From CIO to VC Advisor: Michael Dunn’s Blueprint for Strategic Advisory Boards

Michael Dunn, a veteran technologist and executive advisor, has held top roles including CIO, CTO, and board advisor across enterprises like Dell, RingCentral, and Brightcove. In this insightful conversation, Michael breaks down the mindset shifts that propelled him from IT leader to trusted VC advisor. He shares actionable strategies for building effective Customer Advisory Boards (CABs), fostering executive engagement, and driving innovation through trust and collaboration. Whether you're a product owner, founder, or enterprise leader, this conversation is packed with frameworks for turning customer and technical advisory boards into engines of growth and strategic alignment.

From CIO to CTO to VC Advisor: Michael Dunn's Pro Tips for Building Strategic Boards - Transcript

Irene Yam  0:00 

Hi everyone. I am so excited today I have joining me Michael Dunn. He's a first and foremost a technologist that has led in the C suite in both startups up to enterprises. He served in several advisories as an advisor to not only, you know, tech companies, but also to VCs on or Ring Central Sun, Microsoft, bright Cove. And I wanted to sit down with Michael, because he's been to over a dozen and he's really taken his C suite journey into being a true advisor, and he really gets value out of cab. And I think a lot of people don't know how to ask questions or really build themselves up, connecting with people and building their network. And it's Michael for being here, you bet. Yeah, well, we, we had a little chat. You're really big into mountain biking. So I wish we could talk all about that. That's really that's really cool, by the way. Um, but let's kind of share a little bit about your background. You you sit on a lot of boards. You even sit on bank boards. So maybe if you could share a little bit about your journey.

Mike Dunn  1:18 

When I started my career, there was mostly the track, was it? And CIO was sort of the top role you could get. And I was lucky enough in my career path to be involved with companies that wanted that had technology as part of their product. And so this new role came about, called the Chief Technology Officer, and it was a in a sort of parallel aspect to what CIOs are doing. So to me, and I, I hear this defined a lot of different ways, but to me, a CIO is sort of running the systems of the business, yes, and the CTO was using technology to help the product of the business, or to be involved in the product of the business, and so much more involved in the strategic direction of the company, versus just fulfilling the you know, systemic needs of the company. I like the creative side of it. I like the innovative side of it. I've had many jobs where I've been responsible for both CIO duties and CTO duties, and I liked building teams of developers and product managers. I always felt like I was looking for the next paradigm shift. So I was involved with when mainframes went to mid range and then went to land systems. I was involved in that shift, when, when the web first started. I was involved heavily with providing websites. I happen to be the CTO of a large global ad agency, so I provided early explanation of what the internet was and what the web was, and early websites for our clients, because they viewed it as our clients, and our company viewed it as advertising opportunities, but mostly marketing. And so we needed to guide them and their their IT groups had not, you know, didn't want anything to do with the internet because it was risky, and didn't want anything to do with the web because they didn't understand it. So that was a paradigm shift. And then I took a few different roles. One was CTO at Dell, building their initial e commerce platform. So that was, you know, a big shift, yeah. And then I had most of my career I've spent either in technology or directly or like Dell or big media companies. So big media companies use a lot of technology. Some is sort of old, tried and true, like broadcast systems. And then some is transforming to Digital and Web Solutions, depending on the type of company it was, and all of those had big partnerships with technology providers, and some of the more forward thinking had customer advisors, and some would form them into boards, and some would just have them as sort of individual advisors, or let us in on how you're using our solution, so we can craft Our solution to meet the needs of a customer like yours better. Microsoft and Dell were that way. They were strong partners, and I used a lot of their software for that initial e commerce site, and they they gathered input from us constantly to see how they could do better with with. We were running a, you know, multi million dollar e commerce pipeline for the in the early days of the web, which was unheard of. I think Amazon was the only one that was really at scale at that point. Wow. And so they wanted that feedback from directly from a customer and from developers and engineers that were working on it. So it was a really, really good relationship. As

Irene Yam  5:26 

I think one thing that I just want to pause and talk about is, as a technologist, you have to really be a strong communicator. You have to communicate across your team, and then you have to across your your colleagues to to understand, like business leaders need to understand why you're doing all these things and your vision.

Mike Dunn  5:48 

I had a really good boss early in my career, and I I would talk too much like I would, I would over explain things, and I was very technical, and, you know, I and he said, Look, we know you're a smart person, but we we need you to be able to communicate so people understand it, and so if you're talking to somebody with a certain level of understanding, the others aren't going to get it. And I spent a lot of time working with academic institutes like MIT and NYU Columbia and variety of others, where I've gone done guest lecturing, and that helped me too, because you're talking to an entry level student, and you have all this expertise, but you need to make it presentable. And so I've coached a lot of the people I've worked with that you really need to develop how to talk at a non technical level, so people understand it and make it approachable. We become storytellers, you know, and how we're expressing the value, let's say, of if we're promoting something that we think should be budgeted for and implemented, then we've got to make it approachable, so people understand it and so they feel like they're engaged in a part of it. So, yeah, I always sort of honed that. Thought it was really important. The other thing was to learn how to be a listener. Like, yes, I've met so many engineers. Pick on engineers a little bit, but they spend so much time talking about what they're doing and they're missing that feedback. It's like listening is a it's a such an important aspect of of learning and then offering value. So tried to coach a lot of people to do that too.

Irene Yam  7:39 

Mm, thank you for doing that. I think that makes us all better, and I'm really glad that you had an early boss that pulled you aside to tell you, to tell you that in your ear, because we get to sit together, and we were part of a great Ring Central advisory board. You know, over the course of your career, you've been asked to sit on lots of boards. Let's just focus on customer advisory boards and technical advisor boards, because you have the chops. What was the value to you? Because I think you're you don't just take the CEO's phone number and go home. I want to hear about how you've built these relationships over time through customer advisory board, Technical Advisory Board, and how has it kind of leapfrogged you into all these wonderful opportunities I want to learn from you, if you don't mind. Michael,

Mike Dunn  8:28 

um, sure. So you know, formalized boards, whether it's traditional boards, and I've served on a number of those, they have a process, and they have sort of a way that you you you expect them to function, and then you get into customer advisory boards, technical advisory boards. They're meant to be two way opportunities to communicate and learn. And so the company has it structured as its various responsibilities, depending on if it's a, you know, a SAS model or a traditional product, whether it's a digital product or a physical product. And you as a customer, I think you approach a customer advisory board as I'm using the the what the company offers now, and I'd like to understand the direction that company is going in from a product maturation standpoint, and I'd like to express my needs in my area. If you just, as you said, take the CEOs email and number. You know that's always an escalation. That's always that CEO isn't talking to customers every day, there's there's people in teams that are managing those things, whether it's a product team or a sales and marketing team or a customer support team, yes, and those there's fun, they all have functions that are important. And, and so if you built those, and then you look at people you're partnering with, and they have those in place, you want to actually understand who does what and and fit within the process to gain some traction in whatever it is you're trying to gain. So in something like, I'll use Brightcove as an example, because it was a streaming media platform that we happen to be an investor in, the company I was working for. And so I was representing the investment, as well as representing implementing this, the platform, the solution, as a customer. And then I was also socializing it and trying to influence decisions of some of our partner companies that were part of this big media company, basically, and and so I was selling bright Cove into them as well, not as a salesperson, but as an advocate for the solution. And so as I did that, I I'd see what was missing as a customer that we could implement. I'd see what was on their pipeline, because I was aware of that and influencing that. And then I was also acting as a technical advisor to their engineering and product team as they were looking at progressing that and understanding, you know, if we, if we look, everything's a everything you have to budget for. Everything is an investment in when, anytime you're a company, and when you're doing software development, you have to make decisions around what you're going to focus on, what the high return on investment is, the what it's going to cost you from a team, commitment and delivery pipeline, like, what's the order of things we should be doing? And so being able to collaborate on that is critical in a cab or in a in a technical advisory capacity. And so you do it sort of in a collaborative, collegial way, and that at the end of the day, you're looking to get something that helps you do your job, helps your company get value out of what you invested, in this case, or or you're using as a customer, and then that company wants to be able to Look at input from a variety of different customer segments and prioritize what they're going to be working on to add value to that customer segment, to add value to where they sit within the their competitive landscape. And in our case, you know, the goal was for right Cove to go public, and so it was aimed at what what are the variety of value? What's the variety of value we can provide that will mean the most as we convert this from a private company to a public company? And so that was fun, you know? It was, yeah, we got a lot of value as a customer, I think at the end of the day, like small for compared to today, but I think we're running about 4 billion streams through bright Cove annually, at the time, through a lot of pretty big media entities. And you know now, with all the OTT and streaming platforms, it's much bigger 15 ish years ago, so different time. That was a really rewarding effort, because I was part of the original team that did the due diligence on the investment in bright Cove, and then I stayed as an advisor all the way through until they went public. Jeremy Allaire was the founder and CEO of that of bright Cove. And then Interesting enough, when they went public. He left with within a short period after, and founded circle, which is a blockchain a very established blockchain company. So just and at the time, I knew about blockchain and digital currency, but I had no idea. I'm like, oh my god, this is such a talented guy leaving, you know, this media service industry that he's done so well in and he's going off to this nation now they're, you know, one of the premier circles, one of the premier blockchain enterprises. So obviously, he's a, he's a talented guy. It was fun to work with him.

Irene Yam  14:13 

Yeah, wow. Sounds like you have a lot of stories that you could share, right? So I don't want to, yeah. I would actually, because of our time together, could you share one story that like a cab, that you could they could have done better, meaning you're sitting there, you were excited, you were ready, you're excited, you're engaged. I don't mean to be negative, but there are a lot of times where, you know, we try so hard, but we're not, we're not really getting it. So I'd love, yeah, we could be better at running customer advisory.

Mike Dunn  14:49 

Well, yeah, we talked about this a little bit before we started recording. But the key thing for me with any advisory board, whether it's technical. Customer, whatever is that you're it's a two way communication path. So customer, in this case, customers are communicating and the business is communicating. You're sharing some insights. You're sharing a direction or pipeline, and that you help help both sides understand the process. And then you're going to have a punch list that comes out of that. And there needs to be follow up in that. And it needs to be, you know, land in the right area. So sometimes you bring up something during a cab session, yeah, and it's a sales related thing, and so the sales department is going to go follow up. Sometimes it's customer support has something to do with with CX, you know, customer experience. And so you're getting insight from a customer and how to improve CX. And so you have to do follow up on that. I think the cabs that don't do well, use it as, and I haven't experienced this a ton, but I've seen it. They use it as a sales pipeline, you know, they take notes during the cab and they say, Oh, I can go up sell that. Because I just heard this customer say, it'd be great, you know, if we could have that feature function, whatever. And so then the salesperson, sales team goes and advocates that, advocates that to the product team to increase the, you know, get it into a different place in the pipeline, which may be the best way to do it. I think if you're if your customer and market fit focused sales will follow fine, but if you're driven by just sales opportunity that don't fit with what the product really should be doing, you're not going to get as much value as a company. You're not going to get as much value out of your cab, and then the customers are going to be disappointed as well. And so I know the cabs I've worked with where I actually had, let's say a customer support issue that was really critical for us the follow up we got. You know, sometimes I'd be at the cab, I'd be traveling back to to wherever, wherever I worked, and customer support of that company had already reached out to my team and was already starting to move it forward. By the time I got there, there'd already been progress. I mean, that's just, that's a win, win. That's, that's high value. And it to my, whoever you know my management was at the time, it was able to prove that, hey, being involved in these cabs is really beneficial. Because as a company, instead of just sending an email into customer support and getting a ticket and hoping it gets through, you're getting a direct pipeline to see the wheels are moving right away. And so there's high value in that. And sometimes, you know, business executives don't understand the value of a technical advisory board, especially if you're, you know, you're providing your guidance as a technology team into the solution you're working with. It's that's high value, but you've got to be able to sort of prove it that, hey, this is worth the time. It's worth taking a week, or, you know, 552, travel days and three working days, whatever, to go do this engagement with this partner. Yeah, highly critical.

Irene Yam  18:24 

You just brought this up like now I got to ask you a new question, do you prefer a technical advisory board or a customer advisory board?

Mike Dunn  18:32 

From the maturation of my career, I've done more technical advising, but technical is a misnomer, because sometimes I'm advising startups, let's say where you have early in their career, CTO founder, let's say and they have no idea how to deal with the staffing, administrative side of building a team, how to deal with hiring recruiters, or how to deal with communicating to a recruiter with what their needs are, and then how to deal with the HR side and bringing teams on board and building sort of the patterns and cultural fit that make a team progress. And so I've done a ton of advising on that that's not technical. It's just being a technologist with from a business perspective. And so that's a underdeveloped skill set that some some technical, technical founders need. Then there's the product side. Some engineers don't understand the product side. I've always felt like I needed to understand both and develop teams that could could focus on both, and so those fall into a technical advisory capacity. Sometimes, where you're you have a lot of partnerships. You know, you may have a cloud partner, you may have a service partner, where you're looking at your core competence, and you're looking at what's mundane, or something that's you could outsource. Or you could provide a get from a service. Like, as a technologist, you're always thinking, what's the IP of what I'm about to build? What do I need to understand and own, and what may be patentable, what's a differentiator, and what sort of things I can just bundle together and, you know, get access to like, if you use a lot of open source, you can look at an open source stack, and then how do you take what you're building that's differentiating and combine that with that open source stack? So you're going to do have partnerships with those open source providers, with those SaaS providers, maybe. And so that's more technical advising in the big enterprise jobs I've had, I think cabs came more into play there, because they tended to be really big companies that were, you know, in the top 10 of the customer segmentation for that company. And so you have a strong voice just from sales you're already doing with them. And so having input into what was going what you were using that solution for, and where that company was going to make sure could could keep maturing that and going in the right direction. From a pipeline perspective, I think cabs were hyper critical for that. So I enjoy, enjoyed both, okay, you know, it depends on the role, it depends on the the opportunity, but

Irene Yam  21:31 

and the timing, like you said, of the company where they're at, I think the audience would be really wants to know, how do you become invited to be on boards. What are boards looking forward to be an advisor, like even VCs. Not everyone gets invited to this. So if you could help a upcoming leader, not that you want to share your secret sauce, but you know, you I think it's important.

Mike Dunn  21:56 

I think, you know, it's a good community. Yeah, it's a it's like anything. It's a crawl, walk, run. So, you know, I've when I've had some of the most of the the enterprise jobs I've had. I was also part of the strategic VC group at those companies. So big media companies, big technology companies. I was at Dell when Dell ventures was founded. It was internal first and then spun out. So I was a technologist that was influencing, or, you know, advocating for that at the time, that was in the 90s. And I think so, if you, if you, if you're able to sit and listen to a company that has a concept, and then you can help them take that concept through each step to ultimately being something that's a a new CO and a and a a product and market fit that makes sense. And you can guide them along that, if you do it in a in a useful, informative way, they're they're going to ask you to keep advising them. You know, depending on where you're doing it, I got a lot of traction early on in my career from speaking at universities. And so there were entities like the MIT Media Lab spun out new entities all the time, or their sponsors got access to that IP and created a new CO out of that. We did that at Hirsch when I was at Hearst with E Ink. So came out of the lab and then was spun out into a separate entity, and Hirsch was one of the original investors in that entity. And it's, I think it's one of those scenarios, like I mentored at TechStars as well. And so you go through the program, which is sort of like an incubator, what today would be called the studio, and so you're helping them through that program. But then if you've added value, sometimes the companies are going to say, Hey, can you stay on as an advisor after we leave this program? Or even, can you join our board? Because we'd like to have you as an outside board member, which I've done a number of times. So sometimes you end up serving on boards as an aspect of your role, and then sometimes you're just involved because they got value when you're going through some program, and then you you were able to, you know, show that you added value. And it just sort of becomes organic. I think you know where I am right now, in the in the Bentonville area, northwest Arkansas, there's, it's a phenomenal environment and culture. There's lots of the ecosystem for innovation and and growth is really strong. On. I told you, it feels a little like Austin back in the day before Austin had its boom. Yes, I happened to live in Austin during that early boom time, and I'm seeing it here in Bentonville as well. But it's a little more structured than it was in at the time in Austin. So there's some great programs, and I've been involved in some of I've done some. Been involved in some accelerators or innovators or incubators or studios where I just act as a mentor. And then again, if there's if there's if they want me to hang around and provide advice, more than it, you know, matures into a formal advisory role, which I've done for for a few and I really enjoy doing.

Irene Yam  25:49 

Yeah, no, you're great. I remember at RingCentral. So I joined Ring Central later when it was trying to move up market. Yeah, and I know you were really early on as one of our first inaugural customer advisory board members who really gave us feedback that we really needed to hear to build our platform to get to small, mid and into enterprise. So I want to thank you for that, because you were a part of our journey of of scaling, and you were

Mike Dunn  26:28 

fun, fun cab, and it was run, was really well done, and access to the entire team, and again, from my perspective, a lot of note taking during the meeting by the Ring Central team members and lots, lots of good follow up. Yes, we had an interesting implementation of Ring Central, and it was, I was changing a lot within the company that I was working at. And so it was really great to, number one, get that exposure to the RingCentral team through that cab, and then be able to go back and and use some of what was changed over time to be able to, you know, add to it. And, yeah, RingCentral was going through a growth phase, I think, at that point definitely pretty, pretty

Irene Yam  27:24 

interesting. Yes, and big shout out to Anita, who she was first, who started the boards and then hired me later, and she she's a great mentor of mine as well. I Okay, we have, like, two more minutes, if I don't mean put you on the spot, but I really want to talk about, you know, there's a lot of uncertainty in the world, so people are kind of figuring out budgets. People in even Marketing Land, are trying to figure out if they should have in person meetings or virtual cabs. I just want to throw it out there. Do you benefit from a virtual cab? Or is it okay, sure, sure, go to those. Or should you you want more in person? I just like your feedback because you have you send in probably dozens or 10s of dozens of customer advisory boards. So I want to get your feedback, please.

Mike Dunn  28:13 

So the the difference between a virtual cab and a in person cab or the outside of the meeting, conversations and relationship, going out to dinner, talking outside the structure of the room, sort of informally. And so that's, there's huge value in doing that physically, but virtually. You can still gain value out of it, because it's still basically, you know, you have your market segmentation as a company, you have your customer categories that you're working with, and you can still address that during a virtual session. And you can probably do a virtual session easier and quicker, more often than you can with physical but there's, there's high value in that, and that's the same at every conference, right? You go to a conference and you sit through this panels and the sessions, but probably the most value you get out of it is that impromptu meeting, you know, meeting something in the hallways, or going out to dinner with people and talking that way. And we sort of lost that during the pandemic and the lockdown. And I think now it's now, it's coming back. And so there's, to me, there's value in in both. And I, I think we have great virtual tools now. I think you can do both, either or, yeah,

Irene Yam  29:38 

well, I think you those are really good points. I think, for me, virtual, if you, if you want to do virtual, is that you have to keep reminding everyone to pipe up and talk and but now that, after you end have encouraged people to have one on one conversations, it's okay to, like, just hop on a zoom like you say, like, have your. Virtual side coffee or wine. I mean, just keep engaging, because I think there's so much momentum from a cab and then after, it's like, mer, but no, keep going. Keep talking like that's the best part. Absolutely you can connect, right? And that's what it's about.

Mike Dunn  30:16 

Yeah? 100% totally

Irene Yam  30:18 

agree, yeah. Well, Michael, thank you so much. Really good. Catching

Mike Dunn  30:23 

up with you again. I always enjoyed working with you. I know you're a very strong expert and advocate for cabs, and I, I'm just glad to be participating with you and sharing my thoughts on my experience with cabs as you, as you grow your business, because I think it's, I think it's very useful.

Irene Yam  30:42 

Thank you. Thank you. And thank you for being the OG not not only in mountain biking, but high five. And thank you so much for your time. I'm going to come out and visit you in Bentonville. Absolutely.

FAQ 

1: What is the difference between a CIO and CTO, and how does that impact CAB participation?

 According to Michael Dunn, the CIO typically manages internal systems and operations, while the CTO influences product innovation and external technology strategy. CTOs are often better positioned to participate in CABs and technical advisory boards because they focus on product evolution and customer impact — both critical to strategic board engagement.

2: What makes a Customer Advisory Board (CAB) or Technical Advisory Board valuable?

The best CABs foster two-way communication, where companies share product roadmaps and customers give structured feedback. Michael emphasizes that follow-up is critical: insights must reach the right teams (e.g., support, CX, product) and lead to action. When CAB feedback turns into real product or service changes, it deepens trust and drives customer loyalty.

3: How should companies follow up after a CAB session to maximize value?

Effective CABs don't end when the meeting does. Michael notes that when feedback turns into immediate action — such as customer support proactively following up within hours — it validates the customer’s time and input. He warns against turning CABs into sales traps; real value comes when feedback drives the roadmap, not just revenue.

4: What’s the best way to get invited to serve on boards or advisory councils?

 Michael advises upcoming leaders to offer real value early and often — especially in incubators, accelerators, or university spinouts. Contribute meaningfully, be a great listener, and communicate clearly across technical and business lines. Most advisory roles come organically when others recognize your insight and trust you to guide growth.

5: Virtual CAB vs. In-Person: Which is better for executive engagement?

Michael believes both formats offer value, but in-person CABs unlock richer dialogue through informal side conversations, dinners, and hallway chats. However, virtual CABs are efficient, scalable, and more frequent. The key is to encourage ongoing post-event connections, whether virtual coffee chats or follow-up Zooms, to maintain momentum and human connection.