9 Sales Gems From Josh Gillespie Part 1

You made it! If you missed the introduction post from Josh (our OG of sales), click here.

Here are the first 9 gems that will help you along your sales journey. I recognize there isn’t a one size fits all approach to sales for every team, org, etc. But, these tips can help you along the way. Take what is valuable to you and use it in your daily life in sales.

Necessity breeds success

For me, I only became successful in my sales career once I had to be. We always want to be great at what we do…but ask yourself what would cause you to have to be great. Becoming a bonus dad to my stepdaughter put my sales role in a new, opportunistic light. Add in a mortgage and there you have it…necessity!

Be ethical

There are a million ways to get to the finish line and close a deal. But there’s usually only one right way. There are good actors and there are bad actors. If you assume there’s any grey area, then you’re not a good actor. In most sales roles, we are “losing by design” and ultimately lose more than we win. There’s a right way to lose that is conducive to future success. After 9 years at PandaDoc, roughly 20% of my new business revenues come from “boomerang” opportunities that I previously lost. In the SaaS subscription game, we get another chance with the same prospects nearly every year. Lose with class and shake the other team’s hand. Ask for feedback, “What could we have done better that could help us improve our services for others moving forward?” 

Authenticity is the highest-valued feature of any sales transaction

The only way to build trust consistently is to be 100% your (best) self. The best way to build trust is to attempt to disqualify a prospect early. It’s essentially the strongest method of showing that you actually care about your respective time. And while we’re on the topic of disqualifying…

Disqualify all misuse of our time

This one is tough and takes time to master as in sales, we often think we’re in the business of being accommodating to others (both prospects and internally). That may indeed be the case, however, we should first be in the business of disqualifying opportunities. Our limited time has to be spent wisely and in the right places only. Don’t confuse likeability with durability and know where to spend your time based on the principle of…

Reciprocity

The best business relationships are mutual collaborations. Only spend time where time is being spent. Prioritize the opportunities that display the highest levels of engagement. Protect your time through professional courtesies like Mutual NDAs and calls to align the Executive Sponsors from each side. If a prospect is unwilling to engage with an NDA, they’ve just proven an inability to execute on an MSA to follow.   

Stay motivated

Perhaps the toughest thing in life is to stick with it. Change is often the easier path. I’ve seen many reps jump around every 1-2 years and it’s always strange to me. Sales gets easier the larger your book of business becomes. Every year I’ve been with PandaDoc, lead generation becomes less arduous thanks to my existing book of business and the referrals it produces. How do you stay motivated? It's a highly personal question, but for me, I like to find every chip I can to put on my shoulder. I can revive memories from every time I was doubted, passed up on, insulted, offended, or denied. I remember an interview where I felt personally attacked. The VP didn’t want to hire me because of my use of “colloquialisms” and he preferred to hire Stanford grads. My father was an English teacher and my entire family went to Stanford except for me, so that one hit a note with me in a way that still fuels me on calls today. 

Only give discounts in exchange for referrals, case studies, and/or customer reference calls

There are several ways an existing customer can help you grow your book of business. Inevitably everyone asks for a better price when dealing with a salesperson…the response should always be an ask in return to help you at a more partnership level. Customer reference calls especially have been a huge tool for me over the years. A happy customer will typically take a call if you just ask them nicely (and send them some swag as a thank you!) 

Research is key

It’s always worth an extra 5-10 minutes to go online and research every lead or opportunity before you jump on a call. If sales is a numbers game to you and you are skipping this step, it’s not sales. Sales is the process of adding value to a buyer’s journey. One simply cannot do this effectively without first gathering intel. No two apples are exactly the same, it’s your job to find what makes them unique (and this will convey genuine interest to your prospects). 

Data entry is key

I bet you weren’t expecting me to say that. I cannot stress how important it is to stay organized. For me, it’s a constant process that requires attention every single day. Roughly 20% of my day is spent updating my records, which is also a good sign of how many activities I am logging. We have to commit ourselves to mastering the unglamorous parts of the job, otherwise, we’re giving credit of our successes to luck and happenstance. What separates great from good sales reps is due diligence in this regard. 

Recap

Tell me about your experience with these 9 gems that I shared above. Are there any that you strongly resonate with? Are there any that you are surprised they are on the list? Let me know in the comments.

Ready for Part 2? Click here!