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Sales Insights



Clocks vs Timers

Immediately upon entering Sales you'll find that Clocks turn into Timers. You'll never again look at a clock and feel like the day/week/month is never going to end. You will now have a 90 day timer that you will always wish was longer. In high pressure organizations, if you do not see success in 90 days you'll get one more chance before you're let go. This timer will vary depending on Sales Cycle and maturity of the organization...but it will always be there. The key to handling this is to stop attaching any emotions to the timeframe and work to build a good foundation of opportunities - always trying your best and working consistently so the highs and lows aren't so drastic.


You'll find this Timer concept so pervasive that it will infect many other areas of you life that are not work. It will be very important that you compartmentalize this concept. In reality there is plenty of time in your personal life to accomplish things without rushing. Something that I have to work everyday to remind myself. (There's a good book on this called The Ruthless Elimination of Hurry. A few holes in parts of it but generally gets it right.)


Depending on your age, family, responsibilities you'll be faced with two Healthy ways to deal with this Countdown Stress - 1. Find something more intense that demands absolute focus OR 2. Find something that slows you down


Examples of 1 I've found include: rigorous workouts, Brazilian Jiu Jitsu (although I don't recommend this unless you have calmed your ego and can dedicate 4 classes per week), marathon running, any kind of anaerobic sport.


Examples of 2 would be: Yoga, meditation, reading, hiking, anything that keeps your heart rate below 60% max It's imperative that you and your personal relationships understand the emotional highs and lows - as well as you being honest with yourself that this level of survival stress generally will drive your negative decisions - alcohol intake, personal choices, manner in which you treat people.

Committing to a Startup


As a Sales VP or Sales Associate at a startup it's very important to have a complete company and market background before committing to the organization. Startup life is fun and exciting, but high growth expectations and lack or resources will put more pressure on you to perform. If you work better in this environment, trust your instincts, and feel like you know a way to "do it better" you'll be a good fit for a start-up Tech business. However, these lows will take its toll on you and will never find the pinnacles of startup success by jumping ship when the future looks bleak. A few things that may help before taking the position:

  1. Develop a Personal Relationship with the Founding team

    1. 1. You'll need to really understand how these Founders behave in their personal lives and how they view the world before starting. If anyone on the C-Staff believe in a very Machiavellian way to business that involves a Zero-Sum game, you'll be sure they'll screw you when times get tough

  2. Deeply Understand the Comp Plan

  3. Negotiate your Severance before starting (in a Leadership Position)

  4. Understand the Market

  5. Understand the customer

  6. Understand what the company does not do well

  7. Ensure your boss is would be happy to pay you large sums of money

    1. There's a naturally greedy instinct with some CEO's and CFO's that don't want to cut commission checks larger than their own Salaries+Bonus. That should never be the case. If you make a large commission check, it means you've also made the company a lot of money. If you find that the Leadership does not value paying their sales team well - do NOT take that job.

  8. Talk to customers 1 on 1 and understand why they bought the solution

When considering taking a job at a new VC backed startup, it will be a very emotional period where you may get over excited and just believe everything is going to go great. Three months in you'll find the problems and will have buyers remorse if you don't carefully vet the opportunity and be willing to walk away at a moment's notice.


Whatever you do, don't expect to fall into a job at a company that is <1 year away from getting bought and expecting a multi-million dollar payout. You'll need to expect to put in the work to make that company valuable...which is the only reason you should receive any payout during and Acquisition or IPO.


Listen to the RSnake Episode "The Sales Game" with Kyle Kephart




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