Buyers Boutique

7 questions to ask before you leave tech sales

Your vest lands next month. The share price is still under where it was when you joined, and Sydney is still out of reach. Start with these seven questions.

Send me the 7 questions
Mike Wingfield

Who wrote this

For more than ten years I ran APAC sales teams at Twilio, New Relic and Deel. I enjoyed the work, but the targets kept climbing. My wife Jaq and I built property alongside our careers, and that gave us the choice to step away. These are the questions I wish I'd asked earlier.

The seven questions

  1. What does my life actually cost each year once the salary stops?
  2. How many unvested RSUs would I walk away from on my last day?
  3. How much of my wealth is sitting in one ticker?
  4. How will a lender read my bonus and commission history?
  5. Should I lock in my borrowing while I still have a payslip?
  6. What tax will I pay when my shares vest, and when I sell?
  7. What does my next property need to do: income, growth or both?

Three of these belong with your broker or accountant. The email tells you which, and why each one matters.

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