50 Things I Learned About Sales Working With Start-Ups

We help our customers focus oSales Learningn building the right type of sales organizations for their unique and products and services. We focus on The 4 P’s: People, Performance, Process, and Planning. Whether you are building an Inside Sales Team, a Lead Gen Team, or an Enterprise Sales Team we continually see the same things across all clients no matter how big or small.

With this in mind we have collected some of the things we have learned and wanted to share them with you.


    1. More often than not athletes are not always built for sales.
    2. Sometimes people with less experience and better attitudes are better than those with a ton of experience.
    3. Invest in Customer Success very, very early, they are the lynchpin between sales, support, marketing, and product development.
    4. If a candidate cannot remember their best reward for selling, they are not a real sales person.
    5. A real sales person will admit money is a motivator but recognition means more.
    6. If your sales people tell you they hate recognition, stop recognizing them and see what happens.
    7. People who can admit to being a manipulator tend to be the strongest sales people.
    8. Your top sales person will rarely make a good manager and should only be promoted if they have first had a team lead role.
    9. Millennials like money, but they value more than just money in a job.
    10. Millennials need to understand why, not just told why.
    11. If you are just beginning your sales career get experience selling some Saas product ASAP.



    1. You cannot teach someone how to hate losing.
    2. Sales Leaderboards should be shared with the entire company at least once a week if not more.
    3. As a sales leader you should always be working your own book of business.
    4. Every person on the sales team needs a dashboard emailed to them 3 days a week at minimum.
    5. If you do not know the difference between motivation and inspiration then you not a good sales leader.
    6. Spiffs work, quit complaining that you are “paying people” to do their jobs
    7. No matter how much experience a sales person has, it’s not unusual for someone to forget one simple thing, ask for the sale!
    8. Any sales rep who cannot tell you “how they sell” will be become cancerous when they inevitably hit a slump
    9. Your war stories about “back in the day” are really for your entertainment, not your teams’, and should only be told in social situations. Preferably after the 2nd
    10. A good sales person in an interview will be able to tell you their best sales win and their worst sales lost stories without hesitation.
    11. If you are a sales rep and your company does not provide tools like Salesforce, InsideView, ToutApp, SalesLoft, Hoopla, etc.,  get out now why you still can and find a company who understands the value of time management, motivation, and inspiration.
    12. Too often Saas companies think their sales reps understand the value of Saas but when asked directly they often times have no clue what Saas even means.
    13. Customer Success will help you close more new business than you can even begin to imagine.
    14. Customer Success personnel are not closers in the tradtional sense of sales. Give them support.


    1. Subscribe to a single sales philosophy throughout the entire organization. (Sandler Sales and The Challenger Sale are two of our favorites!)
    2. Make sure your sales process in your CRM mirrors your overall sales philosophy.
    3. The sales process is no longer a chess game. It’s a 3Dimensional chess game called Strato-Chess made popular by Star Trek.
    4. In today’s democratized sales buying process one must be astutely aware not only of the milestones that need to be achieved in your sales cycle but also the attributes that surround those milestones.
    5. You have to earn the right to ask your prospects questions.
    6. You must be willing to politely challenge your prospects status-quo, even if they initially disagree.
    7. Your prospects do not actually care about you, what you do, or how you do it. They only care about results.
    8. Your process means nothing, the buyers’ journey means everything. Marry the two.
    9. If you spend the first 10 minutes of your pitch talking about yourself you sound just like your competition.
    10. Sales prospecting should belong to dedicated personnel.
    11. All AE’s should be responsible for prospecting activities in their targeted “hit list”.
    12. In a competitive sales situation winning the sale will not always be about what you do but how you do it.
    13. CEO’s who help close deals often do not realize it is their title and vision that people are buying in addition to the product or services.
    14. Remember to ask for the sale.


    1. Hire slow, fire fast.
    2. Do the math, a bad hire costs over $100,000 in their first 90 days.
    3. Only playing Monday morning quarterback after a sales call does not make you a good sales leader.
    4. Scaling a sales team does not mean throwing more bodies at the revenue target.
    5. Fill the funnel first before you hire more closers.
    6. Sales training does not equal 2 days with a product manager and being told to make 90 calls a day.
    7. If you have a cancerous sales rep, remove the cancer as soon as possible and do it with compassion.
    8. Sales training is continuous and should be done 4-6x a year.
    9. The moment you think you know everything about sales is the tipping point for when sales begin to decline.
    10. It is your AE’s responsibility to help groom your SDR/BDR team to become real sales reps.
    11. If you cannot stomach how to make the “sales sausage” it’s best you stay out of the kitchen.


Yes, we know this is a lot to digest here. Our recommendation is to choose one of the 4-P’s you want to focus on for a specific amount of time. Implement a solution, measure it, iterate, and then move on to the next one. Unsure where to start? Contact us and we gladly point you in the right direction.


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