CIOs and venture capitalists (VCs) sit at different ends of the technology implementation spectrum: VCs are the initial investors and vendor catalysts. CIOs are the buyers when a technology or concept becomes productized. The two groups often come together, however, to discuss possible deals, explore technology trends and seek each other\u2019s expertise.\n \nFrom left to right: Vala Afshar, CMO of Extreme Networks; Brook Colangelo, executive vice president and CTO of Houghton Mifflin Harcourt; Michael Skok, partner at North Bridge Venture Partners; Michael Krigsman, CEO of Asuret; and Maryfran Johnson, editor in chief of CIO magazine and events.\n\nOne of those exchanges took place at the CIO Perspectives Boston event last week when Michael Skok, a partner at North Bridge Venture Partners, and Brook Colangelo, executive vice president and CTO at Houghton Mifflin Harcourt, connected for CXO Talk, a panel discussion and live Google Hangout, to discuss VC investment trends. The session gave CIOs a fresh perspective on what they should keep in mind when evaluating technology trends, putting together deals, and working with employees and customers. Based on that discussion, here are five things CIOs and VCs can learn from each other.\n\u00a01.Think about cloud like a futurist\nThe cloud is still one of the most important enterprise technologies, but it\u2019s also one of the most hyped, especially given the buzz surrounding the SMAC (social, mobile, analytics and cloud) stack. Skok of North Bridge Venture Partners said the cloud is entering its \u201csecond front\u201d and is no longer just a way to host HR or CRM systems. \u201cIt\u2019s the one [technology] that enables all the others,\u201d he said. \u201cThey\u2019re only all possible because of one particular huge disruption that\u2019s going on that\u2019s a tidal wave. And that\u2019s cloud.\u201d\nSkok said the cloud is what enables most modern mobile applications and cites Uber as a prime example. \u201cThe services that are available today are location services, payment services and communication services, and what\u2019s born out of that is apps like Uber. [Uber] would be impossible without cloud,\u201d he said. He added that cloud disruption is far from over and has yet to reach its full potential in the enterprise so CIOs should still pay close attention.\n2. Enterprises need to deliver easy-to-use technology for employees and customers \nDeploying new enterprise technology used to require many hours of implementation and training. But now with the emergence of consumer devices, employees have come to expect that technology at work will be new, easy-to-learn and easy-to-use.\n\u201cThe CIO\/CTO [role] is to change and deliver new technology and new functionality to your customer at least every three months,\u201d said Colangelo of Houghton Mifflin Harcourt. \u201cYou can\u2019t do that if you have an 18-month selection, a bid process, all of that.\u201d\nColangelo said he doesn\u2019t always take cues on technology from experts. In one instance, he began exploring storage technologies because his customers were already using them on their own, for free. \u201cIf you have to do something [that requires] a day\u2019s training, you\u2019ve already lost,\u201d he said. \u201cBeta testing is happening already in less-controlled environments. If you sit there and be the \u2018no\u2019 guy, eventually the powers that be will overthrow you.\u201d\nColangelo urged vendors to roll out new versions of their products as technology evolves and new methods emerge; otherwise they will be left in the dust by users and competitors. \u201cDeliver it quickly (every three months) and iterate and change,\u201d he said. \u201cThis is a demand based-economy and that goes for vendors, too.\u201d\n\n\u00a03. CIOs need to put the customer before the technology \nSkok said he meets often with CIOs who are trying to figure out the next greatest technology to adopt. While he can advise them on many technologies, he said CIOs should take a step back and consider something else first. \u201cThe great companies understand the customer mindset,\u201d he said. \u201cI try to invest in companies with people who particularly understand the business problem of the CIO. The companies that can really understand the customer\u2019s point of view are going to be the best to deal with.\u201d\nColangelo said the new economy is fast, agile and based on demand. He said he looks to work with companies that live by these rules and helps them build iterative organizations. \u201cI\u2019m not signing a five-year deal again,\u201d he said.\nFrom the VC perspective, Skok recommended that CIOs look for companies that don\u2019t just present technology but lay out a plan for how they will build a unique relationship with your company in order to best serve your customers. Once that\u2019s been established, zero in on companies with \u201cfundamentally disruptive technologies, not incrementally disruptive.\u201d\n4. VCs shouldn\u2019t think of crowdfunding as a threat\nThough it\u2019s a disruptor to VCs, Skok said he doesn\u2019t think crowdfunding will put him out of business. Instead, it's a positive thing for all sides of the technology landscape. \u201cIt\u2019s a good collaborative means for people to get access to capital,\u201d he said.\nHe said VCs are not just about capital but serve as advisers to technology companies. \u201cMy resources are my time, energy and commitment to help build a company. Capital is a small piece of that.\u201d However small the capital, Skok said he doesn\u2019t mind the help. \u201cIf you could get customers, partners and suppliers to contribute capital, [then] they are putting money where their mouth is,\u201d he said.\n5. CIOs shouldn\u2019t ignore open source\nWhen asking how many of the CIOs in the room used open source, only a few hands went up. \u201cFor recruiting and retaining talent, open source is critical,\u201d Skok said. \u201cEmployees today, when developing any kind of system, whether it\u2019s internal or external, want to be involved in the latest technologies. Gen X and Gen Y care about making a difference, and if you want to retain the best developers, they\u2019re going to want to contribute to open source projects.\u201d\nSkok added that showing that you\u2019ve been involved in open source can be a competitive differentiator for companies and a way for developers to create a personal brand. \u201cMany enterprises are now getting kudos for the fact that they\u2019ve contributed to [open source] projects,\u201d he said.