Jerry Swain

Career coach · Solana Beach, CA · virtual

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"Coaching here is not advice by the hour." (in their words, on their website)

Services

ServiceWhat is includedPrice
Compass: Financial Reporting and KPI Dashboard
CFOs and CEOs of growth companies		 Improve reporting quality, timeliness and efficiency · Develop KPI dashboard, trend analytics, and data analysis · Move from lagging metrics to leading indicators e.g. sales forecast, cashflow forecast on request
Multi-Point Financial Review and Plan Development
CFOs and CEOs of growth companies		 Business valuation model prepared with industry comparables on request
Positive Cash Flow (PCF): Business Restructuring and Profitability
CFOs and CEOs of growth companies		 Assist with discussions with Bank to permit time to prepare a plan · Extensive cash flow and financial analysis and guidance to create a full business restructuring plan · Restructure ready and support through the changes · Analysis and support to the break even point and path to profitability (month-end reviews) on request
CFO Coaching: Financial Coaching and Support
CFOs and CEOs of growth companies		 Coaching 4 hrs/month · 2 hrs/month of offline support with data analysis, modelling and review as needed · Extensive financial planning and analysis, including capital structure · M&A preparedness · Internal controls, budget process, and corporate governance on request
Executive Coaching
CEOs and their teams		 Individualized coaching focused on business growth · Neutral sounding board without judgment · Annual and quarterly planning built into every engagement · Coaches who are former CEOs or Presidents from $100M+ companies · Proven methodology called Make BIG Happen System on request

As published on their website, read Sep 30, 2026.

Where they fit

StudentsEarlyMidManagerDirectorVP / C-suite
Resume and LinkedInnononononono
Interviews and offersnononononono
Job search strategynonononoyesyes
Career direction and changenononononono
Leadershipnononononono
Personal brandnonononoyesyes

How they work

Process
Understand client goals, challenges, and opportunities · Clarify vision · Assess current situation · Develop plan
Assessments
The BIG. CEO Score, Business Diagnostic
Before coaching
CEO, various companies; Investment Banker, Investment Banking Industry (25 years)

Do it yourself, or hire a coach?

Doing it yourselfUsually enough whenA coach earns the fee when
Job searchA target list, a weekly plan and steady outreach. Callings builds the weekly plan and tracks every application, free.Interviews are coming in.Three months without traction, or a senior search that runs on your network.
Personal brandA consistent story across your resume, LinkedIn and a personal page. Callings builds the page, free.The role you want does not depend on visibility.Visibility or thought leadership is part of the role.

Times are our estimates. Try Callings.

Questions to ask before hiring

  1. What does it cost in total, and what is included? (no published price)
  2. What are your cancellation and refund terms? (no refund terms on their site)
  3. Who do you usually work with, and how long does a typical engagement last? (always worth asking)

What they publish

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