Transitioning Executive

Chief Marketing Officer

Jessica Cohen, 50, Chief Marketing Officer (CMO)

Jessica Concern

Jessica had spent almost 20 years working for a leading company as a brand executive.  She had hit what felt like the “glass ceiling” and was offered a Chief Marketing Officer (CMO) position from the CEO of a younger and growing company.  She had worked with the CEO previously at her current company so they had familiarity working with one another.  However, she wanted to understand where she was at as far as benefits and compensation so she could compare and negotiate and make good decisions about her potential future.  She also wanted to be smart about her wealth and get it on track to support the future she envisioned for herself.

Primary Goals:

  • Financially independent by 60, making work optional and spending time how she wished
  • Outsource wealth responsibilities to an expert
  • Devise a plan that optimizes her investments and benefits:
  • Profit sharing assets
  • Personal assets
  • Deferred compensation plan
  • Equity compensation (in the form of options, restricted stock units (RSU’s) and Performance-Based Restricted Stock Units (PSUs)) and employee stock purchase plan (ESPP)
  • Disability insurance
  • Life insurance
  • Health insurance
  • Directors and officer insurance
  • Property insurance.
  • Evaluate her stock concentration and create and implement an investment plan that removes some or most of the risks.
  • In case of an untimely death ensure her family can continue on with their lifestyle and education
  • Reduce taxes where possible
  • Provide guidance on her current planned transition

Results Executed:

Transition Planning

  • Created a compensation and benefits score card to compare to her offer. Used this to help structure the compensation and benefits negotiations.
  • Asked and negotiated for a severance package if things didn’t work out with the new firm.
  • Reviewed non-compete clause and separation policies of current and old firm to evaluate risks on new employment.
  • Reviewed negotiating approaches to consider when negotiating for a new position.
  • Reviewed and advised on the tax implications in the transition and used those in negotiations.

Wealth Enhancement and Tax Planning

  • Removed stock concentration risk and created one diversified portfolio across all accounts (reducing taxes) that attempted to maximize expected return and considered Jessica’s specific risks.
  • Evaluated Jessica’s cash flow and reduced income, taking full advantage of her benefit programs to reduce taxes. Additionally, minimized taxes on equity transactions and harvested losses when possible.
  • Utilized a Health Savings Account to reduce current and future taxes.
  • Developed a Roth conversion planning strategy to reduce life time taxes.

Asset Protection and Estate Planning

  • Evaluated insurable risks both inside the benefits at the new company and personally and, collaborated with Jessica and other experts on the best policies and mitigation for her.
  • Evaluated uninsurable risks and collaborated with Jessica and other experts on how to mitigate those risks in the form of legal structures and best practices.
  • Evaluated the protection and safety of assets, collaborated on costs and other approaches to protect the exposed assets.
  • Evaluated estate wishes and taxes, collaboratively developed a plan prior to bringing in an estate attorney with the appropriate experience to provide the expertise and execute the plan.


Note: The above case study is hypothetical and does not involve an actual Pacific Capital Works client. No portion of the content should be construed by a client or prospective client as a guarantee that he/she will experience the same or certain level of results or satisfaction if Pacific Capital Works is engaged to provide investment advisory services.

still have questions?