After just a few years on the job, most CIOs will typically have heard ~100 sales pitches. And 7x CIO Mark Settle has heard the good, the bad, and the ugly.

While there’s no magic formula for an effective sales pitch, over his tenure vetting and purchasing software from startups, along with many conversations with fellow CIOs and technology buyers, Mark’s developed a proven method for startups to efficiently define their value and close the deal.

Before diving into Mark’s “formula,” it’s important to understand that while CIOs may be senior gatekeepers to a company’s technology budget, they’re by no means the only gatekeepers. Traditional top-down sales is commonly thought of as the preferred strategy to collapse the sales cycle. If you “wow” the CIO, most of your hard work is done. However, this is also a high-stakes, calculated risk because if you’re unable to garner the CIO’s enthusiasm off the bat, your campaign could be dead in the water. But nowadays, many stakeholders (including the end user…hello PLG) are involved in the decision to invest in new technology and different VPs hold their own budget authority.

For those who have decided the CIO is the right sales entry point, here is a recap of Mark’s top tactics as well as a recording of his webinar on the topic.

Get a Meeting on the Calendar

While booking a meeting with a CIO may sound easy, Mark confessed that sending a cold email is a challenging and often failed approach in breaking through the noise of the CIO’s busy inbox. Instead, look for warm inroads - aka a recommendation from another CIO, trusted VC, or respected member of the company’s IT team. In that initial outreach, you should include:

• An intriguing and relevant business use case
• A new technical approach to doing something I already do
• A product/service that more than pays for itself - according to Mark, this will always get his attention
• A product/service that allows me to rationalize my current tech stack

Note: If a cold email is your only option, make sure it is extremely well researched and personalized. Do not copy and paste generic messaging from previous pitches. 

Congrats…You Booked a Meeting! Now What?

With most meetings lasting just 30 to 60 minutes,* Mark warned not to follow Alec Baldwin’s famous advice to “always be closing.” Instead, focus this precious time on booking a second meeting, not closing the deal. To do that, he recommends following these five rules:

• Rule 1: This is not a sales meeting – it’s a relationship meeting.
• Rule 2: The ultimate goal is obtain a 2nd meeting with the CIO and/or their team. This is a conversation about having a conversation.
• Rule 3: Determine 2-3 learnings you want the CIO to take away from this conversation beforehand.
• Rule 4: Determine the 2-3 learnings you want to obtain from this conversation beforehand.
• Rule 5: Don’t get trapped in a lot of slides. Slides can often bog you down with overly technical and long-winded details, distracting you from the time and relationship management component of the meeting.

*Note: 30 minutes minus 5 minutes if the CIO arrives late minus 5 minutes for introductions minus 5 minutes to determine next steps = 15 minutes or less to actually engage the CIO. 

Drive An Effective Conversation

What do vendors typically want to know?

• What are your current pain points?
• What are you doing to address these pain points?
• Are you satisfied with the tools you’re using to resolve these issues?
• Are you looking at any other new tools to address the current pain points?

What do CIOs typically want to know?

Never assume the CIO has been pre-briefed on your meeting. Instead, quickly establish context and relevance before diving into more specific product information.

• Who are you? Ie. VC funding, other customers, team background.
• How did you get here? Have you had conversations with any other member of the organization?
• How are existing customers using your product? Do not focus on “what problems can you solve?” Mark’s worst sales experiences were when sales leaders tried to educate or lecture him on generalities of his own problems (Ie. Breaches are becoming more frequent and expensive). The CIO knows the major pain points of their business. It’s more important to show them how you can repair those pain points vs. show them that you know the pain points exist.
• Where do you fit in the universe of IT vendors?
• How does your product actually work? How is it different? The role of the CIO does not often require a highly technical background, therefore it’s more impactful for them to understand the secret sauce that makes your product different from competitors vs. a technical dissertation on how your product functions.
• How would I build a business case to buy your product?
• What can I get rid of if I buy your product – now or in the future?

Don’t waste time:

• Providing exhaustive information about founder backgrounds and company histories
• Describing generic pain points that are common knowledge
• Providing a technical treatise on the inner workings of their product
• Conducting demos to illustrate points that could be illustrated more clearly and in less time with slides

Always End With Concrete Next Steps

Ensure there’s enough time for a thoughtful conversation about ‘next steps’ at the end of the meeting.

If there’s a specific request for additional information or follow up activities, make an explicit commitment as to when that will be done and report the completion of those requests/activities after they’ve occurred. If there’s no explicit request, ask for a homework assignment or preemptively commit to certain actions based upon the conversation.

Happy selling! 

If you’re thinking about launching an enterprise software or SaaS startup or have already taken the leap, it's never too early to connect with us. We’d love to meet you to learn more about what you’re building, share our best feedback, and plug you into our enterprise community where helpful.