PODCAST 146: Why Following Your Passion Is Bad Advice (and what the good advice is) with Callie Moriarty

If you missed episode 145, check it out here: Lessons Learned From Winning by Design with Jacco van der Kooij

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Show Agenda and Timestamps

  1. Show Introduction [00:10]
  2. Who is Callie Moriarty and what is 6 River Systems? [3:00]
  3. Lessons learned from nine months in enterprise sales [10:18]
  4. Taking the right approach to diversity [13:48]
  5. Cold outreach strategies that generate engagement [18:02]
  6. Why “follow your passion” is terrible advice [21:31]
  7. Who influenced Callie [25:17]
  8. Sam’s Corner [27:27]

Show Introduction [00:10]

Sam Jacobs: This week on the show, we want to put a spotlight on account executives, people like you that are in the trenches making sales. We’re talking with Callie Moriarty, an enterprise account executive at 6 River Systems, which is software that manages robotics platforms that help pack e-commerce shipments. We discuss how Callie stumbled into sales and why the popular advice to follow your passion doesn’t work. She also talked about knowing where your intellectual interests and curiosity intersect with work so you can line up with your lifestyle and financial goals.

Now, before we get there, we want to thank our sponsors. Our first is Revenue Grid. What’s your sales organization’s biggest challenge right now? Remote work? Buyers tightening budgets? Guided selling with Revenue Grid allows you to guide reps step-by-step through every deal, reducing guesswork and increasing consistency so your teams have the best odds with every opportunity in the pipeline. See how you can put your sales teams in the best position to win now at revenuegrid.com/saleshacker.

Second sponsor is, of course, Outreach. Brought to you by Outreach, the leading sales engagement platform for the modern sales org. I’m not here to sell you anything, but I am here to share good ideas, and Outreach, it’s a great idea for nearly any sales leader. You don’t have to trust me you can talk to Chris Pierce, the VP of Sales at Tableau, who says they run their entire business from Outreach. Or Nicolette Mullinex, Snowflake’s enterprise sales director, says Outreach is the pillar that supports their ability to scale. Want to see what the number one sales engagement platform can do for your business? Head to outreach.io/saleshacker.

And without further ado, let’s listen to my conversation with Callie Moriarty.

Who is Callie Moriarty and what is 6 River Systems? [3:00]

Sam Jacobs: Hey everybody, it’s Sam Jacobs. Welcome to the Sales Hacker podcast. Today on the show we’ve got Callie Moriarty, a solutions executive for 6 River Systems who has transitioned into the world of enterprise sales from a previous background in customer success. We’re going to be talking about that transition. We’re also going to be talking about how to build and really develop a proactive approach to diversity when it comes to building and scaling your organization. So Callie, welcome to the show.

Callie Moriarty: Hi Sam. Thank you for having me.

Sam Jacobs: We’re excited to have you. So we’d like to start with a baseball card where we learn a little bit more about your background. We know your name, give us your title.

Callie Moriarty: My title is solutions executive at 6 River Systems, and that’s just what we call an enterprise sales rep.

Sam Jacobs: What does 6 River Systems do?

Callie Moriarty: 6 River is a software solution that enables our mobile robots for each picking in warehouses.

Sam Jacobs: Oh, that’s cool. So tell me more about that. What does that mean exactly? So you sell robots to Amazon, to Shopify, who are your customers?

Callie Moriarty: Not Amazon. Amazon bought Kiva Systems, which is their robotics provider. Shopify actually acquired 6 River in the end of 2019. So they are our parent company. And in terms of our target market, we are selling to either third-party logistics companies, retailers, anyone needing e-commerce fulfillment with the goal of optimizing how their warehouse functions, so that people picking orders can pick them faster and increase the overall throughput of the warehouse.

Sam Jacobs: How did you get into this? Tell us a little bit about your background.

Callie Moriarty: Interesting route here. When I graduated from college I started in public service advertising at a nonprofit, and I wasn’t really sure what I wanted to do. So I landed there and had a lot of ideas for doing things differently and increasing revenue, which didn’t really land particularly well. And to be fair, they probably weren’t very good ideas because I had no experience.

Sam Jacobs: Don’t sell yourself short, we don’t know that.

Callie Moriarty: Okay. It just caused me to crave an environment that was really fast-paced and a little bit less risk-averse. So from there, I went back to business school to get my MBA with the goal of shifting to a focus on entrepreneurship.

Sam Jacobs: Where are you from originally, by the way?

Callie Moriarty: I’m from Newton, Massachusetts. Right outside of Boston.

Sam Jacobs: Cool. I have friends that live there.

Callie Moriarty: I used the business school to shift to entrepreneurship, and after I graduated I joined a really small startup that was pre-product, pre-funding, pre-revenue, pre-everything really. And I was there for about eight months and it just wasn’t what I was envisioning and I didn’t feel like I was being treated fairly. So I quit on the spot one day. I just walked in and quit, which is not something I would probably recommend, but felt it was important for me to do at the time. And then I became really intentional about, okay, what’s my next move going to be, and how can I go about it with a long-term view? I didn’t want to be bouncing around anymore, and I really wanted to find that startup environment that I was looking for.

Sam Jacobs: Can I ask, what made you quit?

Callie Moriarty: I felt like it wasn’t really moving at the pace that I had in my mind for startup moving. It was so young, and I think that can happen sometimes. But I guess I just didn’t have full confidence in the leadership team, and I thought there was something that was a better fit for me out there, that was more in line with what I was expecting.

Sam Jacobs: Fair enough.

Callie Moriarty: I started talking to venture capitalists with the goal of building a list of the most promising startups in Boston. And one of the people I met with is named Paul Mader. He’s the founder of Highland Capital Partners. And he said, “You need to identify a rocket ship and then become a rocket ship within it.” Meaning, if you identify a startup that’s very promising and are a mediocre performer within it, you’re going to limit your success. And conversely, if you are a really high performer at sort of a mediocre startup, you’re also going to limit your success. So the first step was to identify a promising startup, and I did that through a bunch of different conversations and research online about the fundraising track record.

Sam Jacobs: What was the criteria when you were making your list of great startups? Besides how much money they’d raised?

Callie Moriarty: I was basically leaning on how much money they had raised in what timeframe.

I’d made that list of startups and started interviewing with basically no regard to what lined up with my experience, which at that point was kind of random anyways. But I was applying to consumer insights and data analytics and customer success. I really just wanted to get into a “rocket ship” based on this advice. And as you can imagine, that strategy led to quite a bit of rejection. Also, a strategy that I’m not sure I would recommend. But when I got to 6 River, it was a different story.

So as I mentioned, 6 River is a mobile robotics solution, and there was an open customer success role, which I applied to with no experience in robotics or customer success or logistics and warehousing. I still remember the email from our CEO that was like, we think you should join the team. And I was so, so thrilled. I didn’t know what I was going to do in terms of figuring out how all those different aspects work, but that’s how I landed in customer success at 6 River.

Sam Jacobs: What was the original context for you deciding that you really wanted to work at a startup?

Callie Moriarty: I think just based on my own risk tolerance and sort of things I’ve read and seen and heard that seemed like the startup was full of people who were just really grinding and doing something new. And I had so much energy, and still do, and so much excitement and was ready to just throw everything I had into my next company. And I wanted to be in a place that would kind of welcome and appreciate and require that.

Sam Jacobs: Fair enough. So you got a bunch of rejections, but you got one acceptance at 6 River in the role of customer success. At that point did you know what customer success did or how did you think about it?

Callie Moriarty: I thought about it as effective account management. I think in 6 River’s case, especially at that time, the company was founded in 2015 and I joined in 2018. So the customer success team, which there were only two of us at the time, required more of a technical depth that I also didn’t have, but that would be just one nuance of customer success at 6 River. I think in general, I’d put it in the same category as account management. So from there I started thinking maybe 6 River could be my rocket ship and now I need to focus on my own career development and path. I read in a Forbes article that enterprise selling is the most common experience that Fortune 500 CEOs share. I figured, regardless of where I end up, it’s a pretty compelling reason to go out and try to get some experience in that.

Sam Jacobs: Did you do customer success for a couple of years? How long have you been doing enterprise sales?

Callie Moriarty: I did customer success for two years and then, with the help of the folks at 6 River and the person who is now my sales leader, I shifted to enterprise selling this past April. So I’ve been in the role for nine months now.

Lessons learned from nine months in enterprise sales [10:18]

Sam Jacobs: There are a lot of folks out there that probably want to move into enterprise sales. What are the things that you’ve learned over the last nine months? What are the things that are surprises and things that you fully expected?

Callie Moriarty: I love the metric-driven nature of sales. I think to a lot of people it seems like a scary role to take on because you’re carrying a number and you’re expected to hit it. But I think what’s less commonly represented is that there are so many leading indicators that factor into that number, that it actually makes it, from my perspective, much easier to identify where you need to focus. Or if you’re struggling in a certain area, it shows up and is exposed in the numbers so quickly that you can address it. So I think that’s something that some people view as a negative that ultimately works out as a positive in terms of your own development and understanding of success.

Sam Jacobs: When you’re thinking about your own activity and driving towards, do you have an annual quota at 6 River or a quarterly quota? How do you think about hitting the number?

Callie Moriarty: Our quota is annual.

Sam Jacobs: How are these 12-month sales cycles? I imagine buying robotic systems is a pretty intensive investment on behalf of your prospects. So tell us about your sales methodology. Is it highly regimented? And when you think about planning out your day, that’s something that a lot of salespeople sometimes struggle with, what does effective time management mean for you?

Callie Moriarty: The interesting thing about sales is the metrics and that helps inform the time management as well. So if I think of my day today, I need to be doing every day what I need to do to hit or exceed my quota. And that breaks down into the leading indicators. So I can determine, basically by comparing my conversion metrics, both to myself in the previous quarter or year and to others on my team, I can identify what I need to focus on in the long-term strategically and in the short-term tactically. I’ll give you an example just to ground what I mean here. So as a newer rep on the team, my conversion rate at the top of the funnel is lower. So in the long-term, I need to work with my sales leaders to increase that. And in the short term, I need to bring in, say, double the amount of leads at the top to make up for that for this year.

Sam Jacobs: When you talk about your conversion at the top of the funnel, are you doing all of your own prospecting, is marketing serving up leads? How do you fill the funnel in the first place?

Callie Moriarty: Marketing is certainly serving up leads. We have a business development team that is contributing to that. We have events. I’m putting that in quotes because this year it’s all virtual of course. But the reps at 6 River are also expected to be doing their own prospecting as well. So I would say it’s a mix of all of it.

Sam Jacobs: Makes sense. When you think about improving your conversion rates? What are the things that you’re working on to help you do that?

Callie Moriarty: I think identifying the critical point in time, or critical area that needs work. And then we do a lot of training sessions on those stages, role-play. For me, as someone newer to the industry, I spent a lot of time building my expertise around warehousing and logistics. So making sure I’m credible when it comes to other technologies, potential competitors, existing setups. I would say a mix of role-play training and research just to bring up my credibility and understanding in any areas that it’s lacking.

Taking the right approach to diversity [13:48]

Sam Jacobs: You’ve talked about how companies need to take a proactive versus a reactive approach to diversity. And how does being a woman account executive trying to sell into warehousing logistics, tell us about what you define as proactive versus reactive, and how companies should think about it?

Callie Moriarty: In previous interviews that I’ve listened to, it’s been referenced that diversity is important because you want your sales force to represent or reflect your buyer group, which I think totally makes sense. Except for, what if your buyer group is not diverse? And I think in that case, based on sort of commonly understood wisdom that diverse teams perform better. So if we think about increasing sales as a discipline and the power of that, and we want that to something, over time, that becomes very diverse, sales leaders who are selling to non-diverse buyer groups basically need to be prepared to do the opposite. So in my case, I am a female in my twenties selling almost exclusively to males in their forties and fifties. And in the interest of making progress from a diversity front, it’s exciting, for me, that sales leaders at 6 River are prepared to not match up the sales force to the buyer group.

Sam Jacobs: Absolutely. And when you think about finding common ground with some of these folks, what are your strategies? I imagine it must be, as a woman in your twenties, it must be difficult to try and create opportunities and have a peer-to-peer conversation with some of these folks within the warehousing space. What do you do to overcome? I don’t know if it’s a gap or a challenge, or if it’s actually a benefit or an advantage that you have?

Callie Moriarty: Commonalities are basically irrelevant. Eight months ago I started and I thought, okay, let me track through what type of chit-chat comes up most frequently and try to build that into a conversation. So one example easily is sports, and that’s not something that I follow. And to make matters even more challenging, I wasn’t allowed to watch TV or listen to the radio or do any of that growing up.

Sam Jacobs: You weren’t’ allowed to watch TV? Were you allowed access to the internet?

Callie Moriarty: I was. The goal was to avoid any exposure to advertisements. My dad is a professor and didn’t want me exposed to advertisements. My only point being that anyone who thinks they’re behind on sports and pop culture, I’m about 12 levels behind.

Sam Jacobs: Do you have a smartphone?

Callie Moriarty: I do. I joined the world in 2020. It’s just, there’s a lot of years to try and catch up on. And when I started in sales, I thought, okay, I can not compete if I don’t follow all the sports teams.

Sam Jacobs: Especially in New England.

Callie Moriarty: Yes. And what I basically realized is, that’s not true. I think commonalities are useful for perhaps getting someone’s attention in prospecting, or building rapport. But I think in terms of building trust, which is the foundation of enterprise selling, it’s actually not relevant. And one of my mentors is Joel Peterson. He’s a former chairman of JetBlue and has written two books, both of which I’ve read and would recommend. But my favorite is the 10 Laws of Trust, and his thesis states that in order to build trust, you need to establish character, competence, and authority.

So for example, let’s say you’ve decided that I’m someone with good character, hypothetically, if I make a claim that I just don’t have the authority to execute on, you can’t trust me. Similar with authority. So I think for a sales process, it’s helpful to have commonalities for building rapport, but I don’t think it’s necessary. And it’s something that I shifted away from in terms of thinking about efficiency and how best to spend my time. I don’t think it’s Callie trying to catch up on 20 years of the Patriots or the Red Sox or other popular teams.

Cold outreach strategies that generate engagement [18:02]

Sam Jacobs: I think that’s fair. And there’s a lot of different points of view on this, but I’m in your camp. I don’t think it’s as critical as some people think. So what does work for you when you’re prospecting, or when you’re trying to establish rapport? I guess when you’re working towards competence, authority was the first one, character. I think you come across as a person of high character, but when you’re trying to establish competence or authority, what are the strategies you use, and what are the strategies you use, or tactics you use, when it comes to cold outreach to generate engagement with people?

Callie Moriarty: In terms of building character, trying to be extremely rigorous about doing what you say you’re going to do. Make sure anytime something that comes out of your mouth that has even the smallest level of commitment, you are doing it. And then in terms of competence and authority, I think it’s building credibility as a consultative seller. So as nice as it is to speak to a salesperson who is likable and fun and has interests in common, at the end of the day, B2B sales is about making an economically compelling business case. So if you can speak to what your prospect is interested in, and what type of value your system or solution is going to deliver in a credible way, that’s really the only thing that matters.

Sam Jacobs: Got it. And so for you to be, I love what you said, just about everything that comes out of your mouth. If you make a promise, you’ve got to do it. When it comes to credibility around the buying decision, is that just you studying up on robotics and you using the sales enablement or sales readiness team at 6 River to get smart on robotics? Have you done additional research or learning? How have you gotten smart on the industry?

Callie Moriarty: I do a lot of research on my own. I present to my boss every month on a new-to-me technology to make sure that I understand how it fits. If someone has this, what does that likely mean their operation looks like? So a lot of research. And speaking to people from my company like interviewing those who have 30 years of industry experience. I think that’s helpful in terms of building credibility. And then also just being okay if a prospect asks me a question that I don’t know the answer to, just saying that I don’t know and never trying to wing it.

Sam Jacobs: What are your career goals? I’m just curious. As you think about it because it seems like you’ve been very focused. You ran a great process in terms of picking which company you wanted to work for. You’ve developed mentors that you’ve mentioned. What do you want from your professional life over the next 10 to 20 years?

Callie Moriarty: I would eventually like to lead a company so my goal is to be CEO. I think Clayton Christianson published a book called How Will You Measure Your Life? And in it, he talks about deliberate versus emergent strategies. And basically says you should come up with a deliberate strategy, but be open to letting it evolve. So I would say, I don’t know if in five or 10 or 20 years that’s where I’ll be, but at this point, my focus is learning the relevant disciplines that I need to become a leader of a company, and also learning management and leadership techniques alongside that.

Why “follow your passion” is terrible advice [21:31]

Sam Jacobs: You mentioned that you think “follow your passion” is terrible advice. Why do you think it’s terrible advice and how might you modify it?

Callie Moriarty: I do think that’s terrible advice. I also think it’s confusing advice for young people. Two reasons. First of all, “follow” implies that they’re moving along after something that’s already surfaced. And then “passion,” if you read about definitions of passion, they’re all really emotionally driven. I think what I would modify that to, is identify an area where your intellectual interests intersect with a place that lines up with your financial and lifestyle goals.

I think that’s much more realistic. And when you think about following a passion that you develop maybe when you’re a kid, only about .001 percent of people can actually sustain themselves in roles like actors, artists, or professional athletes. All of which are admirable professions, it’s just not realistic to think that by following that passion, people are going to be able to sustain themselves in the way that they want. I also think in many cases, people follow a passion for a certain amount of time and end up just resenting that passion. Let’s say, someone who’s going to be a professional athlete, is that turning an avocation into a vocation? Will it build resentment and lead you to not like your passion anymore?

Sam Jacobs: That’s absolutely true. How has the career path that you’ve chosen, does that line up with the advice you just articulated in terms of intellectual interests? And does that divert from things that are passions for you outside of work?

Callie Moriarty: I wandered during the early years of my career and I absolutely love sales. I think it’s a great fit for me. I love thinking about individual and psychological behavior and sort of seeing if I have the ability to influence it. That being said, when I was younger, I was never thinking my passion is sales. I would say I have discovered that passion, but I didn’t follow it. And conversely, I loved distance running, and still do. And I ran in college and it just got to a point that I had to produce at such a high level that it made it not fun anymore. And my whole life was centered around running, and then I just didn’t really like it anymore. And luckily I recovered and I love it now, but I think it’s much more realistic to work on discovering something that you’re intellectually interested in, than following what you happen to be good at when you’re 12 or 15 or something.

Sam Jacobs: I’m somebody that runs on occasion. What advice do you have for runners out there that want to be better? When you think about things that have really impacted your training in an effective way that helped you run your best races, what are the things that come to mind?

Callie Moriarty: There’s a whole different feeling from running once you’re in really good shape. So if you’re not used to running and you go for a run, I agree, it’s terrible, not fun, not something that anyone wants to do. But once you build up enough base that your body gets used to it, I think it’s great physically. It’s very mentally cathartic. I think it’s a very holistically helpful activity. So I would just say, if you can stick with it to get to the point where you feel like you’re in pretty good shape, it gets a different level of fun after that.

RELATED: Career Advice from the Pros

Who influenced Callie [25:17]

Sam Jacobs: Callie, we’re at the part of our conversation where we like to pay it forward and share mentors. You’ve mentioned a few, but people that you think we should know about that have had a positive influence on you. Talk to us a little bit about some of those folks and why they’re important to you.

Callie Moriarty: I would start that by saying Jerome and Rylan, who are the co-CEOs and founders at 6 River. And I think they just really lead by example in terms of building a company culture that’s focused on the interest of the company, and not building a group of people that are focused on their individual career paths. So those are my current co-founders and CEOs. You probably hear that one a lot. So I’ll give another one.

Sam Jacobs: Not often enough

Callie Moriarty: I would also add Hanko Kiessner. He is the founder of Packsize, which makes right size packaging solutions, sort of peripheral technology to 6 River. And he is also a marathon runner as I am, so obviously appreciate that in him. But I’ve heard him tell great stories about going to the floor as a technician in the early days, and then coming back out and putting on a suit and going back in to meet with the CEOs, or whoever he was speaking with back when the company was founded or close to it. So always love hearing about those people who really were getting their hands dirty and ready to do whatever it takes. And then I already mentioned Joel Peterson, who I’ve learned a lot through his books and followed, he’s a venture investor, so just followed his philosophies over time.

Sam Jacobs: Awesome. Callie, if folks want to reach out to you, maybe they want to hire you, maybe they’re fellow people on their way up on the career ladder, how do you prefer people get in touch with you?

Callie Moriarty: Yeah, I would say my LinkedIn. I’m Callie Moriarty. Or can always feel free to shoot me an email, cmoriarty@sixriver.com.

Sam’s Corner [27:27]

Sam Jacobs: Hey everybody, Sam Jacobs and you’re listening to Sam’s Corner. It’s always great to hear from people that are on the early part of the upward rise in their career trajectory. And Callie had a lot of really great things to say. Two things that come to mind that I just want to highlight and point out. The first is this concept of following your passion. How do you know what your passion is? Most people don’t. The second thing is oftentimes your passion is not something where there’s a commercial opportunity, right? I’m passionate about writing sad folk songs, but that does not mean that I can support my family or my lifestyle, or pay my rent by writing sad folk songs. Particularly because they are all C F and G, they’re using exactly the same chords. It doesn’t really work. So following my passion doesn’t really work.

Instead, Callie talks about, where do your intellectual interests line up with where there’s a commercial opportunity that can meet your lifestyle and financial goals? And I think that’s just great advice because again, so many people don’t even know what their passion is. And then assuming that your passion is something that can pay your rent is sometimes a bad assumption. And then I guess the final thing I’ll say is that people just misdiagnose the core activities. You know, when I write songs, I like the act of creating. I like the act of having ownership over an idea and watching that idea come to fruition. That doesn’t need to just happen in music. It happens in a company all the time. If I have a great idea and I can work with people to execute it, that’s really scratching the same itch for me.

So I think it’s great advice and Callie demonstrates a lot of wisdom when she explains it like that. The second thing that she said, and this is more controversial: her dad didn’t let her watch TV, which is amazing. And she wasn’t allowed to be exposed to advertisements, also amazing. The US economy runs on consumerism. So she was being excluded from the engine that drives all of our wellbeings. But anyway, that’s not the point. The point is that commonality wasn’t going to work for her because you know, she’s from Boston. Talking about Bill Belichick and the Patriots wasn’t going to work. She doesn’t follow football or care particularly about it. So she referenced a framework from Joel Peterson, the executive chairman, former chairman of JetBlue, talking about the three things that go into establishing trust.

Those things are character, competence, and authority. Part of how she described competence is just always doing what she says she’s going to do. Anything that comes out of her mouth, if she says, I’ll get that to you by the end of the day, she always gets it to that person by the end of the day. And I think that’s fantastic. And frankly, what I look for when I’m hiring people is exactly the same thing. All we need, if everybody at the company just does what they say they’re going to do, we will be an incredible company, and every organization will be great if all you do is what you say you’re going to do. So, that’s Sam’s Corner.

Don’t miss episode #148

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