1.5 years in sales!

It is hard for me to believe I have been back in the US working for over 1.5 years already. To some extent I feel like I just got back from living abroad in Spain. Walking downstairs everyday to take the metro to work, speaking Spanish, and just enjoying the European way of doing things.

At the same time though, the past 1.5 years have been full of priceless experiences. As I work in enterprise sales, I wanted to write a brief post talking about some of the lessons I have learned so far.

I am by no means any sort of thought leader, I just wanted to share some of my reflections from my experiences. In short, this post will be broken down the following way:

  • Takeaways from 1.5 years in enterprise sales
    • The importance of hustling
    • Smart persistence is key
    • Staying relevant to your customers is important!
  • 3 actions I’ve taken to start implementing these ideas

Takeaways from the past 1.5 years

Hustling leads to results

This lesson is one of those I really wish I had learned at an early age – however, the overall takeaway here is it really seems like those who put in the hard work tend to be those who reap the rewards (this isn’t ALWAYS the case as sometimes just being in the right place at the right time works out, but that seems more like the exception than the rule).

If I had to come up with a definition of hustling I would say something like it is a quality in someone where that person finds a way to accomplish a goal, or at a minimum they put in 100% of their energy, regardless of what obstacles may arise. That person will think outside of the box, get in early and leave late, be aggressive when it counts yet also charismatic when the situation calls for it, and this person doesn’t make excuses.

When I look around at the top salespeople at work I think about 5-6 people who stand out from a crowd of about 30. One of the biggest. What really sets these people apart from the rest is their hustle. They just want to succeed more than the rest of the salespeople and they show it through their actions.

The rest of the people may say they want to make sales but then they leave early, they don’t go to events, and they aren’t studying the trends to make sure they are on top of their game.

Smart Persistence is key

You gotta throw some jabs before you throw your right hook.

-Gary Vaynerchuk

This lesson was a hard one to learn as in the process of learning it myself there wasn’t much feedback to tell me whether I was on the right track or not…After receiving a few responses from prospective customers after continuously jabbing them 6-7, with no response during those 6-7 follow ups, I finally began to see the power in it though.

In short, people are busy, and timing plays a big role in when I was able to get a response from prospective customers. With that in mind, I continued to follow-up with these prospective customers, EVEN if they weren’t responding to my emails, until they either told me to stop or they finally got back to me about setting up a call.

What I tried to keep in mind in this process was to not just send follow-up emails saying “Hey Mike, just following up here, do you have time for a call next week?” over and over. Rather, I would try and think about how I could provide value to this prospective customer – as in, what kinds of events might this person want to be aware of, or what kind of news would be very relevant that I could share – and then send those as a conversation starter.

I can’t tell you the amount of times I would get a response on the 8th email saying “Miles, sometimes it helps to be persistent, please forgive my delay, things have been really busy. How’s your schedule next week for a call?”

Now, I stay very organized with all the people I am in contact with (as I may be trying to contact upwards of 300 people at a time) and track when I last messaged this person AND what would be relevant to send him or her next.

Staying relevant to your customers is important!

A wise man adapts himself to circumstances, as water shapes itself to the vessel that contains it. –Chinese Proverb

A huge problem my organization is facing is many of our partners who have been with us for more than 2-3 years tend to end their partnership with us. Although we are making a decent amount of new sales which moves our revenue numbers up, the fact that we are losing so many members keeps our total revenue stagnant as we lose just as many partners as we are adding.

When you really look into the product we are offering though one of the biggest things you notice is our core offering isn’t THAT much different than what we offered a few years back. Therefore, once a corporation no longer needs our core product there really isn’t a reason to continue doing business with us.

One way we are combating this though is to use what some people call the problem-solution method. In short, the problem-solution method simply means you are constantly evolving your product to match the problems your customers are facing. In our case, we are taking time to understand once our customers no longer need our core offering, what other problems are they facing that we can potentially address using our network and knowledge.

The beauty of this method is it drives innovation through needs of your customers – rather than trying to come up with solutions based on what you think the customer may want.

3 actions I have taken to start implementing these ideas


As far as hustling goes, what really helped me light that inner fire was coming up what my ideal life would look like in 5 years. I had to sit down and really think about this one but after allowing myself to dream a bit I came up with a nice idea.

Then, I turned this idea in to actual goals that I would like to achieve. Goals like where I wanted to be financially, the type of house I wanted, where I would be living, and so on.

Once I had all of this written down, it gave me something to work towards. Now, work is jut a means to an end for me instead of something “I have to do.”

I try to bring my A-game to work every day because I know all my effort is bringing me closer and closer to my long-term goal.

Smart persistence

As far as persistence goes, for the time being the biggest things I am currently doing are:

  1. Staying organized
  2. Following up regularly

The first one is pretty self-explanatory. It is important to mention though because during my first 6 months I wasn’t that organized and I had a hard time tracking who I was talking to and where I was in the conversation.

For following up regularly, a big part of this is to truly try and empathize with the person you are trying to reach and think about the types of things that he or she cares about. I’m still trying to perfect this one myself but I have a better idea of what I need to do, I just need to get out there and actually get to know my prospective clients better!

Staying relevant to my customers

Along the same lines of what I stated above in the smart persistence area, truly understanding the wants and needs of your prospective clients seem to be a good way to be able to deliver the solution that best matches him or her.

Therefore, I’m working hard with my team to understand what the wants and needs of my current customers are. With that information we hope to find out how we can improve our product to best serve our clients.

In closing

I’ll be sure to continue to share thoughts and lessons learned from my journey as they come.

In writing this blog I am starting to wonder if I should consider changing the medium of delivery to video or audio instead of or in addition to a written blog. The reason for this is I personally don’t have time to read long blog posts. However, I do have time for bite-sized podcasts or articles that are consumable on commutes. Lets see!

Feel free to leave any thoughts or feedback in the comments below! Until next time.

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