Podcast 140: True Enterprise Selling With Ian Koniak

What is true enterprise selling really like? Ian Koniak is crushing it at Salesforce selling 7 and 8 figure deals and we’re pleased to have him on the podcast to understand how he’s doing it.


What is true enterprise selling really like? Ian Koniak is crushing it at Salesforce selling 7 and 8 figure deals and we’re pleased to have him on the podcast to understand how he’s doing it. This is true enterprise selling, very long deal cycles and multi-million dollar deals that are long term contracts. It doesn’t get much harder than this in software sales. Sales reps in any industry, with any deal size or length can learn from how enterprise selling really works. Even if your process is a slimmer version of Ian’s, you can over-deliver if you take things to the next level. This was an interesting one…

In This Podcast You’ll Learn:

  • Product Sales to Service Solution Sales
  • How to Approach Enterprise Selling
  • Selling to All the Levels

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Product Sales to Service Solution Sales

John: You took what you knew at Xerox and it was a numbers game, but now you’re doing enterprise selling. Walk me through that experience, that transition of product sales to service solution and SaaS sales and anything you realized pretty early on.

Ian: So I hit my number my first year by being extremely persistent with this one account for a big hospital. A multimillion-dollar deal just by calling and emailing the CIO constantly with all different messages. I ended up getting this big deal and I continue doing that. And a couple of years after that, that’s when I really struggled. I didn’t hit my plan and I had always treated activity yields pipeline, real yields, results.

I learned through unfortunately through a common symptom among salespeople thinking “you’re only as good as your performance”. So if you’re hitting your plan, you feel great about yourself. If you’re not, you feel like you’re a sh*tty person, and that translates to everything. I was number one victim of that. That’s kind of what propelled me in my journey to self-development. I was so down on myself cause I wouldn’t hit my numbers. I missed my numbers two years in a row. It made me look at Microsoft, I was going to change companies rather than look in the mirror.

Finally, I met a woman named Jen LaGaily and she was in another division at Salesforce. She actually gave me an opportunity to switch to the commercial division, which was a little more at-bats. It was going after a little more accounts. And I said, maybe I need this because of the way I sell at high velocity. Basically I took that approach which was a little more suited towards selling to the small business and I took it to commercial. I finished like 97% that first plan.

I realized this way of selling this high activity, hard closing, hard-charging, go to the next one after you sell isn’t working for me, I need help. And I ended up joining a sales training program where I invested 20 grand that first year in my own training and development and then I’ve invested over 50 grand and it’s been three years and I’ve continued. I got a coach, I joined a mastermind, I started reading, I started changing so many things and that was when the change took place. That first year I finished number one in all of Salesforce enterprise and sold more combined than I had in those first four years and just crushed it. Since then, I’ve really changed the way I sell and learned what was different. That was my transition.

How to Approach Enterprise Selling

John: With huge organizations, how do you even approach them? Do you just go straight to the CEO and be like, what’s up dude? What do you do to even get into an account like that?

Ian: In sales, you want to hit charge, get in your accounts, go through, but where sales reps don’t spend a lot of time (where I certainly didn’t for my first few years when I wasn’t performing) was on that research and prep. Whether it’s for an appointment or a presentation, you can spend a couple of days preparing for a 30-minute meeting in the enterprise space. The same way that I prep for a big deal, I’m working on actual prep for an account that I’m taking over.

So when I want to identify, there’s a lot of things we do, but at its core, there’s research on the company, which is looking at the people in the company that matter. You have to talk to a lot of people and something I do is I look at what they’re saying in the news. I’ll look at their interviews, I’ll look at any article, and I’ll make comments and they’ll talk about initiatives. Then mapping what you sell your product or service to what they’re trying to do. So you’re coming in with a very pointed message and that takes a long time to do that research.

Selling to All the Levels

John: How do you balance and maintain consistency in an enterprise sale? How do you maintain that control of such a complex sale with so many moving parts and alignment with the executive side?

Ian: In some cases, you can’t. In some cases, there are things outside of their control. I would say there are some times literally where a company can get bought out or there are just some things that happen that are out of your control. So kind of knowing what you can control and knowing what you can’t is really important.

The key is when you get to that executive and you map out kind of here’s what needs to happen, you have to control the process. You have to define, “Hey, our process is X. We need to look at your current systems. We need to understand your contracts and where you’re at. And we need to understand your KPIs.

We’re going to put together a business case and we need your finance involved so we can map the value”. Just asking them how are decisions really made? Have you done this before and got something approved? Who runs the company? I think identifying upfront, like how do decisions really get made at your organization and keep asking “who else?”. Then kind of doing that sniff test where you can ask: have you done something like that before and got approved? Tell me how that went down. What had to happen? It’s a really kind of gave you that upfront.

And then you go into your diligence, you do your discovery, go back in a month or two and you do the readout to the executive again. It’s all about setting up that next, so we’re going to need three, four weeks, maybe longer. The more information you gather, the more you’re actually going to get to the truth. Because executives often don’t even see it. You’ve got to do the lower levels, even down to the user in some cases then come back up and say here’s what we heard, here are the challenges, here is the biggest opportunities, and then really show a plan of here’s how we’re going to get there.

That’s a wrap. Join us next time

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