Episode TwoHundredSixtyNine

Building Your Sales Career

Guest: Jesse Rothstein, Global Account Manager for LinkedIn Sales Solutions

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About This Episode

Building a career in sales comes down to three simple things: knowing yourself, relationships and choosing your tactics.

I am joined by Jesse Rothstein, Global Account Manager for LinkedIn Sales Solutions, to discuss these things in more detail so you can use them to enhance your sales career, starting right this moment.

Let’s dive in!

Useful resources:

Distilling the purpose of sales

There are a lot of elements and processes involved in sales, but Jesse’s approach is about doing the simple things really well over time.

He mentions that sales is about helping people solve their problems. 

Problems they may or may not be aware of.

So, in the process of distilling the purpose of sales, it’s wise to also look deeper at why you’re in sales to begin with.

Key themes from ‘Carry That Quota’:

Jesse’s learned so much throughout his career, in startups and in MNCs.

He was inspired to go ahead with his long term goal of putting his knowledge down for people all over the world, today and for generations to come, to benefit.

We got some time during today’s conversation to talk about the three key themes from inside Jesse’s book: ‘Carry That Quota’.

3 key themes:

Here are three key themes, or pillars as Jesse calls them, from his book:

  • Knowing yourself: self-awareness and self-confidence are critical for success in a sales career, as well as knowing how you personally process rejection, because it will happen.
  • Relationships: this includes clients, co-workers, partners, managers – everyone in your ecosystem. Relationships are the currency of business, and need to be maximized, nurtured and developed.
  • Tactics only experience can teach: learn by doing, and by how others do. Maximize your productivity to become the best you can be. Jesse’s book shares tactics that can’t be found anywhere else.

Advice for people building their sales careers:

It’s important to remember that building a sales career isn’t limited to entry level positions. 

Jesse and I discuss his three pillars in the context of anyone looking to embark on the journey that is a sales career, including those who may have just started or have been in this space for decades and want to take that a step further.

Knowing yourself

Before you can build relationships with others, you need to define your relationship with yourself:

  • Develop and expand your sense of curiosity
  • Invest in introspection from time to time
  • If you can’t see yourself handling rejection well, sales might not be the space for you
  • Understand why you’re in sales and what it means to you – what’s driving you?


I asked Jesse for advice specifically for learning how to navigate relationships early on in a sales career, before there are many relationships. His advice was:

  • Be memorable
  • Be different from the other sales people you see
  • Personalize the buying experience for your customer
  • Engage in a way that etches a memory for both you and the customer, that can be recalled between 5-20 years from now – help that person or team to that extent and in a manner that you, and that buying experience, stays etched in everyone’s minds for as long as possible (in a good way)

Tactics from experience

In this episode we focus on one example Jesse highlights, which I think we all really need more knowledge about but doesn’t formally get taught very often: time management. 

The context for this example is that when you look at your calendar, you see all the meetings you have scheduled, probably up to a few weeks in advance:

  • Set time in your calendar to execute follow-up tasks from those meetings or calls
  • Include the follow-up as an action point on your own meeting agenda or notes
  • If you can follow up on the same day, that’s amazing, but try not to leave it longer than 2-3 days out
  • Thank the prospect or customer for their time in your follow-up communication

Get in touch with Jesse Rothstein about this topic on LinkedIn.

About The Podcast

The Sales Engagement podcast is the #1 podcast focused on engaging your customers and prospects in the modern sales era. This show features real-life stories and best practices from revenue leaders doing the job day in and day out, in a casual, radio-like talk show.

Each episode features modern tactics, strategies, hacks, and tips to get the most out of your sales engagement strategy and help you navigate the next generation of sales. You’ll find energetic talks that will provide you with real actionable value around building meaningful connections and creating a better selling experience through authentic conversations that you can measure.

The Sales Engagement podcast is here to help B2B sales leaders, customer success leaders, and marketing leaders innovate and usher in the next era of modern sales by building pipeline, up-selling customers, and ultimately generating more revenue with more efficiency.

Hosted by Joe Vignolo, Senior Content Managing Editor at Outreach, and Mark Kosoglow, Vice President of Sales at Outreach.

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