Portfolio and Trading Specialist

Hiring Firm:
Oakwell Private Wealth Management
Hiring Manager:
Brian Luper -

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.

• 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

• 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…