accounts, and multi-year tax-budgeted allocation transitions.
• Transitions and client situations. Tax-aware transition plans prepared before assets move, and implementation plans for real life: a business sale, an inheritance, retirement income, a large withdrawal.
• Firmwide trading. Trade ticket review and reconciliation across the firm’s accounts on a cadence confirmed through capacity validation and phased in as household implementation stabilizes, error documentation and escalation, and provider coordination, one accountable owner for the details that protect every client.
• Advisor partnership. Implementation strategy documents and plain-language education support for every qualifying household, with proactive briefings when milestones, risks, or opportunities need attention.
• The operating documentation. The procedures, household logs, and implementation records that make this function the firm’s rather than one person’s, documented to a standard that lets a successor assume the role.
• Priority under pressure. Daily reconciliation carries a deadline and household tax work does not. The role specification names in writing what yields first when volume spikes, and who covers it.

What You Bring

• 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.
• A documented-process mindset where accuracy, fairness, and efficiency take priority over speed, and the 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, and supports a later-phase capability rather than a first-year duty.
• Employment is subject to the firm’s Code of Ethics, personal trading pre-clearance, outside business activity disclosure, and a background check.

What Success Looks Like

• First ninety days. The trading SOP learned end to end, reconciliation running clean, and implementation plans drafted for the first wave of qualifying households.
• First year. Every qualifying household on a written implementation plan, harvesting and household-wide wash sale surveillance running on the agreed cadence, and the first transition wave complete.
• Throughout. Errors and exceptions documented and resolved, realized gains managed inside each household’s budget, and advisors briefed before they have to ask.

The role reports to Financial Planning Manager, with investment oversight from the Investment Committee. Trade authority, approval thresholds, and escalation are defined in the role specification.

The Process

Qualified candidates will start the process by having a 15- to 30-minute zoom interview conducted by our consultant (the hiring manager for this position). If there is ground to move forward, you will be asked to fill out a Career History Form and if you are selected to advance in the process, you will meet with the firm. Qualified candidates will be asked to take assessments.

Ideal Start Date: January 2027

We are an equal opportunity employer.