Yousuf Khan
Technology vendors who have been successful over the long term all have something in common: they know how to sell to chief information officers.
They understand that the work isn’t over after the handshakes and signatures — effectively managing and nurturing a vendor-CIO relationship requires attention.
I’m a VC now, but my five CIO stints over the past two decades have taught me plenty about the before and after of the enterprise sales process. My daily conversations with existing CIOs reaffirm these insights and shed light on other important steps.
I’ll tackle the relationship-nurturing piece further down. First up, here is what CIOs look for in solutions and how you can tailor your sales approach accordingly.
CIOs sponsor and decide, not buy. CIOs rarely make decisions unilaterally. They will most often sponsor a buying decision in collaboration with key members of their team. The mistake most companies make is going straight to the CIO without buy-in from the leadership group immediately under them. Build confidence with that team first. From there, you’ll have better insight into whether the product you’ve built fits into the overarching strategy the CIO has put into place.
CIOs care about value. Make sure your ROI is definitive. People are always willing to pay a premium to solve problems, but you have to be prescriptive about what you do. And whatever that value prop is, be sure it’s aligned with the CIO’s larger vision. CIOs want solutions for the longer term, so think about how you position your product as a long-term solution rather than a reference-point solution.
Most CIOs already suffer from tool fatigue, managing a budget that includes hundreds of SaaS applications. If you want the CIO’s attention, position your offering as one that will continue to add value over time. Show that your solution can scale and that you have a vision for the future. CIOs are often wary of procuring products they think may disappear or be acquired.
Talk about your deployment plan. Make sure you have a clearly articulated plan for deployment and change management. Many CIOs will say no to a solution simply because their teams aren’t set up to deploy well. Think about how you can deploy a solution and add value without relying on the customer’s resources.
Remember that a CIO’s team has been building, buying, deploying and managing solutions long before you showed up. How does your solution fit into the team’s process and, more importantly, how do you deploy successfully?
Have your references ready. Have a reference that’s relevant to the CIO before you reach out. CIOs expect to be sold to and cold-called; it’s not a surprise when it happens, nor is it jarring. But it happens a lot, and to break through the noise, it really helps to have a peer CIO who can reference the solution.
CIOs want to hear about you and your company. Don’t rely on the customer’s competition as a reference point — you don’t know what they think of that competitor. When I was a CIO, I had vendors call me and say they were helping a competitor do X, Y and Z, while said competitor was still losing ground to my company. My first reaction was always, “If we’re already beating them, why would we want to replicate any part of what they’re doing?” It puts the CIO on the back foot immediately.
Their priorities and operational headaches are ever-changing. Most companies hear “no” and move on, but it’s crucial to play the long game. CIOs have a lot on their plates and are always budget- and resource-constrained. Sometimes their strategy is still being developed, so make sure you’re approaching them at the right time, and start with relationship-building. That no could easily become a yes someday if you put in the time and effort. Track their company’s progress and build rapport with the CIO’s leadership team: The more you understand the company and how you can be successful, the more likely your solution will become a priority for the CIO.
Now you’re rolling. You made your pitch and knocked it out of the park. But your work is far from over once the CIO and their leadership team say yes.
The next step is to strengthen your relationship with the CIO for the long haul. As CIOs rely more and more on the startup ecosystem to differentiate and make decisions, the relationship between CIOs and founders will become increasingly symbiotic for those who properly nurture the connection. Here’s how to do just that.
Begin by getting alignment on the actual deployment. How are things working? What could be better? What’s better than expected? Starting here signals that their needs supersede your own.
Be prepared to talk about where you are as a company. Elicit feedback and show that you’re responsive. Talk about where you’re going, and use that as a low-pressure environment to gradually upsell or talk about renewals. When I was at Pure Storage, the founder of a startup that had recently won our business went out of his way to sit down and listen as I reiterated my feedback. He focused on the product road map rather than renewal, and was able to illustrate to me in very clear terms where the company was going. He knew he had a solid product, but was candid about where he thought the shortcomings were and solicited feedback on how to strengthen those areas. Needless to say, renewal — and significant expansion — followed naturally.
Understand the CIO’s business inside and out. Provide a vantage point on their competition or industry. Go beyond what they expect, and when it comes time to create yearly budgets, your line item will be a no-brainer.
Look for opportunities to help that go beyond the scope of your engagement. Understand the CIO’s hiring needs and what gaps they have. When appropriate, give them referrals. Never underestimate the power of being personally helpful. If you can connect CIOs with potential customers, peers or talent, do it every chance you get.
Get to know their leadership team and build a rapport with them, too. Understand succession planning within your customer’s organization, and get insight into who’s influencing the decisions. Identify the people who will continue to allot budget toward you as the key internal players change and evolve.
Escalate problems early, and be proactive in finding quick resolutions. At another previous company of mine, we’d bought a new solution and the deployment just didn’t go well. The value prop was great, we loved their team, but due to unforeseen issues in both their environment and ours, things simply didn’t work. I’d taken a risk, and the founder knew I’d ultimately have to answer to my bosses for the wasted spend. Proactively, the founder refunded every dime, with one condition — that we’d give them another shot when the kinks had been ironed out. A short while later, they came back with a better product and we successfully deployed it together.
As a startup founder, access to power and influence within a customer’s organization is critically important. Knowing how CIOs think, the ins and outs of their business, and how best to fulfill their needs will not only help you sell more today, but help you build for the future.
Your job as a founder is to keep that door permanently open. Good relationships with executive buyers can help shape your company as it grows, ultimately serving as an unofficial advisory board of the top leaders and experts within your customer base.
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