How to Sell to Large Companies

The following is a transcript from my appearance on the $100 MBA Show.

Read this if you want to learn:

  • Why selling to companies is hard
  • How you should define your target company profile
  • How to determine how your target customers make purchasing decisions
  • Questions you can ask to qualify leads
  • Why initial meetings should be all about the target, not your product
  • How to use online tools to scout for warm leads that are much more likely to convert
  • The power of reciprocity
  • Defining your stories
  • How to arm influencers in an organisation to sell on your behalf
  • How to use a VA to 10X your outreach efforts and 10X your leads and conversions
  • Why you should follow up, relentlessly
  • How to differentiate your pursuit from competitors
  • Sales cycle times and resilience

If you’re a startup, selling to large corporates can be hard. They tend to move slowly, have multiple stakeholders making joint decisions, corporate budgets that mightn’t align with financial objectives and they’re inundated with cold calls and emails on a daily basis so getting an initial meeting can become incredibly difficult.

It’s not like you can run a simple facebook ad and convert a corporate client as you might with a B2C customer, they usually require multiple exposures to your brand or product. They need to build cases to sell things internally and this can take months! Oh, and many are likely to take meeting after meeting with you but if you’re not careful, this will only amount to them picking your brain, getting out of the office for a coffee and wasting your very precious time.

I’m the founder of a corporate innovation consultancy called Collective Campus that despite having just 6 employees is working with companies that have more than 6,000 employees. So today, I’m gonna teach you how to take the pain out of selling to large companies. Let’s get down to business!

Define Your Target and their Drivers

First, you should already know what kinds of companies you are 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 one of four ways. When you break this down are you targeting the user or influencer or are you targeting the buyer or decision maker.

I like to optimise my time and go straight to the decision makers. Say I’m selling a Human Resources software package then I’m gonna go straight to the Head of HR and twork my way down the org chart until I get a bite. The further down I go though the more likely I find myself in influencer or user territory and the longer the time to close.

Understand their KPIs of who you’re targeting so you can speak their language, understand their challenges, how they make purchasing decisions (price is just one factor -, others might include but would not be limited to switching costs, quality, brand awareness and trust, security, social proof and compatability of your offering). You also want to understand where they hang out online AND offline so you can effectively target them with your marketing.


First, reconnaissance — would you rather invest your time on prospects that are a 1% chance of converting or a 25% chance of converting? You only have so many hours in a day and you must guard your hours with your life. This is where reconnaissance comes in handy.

You can use tools such as Google Alerts and BuzzSumo to monitor mentions of keywords for you. Keeping with the theme of HR software, you could subscribe to the Google Alert for keywords such as “HRtech” or, “human resources technology” and on a daily basis be kept up to date of any company mentions in the news for this topic. If they’re in the news chances are they’ve got appetite and are investing in HR technology and are far more likely to convert.

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 HRtech into buzzsumo, I get 41 pages of results. The very third result on the first page tells me that Randstad, a recruitment company, has bought Monster, the online jobs board, for $429M. Clearly, they have an appetite to invest in growth. When I click into the article, which takes me to TechCrunch, I can see that Jacques van den Broek, CEO of Randstad, has been quoted in the article.

Targeted Outreach

My next step is to then reach out to either Jacques, his underlings and other people at Randstad who fit my target role profile. Where you can, always look for mutual contacts to make introductions via Linkedin instead of sending cold InMails or emails and if you don’t have any mutual contacts, see if you can find some — this is ALWAYS way more effective than cold outreach.

When you first reach out to your prospects, mention the news you found, briefly introduce who we are and ask for just 20 minutes of their time, framing the intro all about them, getting to know them and their challenges. Don’t worry, if they agree, you’ll get more than 20 minutes!

You might have an initial phone call, in which case, your job becomes to ask REALLY GOOD QUESTIONS, good questions = good answers, and your whole objective here is to understand the company’s situations, their objectives, challenges and where your product might fit into that. Chances are, if you’ve made a good enough impression, you’ll either be asked for a face-to-face meeting or to submit some kind of proposal, outlining your offering. This proposal should build upon all of the insights you collected when you were asking all of those amazing questions so it speaks to the core of what they need and what their pain points and gains sought are. Don’t pitch features they don’t need. Don’t fall into the trap of pitch the flower in Super Mario Bros, pitch the fact that it gives you the ability to shoot fireballs!

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Be Memorable

But don’t stop at a PDF proposal sent by email. Be memorable. Send a hardcopy along with some kind of tiny immaterial gift that you just KNOW your prospect will appreciate. But think outside the box, there are many ways to novelise your proposal so you stand out from the pack — oh, and there will be a pack. If the proposed contract value is above $50K you can be sure the corporate will be shopping around more often than not. This gift might even extend to a free keynote talk or a simple online tool your company has developed. Whatever will play to their innate human desire to reciprocate.

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 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 podcast that you just KNOW they’d derive some value from and share it with them. Maybe just tack onto the end of that email that “oh by the way, I understand you guys are reviewing our proposal but feel free to let me kno wif you have any questions in the interim” — easy and not too cheesy.

And don’t forget to follow up, ensure you’re either 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 Followup.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 virtual assistant. I love to the platform Supahands cause it costs me just $4 per hour and I can get lists built super quickly. The VA can also go a step further and use a tool like Rocketreach, or Clearbit Connect to identify the user’s email address, giving you another pathway to the prospect and you guessed it, send emails on your behalf. Anything that can be codified, that isn’t mission critical should be outsourced and this includes your outreach efforts.

So like I said at the top of the show, the LAST thing you want to do is to waste your time on unqualified leads so have some questions handy to qualify any leads that come back and agree to an initial call.

Qualify Leads

In this case, ask things like “have you worked with any other companies like us?”, “do you have budget to explore this?”, “what’s senior management appetite for HR software” and so on. You don’t want to waste your time on companies that have no real appetite to invest and are just taking your call because they’re bored and want a show and to stroke their own egos. You’re the one with the limited resources, not them, don’t squander it!

In some cases, you might not get a direct line to decision makers and you’ll have to work users and influencers. Seed them with a story and with materials that they can use to sell the product on your behalf internally. Understand WHAT information they need and get it to them. Make their job easy.

After Care

Sold a deal? Congratulations. Don’t just end there. Follow up, your easiest deals are to existing customers. Get on the phone, catch up with them reguarly, buy them lunch, maintain and strengthen your ties and upsell and crosssell them on other stuff you’re doing. Give them special offers that align with your busines model. Use them as a testing ground for new offers where possible. Never lose a client because you were 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 1 yes, you’re probably going to hear no 19 times or more to start with, at least that’s been my experience, so embrace each no as an opportunity to learn and get better. Always ask WHY your proposal was unsuccessful. Take these learnings on board and optimise your approach so that you can turn that 1 out of 20 into a 2 out of 20 and effectively double your revenue in the process.

I hope you found that helpful. For more insights on innovation and entrepreneurship, head to www.theinnovationmanagershandbook where you can pre-order my new book as well as sign up to a bonus bundle which includes a free digital copy of my first book as well as an exclusive invite to a live Q&A webinar with me. I’d love to speak with you then.

Tools mentioned:

  • Google Alerts
  • BuzzSumo
  • RocketReach
  • Supahands
  • Clearbit Connect
  • Hubspot
  • Followup.CC
  • Linkedin
March 28, 2017




Steve Glaveski


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