I am currently actively looking for a role with not a lot of luck given the landscape. My goal this year 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?

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, 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.

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.

You’ve got to start to pull out what’s relevant. We’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. In this scenario, we would focus on the fact that we’ve worked with legacy buyers and industries that moved slow. We’d try to highlight our work experience in a way that is parallel and is actually relevant to the new industry. This is what we 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.

Enterprise sales is my goal. What resources/ industry knowledge tools can I utilise to prepare me for that role?

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 our number one piece of advice for being in enterprise sales. You can’t just worry about your champion. You’ve got to realise 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.