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Keeping it Simple is Hard Work with Dennis O’Malley {Hey Salespeople Podcast}

It takes a lot of work to keep things simple.

Dennis O’Malley, CEO at Caliva learned that first hand as he transitioned from an enterprise organization to a vertically integrated cannabis company.

Dennis and Jeremey discuss how authenticity, consistency, and transparency are key to any thriving business and how to build a rhythm of a high-performance culture. Make sure to catch Dennis’s four ways to get teams ramped up and what he sees in all successful salespeople. 

dennis o'malley podcast

Listen to this episode for answers to questions like: 

  • Is getting an MBA that important for a salesperson? 
  • What is the biggest missing piece of sales today?
  • Can too much passion for the product you’re selling be a bad thing?
  • Why should you never give prospects advice? 
  • How did Dennis navigate the move from an enterprise company to a vertically integrated cannabis company? 


Is an MBA Worth it?

Jeremey: Salespeople ask if they should get an MBA. Should they go full time? Should they go part-time?

Based on your experience, what would you recommend to B2B sellers who are early in their careers?

Dennis: It’s all different. Based on what people wanted to do for a very long time, I felt that sales was a myopic place to be if I wanted to be a general manager and wanted to start a business someday. So that was the first impetus around why I went into an MBA.

It was super helpful for me going the part-time route where I was able to take real-life problems and get 30 smart people actually commenting on them and bringing that back into work. The next day was phenomenal.

It’s always been a huge help understanding everything from territory management to which companies were doing better, which companies had money, the fastest-growing companies, what their problems were, what questions to ask and then helping them craft solutions.

That was what changed the impact that I had in sales and really reinvigorated me of, of understanding what generating revenue really meant,

Getting Teams Ramped Up

Jeremey: As you’ve led teams, and now that you know the importance of business acumen and asking great questions, what do you do with your teams? Because you obviously can’t send everyone to business school. How do you get your teams ramped up to be able to have those same level of conversations and ask those same depths of questions?

Dennis: The first thing, is to go out and immerse yourself in whatever prospect customer that you are going after. It is mind-boggling to me how many salespeople sit behind a computer and a phone and think that that is selling.

Unless you’re getting out to traffic, you’re going to their stores, you’re buying their products, you’re seeing their offices, you’re talking to their people, you’re seeing where their products are sold, unless you understand where and how you know your prospects or customers make money, there’s no way you’re going to be effective in terms of a sales cycle.

I think that’s one critical aspect.

The second critical aspect that you can apply is that companies are focused on rapid growth at the expense of all costs. Revenue growth is a key thing.

If they’re pre-revenue, or they’re something else, whether it’s a social media company or biotech company, they may be focused on growth, but it’s not in revenue. It’s maybe in users, or in clinical trials.

There are not too many different things that businesses do there. There are only a couple of things that the CEOs are tasked to do.

You can almost break down every single company into what its ultimate goal is. That’s really those four things: growing revenue, saving costs, taking market share, or growing enterprise value some other way.

And then, what are their longer-term strategies against those goals?  What is that person tasked to do to be able to contribute to those strategies?

I’ve always found the most successful sales reps are really focused on those tangible initiatives and understand what the obstacles are for those tangible initiatives to somebody who’s personally going to allocate budget against the initiatives.

THERE’S A LOT MORE TO HEAR! Listen to the full podcast for more on driving strategy.

If you have a passion for the art and the science of sales, are looking to further your career, or just want to hear some great, practical tips, ‘Hey Salespeople’ is the podcast for you. Subscribe so you can follow along as Jeremey interviews the brightest minds in modern sales to bring you immediately actionable advice. Listen and subscribe here.

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