Bonus: Guest Teacher Steve Glaveski – Selling to Big Corporates
2 Feb 2026 · 14 min
Podcast bonus episode (host Omar Zenhom) featuring guest Steve Glaveski delivering a practical lesson on selling to large corporate clients. Glaveski covers how to choose target companies and decision-makers, perform reconnaissance (Google Alerts, BuzzSumo), reach out (mention news, ask for a 20-minute meeting), qualify leads, craft memorable proposals (hard copy + small gift, offer value), follow up effectively (share relevant content, use CRM/FollowUp.cc), outsource outreach tasks (VAs, Superhands, RocketReach), and maintain resilience (expect many rejections; ask why to improve). Transcript includes host intro/outro and multiple ad reads (Intuit QuickBooks, Dell, McDonald’s, ADP, CarMax).
Chapters
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Hey oh. Welcome to the Hundred Dollar MBA show your go to podcast for practical business lessons. I'm your host, your coach, your teacher Omar Zenholm. I'm also the co founder of the Hundred Dollar MBA and webinar Ninja and today's episode is a bonus episode. We have a guest teacher on today's bonus episode so Steve Glovesky. Steve is the founder of CollectiveCampus US and he's the host of a great business podcast called Future Squared. And I was a guest recently on Future Squared. It was a great conversation and today Steve's gonna deliver a lesson on selling to big corporates. If you're a B2B where you have to sell to other businesses and you wanna land some big clients, this is a great lesson. He's gonna give you his formula of how to reach out and contact somebody in that company and and sealed the deal. Can't wait for Steve to jump right into it. So let's get down to business. Steve Lewsky has secured some pretty big clients over his time even though his team is a small one, only six employees and he wants to share with you his formula, his strategy to reaching out to these big corporations, who to speak to, finding that decision maker and how to follow up so you can nail the deal. I'm going to hand it over to Steve now, but I'll be back to wrap it up and give you a freebie from Steve. A great downloadable, a great book. I'll be sharing that with you shortly. But for now, take it away, Steve.
Hey guys, Steve Gloveski here. Thanks for joining me. If you're a startup, selling to large corporates can be really hard. They tend to move really slowly. They've got multiple stakeholders making joint decisions very slowly, corporate budgets that might not align with your financial objectives and they're inundated with cold calls and emails on a daily basis. So just getting an initial meeting can be really difficult. It's not like you can run a simple Facebook ad and convert a corporate client as you might with a B2C product. They usually require multiple exposures to your brand or product. They need to build case studies to sell things internally. And this can take months. And I should know, sometimes it's taken me up to 18 months to close a client. Oh, and many are likely to take meeting after meeting with you. But if you're not careful, this will usually amount to them doing nothing more than picking your brain, giving themselves an opportunity to get out of the office for a coffee and wasting your very precious time. So I'm the co founder of a corporate innovation consultancy and despite having just six employees, we we're working with companies that have more than 6,000 employees. So today I'm going to teach you how to take the pain out of selling to large organizations. So let's get down to business. First, you should already know what kinds of companies you're targeting. You should know the industry, company size and where they're located. Second, you need to know who you're targeting in the company, which can go a number of different ways. When you break this down though, you're targeting either the influencer or or the user or you're targeting the buyer or the decision maker. I like to optimize my time and go straight to the decision maker first. So say I'm selling some type of human resources software. I'm going to go straight to the head of HR and work my way down the org chart until I get a bite. But bear in mind, the further down you go, the more likely you'll find yourself in influencer territory and therefore the longer it will take to close. So you've got to understand the KPIs of who you're targeting so you can speak their language, understand what their challenges are and how they make purchasing decisions. You know, price might be one factor, but other things that companies consider when Making purchasing decisions could include things like switching costs, the quality of your brand, the reputation, brand awareness, trust security, privacy concerns, social proof, compatibility. There's so many different things going on when they're making purchasing decisions. Just being cheaper isn't enough. And you also want to understand where your target customer hangs out, not just online, but also offline, so you can effectively target them with your marketing. I mean, if you're selling something to seniors, looking to sell them on Snapchat probably isn't the best channel. So once you've got a concrete idea of who you're targeting, you can start to do some of what I like to call reconnaissance and outreach. First up, reconnaissance. Would you rather invest your time on prospects that are a 1% chance of closing or on prospects that are a 25% chance of closing? You only have so many hours in a day and you must guard every hour with your life, especially as a startup founder. This is where reconnaissance comes in handy. You can use tools such as Google Alerts and Buzzsumo to monitor mentions of keywords for you. So keeping with the theme of HR software, you could subscribe to Google Alerts for keywords such as HR tech, human resources technology, human resources software, and so on. And on a daily basis, you'll be kept up to date of any company mentions in the news for this topic. So if a company is in the news for HR technology, chances are they've got an appetite for investing in this type of software and are far more likely to convert that companies who don't know a thing about HR tech. Similarly, you can use Buzzsumo to see who's talking about a particular keyword, be that on blogs or on social media. For example, when I type in HR tech in into BuzzSumo, I get 41 pages of results. 41 pages. The very third result on the first page tells me that Randstad, a recruitment company, has bought Monster, the online jobs board for $429 million. Now, clearly they've got an appetite to invest in growth. So when I click into the article, it takes me to TechCrunch. I can see that Jacques Van den Brock, who's the CEO of Randstad, has been quoted in the article. My next step is to then reach out to either Jacques, his underlings, or other people at Randstad who fit the target profile and this article where you can always look for mutual contacts to make introductions via LinkedIn instead of sending cold emails and cold emails. And if you don't have any mutual contacts, see if you can find some. See if you can add some of their existing contacts. This is always way more effective than cold outreach. So when you first reach out to your prospects, mention the news you found, briefly introduce who you are and ask for just 20 minutes of their time, framing the conversation as all about them. Like you don't want to go in there selling your product, you want to just go in there talking about them, the article and all the amazing stuff they're doing and how you'd love to find out more. And that 20 minutes will do. But don't worry, if they agree to the meeting, you'll get a lot more than 20 minutes. So you might have an initial phone call, in which case your job becomes to ask really good questions. Good questions equals good answers and your whole objective here is to understand the company's situations, their objectives, their challenges, and where, if at all, your product might fit into the equation. Because you don't want to sell a square peg for a round hole, you don't want to waste your time doing that. You want to hit home runs and do amazing things for companies that are going to use you time and time again and be happy to get up on a megaphone and talk to the world and talk to their clients and friends and peers and associates about how awesome your company is. So chances are, if you've made a good enough impression, you will either be asked for a face to face meeting or to submit some kind of proposal outlining what your offering is, how much it costs, and so on. So this proposal should build upon all of the insights you collected when you were asking all of those amazing questions earlier. So it speaks to the core of what they need and what their pain points and gains sought are never pitch features they don't need. This is a waste of time and takes away from your key message. So don't fall into the trap of pitching the flower in Super Mario Bros. Pitch the fact that the flower gives you the ability to shoot fireballs. But don't stop at a simple PDF proposal sent by email. Be memorable. Send a hard copy along with some kind of tiny immaterial gift that you just know your prospects will appreciate. Think outside the box. There are many ways of novelizing your proposal so you can stand out from the rest of the pack. And there will definitely be a pack. If the contract you're pitching for is worth more than $50,000, you can be sure that a corporate will be shopping the project around town. So do what you can to stand out from the pack. Maybe even consider giving away a free 30 minute keynote to inspire people in the organization or a simple online tool your company has developed. This will play to the innate human desire to reciprocate when given something. So what happens now? Days and weeks might go by, but never fear. Like I said at the start of the show, large companies can take a very long time to make a decision, so keep the prospect warm rather than just follow up with a boring old Hey, I was just calling to touch base phone call or email. Find a relevant article or a podcast that you just know they derive some value from and share it with them. Maybe just tack on to the end of that email or call. Oh, by the way, I understand you guys are reviewing our proposal, but let me know if you guys have any questions. I'd be more than happy to answer them. That way you're not coming across as cheesy or desperate. And never forget to follow up. Ensure you're using a CRM such as HubSpot or a tool like Followup CC to prompt you to follow up. If you've not even reached the proposal stage, then Follow Up CC can send automated messages on your behalf at a given interval with something simple and pervasive such as hey, just wanted to see if you received my last email. So aside from reconnaissance to generate leads, you want to use tools like LinkedIn to put together a list of target prospects. But wait, don't run off and do this yourself. Give the instructions to a va. I love the platform Superhands because it cost me something like $4 per hour and I can get lists built super quickly, super cheap. The VA can also go a step further and use a tool like Rocket Reach to get the user's email address and then reach out for you. Anything that can be codified that isn't mission critical for you should be outsourced and and this definitely includes your outreach efforts.
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So like I said at the top of the show, the last thing you want is to waste your time on unqualified leads. So have some questions handy to qualify leads that come back and agree to an initial call. In this case, ask things like have you worked with any other companies like us? Do you have a budget to explore this? What's senior management's appetite for hr, software and so on? So don't waste your time on companies that have no real appetite to invest and are just taking a call because they're bored and and want their ego stroked. You're the one with limited resources, not them. In some cases, you might not get a direct line to decision makers and you'll have to work users and influencers. See them with a story and with materials they need so they can sell your product on your behalf internally. Understand what information they need and get it to them in the simplest form you can. So if you've sold a deal, congrats. Don't just end there. Make sure you follow up. Your easiest deals are to existing customers you get on the phone, catch up with them regularly, buy them lunch, maintain and strengthen your ties and upsell and cross sell them on other stuff you're doing. Give them special offers that align with your business model. Use them as a testing ground for new offers where possible. Never lose a client because you are too lazy to maintain the relationship. And finally, it's become almost cliche. But be resilient. This is absolutely critical. Selling to business is not easy and for every one yes, you're probably going to hear no 19 times or more. So always ask why your proposal wasn't successful. Take the learnings on board and optimize your approach so that you can turn that 1 out of 20 into a 2 out of 20 and effectively double your revenue. Well, that's it for my guest lesson on how to sell to large organizations. I hope you found that helpful. For more insights on innovation and entrepreneurship, head to theinnovationmanagershandbook.com where you can pre order my new book but also download a free bonus bundle which includes a copy of my first book as well as an exclusive invite to a live Q and A webinar with me. I'd love to speak with you then. Well, that's it for me. It's been super fun hanging out with you all. Back to you Omar.
What a great lesson by Steve Glovesky. Thank you so much for giving us that guest lesson. If you're trying to book those big corporate clients. Try this out. This works. Re Listen to this episode if you have to. And don't forget, you can download Steve's great free gift, including a free book over@the InnovationManagersHandbook.com Again, that's the Innovation Managers Handbook.com thanks again Steve for that great lesson. Listeners, you have to hit subscribe so you can get these bonus episodes. We try to sprinkle them in and surprise you. And if you don't want to miss a beat, make sure you hit subscribe so you get them automatically right on your device. That's it for me today guys. But before I go, I want to leave you with this. Even though you are a B2B, even though you're trying to secure business from a large corporation, as you heard from Steve, you're just trying to secure business from one person. You have to convince the decision maker. This helps you put things in perspective and realize, hey, this is not as big as I thought it had to be. It's a sales conversation. It's a one on one conversation. Now obviously a decision maker may get the feedback of their team or discuss it with other people, but at the end of the day, you have the chance to influence that person. That one person. That's definitely doable. Especially now that you're armed with Steve's strategy. All right guys, that wraps up today's lesson. I'll check you in the next episode. Take care.
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