Burning Career Questions Answered

Jake + Friends: Building Your Career  Original Air Date: July 13, 2020

Watch the recording of the original session to hear more career advice on how to get to where you want to go in sales and how to prepare for the interview, the role, and the journey.

We had some great questions from this LinkedIn Live session. But I wasn’t able to get to them all, so I put together some quick videos for each of these guys, because who doesn’t prefer to watch a short video? 

Question 1 from @Geoff W: I am currently actively looking for a role with not a lot of luck given the landscape. My goal in 2020/21 is to move from an IC to sales leader / sales operations. Focusing more on the strategy, coaching, and process implementation side. How do I make that transition?

To Geoff - There are two things you need to do now to prepare for this transition.

#1 - Start to get the skills you need for this role right now that you don’t have. If you’re looking for a sales operations role, go through the Salesforce Admin certification and get certified in everything you can. Don’t wait to get picked for a role to learn.

#2 - Start reading leadership books and networking your face off. Talk to multiple sales managers and ask them what made them successful, what worked, and what didn’t.

Question 2 from @Tony Johnson: Hi, my name is Tony, and I currently work at Director level in Mobile Accessories, selling to retail. I'm looking to transition to SaaS. What's the key sales differences I should be aware of?

To Tony - Great question, man.

SaaS sellers like to think SaaS is so different, but it really isn’t. I came from a lot of different industries before going into SaaS. It’s not that different.

BUT. The key thing you’ll want to highlight when applying for this role is how you built repeat customers. 

Why SaaS is so nuanced is it’s all about monthly recurring revenue. If I was hiring you, I’d want to see someone who knew how to sell something that had repeat customers.

So that’s where you should focus as you apply and interview. 

“My job was to build rapport. Here’s how I established relationships with businesses. Here’s how I built recurring relationships. Very similar to Saas,” said Tony.

Question 3 from @Mathew McComb: Can you give an example of how to create a business case for an interview or other promotional needs?

To Matthew -

Step one, Matt, is to go to g2.com and compare different softwares and competitors. Look at how people talk about this company in the market.

Step two, is go to the company’s website and see how they position themselves in the market and what their customers are saying (both on G2 and their website).

Take this information you’ve gathered to the interview and position it like this:

“Here is how I’m going to sell your product because I know what it is, and I know who the target buyer is. Then, here is how I’m going to competitively differentiate between these three companies. These are my initial thoughts from what I’ve been able to gather, and I’m going to build on that as I come in and work for you.”

Do this and I guarantee you’re going to stand out.

Question 4 from @George R Hauffe: I would like to know how to approach an opportunity I know of, it’s completely in a different industry that I am accustomed to, but I see an opportunity to lead.

To George -This is very similar to my advice to Tony. You’ve got to start to pull out what’s relevant. I’ll give you an example. 

Let’s say this industry with the new opportunity is in oil and gas and you’ve worked in insurance. (I’m completely making this part up, obviously.)

In this scenario, I would focus on the fact that I’ve worked with legacy buyers and industries that moved slow.

I’d try to highlight my work experience in a way that is parallel and is actually relevant to the new industry. 

This is what I don’t see enough people doing when trying to transition. You’ve got to do a really good job of making it really easy for the new opportunity to see the correlation between what/how you used to sell and how it actually is similar to what you’re applying for.

Question 5 from @Luke Shaw: Enterprise sales is my goal. What resources/ industry knowledge tools can I utilize to prepare me for that role?

To Luke -I love enterprise sales. It’s my fave.

For resources and tools, I got you. DM and I’ll send you an online course we have and a training deck called Navigating Complex Deals.

The key to enterprise deals - really the only thing - is there are a lot of different stakeholders. 

If you want to be really, really good at enterprise sales, you can’t rely on a champion. You have to pull in the right people when you need to.

That’s my #1 piece of advice for being in enterprise sales. You can’t just worry about your champion. You’ve got to realize that your champion is over here and you’ve got to find the five other people you need to work with to close the sale.

That’s what’s up, my friend.

Question 6 from @Benjamin Roach: Getting burned out in the start-up world. Best advice for making a transition into the traditional cooperate world? (BD management).

To Benjamin -

First off, that’s smart, Benjamin. You have to spend some time in the corporate world, preferably in the beginning of your career.

I started off in kind of small sports for smaller teams. Then I went into corporate when I started at CareerBuilder. When I went back into Startup, I was at a much higher level.

Here’s my advice when making the transition: Sell out. 

That may sound like the worst advice you can get, but there is a reason that corporate companies train the way they do.

Let me tell you my story about how I came into my first corporate job.

I was Mr. Tickets when I was in sports. I was crushing premium seats. I was the man. 

Then I went into tech and what ended up happening was I was slow to sell. I didn’t know what changed. I was naturally good, but I was struggling.

My boss at the time (really my boss’s boss - the Director), eventually asked why I was trying to reinvent the wheel. He had listened to my calls, and wanted to know why I wasn’t following any of the scripts or messaging.

I was like, scripts? I am Jake Dunlap, I don’t need scripts! 

He said something I’ll never forget. “Do you think we train 1000 reps on this process because it’s stupid?”

I said, “No, that would be bad.”

He said, “Exactly. just read the script.”

I closed $60K in new business the next month. I was promoted to leadership two months later. And I realized sales is a science.

So even though it sounds like bad advice, buy into the system. Take the skills that you had, but focus on what they’re teaching you and buy in.

Have a specific question I didn’t answer in the videos?

DM me or drop them in the comments. I’ll get to as many as I can.

-Jake Dunlap