Customer Acquisition & The Future of Prospecting with Ryan O'Hara [001]

Written By Gus Joseph

Episode Summary

In this debut episode of the Founder Facing Podcast, we're joined by Ryan O'Hara, a marketing and sales expert who shares his journey from being the first go-to-market hire at Lead IQ to founding Pitchfire. Ryan discusses the evolution of prospecting, the challenges of modern B2B sales outreach, and how his company is creating a marketplace that pays people to respond to sales pitches.

Key Topics

  • The declining effectiveness of traditional cold outreach
  • How "cognitive switching" impacts productivity
  • Building a two-sided marketplace in B2B sales
  • Marketing strategies for early-stage startups
  • Finding the right angel investors for your business

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Full Transcript

Introduction

Gus: Ryan O'Hara, thank you so much for joining us on this episode of Founder Facing. We're really excited to have you and talk about your journey through your career, the different opportunities you've had, all leading up to your current business, which is Pitchfire, right?

Ryan: Yeah.

Gus: Can you tell us a little bit about Pitchfire and what problem did you set out to solve with your current company?

Ryan: So ever since I was a little boy in the mean streets of New Hampshire—I actually grew up in Massachusetts originally, but I live in New Hampshire now. So if you want to come rob me, that's where I am, for listeners out there at home. My address is... No, I'm just kidding.

Anyway, when I was a young little lad, I always kind of liked doing my own thing and making my own thing. I always wanted to get there and do something like that. So at the back of my head, I was like, "I'm going to make a startup someday. I'm just not sure what it's going to be."

I worked at my last job as VP of marketing at Lead IQ. I was the first go-to-market hire. When I was there, I was literally the first hire they had that wasn't an engineer. And we blew up. Things went crazy for a couple of years. I can't share revenue numbers, but when I left, there were over 200 people working there. We had raised a $48 million Series B round. The company did really well.

The Problem Pitchfire Solves

Ryan: One of the things that happened while I was there—Lead IQ made software that helps you find contact information from LinkedIn and send it into your different sales tools. Every year we did these state of prospecting surveys with our customer base, asking things like: What's your reply rate? What's your connect rate when you do cold calls? How often does it take for someone to get back to you?

I saw these numbers from 2016, when we first started doing it, to 2020, just plummet. The first year I was at Lead IQ, the average person had a 6% reply rate on cold emails. My last year it was 0.7%. When people did cold calling, prior to COVID, the average connect rate on a cold call was almost 10%. So you'd call 10 people, one person would answer. My last year there was 3%. So you'd have to call 100 people and you'd hear back from only 3. Really, really bad.

"People send so much stuff over cold email now that people don't even check their inbox. There's a reason your company bought Slack or Teams—it's because the inbox is full of so much noise."

– Ryan O'Hara, Founder & CEO of Pitchfire

Ryan: I started to investigate this more and ask more people about it. I ended up finding out from the sales side that the things that we used to do for sales prospecting just don't work anymore.

Dude, I've done so much cool stuff that we can definitely talk about in this episode for prospecting. I kind of got my name on the map. I did a campaign where I made music videos for prospects in 2012 before people were even doing video prospecting when I was at Dyne, which got bought by Oracle in 2016. So it's like erased from the internet, but you can still see articles if you Google it.

I made music videos for these prospects and six of the seven that we made music videos for turned into customers from it. One of the people I prospected was Jason Killiar, who is the CEO of Hulu. He forwarded my cold email to his entire press list and said, "check out what this kid's doing." And I got published in all these publications talking about this prospecting thing.

You could never do that now. Because if you sent music videos to somebody over cold email, only one in three of those emails are actually going to get delivered. And everyone's sending so much...can we swear?

Gus: Oh, yeah. Go for it.

Ryan: People send so much shit over cold email now that people don't even check their inbox. And if they do, I can prove it to you. How many of you listening to this at your workplace are on Slack or Microsoft Teams right now? There's a reason your company bought that. It's not because like, "oh, chat's modern and all that stuff." It's because the inbox is full of so much noise.

So I started to see this problem with sales. And I was like, well, if I were to reinvent prospecting today, how do I make it more beneficial for a buyer?

I started diving in and reaching out to all these people that I knew who get hammered with prospecting. I mainly focused on accounts like sexy accounts that I know sales reps want to sell to. So I talked to people at companies like DocuSign, Dropbox, Google. I talked to someone at Netflix. I can go down the list. Any of these companies you probably have heard of. I talked to a variety of people at these companies and just found out that like, yeah, we hate getting prospected. It's really bad. Some people I talked to were getting prospected over 300 times a day.

Gus: Wow.

Ryan: Yeah, which is nuts. And I was like, what do you do? And they're like, well, I delete it.

And I know from working on the sales side that when you delete an email, all it does is—because you open the email—it makes your lead score go up in their marketing automation system. When your lead score goes up, what do you think happens? That rep says, "oh crap, I got to actually do more outreach" and marketing will go run some targeted ads to that person too, if they're running an effective ABM platform program.

What sales does is they put you in a cadence or sequence, so they're just going to keep emailing and calling you anyway. And the only way to get out of it is you can unsubscribe, but you'll just get passed to another rep in 30 days and that unsubscribe isn't global. Or you could reply back.

I was thinking, you can't reply back to all these emails, it would be terrible. So that's kind of how Pitchfire started. It's basically this problem that buyers get hammered by tons of outreach. And there's actually a huge problem with that, that I could go into afterward. I don't want to get pitchy, but there's this thing called cognitive switching that causes that—it really impacts productivity at a company when you're getting called and emailed by sales reps all day.

Gus: Is that like the investment of your mental efforts to move from one task to the next?

Ryan: Yeah. The thing that we kind of discovered, I didn't even think of this when I was doing discovery. I was always like, "how do I make something that's more beneficial for everybody?"

What we found out is that when someone gets cold called or cold emailed, the problem isn't that they get that interruption because you could just delete the email and be like, "Oh, it's not a big deal." The problem is not only is that rep going to reach out to you on average six to 15 times before they give up, and then they're going to pass you to another person and then pass you to another person on that team to keep prospecting you.

The other issue is if you're a millennial or you're Gen Z, which most of us in the workforce are now—that's who's primarily turning into decision makers. Average decision maker right now is close to 31 years old. So they're right in the smack dab of the generations there. We're conditioned to check notifications even when we don't have any.

And that cognitive switch makes it so that when you get to a critical task like, let's say, working on a really good project, let's pretend that you're like, "I'm going to redo and restructure my podcast," right? That takes a lot of thought, a lot of thinking. What ends up happening is because you go and switch all the time, you get in the habit of answering cold emails or deleting cold emails and keeping your inbox at zero and checking LinkedIn and phone and all that stuff. You actually end up getting worse at doing the critical task long term. And you condition yourself to check for notifications even when you don't have any.

Gus: Dude, I mean, I feel that every day, like I'm sure everyone listening to this feels that pull. And it is interesting how that can really turn into a pattern where it's like, OK, I'm now sitting down for focus time. And then your brain immediately just says, well, now it's time to check my Gmail notifications and all that. That's super fascinating.

And again, I don't want you to feel like you're doing too pitchy of a situation for your business. But how does Pitchfire try to address this? I've done some research on the website, but it looks like a really interesting platform that connects different incentives from buyers and people who are looking to sell.

Ryan: Yeah. Not to stack all these problems, but the other phenomenon that happened is in 2020, the separation of work and personal life became one thing. I mean, most people are working from home that are in our space, right, in the B2B space. You're on Zoom calls and your kids are walking into the frame. You're answering work emails in Slack on your phone, even though it's your personal cell phone. And the reps that are cold calling you are cold calling you with your personal phone.

What we did is we built a B2B marketplace that any B2B professional can sign up and join. It's free. You list yourself on Pitchfire and salespeople come in and look for you on Pitchfire and send pitches to you and they pay you money to respond to their prospecting. It's really, really simple.

The other element that we did, and this is kind of a little growth hack, which is cool because people are like, "oh, cool. I'm going to go do that." We wanted to create network effects because when you're building a two-sided marketplace, it's really hard to zig and zag and get everybody.

We built an Outlook and Gmail plugin that you can install on your inbox at work. And anytime you get prospected, you can in one click reply back with Pitchfire. And when you reply back, if most companies that are prospecting are using sales engagement, which they usually are, when you reply back, it actually pulls you out of the automation. So 19 emails that would have gone out to you over the course of 60 days turns into one email only. And the LinkedIn messages and cold calls that would go on that rep's list to do the next day disappear because you replied back.

So that's how we built it. It takes about 85 people that you send to Pitchfire to come in and actually send you a pitch. So we're reducing that a ton and getting people in the habit of not getting hammered and interrupted a hundred times throughout the week.

Marketing Strategy

Ryan: One of the things that I really like doing is disruptive, cool marketing stuff. And I love doing crazy shit to get in front of people. But one of the downsides is the first year and a half of doing this, we're going into year three in January, I have to teach people what this is. So I can't do some of the shenanigans that I want to do because it's too hard to stuff in information about Pitchfire.

I don't want to talk about Pitchfire. I want to do crazy stuff, get your attention, and then get you to go, "what the hell is this guy doing? Where does he work?" And then go click and check. That's the ideal flow for us for marketing. But I can't do that the first couple of years because I got to be an ambassador and teach people what this thing is and why it exists.

Gus: I mean, that's my world, content marketing, content strategy, and all that stuff. And it is very interesting to not only talk to and work with founders who all have differing philosophies on their marketing approach and what they think that their customers want to hear versus what they actually want to hear and things like that.

I really wanted to kind of dive into that. And you were head of growth, so you know your marketing chops. And I do love a good old moonshot marketing attempt. Just doing something crazy and throwing it at the wall. But as you look at the marketing for Pitchfire, and I guess maybe even more generally, just as a startup, right? Let's say you have some capital, you're gaining new customers, you have momentum. Where and how do you think about allocating those marketing dollars? And what's the thought process for you to get what is the best ROI for that marketing spend? How do you approach that?

Ryan: Yeah, without giving away the farm on Pitchfire in general, I'll kind of say my approach to it and then I can give away the farm, I will.

Gus: We love that.

"I'm a big believer that there's kind of three areas that you need to do in marketing today: frequency, persistence, and impressions. The thing that really sticks with marketing in a startup and a new product is persistence."

– Ryan O'Hara, Founder & CEO of Pitchfire

Ryan: So I'm a big believer that there's kind of three areas that you need to do in marketing today. Most people think, I want to get in front of as many eyeballs as possible, which by the way, every time I get on a conversation with someone about Pitchfire, the first thing I say is, I hate that I didn't come up with this first. Because I mean, you're not only cutting down interruptions, you're getting paid to get pitched because you make money if you answer a sales pitch on Pitchfire.

I could just go get in front of people once. But the thing that really sticks with marketing in a startup and a new product is persistence. So it's frequency, persistence, and impressions. The persistence is doing things to stay in front of the person that you got in front of the first time. The persistence is consistently making excuses to get in front of that person. And then the third part of this is, how do I get in front of the person for the first time so that I can do the other two parts?

And that's sort of how we strip it down. All these people waste money on marketing attribution software and stuff and be like, "I want to track where everyone came from." The easiest way to find out where people come from is to write a survey and send it to everyone and say, "how'd you hear about us?"

And for us, our first year, it was pretty much, "saw your content on LinkedIn." That's usually what we'd hear or "have followed you on LinkedIn" or "follow someone at your company on LinkedIn." We're shifting to some other strategies.

One of the things that's actually been working really well for us right now is YouTube Shorts. So Google is going completely bananas trying to compete with TikTok because they're hoping TikTok gets shut down. So if you post content that's under one minute on YouTube and it's vertical, they are automatically feeding Pitchfire videos into people's feeds. Anyone that works in sales is seeing stuff that's sales content. Anyone that's seeing things about life hacks and productivity is seeing Pitchfire content that's about the inbox side and the buyer side. And that's been one of the channels we've been growing really well on.

And then the other thing we do is if someone comes to our site and they don't make an account, we follow them online. We retarget them. And that's how we're keeping the frequency, but I'm not following them around with more crap about Pitchfire. What we're doing instead is giving best practices to stuff for both sides and following them around with that content. And all I'm doing is I'm trying to build up that brand affinity so that they're loyal not just to Pitchfire, but the people that work at Pitchfire. And if they are and they like the team that works here and the people, they're going to want to do stuff to help us out.

Challenges and Fundraising

Gus: What would you say is the biggest challenge for you, throughout the past year? What were some of the hardest challenges for you to either think through or engineer or just getting sales? What were some of the biggest challenges?

Ryan: So there's—do you ever see the early adopter curve thing? Like you know how they have that? It's like you have an early adopter, then you have disruptors, and then it's like mainstream. And then it's the laggers. Like, that's how they arm it all out.

The hard part for us is the behavior of someone getting paid to answer a sales pitch. When we talk to some people that are risk adverse, for example, we had a whole three week period where we thought we could sell this to HR, HR is not risk adverse, don't sell to HR. If you're trying to sell something that's a little risky—Pitchfire is not risky. But the idea of being like, "oh, my employees are going to get paid to answer sales pitches" sounds super abrupt and blunt and crazy.

If you're someone that like has made a living working at the same place for 10 years and doesn't rock the boat too much and likes to chill, like, yeah, that's not the person we need to go after. So it's like, I think the hard part of that is doing marketing that lands with the right type of person. That's an early disruptor and early adopter.

I think the other part was obviously fundraising. There are tons of companies that are out there, marketplaces are really tricky. We did raise some funding. What's cool is I can talk about it now. Not because of a cool reason, I'm going to tell you why in a second, but it's actually really crazy.

So one of our reps, Jeremy Levy, cold called a CEO of a company. And that CEO was like, "oh, I know you guys, I used to see your stuff from Lead IQ and all this stuff. Get me a call." He messaged me on LinkedIn and said, "can we talk?"

Anyway, the investor's name was Michael Mbardo, he's CEO of Glide Fast consulting. And Mbardo really believed in us and loved what we were doing. So we raised some funding from him in October of last year—it'll be a one year mark.

Michael's story is crazy. Michael dropped out of high school and learned how to program and then built out this company called Glide Fast. It's like the biggest service provider for Service Now in the United States—they work with all these huge enterprise clients. And in 2022 or 2021, he got diagnosed with stage four lymphoma and thought he was going to pass away. So he's like, "oh, you know, me and the Glide Fast family, we're going to sell our company." And he sold some of the company to a big company and had a nice little exit for himself. And then he beat cancer.

So he had all this extra money lying around and he was like, "yeah, I want to do some angel investing." So he did angel investing in a couple of companies, including us and I think two more. And sadly Michael's cancer came back and he actually passed away about a month ago.

Gus: I'm sorry.

Ryan: Yeah, I'm like, I'm going to get teared up talking about it, but he helped us a lot with stuff in the product and ideas and gave me introductions to people that they worked with and was just super, super helpful. He pushed us and made us a lot better on some things and leveled me up as a person.

But before that we would go and do fundraising rounds and talk with people and we got pretty far with a bunch of different companies. The problem is a lot of the companies that we'd talked to on the VC side were people who do sales tech, but we're kind of sales tech, but we're also buyer tech. And then some of the people we talked to would be buyer tech. And we kind of got put in this in-between spot for people.

Startup Karma

Ryan: I think—this might sound kind of hippie dippy—but I think a big part of this is, there really is startup karma. So when I was at Lead IQ, even after Lead IQ, even before Lead IQ, I used to just go help people do stuff all the time. I'd help with intros, I'd help with sales training, marketing training, I'd give advice. I never held anything back. I didn't put anything in a course—not that courses are bad, I'm not saying that there's a problem there.

It kind of felt like everyone wanted to help me out cause I helped them. And that's a thing that I think founders don't—there are a lot of founders out there that are selfish assholes, sorry. And by the way, just posting about your company isn't going to do it either. You got to do stuff. You got to be an expert in your area that you know.

"If you can help one person a day, that's 220 people you're helping in a year. That's 220 favors I can use when I'm really in a jam and I need help with something."

– Ryan O'Hara, Founder & CEO of Pitchfire

Ryan: I know a ton about marketing and sales. I know a ton about productivity and I went from being a small four person company at Lead IQ to being like a 200 person company getting hammered away with prospecting. I understood the pain.

I feel like if you want to be a successful founder somewhere, I'm not successful yet, but if I want to start being successful, I'm building off of stuff that I did by just helping people for years. So I think like if you can, a good way to think about it is like if you can help one person a day, that's—let's say you're not helping them on weekends, let's just assume you're not helping too many people. But if you could help someone in your space and business once a day, that's 220 people you're helping.

And if you help 220 people cause there's 220 business days in a year, that's 220 favors I can use when I'm really in a jam and I need help with something. And that's how you need to think about it. I think that's like the best advice I could give you. Find a way that you can help people.

Gus: For sure. Yeah. Some calculated karmic buildup, I guess. Right. And it's always good to help people, but people have finite time, but I think that you're a hundred percent right. Especially for my business, there's a lot of just favors, you know, doing things for people who may not be customers may turn into customers in the future who just needed something. And I said, sure, absolutely. They come back, they give me three referrals, you know, the business value is exponential. If you can really help people with a problem that they need to solve, even if they're not your customer or even ever going to be your customer, because you're going to learn from that. I think that's really, really strong advice and makes for a better founder ecosystem as well.

Ryan: And the other thing is you don't have to favor stack either. Like you can kind of just pick one thing that's really important. Like right now we're really trying to learn how to get—if you're listening to this and you find this helpful—we're really working hard to try and get not just a person to sign up on our site, self sign up, but to go through the motion of working with their IT team to implement this as a policy for all outreach. And I'm asking that for favors from people that we've helped before. And I haven't asked a favor from those people in six months. Some of those people—I, so you got to do a balance. You got to help people. You can't just take, you got to give as much as you can too.

Gus: That's awesome. Thank you so much for those wise words. Ryan, anything else that we didn't touch on? I really love this conversation. I think you got a lot of great knowledge up in that brain of yours.

Ryan: I think the only thing that I would say is on this end, what you're doing right now is extremely valuable because we're making this content, but we're also getting to know each other while we make this content. And I think that if you're listening to this and you're like, "oh man"—I'm not saying go compete and make a rival podcast called Better Founder Facing or Even Better Founder Facing. But like, if you're listening to this and you're like, "oh man, just go do mini interviews with people where you ask one question, record it and throw it up online or something." You'll get to know a lot of cool people through content creation. I think it's really a magical experience.

Gus: One of my favorite results of content creation is the different communities that I've just gotten so deep with. Like some of my closest friends are people who live in Australia and now have 8 million YouTube subscribers and stuff like that. And I'm like, damn, you know, I wouldn't have known you had I not been doing this content thing. And yeah, Ryan, so where can everybody find you? Where can they find Pitchfire?

Ryan: pitchfire.com, you can make an account. If you really want to do a favor for the right guy, don't worry, I don't really call myself right guy. That's making fun of myself. Like, I just put a slick back where I'm like, "Hey, what's up guys there." You can write an email over to me, ryan@pitchfire.com. I would love to pick the brain of whoever runs your Google workspace or Outlook instance. If you could hook me up with that, I would weep. I'll put the tears in an envelope and send them to you and you'd be like, "this is super gross. Why the hell did you do this?" But you know, that's what I'll do. So if you want tears of envelopes, envelopes of tears, shoot an email to me. Seriously, it's free. It's a lifesaver. If you get hammered away with prospecting all the time, or you make some money too.

Gus: Come on. Yeah. I mean, I got one guy that's getting married and he has contributed a couple thousand dollars this year in pitch money that he's received just using Pitchfire. I don't like to lead with the money, but it's a secondary thing, you know, but still pretty cool.

Ryan: We buried the lead on that. I'll be sure to mention it in the intro, but Ryan, thank you so much for coming on, man. I'd love to chat with you again too. So maybe we'll have you back on sometime in the next couple of months. See how you're progressing on everything.

Gus: Sounds good. Thanks man. It's nice talking to you.

Conclusion

That wraps up our first episode of the Founder Facing Podcast with Ryan O'Hara. If you found this conversation valuable, please subscribe to the podcast and check out Pitchfire at pitchfire.com to learn more about how it can help with your sales prospecting or reduce the noise in your inbox.

Stay tuned for more episodes where we'll be talking with other founders and business leaders about their journeys, challenges, and insights.

Resources Mentioned

Gus Joseph
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