How to Evolve Your Digital Strategy with Kira Singer from Oak Street Funding

Lindsay Tjepkema: Welcome to the Casted podcast. I'm Lindsay Tjepkema, CEO and co- founder of Casted. And I'm bringing you the conversations with the most innovative and forward- thinking podcasters in the B2B world. These brilliant marketers are harnessing the power of podcasting to reach their revenue goals, to rev their thought leadership engines, and to amplify their voices in the marketplace. Let's dive in to this week's conversation. Okay. So, just to get things started, tell me about the origin story of your show. How did it begin? How long have you been doing it? Give us the backstory of how this whole thing got started.

Kira Singer: Yeah. So, I guess starting from the very beginning, I started at Oak Street Funding in January of 2020. And I was the in- person event coordinator. Then two months in, pandemic hit. And it was kind of like, " What are we going to do, to not only fill the leads that we get from in- person events, but also what am I going to do with this role" So, we really quickly pivoted to do focus on digital assets, which we had done before, but not quite in the same intensity. So, we did a lot of webinars, videos, and things like that, just with our laptop from home. We ended up seeing a lot of really great positive interaction, ROI. And as we were coming out of working from home moving into more of our regular activities in 2021, we already had a construction project on our 18th floor to turn it into, move the kitchen and some meeting rooms up there. And our CEO, who was on a lot of the webinars with me and other thought leaders in the space was like, " Let's just invest and let's build a media studio. Let's get cameras. And let's do it right." So, that kind of started this whole process. And as we were talking to different consultants about what should be in this room, because none of us really have this background, we were like, " Let's make it flexible so as our media grows, it can grow with us." So, we thought about, " We're not doing a podcast, but we might one day." And so, we started adding microphones that would work for podcast being and for webinars. We got a teleprompter. We got some cameras. So, that's how this started. And then we were challenged to, " Now, we have this studio. We've been doing webinars. But what are we going to do in addition to that since we made this investment?" And that's where the podcasting conversation came about.

Lindsay Tjepkema: Okay. So, a little bit different, although not hugely uncommon path into podcasting. So, you started with webinars, saw some success, built out a studio, and then said, " Okay, let's do this. Let's venture into podcast land." And it sounds like it was kind of led by your CEO, right? So, you had that executive buy- in from the get- go.

Kira Singer: Mm- hmm. Yeah. It was really great to have the advocates at the executive level to not only build out the studio, but also to be some of our guests on the show frequently as well.

Lindsay Tjepkema: Yeah, definitely. You had the infrastructure and you had this webinar background. How did the show come together? I would love to know who was involved, how did the concept come together? Once it was like, " Okay. It's mandated. We're going to do this thing. We have the support," where did you go from there? How did it come together?

Kira Singer: So, we initially had to go on a lodge in 2021. But as so my teammate Morgan, who works in our strategy and innovation team, was really leading the strategy behind what really is a podcast, a business podcast, and what are other people doing? And so, she headed up the research on the strategy side, while I was figuring out what do we need to create and produce a podcast? So, we were working in tandem. But Morgan really led the strategy. And through that strategy, we were looking at competitors, looking at different B2B financial podcasting, and realizing we could really stand out and be one- of- a- kind in our space by having a podcast. And one of the things we really debated was who hosts our podcast? And we set it on, " Let's see if we can hire a contracted person to become the voice of Oak Street. That way, one, if people leave, we're not taking the voice of Oak Street with them. And two, we have some great people and truly who would do it, but they have other goals tied to meeting their own KPIs and things like that. And using them to record a bunch of content is probably not most efficient." So, Morgan found a woman who's been our host and voiceover for all of our content since. And she actually has a theater and voiceover background. So, she's a great host to add some great conversational aspects to our podcast. And I think that really helped us stand out. And then from there, we worked on, " Who do we want to be in our episodes and what stories do we want to tell?" We had this content with webinars that was very thought leadership, very what's going on in the market, and we didn't want to just have the exact same content in our podcast. So, we initially started with a lot of our partners are also founders of their company. So, we had launched this founder story, which begins every season. And then we would record a founder's story with them, and then an additional topic about what they're passionate about talking about. And it kind of just came together. We would be doing a webinar with someone, and while they were going to our to be recording, we were like, " Let's figure out how we can get a podcast that's still with you as well." And kind of started rolling that way. And now, we're three seasons in. Yep.

Lindsay Tjepkema: Which is really, really great. So, a couple of things that stand out to me is on, we hear a lot, and I'm sure you hear it a lot too, is how are we going to find a host? Who's going to host it? How are they going to find the time? Quite often, people look at executive leadership, and that's where a lot of the thought leadership comes from. But there is concern about time. But you didn't let that stand in your way. You found a workaround. How's that going? How is having an external voice literally and figuratively running your show, how's that working? How has that been? What kind of advice would you have? Do you think it's for everyone? Tell me more.

Kira Singer: Yeah. So, we've had nothing but a positive experience. One, I think she just fits in great with our company and the people that we interview. And she doesn't have necessarily a history in financial services, but she's a great conversationalist, and she's an actor, so she can put on that persona. And we started using her as our podcast host. And now, we've launched into, she's doing voiceover for videos, she's hosting our webinars. So, we've really brought her on for even more things. It's been going really well. I do highly recommend, one, it just helped with, I mean, we're experiencing turnover. I'm sure everyone is experiencing turnover. And I just couldn't imagine if in the middle of the podcast our hosts left and we had to start from scratch. Old podcasts that had been produced, but hadn't been shared. It'd kind of be, " What do we do with them?" So, it's great from that standpoint. It's also just a consistent voice that once we maybe start doing marketing videos and things like that, the voice should be recognizable as Oak Street Funding. And then the timing is great because this is her full- time role, not just with us, but doing voiceover, and podcasting, and things like that. So, she's available, even when we have panelists or internal panelists who aren't. So, she can do one segment with our internal panelists and then come back to do the external panelists. And so, it's been great. She's also local. So, she does come in to do our voiceover and things in person. But we have had nothing but great success doing it that way.

Lindsay Tjepkema: Yeah, that's so great. And I love that you tried it. I mean, you don't know until you try it. You've got to test it out. And three seasons in, it seems like it's working. And it sounds like it's scaling across other areas of the business too, which is really interesting. So again, we get asked about that a lot. So, check out Oak Street Funding and what you're doing, because you're a great use case of how that can work really well. Okay. So again, three seasons in. Let's talk a little bit more about the origin story and then I want to see how it started, how it's going, right?

Kira Singer: Yeah.

Lindsay Tjepkema: So, when it started, what if anything, were you looking at? What were you measuring? What were you hoping to measure? What were you thinking of as, " This is what we'll think of as success," even if it was intangible, or in the back of your mind? What did success look like in the very, very beginning?

Kira Singer: From the very beginning, it was difficult for us to create KPIs that we wanted to commit to tracking because one, we hadn't ever done it before, and two, we didn't have a lot of direct competitors doing this either to see what they were tracking. So, we started with goals for starting with the number of episodes we were going to produce. That was an easy goal to wrap our head around. And then reevaluate, what did we gain from doing these episodes, and what can we change? So, we started that way. And then realized through the power of Casted and the other platforms that we were distributing on, like social platforms, that helped us uncover what we wanted to be trackings. So, at the beginning, we are tracking the actual content. And now, we're tracking listeners, where they're coming from, how long they're listening, because that's been helping us with one, what our episode link should be ideally, and two, where they're listening in the podcast. So, what topics are interesting, which speakers we've had on that they're really listening to. And then the channels that are successful in bringing listeners to our podcast to create a content marketing plan that involves podcasting as we go into the next year.

Lindsay Tjepkema: That's great. So again, as we look at the maturity curve, not unique. Again, when you get started, quite often it's what things can we control? Let's have the goal be establishing this show, and a regular cadence, and making it successful, and making it good, and getting all of our processes worked out. And then it starts to evolve to say, " How do we focus on audience growth? How do we better understand who our audience is and fine tune who we want it to be?" So, it's very interesting. So, tell me a little bit more about how you are leveraging this content in other ways? And if your webinars and podcast work together, tell me kind of how this fits into your whole content ecosystem?

Kira Singer: Yeah. So, as we were kind of developing this podcast plan, we had started doing it with webinars where we would get the transcripts and utilize that for various things. But our boss is the chief marketing officer at the time liked to call it the Tiffany Box of let's package everything up that we can and use it also as a way to entice partners to work with us. So, we're not just saying, " You can come on and be a podcast guest. But we'll do a podcast episode of your founder's story. We'll also film a webinar, a podcast. And then all of those things will be transcribed. And our content writer takes the transcription and turns them into blog. And from those blogs, embedding different audiograms or videograms into them to make them be able to be consumed various ways. And then taking key takeaways, putting them on social media, tagging these leaders, and then sending it out in an email as well." So, one conversation with us can help amplify our brand and another person's brand almost like sevenfold for each asset, which has been really exciting. Not only for us because we get so much content out of each asset, but it's great to see how it all works together. So, our content writer writes the questions for our podcast so that she can know what type of blogs to produce, working with our SEO person to optimize the transcripts for search engines. And it's cool to see it all work together in tandem and really propel the content that we are producing from each just conversation that we have with a leader.

Lindsay Tjepkema: You've come a long way. I mean, you launched in March. And how far you've come from, " Yeah, we're doing these webinars. And we had the studio now, so we started a podcast too." A pretty sophisticated, what we would call amplified marketing strategy where you're using every single piece. You're ringing things out across multiple channels. You're taking kind of this waterfall approach to saying, " How do we start here and really amplify everything as much as possible?" Tell me how that evolved. I mean, pretty quickly. I mean, we're maybe six months from the launch of the show to everything that you just described today. Is that something that you started with? Or, that you always you wanted to get there? Or, did it kind of come about as processes clicked into place, especially for people who are just getting started and are at that stage one, stage two looking at you and saying, " How do I even get there? I haven't even launched my show."

Kira Singer: Yeah.

Lindsay Tjepkema: What does that look like for you and for your show?

Kira Singer: So, one of the things I think that really helped was that we had this goal to do this before we even started podcasting. So, when the pandemic hit and we started doing so many webinars, we have a lot of time invested in these, how do we get more out of them? And that's when this Tiffany Box idea came with kind of like, " What can we get out of each thing? And what can we promise speakers they'll get every time?" So, they'll get the recording. They'll get usually an edited version that's shorter. And then a transcript. And it started with just the transcript. And then they'll get sent out in an email. And so, as we found Casted and the ability to amplify was one, it made easier, and two, quicker, we were like, " We can add transcripts. We can add blog." Because you can just take the transcript, and key takeaways, playlist, and all these things that we can do. And it really just stemmed from honestly being a small team, and how can we get the most bang for a buck? I don't know if the same idea, it probably would've come about if we had a big team. But I don't know if it would've come about as quickly as it did, then how can we do all these things, instead of just producing more, and more, and more? How can we get more out of what we are producing because we don't have the bandwidth to make 17 blogs and five videos every month.

Lindsay Tjepkema: So, tell me when you look at processes, and members of the team, and investment, and not only in money, but in time and energy, and people, and headcount, and resources, how did it get started? And how has that evolved over the last six months or so since you launched?

Kira Singer: Yeah. So, our team really has not changed. That was one of the things we kind of knew going in. How do we redistribute either roles or expectations to create an additional panel really, this podcast, but not add to our team, except our contracted host? And so, by finding the right software to one, help with amplify, that was pretty easy. And then we really just started creating a plan that would go out monthly, quarterly, to understand because they really had to be understanding of each other's schedule. So, every time I book a podcast speaker, I add the writer, the content writer, who writes the questions, as optional to the invite as soon as it gets sent out. So, she knows this is the deadline for when we are recording this podcast. And sometimes it might require her to be on a phone call with the guests to understand who they are if we've never done anything with them before. But that's something that then they would schedule offline. And then we have a cadence of a biweekly Tuesday podcast distribution. And so, then that triggered the social, the email, and all of that. And so, it really made us make sure that we were communicating, really was just the key. I think that kind of goes back to the key to everything. We had to be on the same page of what was happening, when it was happening, are we also filming a webinar at the same time? It's tough because we constantly have to be engaging with each other when we all have hundreds of other things to do. And also not wanting to just have meeting, after meeting, after meeting. And we're still kind of working out the kinks. We've had, not really with our team, but we've had some marketing leadership turnover. And so, every time that kind of changes priority, the process. We're constantly trying to pivot and make sure things don't drop. But we all get along very well, so that helps too.

Lindsay Tjepkema: Yeah. And I mean, from this standpoint, not only in this conversation, but the pleasure of being able to hear from the team how things are going, it sounds like you all have really put together a pretty great well oiled machine, great strategy. You're always thinking with the end in mind of this amplification, right, from one many. And how if we're going to get this person, this partner, this guest on the show, how do we make it valuable for them? How do we make it valuable for us? How do we fuel all of our channels? Because you're right, you are a small team. And you've got to be able to really get as great a reach as possible out of every investment you make in creating things. And you all have done a really great job of that. And that's huge. That's awesome. But I want to hear from you what you're most proud of, or the greatest successes that you've seen. And that looks different from everyone, whether it's, " Yep, we closed this huge deal and we can tie it back to a show," or, " I'm really proud of the processes that we have," or, " The steady drumbeat," or, " Brand growth six months in," which again, blows my mind because it sounds so sophisticated and so mature. And you really have done so much in such a short period of time. What are some of the successes that you've seen that you are proudest of?

Kira Singer: Two things. One, before I answer that question, I think part of the reason we have gotten so far was that we went into it having a strategy. And we decided, Morgan and I, we had the goal to launch in 2021. And we had to go back and say, " We're not ready. We want to launch this correctly, not just quickly." And so, we got the approval to push that back to that March 1st of this year. And I think that really helped us be able to be where we are today instead of blindly being like, " We want to start a podcast. Let's go." That was really helpful. But then for success, I think it was like twofold. So, the one on one hand, we didn't really expect it see our origination coming in, things being funded with tieback to the podcast because we weren't sure how long of a lead time it would take for the podcast. But we have had some attribution to the podcast, which has been awesome. And just showing that the investment has been worth it. And then so, the physical leaves, and the money coming in, and the audience growth has been a great success beyond what I expected. Because I thought we were just throwing this small net in this large ocean of podcast world and no one was going to listen to us. But the fact that we have grown our listeners and actually helped the business bottom line has been a big success. I mean two, I think personally, the success of having the people that we've brought on to speak has been so exciting. It started very nervous. I was just a young person telling them what to do. And they're like decade- long industry thought leaders. But learning and developing relationships with thought leaders in the field has been a great success for me. And our executive team buy- in I think is key to the whole success of this podcast. The fact that I can email them and say, " We want a podcast episode in November. Do you have time available?" And they'll just respond giving me three dates. It's pretty incredible. And I don't know where we would be without that.

Lindsay Tjepkema: Isn't that great? So, podcasts are a really great way to create connections with audience in a way that no other content can. You're inviting someone into a conversation, which just really builds trust and authenticity in a way that no other content can, which is great. But then there's this other connection story about, like you said, creating connections with guests and with leadership. And being able to provide value, and this low barrier to entry of working together, and collaborating with, like you said, industry thought leaders and individuals who can really make a big difference for the brand. And also quite often, for the individuals involved personally, which is pretty cool. There's a lot of good stuff that comes out of these shows. So, as a brand that's really kind of in this stage for maturity curve territory where you're really growing the brand through the show, especially in such a short period of time, and you've given such great advice so far. But what are some key takeaways that you have for marketers that are sitting here that they're comparing? They're beginning to your middle for somebody who might want to get started, might be feeling a little bit overwhelmed.

Kira Singer: I think one is really understand what you want to do. Like I said, you still have to be able to jump in, and start, and do it. But having a strategy together and having people work on that with you, I think was key for me to really understand. We have buy- in from my team and the leaders, who will help me get this off the ground. Not only is that just efficient, but it also made me feel, " Okay, I'm ready to actually start producing this show." And we have a plan laid out. And we are ready, no matter how nervous or whatever I was, to actually start recording. And then start with people that you know. So, our first season were either internal thought leaders that I already had a relationship with or external thought leaders that I've done multiple other projects with. And so, people that I felt comfortable reaching out to, who knew that we were launching this, and it was new, and it's not going to be perfect, and were going to be testing things, but that I knew would give me the grace to do so. That made it a great way to start. And just great content when people are comfortable with each other. So, we did have our hosts come in and meet people before she had her first conversation with our CEO, build rapport. And make sure everyone lost their nerves a little bit because she had never done a podcast, our CEO had never done a podcast. I had never produced a podcast. Getting everyone on the same page. And I think being okay of saying, " This is new for us too." So, setting the expectation and really growing together was a big key I think for getting us where we are today.

Lindsay Tjepkema: Got to be willing to try something new and that's vulnerable.

Kira Singer: Yeah.

Lindsay Tjepkema: And that authenticity comes through. And as you are proof of, it can achieve great things. Well, thank you so much for being here. Thank you for sharing your podcast origin story and growth story. And kudos to you all and your team for evolving so much and maturing so much in such a short period of time. It's going to be exciting to watch. You're not even coming up on a year yet. It's been so fast.

Kira Singer: I know.

Lindsay Tjepkema: So, it's definitely been interesting to watch. So, congrats. And thanks for being here.

Kira Singer: Yeah, it's been fun to. Yeah, of course.

Lindsay Tjepkema: Well, that's our show. Thank you so much for tuning in. And if you are ready to harness the power of podcasting for your brand strategy, make sure that you click the link in our show notes to subscribe to the Casted newsletter, and all of our shows, and for all the latest content from our team of experts to yours. Until next time.