Selling directly to the CIO is a challenge, but it’s worth it if you can pull it off. Sell to the CIO and you’re past all the gatekeepers, dealing with a real decision maker. They’re not going to tell you they can’t sign off on the deal after all, or ask you to wait while they bounce it upstairs to someone who has the authority. CIOs are often in a position to push for company-wide adoption with credibility and have the ear of the CEO. And if you’re selling something they have the authority to sign off on, they’re often in control of significant budget.
This isn’t always smooth sailing: sometimes, there’s no CIO. In many small businesses especially, where the whole company isn’t large enough to support or need separate functions, there’s often no-one filling that chair. And some people argue that the role of CIO is becoming increasingly sidelined anyway, In an eye-opening think piece for Inc, Geoffrey James accuses CIOs of being ‘powerless,’ in ‘dead-end jobs,’and ‘standing in the way of technological progress.’
Yeah, you probably shouldn’t lead with that when they pick up the phone…
CIOs might show a preference for older tech, but that’s largely because they have a preference for what works. ‘Let’s try that and see if it breaks everything’ is never a phrase that people who are actually in charge say. CIOs have to both drive and navigate: they’re in charge of keeping operations running smoothly and of strategic direction.
And they might not have the power to decide for the whole company, but they disproportionately have the ear of the CEO when it comes to tech decisions because of their unique combination of technical and business knowledge. If your offering is tech-related, selling to the CIO can be a winning strategy that shortens sales cycles and increases deal size.
Here’s how to go about it.
1. Get The Conversation
How do you get the CIO to actually talk to you or read your email in the first place?
CIOs aren’t busy; they’re swamped, by most folks’ standards, and more so all the time. The average CIO gets upward of 300 cold pitches a week, or 60 a day - a generous handful every hour. Even if yours is unusually good, it’s still almost certain to be ignored. So while cold calling remains a highly effective ‘in’ in some scenarios, selling to CIOs needs a different plan.
You have to offer some kind of value right off the bat, and you have to be in a situation where you can be heard above the noise.
Approaches For CIOs:
Indirectly Through Someone On Their Staff
Many CIOs have a group of staff members who act as their ‘filter,’ making sure that things only wind upon their desk that are worthy of their limited and in-demand attention. Think of this as the qualification process - you get to qualify the target company extensively, so you don’t waste any more time trying to offer something to someone that’s not a good fit for whatever reason. At the same time, they’re qualifying you in terms of your offering, your company and how you sell. If both sides agree, you can move on to the next stage and get an introduction to the CIO rather than shouting to be heard above the noise.
A Pre-Existing Relationship
If the CIO is someone you personally already know, you can make an approach that way. Don’t be scared to state the value prop, but equally, don’t risk damaging your relationship or appearing to regard it as a means to an end.
Salespeople have an uneasy relationship with content, partly because it often seems to be produced by marketers who don’t understand what sales plan to use it for, and most often because they can’t find it when they need it. If you have the choice, talk to marketing about this. CIOs don’t respond well to being ‘sold’ to - they’re professional assessors of IT solutions and processes based on data, so give them some data to work with. You don’t need infographics and fact sheets - you need white papers, case studies and in-depth point-by-point comparisons that lay bare exactly how your offering compares with the competition.
And you need to be able to find this stuff and forward it to the CIO right when you need it.
Word of mouth from a peer is the most solid endorsement a product or service can have. In many ways, CIOs are totally different from consumer level buyers, but in some ways they’re not - they still want someone to solve a problem for them, and they still trust a person like them who had the same problem to recommend a solution. If your own CIO has contacts, ask for them. And if you’ve sold to a CIO before, ask them to help you get the 'in' with your target company.
2. Talk Solutions
The only way you can do this is to know the problems. So we’re back to selling 101: do your homework. The more pressured and specialized a role is, the less interested that person is in spending time on the phone, on email or in person, repeating their LinkedIn profile to someone who wants to sell them something. And the more important it is that you understand what they want before you try to offer them anything.
To do this well you’ll need to understand three things:
Industry And Company
CIOs face industry-specific challenges. Don’t approach them with generic solutions that make no reference to the specific space they operate in. Each company is structured differently. The company structure and the C-level staff especially are the environment in which that particular CIO operates. So know who their colleagues are and what they’re about before you get into a conversation. It could change your whole approach to know that Company X’s new CEO comes from an entrepreneurial background while Company Y is recruiting C staff with experience in the Japanese auto industry, because those differing outlooks and experience sets will influence how business decisions get made.
Goals And Priorities
Typical CIO goals include:
Disaster prevention. Keeping the train on the tracks and stopping mission-critical processes from being interrupted, keeping catastrophes like data breaches from happening. So what’s the big risk faced by your target CIO?
Executive team performance. Fitting in and working effectively with C-suite staff on executive rather than departmental goals. What’s the company’s major goal right now?
Optimizing and streamlining the IT and technical departments. What’s the current state of their IT?
Motivating, training and hiring a great IT department - including a range of skills. Where are they lacking? How can you help?
Hitting management-defined targets - who’s their direct manager?
Securing budget and credit at board and company meetings.
Within all this, certain goals will take priority due to pressure from the CEO or from circumstances. Knowing specific priorities allows you to speak to the CIO’s area of interest right now. If you knew that the CIO’s priority was to cut operating expenses by 15% this quarter, that would change your pitch, right?
Obstacles And Pain Points
When you address the CIO for the first time, you’re at risk of being just another voice in her ear or email in her inbox that wants something. Don’t be another demand on a CIO’s time and attention, that category is already full to bursting. But if you can be a solution to one of the problems the CIO is already facing you’ll be all by yourself in a tiny category: ‘people who made my day easier.’
The value you offer at this point doesn’t have to relate directly to your offering. Your product might make every day easier after it’s installed, but it does nothing for the CIO right now.
As once-CIO, now-consultant Pierre-Albert Carlier told WalkerSands.com, ‘you are always grateful to someone who removes a stone from your shoe.’
‘I have vivid examples of vendor representatives sharing a bright idea with me that had nothing to do with what their company was selling,’ Carlier continues. ‘As a CIO, you will always be pleased with those people. And, one day, you will buy from them.’
3. Sell The Value, Not The Product - Especially If You’re Selling Out Of Your Weight Class
I’m not talking about the sizzle and the steak. I’m talking about CIOs having a hand in your product even if it’s not finished yet. What CIOs have that many other buyers won’t is insight into how your offering can be useful even if it’s still being tested, or it’s incomplete. So if you’re approaching SMB to enterprise level CIOs as a small team with a features-poor, bells-and-whistles-free product, don’t sweat it.
CIOs know that early-stage SaaS products are unfinished. Sell to one at this point and it really doesn’t matter if you fail their usual auditing procedures. They understand they’re not buying a finished product. If they recognize the value you offer, your features-poor, barely-ready product might be fine to start off with. You’re looking at a collaboration rather than a ‘sale’ in the more conventional sense.
Jason Lemkin calls this the ‘social contract’ approach and says you have a shot if you can strike the balance between risks and potential benefits, and if the CIO you’re selling to personally trusts you.
‘No one is going to replace a proven enterprise solution with a start-up that is only 20% better than an existing, implemented, hardened solution,’ Lemkin points out. ‘But if you do something truly unique, and you aren’t mission critical on Day 1 at least (i.e., you won’t be a Career Ending Move for the CIO) … they’ll take a bet on you if it’s a potential game-changer and they trust you.’
That personal trust at high level is really the issue. If you’re shooting for much larger clients you might need to involve the CEO on your end. ‘All three CIOs [interviewed were] citing key, trusted relationships with the CEO/founders,’ Lemkin continues. ‘I found this myself. I had to build personal relationships of trust with all our early CIO (and other key) enterprise customers.’
4. The CIO Might Just Be The Beginning
Selling to the CIO might not be the end of the sales process. Brent Adamson, co-author of The Challenger Sale, observes that consensus sales now typically require an average of 5.4 people throughout the company. ‘When we talk to any B2B company in the world, they all have the same story,’ he says: ‘"We used to sell to X and now we sell to X, Y, Z, A, B, and C." They also tell us, "We used to sell to the Head of Marketing, but now we have an IT component so we have to sell to the CIO too. And now the C suite is involved and now the head of Germany is involved," or whatever.’
When they sit down to talk - whether it’s in a room or over Skype across continents - the CIO’s word will carry the greatest weight in any discussion on tech. Only the CIO can offer both the business and the tech knowledge to answer vital questions such as likely returns, risks and ramp times.
So if you have to convince a larger group of people with disparate skills and knowledge, getting the CIO on your side before that meeting isn’t going to guarantee that you get the deal. What it can do is overcome group inertia. When a group of people has to make a decision, and most of them don’t know much about the subject, they’ll typically revert to risk minimization.
As Geoffrey Walters points out, people in this situation will typically ‘freeze; ...make choices that are least likely to cause a loss; [or] make choices based on a single overriding factor rather than on a number of relevant factors.’
That’s what Adamson has seen too. ‘If these 5.4 people can't agree,’ he says, ‘then they ultimately just settle for what we've come to call the lowest common denominator. What's the one thing we can all agree on? "Well let's try to save the company a buck," right?’
Tim Riesterer, chief strategy and marketing officer at Corporate Visions, points out, 'the salesperson may have to bring the other 4.4 people from 0% to 100%. In actuality, the math to get them all to 100% ready means the purchase decision is really only 10% of the way done when the salesperson is called in.' At that point, the best tool you could have is a convinced partisan in the room who can deliver your sales argument with authority and who the other 4.4 people (!) in the room already trust. Let that be the CIO.
5. Speak To Strategy
CIOs face operational pressures which to some extent we’ve already talked about. But they also face longer-term strategic challenges. Here’s where you get the opportunity to add something rather than take something away - speak to a positive business outcome long-term rather than a short-term fix. And here’s where you can speak to strategic needs.
Avnet CIO Steve Phillips advises salespeople that one of the most effective ways for a salesperson to gain his attention is to have a solution that helps reconcile ‘the consumerization of IT with the need for centralized administration, governance and oversight.’
‘It’s my duty to give employees the tools they need to be effective,’ Phillips continues. ‘But I also need to ensure that Avnet devices are accounted for, backed up and secure.’
CIOs often experience radical changes in how IT actually gets used as massive tension: Bring Your Own Device (BYOD) is a case in point but it’s hardly the only one. If you can help a CIO square that circle, you’re almost guaranteed their attention.
Selling to the CIO lets you deal with someone who will understand your offering and has the authority to sign a deal in many cases. Where they don’t, you can win yourself an effective advocate for a consensus sale. Expect to have to bring your A-game, focus on facts and figures and offer more of a partnership, less of a product sale. And expect that you might have to ‘climb’ a couple of layers to get to the CIO. It’s worth it.
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