Author Archives: Kira Makagon

About Kira Makagon

Kira Makagon is a successful serial entrepreneur and tech industry leader. A graduate of UC Berkeley with both an undergraduate degree in computer science and an MBA, she enjoys sharing her lessons learned from being a veteran “only woman in the room.”

2019: What a Year!

2019 has seen sweeping growth in high tech, especially in the realms of digital transformation products and strategies. As part of that journey, in recent years, technologists have been giving more thought to how technology communicates with its users and vice versa. Looking ahead, 2020 will be the year in which technology will craft more experiences around the way humans want to behave on specific digital channels. Technology also continues to democratize the workplace, facilitating greater diversity in our ranks. I look forward to sharing more about all of these shifts in the coming year — and new decade!

Looking back on 2019, here is where I shared my thought leadership:

On Forbes:

The Growth and Potential of AI

Five Ways to Harness the Entrepreneurial Spirit at Your Company

Want to Satisfy Your Customers? Focus on Digital Transformation — and on Your Employees

Transitioning to a Cloud-First World: Considerations for CIOs

On Fast Company:

How my Gender-Neutral Upbringing Made Me a Better Leader


The Key to Boosting Employee Engagement: A Seamless Communications Experience

How to Implement Tech Perks for an Engaged Workforce

Compare the Cloud:

The Power and Promise of AI in the Coming Year and Beyond

On LinkedIn:

Communication of Things: Embracing a New Era of Collaboration

New RingCentral Survey Exposes Risk of Disjointed Communications Technologies

Building Your Career Curriculum: The Later Years


Considerations For CIOs: Transitioning To A Cloud-First World

As legacy companies transition to a cloud-first world, active leadership of visionary chief information officers (CIOs) will be critical to the success of digital transformations.

Such digital transformation is more than a shift in the specific uses of new technologies — it is also a shift in the mindset around the change, especially for CIOs, who must act in new ways. Specifically, today’s cloud-first tech offers rich sources of information that allow companies to make better, faster decisions; the CIO is the gatekeeper for both this technology and the new information that comes with it.

In light of this role as gatekeeper and its growing importance, hiring a visionary CIO to drive digital transformation is critical for organizations. This CIO will be charged with guiding strategic decision-making to maximize value from the new tech and new information on hand. This article offers my tips for achieving the greatest success with your company’s digital transformation.

First, find the right CIO and give them a seat at the table.

Companies can’t get into the cloud fast enough, as cloud is the newest modality to accelerate business. In order to get into the cloud as fast and as well as possible, placing a CIO at the epicenter of the process is necessary.

Not just any CIO will do, though. Typically speaking, there are three types of CIOs: functional, technical and visionary. For an organization undertaking digital transformation, hiring a visionary CIO is a key inflection point for your organization. If your CIO traditionally has served in a more functional role, like that of a “plumber,” fixing tech that’s broken, that CIO may not be the right type of person to lead sweeping digital change. A visionary CIO will view digital transformation and cloud tech as critical components of a company’s strategic plan for growth and revenue generation. For continued success, the role of the CIO can’t be viewed simply as fixing what’s broken; it’s ushering in a whole new cloud paradigm that fills more than one specific role, and that requires vision to execute from a decision-making seat at the executive table.

Thus, the CIO of your company’s future must be a true executive business partner with a leadership voice. This visionary CIO serves as a key part of the executive team and is charged with making major decisions that leapfrog your organization to success and continued growth for many years to come. Cloud must be part of that for any business seeking to grow.

Next, empower the CIO to implement an integrated solution.

When it comes to digital transformation, companies are often looking to solve the maximum number of problems with one integrated solution. Taking a “solving-one-problem-at-a-time” approach is a vestige of a legacy-systems mindset. If organizations take that approach, their transformation will be both too slow and too piecemeal to be effective.

Digital assets, such as tools that streamline communications and collaboration, are often the only way to do business better, faster and cheaper today; a CIO’s mandate is to support their business in achieving those goals. There are massive platforms out there that can support businesses in achieving all of these goals within one piece of cloud tech.

A mistake I’ve seen large companies and their nonvisionary CIOs make is solving problems in silos, choosing different, nonintegrated systems for different departments or needs. That approach simply doesn’t make sense in a cloud-first world.

At every step of the digital transformation journey, the visionary CIO and the decision-making team must keep their eyes on the prize: fully integrated cloud-first tech solutions as a source of rich information — information that is only as valuable as its accessibility through a unified system. Embracing existing innovation and choosing a consolidated platform is not only better, faster and cheaper — it’s also the only way fully to support the worthy end goals of revenue generation, customer and supply chain satisfaction, and employee productivity.

Finally, remember that digital transformation is holistic, intended to serve both customers and employees.

Often times, the need to improve call center flow is what pushes companies to seek digital transformation to an integrated, cloud-first solution. A recent survey conducted by RingCentral and CITE Research offers data reflecting just how much customers disdain repeating themselves to multiple representatives in order to have their concerns addressed. Such disjointed communication paths drive 41% of consumers to stop using a company’s product or service altogether.

It’s not just customers who are frustrated when tech tools are inadequate, though. Out of the employees surveyed, 75% feel stressed when they can’t collaborate effectively with co-workers to solve a customer issue, hindering them from serving customers as well as they’d like.

The survey showed 54% of workers believe ineffective technology makes them less productive.

These statistics may not seem like primary concerns for a CIO, but they are. A visionary CIO’s job is to make sure that a company’s systems support the goals of revenue generation, customer and supply chain satisfaction and employee productivity. The latter two go hand in hand.

Customers want to be met where they are, on whatever communications channel they choose to use and on whatever device they choose to use. Employees seek to respond just as easily on a single platform that has tools at their fingertips for collaboration with co-workers and the necessary resources to serve customers as a one-stop-shop.

Streamlined communication and collaboration technology serves both customers and employees better, leading to more satisfaction all around. Needless to say, more satisfied customers and employees are better for any business’s bottom line.


Digital transformation yields immediate and lasting results for companies. In addition to the cloud-first world, offering new sources of integrated information, communications and collaboration become much easier for customers and your internal organization.

Being a digital-immigrant to a cloud-first world may seem daunting at first. Ensuring that you have a visionary CIO steering digital transformation will yield the best results for your company. For better, faster and cheaper — and for revenue generation, employee productivity, customer and supply chain satisfaction, the time to get in the cloud is now.

This article appeared first on Forbes.

Risks of Disjointed Communications Technologies: A RingCentral Survey

This week, RingCentral released a new report titled “Overcoming the Digital Disconnect: How Disjointed Communications Technologies Are Letting Customers Down — and How to Solve It.” Based on our global survey of 2,000 customer-facing employees conducted by CITE Research, this report reveals a direct connection between employee and customer engagement. We believe that this is a problem that RingCentral is poised uniquely to solve.

Specifically, the data in our report show that disjointed communications technologies harm employee productivity and morale, and these disjointed communications technologies also hurt customer satisfaction and the bottom line. 75% of customer-facing employees say they can’t effectively service customers due to these issues of disjointedness and that such problems make it difficult to collaborate with coworkers, hinder productivity, and make them unhappy at work. Sadly, this isn’t just a work issue; 50% of employees say they take this frustration home and are more likely to be rude to their family and friends. Considering that customers don’t tolerate poor service, dropping an average of four brands per year for that reason, this is a costly problem for everyone involved.

RingCentral offers solutions. Our seamless platform lets employees navigate easily among all the ways they communicate and collaborate with coworkers and customers. When there is no disjointedness in your communications technologies, you have more satisfied employees and more satisfied customers — and a better bottom line. That’s a win-win-win!

To learn more about this and other findings on AI, team messaging and video meetings, read the full report here.

This post originally appeared on LinkedIn.

2018 Wrap-up

Here is a limited summary of where I appeared in print in 2018:

On Forbes:

The Growth and Potential of AI

On LinkedIn:

The Year AI Becomes Pervasive

Building Your Career Curriculum: The Early Years

Building Your Career Curriculum: Mid-Career

Building Your Career Curriculum: The Later Career Years

Coming Soon: ConnectCentral 2018

Women in Technology: Advice from a ConnectCentral 2018 Panel of Experts

The Five Tools of an Innovator

As the saying goes, change doesn’t happen overnight. It’s not invented overnight, either. A lot goes into the practice of innovation. To become an innovator, it’s important to learn which tools belong in your toolkit in order to build the skills necessary to create and to execute your great ideas. Here, I share my key five:

1. Listening. As a high tech founder, I am being pitched by smaller companies constantly. A lot of those who pitch me have great products and great ideas. Start-ups innovate fast! There is a lot to be learned about an industry or product just by keeping my finger on the pulse of what they’re doing. In listening to their pitches, I hear industry trends, burning questions, and which ideas are coming fastest to market. Hearing what the world needs next is a critical skill, and it comes from careful attention to both clients and to the other companies trying to meet those clients’ needs. No company operates in a vacuum, and, if a client is pitching a widget that would go well with your gadget, there is some kismet to having executed the good listening skills required to pick up on that and then to bridge the two, enabling you to connect things to everyone’s benefit.

2. Reading and Writing. I value inspiration and mentorship a great deal and turn regularly to the writing of other visionary leaders for ideas on how to improve and expand my own thinking, leadership, and creative skills.  You can see how I put this in action by reading this piece, my response to Satya Nadella’s book Hit Refresh. Mindfully considering what other respected leaders of large tech companies have to say helps me to shape my own vision. Of course, I read industry publications and blogs, too, including Techcrunch, Business Insider, MIT Tech Review, Science Alert, and others. And part of the reason I write articles and blog posts myself is so that I can inspire others in turn. Writing down what works for me often gives me new ideas. In fact, if you’re ever stuck in a creative rut, try to write a description of what you’re trying to do. Typing is great, but remember that handwriting and drawing trigger a different part of your brain. Writing out and drawing out creative problems often lead you to picture new solutions.

3. Making time and space for creativity. I’ve written of how my best work days balance productivity and creativity, and key to that is protecting creative space. We all could have day after day after day of meetings and accomplish nothing but talking with each other, but that’s not a path to innovation. Innovating requires the time and space to solve problems and dream up ideas. When possible, I work through my to-do list early in the week so that I can  have as few meetings on Fridays as possible. I give myself the gift of time alone on Fridays so that I can plan and think. It’s a wonderful treat to be able to do so at the end of the work week, and I find that, oftentimes, things I begin considering from that space stick with me over the weekend, puzzled out in my head during downtime. That has the added benefit of exciting me to start another week with new ideas.

4. Collaborating. Good work teams get excited about each others’ ideas and run with them together. To stay connected and on-theme, my teams use our collaboration software, RingCentral Glip, to post and exchange a weekly deck of thoughts. This includes not only what we’re working on but also what’s new and interesting, perhaps something they read in the news or a product they heard about that inspired them to think differently about something we do or make. Great ideas build on each other, and, with all of the tools available now for real-time sharing of information, there’s no reason not to keep conversation going.

5. Practice the art of self-disruption. In other words, disrupt yourself before someone disrupts you. The job of a great strategy team is to sniff out market trends early and to act on them proactively. At RingCentral, we disrupted ourselves in this way with the acquisition of Glip, embracing the idea of a team messaging concept and knowing that we could integrate it well with our existing suite of communications solutions, packaging it all into a unified experience so that people don’t have to switch apps all day. Because of our foresight and quick action, we adopted and adapted something that grew our offerings in the market and meaningfully enhanced the way we communicate and collaborate. Nobody in our industry saw this innovation and its quick integration coming, so our company was able to catch our competition off-guard and grow in a new direction. That’s what disruption is: shaking things up. When that happens internally, forcing change that leads to growth, that self-disruption undoubtedly leads to broader industry-disruption. It’s important for companies not to get complacent or to do things as they’ve always been done in order to be able to forge new frontiers and grow.

Now that I’ve shared my toolkit for successful innovation, it’s your turn to share: what’s in yours?

This article originally appeared on LinkedIn on May 1, 2018.

Looking back on 2017

2017 was a whirlwind year. As this new one is well underway, I’d love to share some of the things that made last year exciting.

First, check out this video from the Dublin Tech Summit of my talk on Predicting Behavior in an Age of Uncertainty. It was an honor to be there to speak.

I felt fortunate to participate in some other wonderful events as well, including as a roundable host for the 2017 Watermark Conference for Women, as a judge in the Startup100 Pitch Competition, as a panelist for the MoNage Conference, and as a panelist at Enterprise Connect.

Writing remains a passion. Here’s where and what I published in 2017:

On LinkedIn:

2016 Predictions Redux, and Foreshadowing 2017

Celebrating a More Intelligent Enterprise

The Vast Value of Good Advisors

Women: To Get Ahead, Compete

Get Your Head in the Cloud

My Game-Changing Career Moment

It Shouldn’t Be Lonely at the Top

Women, Tech IS for You

Honored to be Included: Top 25 Women Leaders in SaaS

People before Process: How to Keep Your Staff

Hitting “Refresh” on What It Means to Lead

On Fortune:

Success Is Still a ‘Boys’ Club,’ but Here’s What Women Can Do About It

Why You’re Not Really Working If You’re Home in Your Pajamas

On the RingCentral Blog:

Revisiting 2016 Predictions and Looking Ahead to 2017

Driving Multinational Growth with Unified Communications and Collaboration

RingCentral Connect Platform Partner Program: Let it grow, let it grow, let it grow

On Huffington Post:

The Value of Gatherings among Women

Kicking off 2018, please check out my piece, The Year AI Becomes Pervasive, on LinkedIn.

The Year AI Becomes Pervasive

Looking back at 2017, it is clear that AI arrived. One development that I found particularly intriguing was when a machine, Libratus, beat four of the world’s top poker players in no-limit Texas Hold ‘Em poker. Considering the nuances of the game of poker in which the machine has to learn how to account for things like bluffing, it is an amazing feat of technology that Libratus could be the success that it was so quickly. The implications of Libratus for things like stock trading are significant. On a more personal level, 2017 saw the advent of AI radiologists at Stanford offering diagnoses gleaned from “studying” multitudes of chest x-rays. This algorithm, CheXNet, is able to diagnose pneumonia better than radiologists at the top of their field. It is a wonderful thing to see AI being embraced increasingly by the medical community, which is often slower to accept change, as AI stands to reduce medical errors significantly, prolonging and saving more lives as a result.

Looking ahead at 2018, this will be the year in which AI becomes even more pervasive. Based on the examples above and many others that unfolded last year, it is evident that the groundwork has been laid for AI to become more ingrained in every facet of our lives, from healthcare to gameplay to work. Part of what’s ahead this year will be the use of AI to deliver more contextual information. One way in which this will come about is via the increased use of voice assistants, as AI helpers like Alexa will move with you from your home to your office. Voice activated business interfaces is just the beginning of seeing conversational modalities interoperate, become smarter, powered by natural language processing, instant transcription, and continuous machine learning. I call this “apps that learn.”ᵀᴹ Business users will need to switch context less and will have their applications surface to them what matters most via these conversational interfaces, streamlining and improving work environments yet further.

As AI continues to grow, expand, and take over, it will be exciting to watch which industries adapt to it most readily. It will also be important to watch how cybersecurity responds to this growth, with new frontiers to protect. Being mindful of our own ethics will matter a lot, too. For example, this report in November 2017 from AI Now “takes an unblinking look at a tech industry racing to reshape society along AI lines without any guarantee of reliable and fair results.” As exciting as the path ahead is for the ongoing ingraining of AI into every facet of our lives, it won’t be uncomplicated, and new ground will need to be forged with regard to holding those who make and use it accountable.

This article originally appeared on LinkedIn on February 1, 2018.