S4E07 - Michaella Gallina from Wave on The Path to CFO: Leveraging IR Skills for Leadership Roles

Your time as an IRO helps instill skills that can set you up for a successful transition into executive leadership. In this episode of Winning IR, Mark Fasken sits down with Michaella Gallina, Chief Financial Officer at Wave, to discuss how her time in investor relations, investment banking, and on the buy-side helped to develop the necessary skills and position her to take on the role of CFO. Michaella shares how her time in IR and the ability to position companies to drive value helped her to become a strategic partner within the leadership team and set her up for success. Listen to the full episode to learn more about:

  • Michaella’s career journey from investment banking and the buy-side to IR and then ultimately to CFO
  • The importance of cross-functional IROs and becoming a strategic contributor
  • How to identify companies that value IR
  • The IRO as a strategic thought partner
  • Mentorship and career development
  • Ongoing learning and professional growth

About Our Guest

Michaella Gallina is the Chief Financial Officer at Wave and the Vice President of Investor Relations, ESG, and productivity at H&R Block. Before taking on the CFO role, she built an impressive track record in investor relations, managing through acquisitions, activist investors, and restructuring. She was previously a consumer and technology analyst on the buy side and worked in investment banking.

Episode Transcript

Mark Fasken: The journey through a career in investor relations unlocks so many possibilities and learnings along the way. Today's guest is Michaella Gallina, Chief Financial Officer at Wave and Vice President of Investor Relations at H&R Block. Michaella started her career in investment banking and was a consumer and technology analyst on the buy side before transitioning into investor relations.

She worked in IR for over a decade before recently expanding her responsibilities to include the role of CFO at Wave. She has taken her learnings from each of her previous roles into the next one, which has made for an incredible career escalation. She has so much great wisdom to share on all aspects of capital markets, from driving value through positioning and storytelling, to financial modeling, to leadership and growth.

This episode is a masterclass on career growth and elevating the role of investor relations, and I'm excited to share her insights with you.

Introduction and Michaella's Career Journey

Mark Fasken: So Michaella, I thought we'd get into some of the real meat of this episode and start to talk a little bit about you and your journey through the world of finance and IR and now into a role as a CFO. And so I think that's probably a good place to start. Can you walk us through your journey, into IR and then now into the role of CFO.

Michaella Gallina: Yeah, happy to, and thanks, Mark for having me. I love these discussions, and I'm so excited to be here today. Let me start by just prefacing that this is just one experience. I think the great thing about today's world versus Wall Street in corporate America 20 years ago is that there are so many different paths you can take to get here. So that's kind of my disclaimer.

Her Time in Investment Banking and Key Learnings

Michaella Gallina: I had kind of a full circle journey of starting in investment banking. And, you know, I think when I started my career, there were really two paths.

If you really wanted to go somewhere, it was kind of an expectation that you either did investment banking or you went into consulting. I did investment banking, which actually was a very different direction than I wanted to go. But I knew it would give me a lot of opportunities to learn and leverage skill sets that I would use for the rest of my career.

And luckily for me, that turned out to be true. I think, you know, in banking, the biggest takeaway I had, or the biggest learning I had, was how companies are valued. I think that's something that I'll talk a lot about today because I feel very passionately that every leader in a corporate finance organization should understand how a company is valued and align their priorities directly to those types of initiatives, and investment banking did that, right?

You learn all the different ways companies are valued, and more importantly, you learn what unlocks value. And so that's something that has stuck with me my entire career, in addition to the PTSD I had from, you know, sleeping at my desk a couple nights a week and working 90 to a hundred hours a week. But it was a great experience. And you kind of do that knowing you're going to be an analyst, do your time, and move on to the next thing.

Transition to the Buy-Side and IR Role

Michaella Gallina: And I was really lucky to land on the buy side after investment banking. I worked for one of the top growth shops in the country at the time I covered consumer and technology stocks for three years.

It was an incredible experience. What I learned there was the art of asking questions to build a model. And so that translates really directly to the role of the IRO. And we can talk about that in a little bit, but, I had an amazing time there. 

We were a top shareholder in Starbucks, and so quarterly, I got to go up and meet with Howard Schultz, and, long story short, I had an interaction with him that made me realize after three years of trading stocks that I didn't want to just trade stocks. I wanted to actually build value. I didn't want to trade around companies. I wanted to be the one doing it.

And so after about five years of what I would call kind of this classical analyst training of banking and working on the buy side, I made what felt like a really natural move, which is simply going to the other side of the table, right? Instead of being the analyst calling investor relations to talk about the company and do my diligence, I was just flipping that role, and I really loved IR, but what I want to make sure we get across today is how to expand the role of the IRO and how to get really good development, and every IRO role that I had was actually paired with either corporate development, working on a venture capital fund, doing FP&A, doing corporate comms, being chief of staff to the CEO.

And that just gave me a broader sense of the strategy within the company. It helped me understand how you work cross-functionally across an organization, and it really gave me a broader base than just being kind of known as the, you know, communications person, which I think some IR roles can really get unfairly cornered into, versus being a strategic role.

So anyway, I did about seven or eight years of doing these turnarounds, getting corporate finance experience. And then about three and a half years ago, this is a funny story because this is not how the world works.

Joining H&R Block and Strategic Insights

Michaella Gallina: I saw a job posting on LinkedIn for H&R Block. Despite doing a lot of these turnarounds and exits, I had only interviewed twice in my entire life because, in every role I'd had, I had met people who then pulled me along or asked me to come join them later on.

And so, I found the HR block posting on LinkedIn and it kept showing up in my feed. And after a while I thought, you know, it might be good to get some blue chip, bigger company experience. And I did a little bit of work on the company, and it was really clear to me that this was a pure play value company.

But they had just done a big analyst day focusing on their big transformation story, and there was a real mismatch in the market. They weren't being valued fairly because they weren't really appealing to their core value investor. And they were putting out a growth story that they hadn't had a track record of being able to achieve.

And so, there were really two things that attracted me to the role, it was: there's a real opportunity to drive value here, and two, it had a tremendous leadership team. And once I interviewed and met with the CFO and the CEO, I realized this was a group of people I wanted to be around. That's a common theme that I'll talk a little bit more about today because I think that's really important in enjoying and thriving in the work environment. And, you know, I've had just a wonderful three years at H&R Block, where we've repositioned the company with the right credible story. We've worked together with a team that's been so enjoyable, and with repositioning and execution, we've increased the share price over 190 percent in that time period.

This year alone, we're beating the S&P by two times. If you look at a 52 week basis, we're beating the S&P by three times. And we have a really simple compounding story, and it's resonated with the market and it's just been the most enjoyable few years of my career. That being said, I was looking for some more development, and luckily I have a management team and a leader, Tony Bowen, who is retiring from H&R Block next month, who's been really supportive of my development, and that's really key in your career is finding a leader who you can build trust with and will support your development.

Current Role as CFO of Wave

Michaella Gallina: And so, H&R Block wholly owns Wave, which is a fintech. They operate completely standalone, but they gave me the opportunity to become the Chief Financial Officer of Wave, which is in some ways a lot of what I did in my prior life, which is doing these turnarounds, and Wave has a tremendous opportunity in the market.

But it is really needing to go through some growth and change to get there. And we're beginning that transformation and execution right now, and it's a ton of fun. So I've been so lucky to be able to get this opportunity and, again, kind of have my career come full circle from pure play finance in the beginning to now being a CFO for Wave.

Mark Fasken: That's awesome. And fun fact, we actually used Wave early on at Irwin. So familiar with the platform and yeah, familiar with many of the people there. That was an amazing summary, Michaella, and I think one of the things that jumps out to me is, I think it sounds like you've been really effective at, to your point, identifying what are those good opportunities, doing some of your own analysis, but you've also had a great network of people who have pulled you along, and obviously that's really helpful from a career perspective.

The Importance of Cross-Functional IROs and Becoming a Strategic Contributor

Mark Fasken: You mentioned something around just, the importance of an IRO being cross-functional, right? And, of having, you know, relationships with your corporate development or treasury, whatever it is, just to sort of get insight into other aspects of the business. How much of that do you think, though, is driven by the company and the company culture, and how much of that do you think is driven by, you know, the IRO themselves? Or in this case, you, like, were you going into these roles saying. Look, I want to do IR, but I don't just want to do that, I want to be cross-functional. Or, were you just looking for opportunities where that's something that the company needed?

Michaella Gallina: You know, I would say for me, I actively sought opportunities where the IRO was a key piece of strategic decision-making. But I've also been in organizations where they haven't been and I've had to really make that change intentionally in the organization.

So I, I think it's a little bit of both. Some organizations already see the value in an IRO and leading strategy in terms of having a voice at the table when you think of the strategic direction of the company, and sometimes you have to show your value in the IRO role, show you understand how the company is valued, put together a plan of what you can do to increase the value from a messaging perspective, and then translate that into what are we going to do from a company perspective?

And I think sometimes, if you're just focused on the messaging, you're in every aspect of the organization, being an investor relations professional, but you're not the one having a voice at the table. You're kind of the output of all of it. The real influential IRO is a part of that strategic decision-making.

And so sometimes you have to raise your hand. Sometimes you got to create a pitch. Sometimes you got to make it known that you want other experiences and you want to be in the room. And other companies kind of have it set up that way. But I think you need to be really intentional about making sure that's the way your organization operates over time and cross-functionally because I think it's completely symbiotic. It works both ways. Your feedback to management develops a strategy that then you package into the story and you have to have a two-way relationship, I think, to have the most effective communication.

Mark Fasken: Completely agree. It's funny, you were talking about Starbucks. We did an episode of Tiffany Willis just a couple of weeks ago, and she's amazing. She's such a great storyteller and she talked a lot about this, of how do you get in there with the management team, help build the story, sort of keep everybody on track.

How to Identify Companies That Value IR

Mark Fasken: And I think, you know, just having that level of access and influence is so important to just being effective as an IRO, but, and I'm sort of putting you on the spot here, cause I'm asking some follow up questions, but how do you actually identify companies that value IR, right? Because you talk to a lot of IROs that you can struggle, right, because the budget's not there, the people aren't there, there's not an emphasis on IR.

Were there certain things that you would do or questions you would ask throughout the interview process, to identify who you thought was a good fit?

Michaella Gallina: Definitely. That was a really key part of my interview with H&R Block. But I'll also say, so let’s put this in two buckets. One, questions you can ask when you're interviewing. And two, if you're in an organization already, that you want to build out that role, how do you approach that? So, one of the things I really seek when I'm interviewing for a job or looking at a company is, will I be valued here as more than just a communications person. And you can do that in a lot of different ways. 

At Block, I just went in and I looked at their values as a company. One of them was straightforward. For me, I'm extremely straightforward. And so in my actual interview with the CFO, I would say things like, Hey, I looked at the company, I see you're positioning it this way. Can you tell me why, would you be open to positioning it X, Y, Z way that I think makes more sense from a value creation standpoint?

And the CFO was extremely receptive to those ideas. And so I think when you're talking to a management team before you take a role, seeing how receptive they are to your past experiences, to feedback you might have on the company, to the analysis that you've done while interviewing is huge.

I think that'll tell you everything because if they will validate or listen to you when you're not even in the organization, that's a really good sign to how they will treat you when you're inside the organization. So I think that's one thing you really have to be critical of is in remembering when you're interviewing for a role, you are truly interviewing just as much for being set up for success as they are interviewing you as a candidate for the role. So, I think that's one important thing that you need, to kind of see how receptive they are to feedback and change. 

And then I would say, if you're in an organization already, and you're finding it difficult, you’ve got to keep raising your hand to get into those conversations. And one great way to build credibility to do that, again, back to this topic of how is your company valued?

Put together a valuation. Put together a list of your peers, put together a proposal of what would lead to getting a greater multiple, and what you can do about that internally. And you know, sometimes that strategy, sometimes it's changing the messaging entirely to, you know, try to get the analysts around, for example, a sum of the parts model versus, just one multiple on the business in general.

And sometimes that means, Hey, you know, we need to make a change in our core business, or maybe we should consider doing acquisitions or spending cash in a certain way because that's going to unlock value. So, building credibility by demonstrating value creation within your org, since you're the one in the company closest to the investors who are valuing your company.

So if you can translate that from the finance or investor speak to the corporate speak, which, by the way, is no small task. I remember when I came over from Wall Street, I couldn't believe how different corporate jargon was and how different the perspective was on strategy. So if you can bridge the gap of those two, you can very easily demonstrate your value and get a seat at the table internally, especially if you're persistent and especially if you do it with the right behaviours to build credibility.

Mark Fasken: That's awesome. That's so helpful. And,  this next question is maybe a bit of a follow on to thinking about positioning and success, you know, when you think about positioning both, you know, yourself and the company for success, you've talked a little bit about this already, but, making sure that the stories align, making sure that, you know, you're, you're speaking the same language as The Street.

How IROs Can Drive the Most Value for Their Companies

Mark Fasken: Are there other areas that you think are important for an IRO to focus on to really drive the most value for the company?

Michaella Gallina: You know, I'm going to repeat this, aligning your roadmap as an IRO to how your company can create value is everything. So, for example, when you're doing investor targeting, are you really being in front of the right investors versus going on the road to support your sell-side analysts with whoever pays them the most?

If that's not helping you drive value to get in front of the right shareholders, host your own road shows. We do this all the time at Block. We go through our key targets, we send them a pitch, and we say, we've got a time with management for you on X day at X time. And that is so much more strategic than just going on the road with your sell-side for example. When I think about the day-to-day messaging, I want to spoon-feed the analysts, right? And so when we have a big news announcement or a quarterly earnings call, I send out to my CRM, Hey, here's the press release from today, I wanted to flag it. Here's the three key takeaways or messaging.

And you'd be shocked at how often taking these really complex topics and distilling it down into a simple message is so helpful to drive value and to get your message understood. You know, it's a lot of just simple items like that, where every task you do as an IRO, even if it's kind of this day-to-day stuff, is it aligned with your strategy? Is it aligned with the way your company is valued? Is it aligned with extending that value? And really, not doing anything else, especially with management's time that doesn't make sense.

 And then, of course, it's making sure that your message is credible. Because when I think of driving value, I don't think of it as, how do we tell this big, sexy story?

When I think of driving value as an IRO, your responsibility is to tell a credible story and build trust with your investors over time that you're going to execute on that story. And you don't have to be a unicorn and be growing at 20 percent to do that. When I think of driving value, it's saying, okay, what should we be valued at? And how do we get The Street to get us to that multiple? And there are just so many ways you can do that. We could probably spend an hour on that topic alone.

Mark Fasken: Well, maybe we'll then have to have a follow-up, a part two to this episode, but that is great advice. And so, maybe shifting gears a little bit cause we've covered a lot of great content on positioning yourself, positioning the company, and how you think about bridging that valuation gap.

Maybe let's talk about now your current position as CFO of Wave, and by the way, for everybody who's listening, Michaella is also still the head of IR for H&R Block, so she's working two jobs, but as you can tell, she seems like she can certainly handle it. How has your perspective on IR changed as you're taking on this CFO role, or maybe even just

you've talked a little bit about this, but how do you think your view on IR differs from others given some of your experiences over the years?

The IRO as a Strategic Thought Partner

Michaella Gallina: Yeah. I mean, I think of the IRO as a key strategic thought partner, without a doubt. I want to lean on an IRO to really dig into the strategy and match up how investors view us versus what we're doing internally.

Sounds so simple, it's actually pretty hard to do, with what I call the language barrier of just how we view things differently. And so I think your IRO is really a strategic finance partner because they're more than just packaging a story, which obviously is clearly important, but if they can get in the weeds and model valuation, they can also help you say, okay, where should we be spending our investment, where do we get the best return on investment? In which initiative that you might be looking at, right? So they can go so far beyond a traditional IRO role.

And also, they are so important in building trust with the analyst community. You know, as a CFO, you're not in the weeds day to day, you need to be put in the right situations. At conferences, at roadshows with your top investors, et cetera. And you need to be even more cognizant of your time. So having an IRO that can get on the phone all day long with your buy-side and your sell-side, and have really great relationships with them, so that I can offload that type of work and trust them fully to handle it is huge.

Mark Fasken: I thought that the point you made on an IRO really sitting down and sort of putting together that case. For, you know, what should we be doing, is really interesting because I mean, I'm sure there's a lot of people listening who have done that and been successful, who have done that, and have probably been ignored or who haven't gone through the effort of doing that.

And, I feel as though just to your point, showing that initiative is such a big part of the development process, right? It's a big part of sort of building credibility, whether or not the strategy that you recommend gets executed on the fact that you did the work, right? Like even in the interviews that you talk about, you did the work to go in and understand these companies so that you could walk into an interview and say, Hey, I think you should make these changes. And I think that immediately builds credibility, even with the companies that you know you're not even working with yet.

Michaella Gallina: Right. And at the same time, it helps you find the right fit because if a management team isn't open to listening to you at that point, they're probably going to run their own playbook, and you're going to be a little bit more of a plug and play having to, you know, tell the story that they're crafting versus being a thought leader. So I think that's really important.

Mentorship and Career Development

Mark Fasken: You also spoke a little bit about mentorship and sort of your career development. So I want to talk a little bit about that. You talked about the CFO that you work with at H&R Block currently, you talked a little bit about throughout your career, not having an interview, which is probably a very nice luxury.

But I think that's because, again, you had a strong network and strong relationships. And so, any advice that you can share on the qualities or types of people IRO should be looking for as mentors just to help level them up and start to think about the next step?

Michaella Gallina: Absolutely. This is such a good topic. I have so many thoughts here. Mentors are so important. I can tell you that I have been spending a tremendous, outsized amount of time with my mentors since I've taken over the CFO role. And they've worn so many hats for me, from giving me feedback on organizational design to handling personnel conflicts to playing counselor, sometimes cheerleader for picking me up when I'm down. And gosh, it has made all the difference in the world. So I would say when you're thinking about mentors, and again, this is just my personal perspective, find someone who doesn't just have a title that you want. Find someone who you truly want to emulate from a values perspective because they're going to help you shape who you are, your leadership style. They're going to help you navigate in a way that they know you best versus just, you know, some outside third-party perspective. And that's going to be crucial to navigating your career in your next step in a way that's true to you. And I think that's going to help you get to a better place.

So again, find someone that you really respect from the way they lead, the way they prioritize, the way they learn, the way they treat their people. And frankly, I think the way they live outside of their work, because we don't talk about it a whole lot, but how you balance roles like being a CFO with the rest of your life is, even being an IRO, is extremely difficult.

And so finding someone who can help you navigate to find the right situation for your, you know, your life is important as well.

Mark Fasken: I'm just thinking about how do you balance being an IRO, a CFO, and also having a life outside of work. But again, maybe that's like a whole other episode, work-life balance, and having like three different jobs.

Michaella Gallina: It is. I can tell you all about my mindset of strategic ops and how I try to navigate that, but it's certainly not easy, and it ebbs and flows.

Mark Fasken: Awesome. Just a quick follow-up question on that. As you think about mentors and people that you lean on, how many of those people or what, what's the split of sort of people within your company and people that you work alongside, and people that are outside of the organization?

Michaella Gallina: Really, really good point. So when I'm thinking about it from my perspective, I would say my mentor, the mentors that I've been mostly talking about lately, are outside the company. So three of them are former bosses and leaders I've had in the past. So they understand the way I work. And they've known me over a long period of time. So they really know my values and who I am at the core. 

One of them is a mentor of mine that I've had since I was in the eighth grade that I've never worked for. They know me, they know my family, and they're a person that I want to emulate. Lifestyle perspective. So it's really a number of different voices that I think it's important to have all of those different opinions, right?

Because each of them have a different perspective based on how they know me or have interacted with me, so I think having a full gamut is really important. And I would also say, you know, mentorship is a two-way street, making sure you're keeping in touch, making sure you're investing in that person too, because I think, if you try to force so please be my mentor and like, let's have a quarterly call that that's not the right way to go about it, but someone who's a little more integrated into your life, and you have a true relationship with them outside of just the workplace, I think is really important.

However, you did bring up a great point about internal mentorship. And I think, you know, as an IRO, trying to get that mentorship from your CFO or, honestly, other business leaders to help get you more steep in the business is really helpful too because they have, again, a little bit more of that inside work track that they can help you with and help champion you in the organization. So that, you know, shouldn't be forgotten as well.

Mark Fasken: That's great. I don't, I don't think there are probably many people that you could say have a mentor that they've known since grade eight. That's, that's awesome.

Michaella Gallina: Very lucky. Very lucky.

Mark Fasken: Very lucky.

Ongoing Learning and Professional Growth

Mark Fasken: And so last question, and we've covered a little bit of this sort of around the mentorship, but how do you think about ongoing learning and education, right, outside of work?

I mean, you know, you think about just all the different skills required to execute in the roles that you're in; are there any particular resources or just ways that you think about ongoing development?

Michaella Gallina: Such a great question. Yes. And this is so important because we've talked about my background in finance and that's great and helpful, and I had a foundation of that.

But if you haven't had that background, it by no means precludes you from learning about it. The thing is, with our profession, you don't really learn that on the job, especially if you come up through the corporate world. But there are so many ways that you can get that skill set so easily. For example, you can take training The Street classes that all the IB analysts go and do their, you know, month before they start their job. Those are all virtual now, you can take those on the side, outside of working hours. Maybe your leader will support you to do it during work so that you can increase your skillset. They're not that expensive. You can go on Khan Academy for free and take classes on modelling and valuation.

But again, it's really helpful if you find a leader that will support it through your work. But anyway, there's tons of outside resources that I just mentioned. And then, I would also say NIRI is a tremendous resource. Your industry partners like Irwin, tremendous resources to help you through that.

And what I love about the investor relations profession is it is the most collaborative and helpful professional network I've ever experienced. And so, if you're going through a tough time, whether it's like, oh, I'm going to have to do a profit warning or, oh, I'm not really sure you know what to think about this analyst model. I wonder how or what I could do. You can learn a lot just by picking up the phone, calling someone, and saying, Hey, I know you've been through scenarios like this, or here's kind of how I'm thinking about handling a scenario. Obviously, you can paint it white and not give material details, but you can say, here's how I'm thinking about it. What would you do? What would you say? So, I mean, the span of what you can learn is just infinite, from going to these classes outside to leveraging your network. And I think you just have to have, you know, a little bit of this introspective culture in you to say, Hey, I want to go beyond my own thinking, and I want to bring other people in, and I want to learn more. But really, the resources are completely unlimited on that front today.

Conclusion and Final Thoughts

Mark Fasken: That's awesome.

Mark Fasken: Michaella, this has been such a great episode. I love your energy and your passion for the roles. So many good insights here that I'm sure our listeners will appreciate. So thank you.

Michaella Gallina: Absolutely. Thanks so much, Mark.

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About Winning IR

Winning IR is a podcast exploring the diverse insights within the investor relations community. Join host Mark Fasken as he discusses the winning strategies, tactics, and shifts in thinking with innovative investor relations professionals who are redefining the profession.

Each episode features a different challenge, innovation, or perspective on the ever-evolving role of IR, giving you real, actionable insight you’ll be able to use to build a better investor relations program. 

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