GTM Advice with Jack Wilson

In this GTM Advice episode, Jack Wilson, EVP of North America at amplify5, answers a fast round of questions and shares her go-to-market advice with you. 

Check out how Jack answered the following questions:

1. What is the biggest go-to-market challenge today? How would you tackle this challenge?
2. Where would you focus your efforts if you had limited resources and had to drive immediate results?
3. How do you ensure there is alignment across all go-to-market functional teams? (i.e. sales, marketing, product, and customer success)
4. What’s the one “dirty little secret” in go-to-market that nobody talks about, but everyone needs to know? 
5. What do you think is the biggest misconception about having a career in go-to-market? 
6. What is one skill that all GTM professionals need to have mastered to be successful? 
7. What is one thing you wish you knew sooner? 
8. What is one piece of advice you would give to someone looking to grow their career in go-to-market?

Transcript

Stephanie Cox: Welcome to our GTM Advice episode where each guest answers a fast round of questions and shares their go-to-market advice with you. Let's hear from Jack. 

Stephanie Cox: What is your biggest go-to-market challenge that exists today, and how would you tackle it?

Jack Wilson: Well, that's a great question. Hey, Stephanie, good seeing you again. My biggest challenge would be that in this go-to-market, fast-paced environment where you've got AI, you've got all these different tools, that nothing is going to replace the human touch of what we do. So I'm a big believer that emails are great, but the personal communication that you can still do to anyone, I still write handwritten notes and I will, and it's amazing to me when someone gets a Jack note, the response that I get back. So I think that the biggest thing that I could just say quickly is the personal touch in this go-to-market world is never going to go away. AI is not going to replace it.

Stephanie Cox: Where would you focus your efforts if you had limited resources and had to drive immediate results?

Jack Wilson: Where would I focus my efforts? I would focus my efforts on continuing, to message the way that I communicate and the way that, I like to communicate is I'm a LinkedIn poster. So I think for me, I can get a lot of messaging out on LinkedIn. It doesn't cost a lot of money to do that. And I'm a big believer. I like to show up at trade shows and not be the person who has a booth.

I like to show up and network with the crowd because again, that's the personal thing. I'm not a scanner. You're never going to see me scanning anyone's badge. I'm a believer that the personal interaction, it's things that people don't do anymore. And I'm finding that people that still have this personal connection, they separate themselves out from the normal salesperson that's hiding behind an email or technology.

Stephanie Cox: How do you ensure there is alignment across all go-to-market functional areas (i.e. sales, marketing, product, and CX)?

Jack Wilson: The only way that there can be alignment is at the top of any organization from the CEO, CRO down, but it's having everyone in these organizations knowing exactly what their job is and how it fits into the bigger puzzle. A marketing person should never go to work and just be focused on marketing. A product person shouldn't just go to work, and say, I'm focused on product. It all attaches somewhere together and making sure that the sales leader, the marketing leader, the product leader, and the CEO are all very much in tune with what the goal is.

Stephanie Cox: What is the one dirty little secret in go-to-market that nobody talks about, but everyone needs to know?

Jack Wilson: Wow. You know, that's a great one. know, I believe the dirty secret is that, you know, senior management, the people making decisions are making decisions not off of actually the reality of what's going on in the field. I think that so many decisions are made in a boardroom, in an Excel file to drive make-believe revenue based on what they want to do in their head. Most of it's never based off of actual facts. And that's a dirty secret that is the absolute truth. I think that these organizations need to ensure that they're setting realistic goals and expectations for sales and marketing and not these unrealistic numbers where 40 percent of the organization makes their number and the rest of them are all put on pips. It's completely unrealistic.

Stephanie Cox: What do you think is the biggest misconception about having a career in go-to-market?

Jack Wilson: Yeah, you know, I get accused of this all the time, you know, me and my sales team. So we, flit around the country, you know, we eat, you know, luxurious meals. We're staying at, you know, top-notch hotels. You know, it's a glamorous life. You know, let me set the record straight. It's a grind. It's, it's extremely challenging to go on these road junkets these days. You know, to always be on, it's a very lonely existence. And, you know, I can say the same thing for marketing, right? The expectation for marketing is, you know, you go to a trade show, we put, you know, a lot of money into this and that things are just going to happen. It doesn't work that way at all. And marketing is just as much under the gun as a sales professional. It's hard out here. It's hard to consistently do this at a level and the perception though is that salespeople are just living this glamorous life and it's completely a misconception.

Stephanie Cox: What is the one skill that go-to-market professionals need to have mastered to be successful?

Jack Wilson: It's the capacity to understand and to push yourself in a very unforgiving environment. I don't know anyone who can be one-dimensional and do this at this rate that I have done for 25 years. So you've got to have passions outside of doing this. Mine so happens to be I'm an ultra runner. So I get a little bit of relief in being able to go and do that.

But it truly is having a mindset that this is a job and this is what pays my bills. This is not truly my identity. I'm way more dimensional than this person that you see. And that people that just take this in the literal sense, it's an unscaling life, meaning that if you're just a CRO and you're just in the weeds of this, it'll kill you because you just can't live this type of pressure on a day-to-day basis without having some relief.

Stephanie Cox: What is the one thing you wish you knew sooner?

Jack Wilson:  Wow. One thing I wish I knew sooner. I wish I really knew sooner, and I probably wouldn't have gone into senior management, how much of the things that are truly out of control of any organization. As a young sales rep, I just always assumed that the people up there making the decisions knew kind of what they were doing.

As I have gotten older and I sit in these boardrooms and I sit in these meetings raising money, what's appeared to me is just the only thing that's happened is you've gotten older and more experience. So out of default, you get into that position. But typically, a lot of these decisions are made in a way that it would just boggle the mind. They're not made off of real empirical data. They're made off of, we just got to grow the business 30 percent because our competitors are and that 30 percent may not fit your model, you may only be able to grow at 10 % due to a lot of factors. I wish I would have known that early on and not taken it so personal.

Stephanie Cox: What is the one piece of advice you would give to someone looking to grow their career and go-to-market?

Jack Wilson: Be patient, find a good mentor. I have been so blessed in my career to have some really good mentors that will take the time, slow down, and give me the facts, kind of like what we're talking about today. I think having these types of conversations, it can only help anyone that's either struggling in their career or wanting to advance in their career to really understand what they're getting into, but to find that mentor, that somebody that has more experience than you, and truly lean into that relationship and hear more than you speak.