Name Dropping, Michelle O’Keeffe, CEO of Engaging.io
By: Hubspot Product Team
Tags: Leadership, Women In Tech, Technology Strategy, CEO, Technology

Name Dropping is a Q&A series that aims to elevate the stories of women and nonbinary people leading in the tech space. The idea came from Angela DeFranco, a VP of Product at HubSpot, who said one way to be better allies is to name drop more women and nonbinary people in discussions of achievement, inspiration, and disruptors in tech, instead of referencing, time and again, the same set of (often male) leaders.

This edition of Name Dropping features Michelle O’Keeffe, CEO of Engaging.io, a HubSpot partner agency.

You’re CEO of Engaging.io, a human-centered digital strategy, design, and development firm. What are the most exciting challenges you’re currently working on?

Things are obviously changing pretty quickly at the moment, as they normally do in tech. With everything that happened this year, we’ve got to answer to the business. We’ve got an agency arm and we’ve got a product development arm. And we were always hoping to build more and more products, some of those associated with HubSpot. Some might be HubSpot plugins. But we build other things, as well. And I think what we ended up focusing on was solving the biggest pain points for our enterprise level clients and turning those into products. We’ve been able to launch two since the beginning of the pandemic, which has been really good. And it keeps our engineers happy, as well. They love building products, as opposed to running multiple agency projects at any one point in time. We’ve escalated this kind of work because of COVID, and because of that recurring revenue model that those products have, versus most of our agency work, which is all project based. It’s been really good. I’ve been really happy and proud about the progress we’ve made there.

When you visit Engaging.io’s website, you list all the ways that you, as a company, are “engaging humans” ⁠ — through intuitive UX, through reporting and attribution, through beautiful websites, etc. What does true engagement mean to you?

We’ve got four directors of engaging, and we’d all been off in corporate doing our own things before we came together about 10 years ago. Our approach with every client is very much, if this were my business, what would I do? We treat every client as if it were our business: these are the challenges, this is what they’re facing, this is what they’ve asked us to solve for. And given that approach, sometimes we reverse-engineer what they’ve asked us for or what the brief was for.

Watch and listen as Michelle answers one of our questions live

But it means that we’re really open and honest. And, you know, most of the time, there is a reverse engineering of the brief as well, which was made at the beginning of the relationship. There might be uncomfortable conversations to a point, but our clients also give us this element of trust. I think that’s why we’re so successful.

We try to instill the same thing in our staff. If you’re talking to a client about the brief, put yourself in their shoes. And imagine if this were my business, and this was my money and my revenue, what would I do?

You also have to say no sometimes, though. If there’s not a good cultural fit between us and a client, we have to say sorry, we can’t help you. Especially right after we see the brief. They may want us to build something we know isn’t going to work. We’ll say look, this is what we would recommend doing. If they don’t want to hear it, we’re not going to build something that we know is going to fail. Not everybody’s used to that approach. But I think it’s the honest way of doing business. And certainly our staff like working on projects that work, and that achieve really good outcomes. And that’s self-perpetuating. We’re 100% referral, because we work that way. That’s the core of engaging: connecting as humans first. What are your business challenges second, and then how can we solve for those?

How has solving for your customers changed, if at all, during the current pandemic?

When everything first hit, nobody really knew what was going to happen, or how we would all be impacted. I think we definitely got off lightly and HubSpot was really helpful, as well. In that sense, it was kind of miraculous that HubSpot acted so quickly, and identified that one of the biggest pain points would be cash flow for organizations like ours. We’re still having the same amount of sales conversations, and we still have plenty of work to do. But clients that we had been working with, their businesses fell away overnight, and now they had to say to us, I know, you’ve done this work over the last three months, but we now have no money to pay you. So that was our biggest struggle.

Now, we’re very, very comfortable with the conversation around payment plans for clients, because their businesses still need to be able to function. We’ve just had to be flexible there in order to help them. And I think, while MVPs in tech have always been an intelligent way to go, it’s much more part of the conversation now: “I just need to get to market with this as quickly as possible. I need to prove that it works.” And then you can build out and adopt an iterative approach later.

What would you say is your greatest career achievement to date?

I’ve done lots of things and been lots of different places. For a while, this was for big corporate companies. And I did some cool things there. I made it to the top of my career space. I was with an organization that paid more than anyone else, and things like that.

From a career perspective, that was great, but at the same time, I was working 120 hours a week, and was not very healthy. This came as a surprise to me at the time, which it probably shouldn’t have. And I ended up just thinking, it’s great to have all this money and everything else with it, but I’ve got nobody to spend it with and nothing to spend it on. I don’t have a life. So I ended up quitting. That was one of the funniest conversations I’ve ever had. Because they asked, Where are you going? And I said, I’m not going anywhere. And they said, I know you’re going somewhere. And I said, I just don’t want to be here anymore. We went in circles for about 20 minutes.

Fast forward to my career now, and my greatest career achievements aren’t on paper ⁠ — they’re about people. We, as directors, we’re all really clear that we wanted to create this environment within our company that acknowledged that work is secondary to real life. Of course, you spend a reasonable amount of time at work, but there’s no reason it can’t be an enjoyable place to be, and we can’t all be nice to each other. It’s like a little mini community.

We’ve always had a great culture, but I think it was really demonstrated for me with COVID. At the beginning of the pandemic, we all said, Okay, everybody work from home. We’re lucky ⁠ — we’ve got all the tools and tech we need to keep things functioning without being in the office. But everyone was working 1,000% because nobody knew what was going to happen. They were working for each other, going the extra mile ⁠ — directors were working really hard to make sure employees were all still getting paid 100% of their salaries, because a lot of their partners had been laid off. In short, we knew that our people were working hard, even from home.

I didn’t think about this too much until I spoke with some other agency owners and they said, I’m really worried, I hate the working from home thing, because I don’t think my people are working. And I thought, How does that happen?

And I sat down and thought about it. I honestly think that would be my greatest achievement: building and fostering this team of people who work for each other and care about each other. Which is what happens with community, right? When you come together, you can do great things. And that’s just not something you can tell people to do or be. That’s something that we’ve built. People feel like they are part of the community, they care about each other. They go the extra mile for each other and the company succeeded because of it.

What advice do you have for those with nontraditional backgrounds looking to break into the tech industry?

In tech, I think it’s a more of a level playing field in the sense that if you build a good product, it doesn’t matter who you are, doesn’t matter what you look like (your end customers can’t see you). But in that context, there’s still the same sort of hierarchical games that you have to play if you want funding, and things like that. And I think I’ve always naturally called that poor behavior and naturally gravitated away from that behavior.

If you’re getting into tech, there still needs to be this awareness and social responsibility. If you’ve got good ideas and good ability, I think that gets you in the door. But once you’re in the door, not everyone benefits the same. Nor is the place you’ve found yourself always a place you want to stay. I think it’s worth looking for those people and organizations that share your values, and gravitating toward and aligning with those people.

While sometimes the money and the bright lights might be somewhere else, going that route instead can equate to selling your soul. Over the course of a career, you might find yourself asking, How did I get here? This doesn’t match with my value system. That’s why people have their midlife crises. It’s really worth finding your niche within tech. People who work in a way that is consistent with your values.

We’re all human beings, and work is a part of our life. And if you don’t like your work, you don’t like what you’re doing, what you’re able to achieve, you won’t be happy in the rest of your life. There’s lots of opportunity out there, almost too much. New products are coming up all the time. You have to decide for yourself where success lies.

I’ve worked in very male-dominated industries, even before I got into tech. I’ve seen some very poor behavior, but I always spoke up and did the right thing by myself. But what I came to realize over time is that not everyone is like that. And that I should be using my voice and my ability to actually help support people who for various reasons feel like they can’t speak up the way I have.

And it’s not just being a female in male-dominated industry. In all of the different contexts that people face, we have a social responsibility to look after those who don’t have the same voice that we have. And it’s hard, and it can feel like it’s going to be career-limiting. But that’s never been the case for me. So if people feel like they have the platform to speak up, then I highly encourage it.

What’s the most important lesson you’ve learned so far from your experience as a CEO?

Apart from that daily feeling of having no clue what I’m doing?

It’s that old adage, the more you know, the less you know. It definitely applies.

Honestly, the biggest lesson has been to look after myself. You’ve got this idea that the buck stops with you, you’ve got to do everything to get there, push yourself to get there. But, COVID brought this lesson to me, because I was just getting exhausted and burned out. And you cannot be of any use to anyone if you’re burned out. They say to mothers, if the mother’s sick, then the kids don’t thrive. It’s the same thing. It’s a little bit counterintuitive, but I honestly think if you, as a leader, take time for yourself to make yourself healthier, then you’re going to have more to give to others, and you’re going to do a better job. I’ve not always been good at it in the past, but it’s so important.

You have a background in teaching Qigong ⁠ — are there any skills from that experience that you use in your current position?

For me, that’s the real stuff. That’s what gives meaning to my life, full stop. Everything kind of underpins that. One of the really good sayings in Qigong is “energy flows where attention goes.” Being mindful about what it is that you’re trying to achieve, and then directing your energies to that will give you success every time. It’s really easy to get distracted and have what they call ‘monkey mind’ and try to do too many things at once. But at the end of the day, if you set goals, just like an organization sets their business objectives for the year or the next three years, you can achieve them.

It’s just as important for a person to set goals as an organization. Put them up somewhere where you can see them, where they are integrated in your daily life, and then they’re something that you think about and your energy goes toward them naturally. That’s been really good for me, that sort of single-minded focus. Filter out the noise and focus on one thing. I think our brains need meditation. It is so rejuvenating, for us to try to slow our brains down like that, especially with the sort of work that we do, and the amount of information that we absorb.

I think it’s really nice to have those big ideas and those dreams. They’re the sort of things that make life exciting for me and give me motivation as an individual. There’s a little bit of mystery around that, as well. It’s great to make money, it’s great to build great things, but at the end of the day, life is always going to be way more important ⁠ — real life, beyond work. That was just a belief that we had when we started the agency, but after living that way, everyone has benefited from it. People love to work here, they stay here a long time, they contribute wherever they can, and I think they feel supported. This idea that the individual is everything just doesn’t work. It’s community. We’ve got this responsibility to look after each other no matter what you look like, or what you do for a living, or what you have or what you don’t have. None of that matters.

I think you can have a business that makes money and still live that way. They’re not completely separate ideas. That was the philosophy that we had. There were a few moments early on, where I thought, Oh, this cannot work. But it does work. It does work. There are plenty of agencies that started at the same time that we did, and they don’t exist anymore. It’s because they didn’t treat their staff well. You need to put your profit into the business and hire more people. Make sure everybody is looked after. That works.

Who’s one woman or nonbinary person you’d like to name drop, and why?

Over my career, I have found that my female bosses were much more difficult for me than my male bosses, who were also challenging. But I’m 44. That was a while ago. And I’d like to think that things have changed a bit since then. We may have talked the talk then, but we didn’t actually walk it.

That said, I don’t have the feeling that I’ve had women leaders in my personal life whom I aspired to. But I do know great women through my own company. We’ve got some great female engineers, who are really open about balancing their real lives and their kids and their work. And they’re just unashamed about it and unapologetic about it. And I really liked that because it normalizes what it means to have these other challenges in your non work life. And I think it’s little things that are brave. So there’s Neema Tiwari, who is a developer of ours. And she’s obviously working from home at the moment. Her family comes first. And she doesn’t skip a beat with work because she uses her flexibility however she needs it. Sometimes that might be doing something at two o’clock in the morning, although we try to try to make sure she doesn’t do that. But I really like that, just this absolute idea that this is who I am, this is what’s in my life. And I can still make this work. And I can still do phenomenal work. I think it’s really cool.

I remember interviewing her. And it was actually the case for all of our women on the team. They were all very outspoken in the interviews about their abilities. I hadn’t heard women be that outspoken in interviews before ⁠ — you hear it a lot from men: Yeah, I can do that. Even if they’ve never even contemplated doing it before. And that was the thing that resonated with me. You are demonstrating to me what your value is. Let’s give this a go and see how far we can take it. I love that. That’s my favorite thing. Empowering each other.

What advice would you give your 22-year-old self?

So firstly, I would not have listened to it.

I’m stubborn. Like I said before, I’ve learned well by making mistakes, but very rarely by following advice.

I would say, don’t work in corporate.

Find something you love. And do that. Regardless of whether you think it’s going to make money or not. At the end of the day, you find a way to support your lifestyle by doing something that you love, and there are so many ways now that we can do that, that maybe I wasn’t aware of back then.

I thought, you finish school, you go to university. But I struggled at university. I did a Bachelor of Arts and thought, why am I here? There was no motivation. I finished, which I think was my greatest achievement ⁠ — actually completing my degree. But then I thought, I need to get a job. That’s what you did. I didn’t have a lot of advice around me. So I was just a bit of a leaf in the wind and ended up finding my own way.

So that would be the biggest thing ⁠ — find what you love and do it, regardless of what you think is right or wrong about it. If you do that, it’s got to be an interesting journey.

Know another woman or nonbinary person whose name we should drop? Tweet us at @HubSpotDev with ideas.