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FintechTalks LIVE: Grace Keith Rodriguez

FintechTalks · 2026-05-12 · 17 min

0:00--:--

Key moments - from our scoring

Substance score

43 / 100

Five dimensions, 20 points each

Insight Density9 / 20
Originality7 / 20
Guest Caliber12 / 20
Specificity & Evidence7 / 20
Conversational Craft8 / 20

Grace Keith Rodriguez leads Caliber, a corporate advisory firm specializing in brand messaging and executive positioning for fintech companies. She describes the core challenge facing fintech communicators: in a saturated market where competitors sound identical, companies struggle to articulate genuine differentiation. Caliber's approach combines the art and science of storytelling - removing jargon-heavy acronyms, identifying white space in competitor messaging, and finding proof points that substantiate claims (especially around AI). Rodriguez draws on her unconventional background reading the Wall Street Journal with her financial advisor father, combined with hands-on experience in marketing and PR, to guide fintech founders and executives toward authentic, relatable communication. She emphasizes that the rise of AI-powered search and content discovery has changed the science of PR; media coverage and quoted appearances now feed search engine trust signals. Most importantly, Rodriguez argues that leadership authenticity - moving beyond hiding behind brand names to showing up as real people - has become essential for fintech executives in a way it wasn't five years ago.

Key takeaways

  • →Fintech companies must move beyond generic AI claims and instead provide specific proof points and use cases that differentiate from competitors' identical messaging.
  • →Executive presence and personal narrative from leaders are now critical because audiences want to see authentic people, not just brand names, especially in the crowded fintech space.
  • →Removing jargon and acronyms from fintech messaging is essential; messaging should be accessible to target customers, not gatekept by industry terminology.
  • →The science of storytelling has evolved: media coverage, quotes, and podcast appearances now feed search engine trust signals, making traditional PR efforts more measurable and data-driven.
  • →Finding 'white space' in competitor messaging - identifying what competitors aren't saying - is often the most interesting angle for journalists and differentiation for fintech firms.

In this episode

  1. 1Introduction to Caliber and Its Mission
  2. 2The Crowded Fintech Landscape and Differentiation Challenge
  3. 3Finding White Space in Messaging and Competitive Analysis
  4. 4Grace's Journey into PR and Fintech Communications
  5. 5Evolution of Storytelling: Art and Science in the AI Era
  6. 6Sources of Creativity and Personal Perspective
  7. 7Networking and Relationships at FinTech Meetup
  8. 8Executive Presence and Authentic Leadership in Fintech

Mentioned

CaliberCaliber Corporate AdvisorsGrace Keith RodriguezHarveySanjeep KolitaWall Street JournalFinTech Meetup

Guests

Grace Keith Rodriguez

Topics in this episode

Media relationsSearch engine optimizationWhite-space analysisCaliber Corporate Advisorsfintech messaging strategyexecutive positioningAI proof pointsjargon removalfintech acronymsauthentic leadership narrative

Questions this episode answers

How should fintech companies differentiate their messaging when competitors sound the same?

Identify what competitors are saying, audit your own message, and find white space - angles or perspectives that aren't being covered by the top three to five competitors. Then support those unique claims with specific proof points, particularly concrete examples of AI or technology in action rather than generic claims.

Why is removing jargon and acronyms important in fintech communications?

Target customers often don't understand fintech acronyms, and using them limits your ability to reach and persuade the audience you're actually trying to sell to. Simplifying language ensures your core value proposition is understood by the people who matter most to your business.

How has AI changed the practice of PR and storytelling?

AI and search engine algorithms now reward media coverage, quotes, and public appearances because they signal trusted sources. This means PR efforts that generate coverage are more directly measurable and feed into search visibility, making the science side of storytelling more data-driven than before.

What's the difference between traditional corporate communications and authentic executive presence?

Authentic executive presence means leaders show up as real people with genuine perspectives, not just as representatives hiding behind a brand name. This shift - from brand-forward to leader-forward communication - has become critical in the past few years and is especially important in fintech.

What skills does a fintech PR professional need?

A combination of deep financial and fintech knowledge, creative storytelling ability, strong relationship-building skills, and the capacity to simplify complex concepts for diverse audiences. Formal PR training is less important than real-world experience and an understanding of the industry.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

9 / 20

The episode offers some useful high-level observations about messaging differentiation and finding 'white space' in fintech positioning, but relies heavily on broad principles rather than concrete, actionable insights. The discussion of AI, acronyms, and competitive differentiation is sensible but not novel - most of these points would be recognizable to anyone in B2B marketing. The conversation lacks depth, data, or specific case studies that would materially educate a B2B operator.

where's the proof behind what you're doing with AI? What are the proof points there?
we try to remove any of that messaging, any of those words that feel you need to know this to be able to understand what I'm telling you

Originality

7 / 20

The core thesis - differentiate from competitors by finding gaps in messaging, simplify complex language, focus on authentic executive presence - is well-established marketing orthodoxy. There are no counterintuitive frameworks, first-principles arguments, or contrarian takes. The advice to strip jargon and focus on proof points is sensible but conventional, making this largely a restatement of standard PR and positioning best practices.

you wanna have a consistency of your own message, but you don't want to have the same message that your top three to five competitors have
we try to remove any of that messaging, any of those words that feel you need to know this to be able to understand what I'm telling you

Guest Caliber

12 / 20

Grace Keith Rodriguez is a relevant practitioner - a 12-year veteran CEO of a PR/advisory firm working specifically in fintech. She has real operational experience in messaging and brand positioning within the target sector. However, she is not a founder/executive of a fintech company itself, nor does she bring the perspective of a high-growth operator who has scaled a core business; her expertise is advisory/services-oriented rather than product/execution-focused. This limits caliber somewhat for a B2B operator seeking to learn from those who have scaled product.

Grace Keith Rodriguez, CEO of Caliber, which is what we call ourselves for short. The long version is Caliber Corporate Advisors
I've been there for 12. Yeah. Really, just we had an acquisition along the way

Specificity & Evidence

7 / 20

The episode is notably sparse on concrete examples, data, metrics, or named case studies. Grace mentions 'AI,' 'search engine results,' and general patterns (e.g., executives needing personal presence) but provides no specific client outcomes, campaign results, numbers, timelines, or named examples. The discussion of an acronym Google Doc is mentioned but not shared. This vagueness severely limits the actionable utility for a B2B operator trying to apply lessons.

coverage of a client or their quote or their announcement or whatever it may be, their award win
I have an entire uh Google Doc of all of the acronyms

Conversational Craft

8 / 20

The host (Sanjeev) asks some reasonable follow-up questions ('how did you wind up at this point?', 'where does your creativity come from?') but rarely probes deeply into claims or challenges Grace's assertions. Most of Grace's statements go unexamined - for example, she asserts messaging changes have occurred but is not asked for specific evidence or pushed on nuance. The conversation is friendly and collegial but lacks the sharp questioning and productive tension that would elevate rigor. Several personal anecdotes (her kids, yoga) drift away from substantive business discussion without being pulled back.

Yeah. So that's where a lot of our early work with clients comes in is we hone in on what are your competitors out there saying?
when a CEO asks you to do something, you usually say yes

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

fintech12different10perspective9caliber8storytelling8thank7sure7message6space6clients6saying6typical6life6meetup5audience5brand5

Episode notes

In this episode of FintechTalks, recorded live from the floor at Fintech Meetup, Sanjib Kalita sits down with Grace Keith Rodriguez, CEO of Caliber Corporate Advisors, to explore what it takes for fintech companies and leaders to stand out in an increasingly crowded market. Grace shares how Caliber helps fintech brands sharpen their messaging, find their “white space,” and communicate with authenticity - especially in a world where everyone is talking about AI, innovation, and transformation. She explains why clear storytelling matters, how companies can avoid sounding like their competitors, and why proof points are essential when making big claims. Plus, Grace reflects on creativity, relationships, and the value of in-person conversations at Fintech Meetup.

Full transcript

17 min

Transcribed and scored by The B2B Podcast Index.

Welcome to another episode of FinTech Talks. Um Sanjeep Kolita. Um and I'm actually at FinTech Meetup. I'm so excited to be here with Grace.

Would you mind please introducing yourself? Yeah, absolutely. Grace Keith Rodriguez, CEO of Caliber, which is what we call ourselves for short. The long version is Caliber Corporate Advisors.

But it's a lot of fun to be here recording on the floor. I never thought I'd see the day. So this is a blast. Thanks for having me.

No, no. Well, once again, thank you for being here. And what what what exactly does Caliber do? Yeah, so we are storytellers at the end of the day, is usually how we describe it.

Um, we focus on making sure that the fintech companies that we work with have the right message out there, that it's consistent, that it's reaching the right target audience, help them determine the right executives to put forward for certain opportunities. Really, the goal is to ensure that the brand and the folks behind the brand are coming across as authentic, but also delivering the message so that everyone can understand what is it that you actually do. Um, in today's landscape of very crowded uh fintech space, it's important that we make sure that clients articulate exactly their value.

And sometimes that can be complex when you're when you've been so focused on it as a founder or as a CEO. You need someone from the outside who still understands fintech well to be able to say, you know what, let's tweak this messaging a little bit. That doesn't quite make sense. So a lot of the work that we do is really to ensure that companies are getting the right message out there and that the the execs behind it feel ready for podcasts like this, for example.

Um, and also just to speak about the importance of what they're doing and the value that they're bringing to whatever that audience is, whether it's consumers or businesses. So when I when I first got into fintech events, um, you know, and I was I'd say more on the company product side before um I was actually so and I my initial role is it was to pick speakers and put together the agenda, and I was a bit surprised at like how everybody sounded the same. And and um and and and so I want to ask you like so that so that is one problem, but then another problem is like you don't want to be like too out there either.

So, like, how do you manage that but and like how do you think about that or how should companies think about that? Yeah, it's interesting. You wanna you wanna have a consistency of your own message, but you don't want to have the same message that your top three to five competitors have. Yeah.

Because where's the difference in that? Where's the nuance? How does how does someone who's choosing between all five of you decide who to go with if you're all saying this the same thing? Yeah.

So that's where a lot of our early work with clients comes in is we hone in on what are your competitors out there saying? Yeah. What are you saying? Where is there a differentiator that we can really work with?

Yeah. And what does that look like? What does it sound like? Yeah.

Um, how does it translate? Yeah. So we make sure that, for example, topic du jour of the year, maybe the next few years, is AI. Yeah.

Okay, well, where's the proof behind what you're doing with AI? What are the proof points there? You can't just say we use AI or we deliver on AI or whatever it may be. That's not enough.

Yeah. It never should have been enough, to be fair, but it's really not enough in today's landscape. Yeah. So what we try to do is take a lot of the acronyms out of it.

There's so many acronyms in FinTech. I like to tell any new member to the caliber team we've got an entire uh Google Doc of all of the acronyms you could ever or never need to know, just so that you understand what someone's saying. Yeah. We read it.

Can I uh you read that sometimes? Yeah, absolutely. I'll send it your way. Um, no, we we've actually only use it internally.

And now that I'm saying it out loud, I'm thinking this is probably a valuable thing that we should give to others because when you enter this space, I mean, even on panels or in conversations at the one-on-one meetings, people drop these acronyms like they're typical conversation topics, and they're not for most people. Yeah. Um, so what we try to do is we try to remove any of that messaging, any of those words that feel you need to know this to be able to understand what I'm telling you.

Anything that feels like it's limiting, we want to remove some of that. Yeah. So a lot of the work we do is we'll say, let's think about this from a different perspective. Or, okay, your target customer is X and Y and Z.

Well, they're not gonna understand that. Yeah. And that's who you're really trying to reach. Yeah.

Um, so that's a lot of the fun work that we do is getting to dig into it and say, well, this word fits well, but this one doesn't. Your competitors using this word, we want to avoid that. Yeah. And a lot of what we do is we call it finding the white space.

So, okay, your five competitors are talking about this aspect of AI, I'll keep going down that train. Well, this one seems to be missing a unique perspective. Is there something we can say there? Is there something unique that we have from a data perspective, maybe, or from a spokesperson perspective, or from clients talking about something?

What can we add that's different to the conversation? Um, that's often one of the more interesting things for journalists is that kind of counterpoint to everything that's out there right now. And and and uh not to go completely off topic here, but and and sort of related, like how how did you wind up at this point and doing this? Like, and I and and I'm interested in like how like life experiences and authenticity sort of got you to this point as well, too.

Yeah, it's interesting. Um I say it's interesting because I am not a typical PR practitioner. Yeah. Um, I actually grew up in a household with a financial advisor, father, and I read the Wall Street Journal with him every Sunday, and that was like our thing that we did.

Um, so I've always been around the financial space and I've always found that really intriguing. I went to college, decided I loved econ and how that applied to finance, so I majored in economics. Yeah. I then went to my first um job and realized that I really liked the ability to communicate what was happening on the financial side.

So taking the complex financial elements that I knew and understood, but making them easier for others to understand. Yeah. So I dabbled into marketing and that turned into a former CEO tapping me and asking me if I wanted to run PR. And I said I don't have any training in that, but sure, when a CEO asks you to do something, you usually say yes.

Yeah. So I said yes. Um, and then I learned as I went. I learned the art and science of PR as I went.

I have no formal training in that, although I think that there's a lot to be said about the real life training that you can get in anything that you do. Yeah. Um, and then I went and got my MBA because, like I said, numbers are my thing. Spreadsheets are my comfort zone, which the rest of the caliber team thinks is hilarious because it's not a typical communications comfort zone.

Um, but I decided that I really wanted to do something with this. I wanted to grow something. And so I had always been in-house at that point in PR communications. So within the entity is the larger company, is the traditional financial services audience.

And I met our founder, Harvey, and had known him for a while. And he was interested in growing caliber. And so I joined and have been on this journey ever since. Um, we've been around for 15 years.

I've been there for 12. Yeah. Really, just we had an acquisition along the way. We've added different services.

We've thought about the way that our clients really need us beyond just the typical agency, because neither of us are typical agency people. Yeah. So that's been something that I have found to be really important in my journey is never just assume that you know where the journey is headed because it could really take a turn. And if that moment in life is right for you, then you jump on and you figure out, hey, this is something new.

And that's that's how I've ended up here. Um, which is not really the typical journey, but I think that's kind of an important way to get to where you are. And and and uh having been at Caliber for 12 years, what how different is the it in in terms of like you know, you mean you mentioned like I caliber is a storytelling. You mentioned storytelling as opposed to like communications or messaging or it's like storytelling.

How different is storytelling now versus like 12 years ago when you first started? Yeah, I think the art of storytelling, I like to think there's the art and science side of storytelling. The art side has continued to be a really critical part of storytelling. The science side has actually found more data points lately.

And I say that because AI, again, here it comes. There we go. Um can't move away from it. You can't you can't avoid it.

So there's that. I'm not trying to, by the way. Um, but when it comes to AI search engine results, right? More and more of our clients are saying, How are we showing up in search engine results?

And the beauty of the work that we've always done from a storytelling perspective, from a media relations perspective, is that coverage of a client or their quote or their announcement or whatever it may be, their award win, their sitting standing on a fintech meetup stage, for example, they're being on a podcast. That's actually feeding the search engines from a I trust the source perspective. So it's helping them show up in the right search results as long as the right messaging is conveyed in all of those elements.

Um so that's where the science has very quickly changed because we're able to, we're able to look at different metrics than we were able to a few years ago. But the art of it is the thing that always needs to be preserved. And it's sometimes the hardest part of it. You need to have the brain space to be able to think about okay, how do we get really creative with this message about a really complex capital markets element?

Um, this new technology that's going to change the way that we see identity, different things like that. Um, that's where the art part comes in, and that's the part that we love to do. Yeah. So actually, the beauty of a lot of these new tools and technologies that have come out is we can focus on that more than we could before.

Yeah. And no, that that's I like that. And um where and and this this question might be a little bit weird, but like as as someone like who used to read the Wall Street Journal on Sundays with her father, where does your creativity come from? My own personal creativity.

Yeah. Oh, that's a good question. Um, well, when I'm able to sleep through the night, which is not every night, I have a five-year-old and a three-year-old, and I love them dearly. Um, but we're in that that phase of life, right?

And that phase of life for anyone who's been in it is an interesting one. Yeah. Um, I actually find that my creativity sometimes comes from my kids. Yeah.

Because when I go to pick them up, I have a regular thing where I pick them up every Friday. It's just me. I pick both of them up. We talk in the car about their days, about their weeks.

I take them to go do something fun. Yeah. There's usually like an ice cream or popsicle associated because why not? Um, it's a Friday, you're able to do that, right?

Um, but seeing how they look at the world and how they think about their friendships and their relationships and how they talk about different things gives me just a renewed perspective on what's important in life. Yeah. Um, and sometimes when I'm able to see how they are with their friends and how they interact, it just helps me think about relationships because at the end of the day, the work that we do in PR and anywhere else is all about relationships. I mean, that's why we're all here, right?

We want to meet up one-on-one in person. Um, so that's something that gives me creativity. Um, and I also like to do yoga and other things to really just stretch my brain and make sure that I'm in the moment and focused. That's great.

It's and stretching your body and stretching your brain. Yes, exactly. Exactly. Yeah.

And and making space. Yeah. No, I I actually I I find that uh like when I'm in the shower and I'm like massaging my head with shampoo, that physical action somehow changes the neur neurons as well, too. So like I think the stretching the body, stretching the mind, I think you're onto something there.

Yeah, yeah, I think so too. I need to do more of that. I'm not as good at doing that as I should be. So so have have you been uh had it been able to stretch your brain at fintech meetup this year?

Yeah, absolutely. Um, I have gone to a few of the panels, um, been able to set sit in on some of the sessions, done some of the one-on-one meetings too, just running into people in the halls, right? All these folks that we know from the many different fintech spaces and conferences, um, and just being able to see our clients in person is such a nice treat, especially when there's a bunch of us in one place, um, thinking about why different folks are here, right? Asking them what brings you here?

Who are you trying to meet? Making sure that we can facilitate some of those networking connections, especially if they're beyond just a traditional media relationship. Yeah. Um, I feel like I've been able to stretch my brain in a lot of that so far.

And there's more days to come, so I'm sure more will happen. Um I have no doubt about that. And and and uh what is there uh something like any something you wanted to get out of fintech meetup that you had in mind like this year? For this year.

I think every year when we come, because we've come for many years, um, even in the virtual format, yeah, during pandemic days, which feels like forever ago now in a good way, um it's always just about having fruitful conversations um and understanding that there is a way to have a 15-minute conversation and have it turn into something more, or just to have a 15-minute conversation and have it not turn into something more. There's a beauty in being able to sit across the table from someone and say, here's what I'm focused on, what are you focused on?

Is there a way that we can help each other? Yeah. Like just coming together to be able to help each other in the ecosystem is nice. And if there isn't, it's been still easy to have conversations.

Um, so I think what I came in wanting out of this year is closer connections with the folks that we already know. Yeah. Um, and then also better connections with the journalists, of course, that are here and with others in the industry that have maybe done things in the past year. Yeah.

Since last year's fintech meetup, that we haven't gotten to see. Um it's all about relationships at the end of the day. Well, I I I I truly appreciate you being here and and thank you for 15 minutes that we had a chance to talk. Yeah.

And uh is there anything you want to leave our audience with? Any words of no, um, thank you for having me. I really appreciate it. This is a lot of fun.

I've never done this on a on a floor, so this is a blast. Um, and shockingly, not too loud either, which is nice. Yeah. No, I mean, I think at the end of the day, when we think about the way that companies and especially executives represent themselves, there's been a change, a needed change, in my personal opinion, from being able to hide behind a brand name to now having to be a person associated with that brand.

So I think that executive presence and executive narrative from leadership is really important now in a way that it maybe wasn't two, five years ago. And so that is something that I think marketers, communicators, execs at all levels really need to embrace is we want to see authentic leaders who are coming across as people not just hiding behind a brand. Yeah. Um, those days are over.

I I think that's a good thing, frankly, because it allows people to be more authentic and to really represent themselves and their company. But that's something that I I know I've noticed in particular be a trend lately. And that's what I would say from an advice perspective, I guess, is what you're asking, right? Lean into the things that make you, as a leader, authentic and able to communicate with your audience that it's going to be a meaningful conversation.

And that's not always easy work. No, that that's soft and hard. That's not. And it's uh I I that's I I think part of how I've differentiated myself and and and and uh so I think that I completely agree with that and and great words of advice, as as always, Grace.

Thank you. Thank you, Sanjeev. Thank you, appreciate it. Thank you.

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