Mastering the Art of Selling with Humility and a Growth Mindset with Jake Cronin

This episode focuses on leveraging AI technology to enhance field sales and foster a growth mindset and humility in the sales process.

1. AI can transform field sales by distilling valuable insights from extensive data.
2. Sales skills are universal and pivotal at advanced career stages across various fields.
3. Authentic leadership, characterized by humility and a growth mindset, drives team success.
4. Embracing sales as a noble profession can dismantle its negative stereotypes.
5. Future sales training may become highly personalized through AI, adapting to individual styles and needs.

1: Introduction

Jake Cronin is introduced and shares his background, transitioning from selling knives door-to-door to founding an AI startup. Jake Cronin: "I started at Cutco at 18, learning the sales ropes, which set the foundation for my career."

2: Evolution of Ciro

Chronicles the evolution of Ciro from a simple tool to a sophisticated AI system aiding sales reps and managers. Jake Cronin: "We pivoted from a basic CRM to creating an AI system that really makes the sales data actionable."

3: The Role of Sales

Discusses the universal importance of sales skills and how they are critical in various professional roles. Jake Cronin: "Everyone eventually sells, whether they're a lawyer, CEO, or senior executive."

4: Future of Sales Training

Explores how AI can personalize sales training to fit individual needs and styles, enhancing effectiveness. Jake Cronin: "In the future, AI could serve as a personal coach, making sales training more tailored and supportive."

1. Embrace technology to enhance productivity, especially tools that distill large volumes of data into actionable insights.
2. Recognize and develop your sales skills, as they are essential in many career paths.
3. Foster an authentic leadership style to better connect with and motivate your team.
4. Consider sales as a service to clients, focusing on building trust rather than just closing deals.
5. Use personal and professional development tools, such as coaching, to continually improve your skills and adaptability.

Jake's Journey: Started in kitchen knife sales at Cutco where he learned to cold call for the first time.
Siro Co-Founder: Co-founded Siro, a platform aiming to provide an AI coach for field sales.

Future Vision: Envisions an AI coach like Siro inspiring salespeople, pushing them to set ambitious goals and providing targeted information for success.

Universal Sales Skills: Asserts the universal relevance of sales skills in any career, emphasizing that those who embrace the sales aspect tend to thrive in their careers.

Hiring Philosophy: Looks for low ego and autonomy, believing these traits contribute to a strong team culture.

Team Culture: Values individuals who can aim themselves, execute great work, and exhibit passion.

Leadership Lessons: Stresses the importance of humility, authenticity, and a growth mindset in leadership.

Role Models: Admires Elon Musk for his bold decision-making and his girlfriend, who is recognized for fostering a culture of bringing one's full self to the team.

Habits and Rituals: Maintaining stability outside of work, investing in executive coaches, and keeping a healthy network of other founders.

People

Jake Cronin

Companies

Ciro

Guest Name(s):

Jake Cronin

Content Warnings:

None

Welcome back to pour over a coffee chat style podcast from Fikaventures. We talk a lot about leadership on this show, as we believe every entrepreneur, every visionary has a unique narrative. It's these narratives that can inspire and transform the way we think about business leadership and success. Your host for today's podcast is Fica partner John Chen, who is joined by special guests Jake Cronin, the co founder and co CEO at Ciro, a company building an AI coach for field sales. Jake's career started in field sales when, at 18, he joined Cutco selling kitchen knives door to door.

He later attended Emory University on a full merit scholarship, receiving degrees in math and computer science and chinese studies while attending engineering classes at Georgia Tech. Upon graduation, he joined McKinsey as a business analyst, working on field service software and tech strategy before founding Ciro. We are thrilled to have Jake here with us today to talk about his leadership journey. We're super excited to have you and the goal of this pod broadly is to try to showcase the different journeys that people have taken towards their leadership role. And we know you've had a very interesting one becoming a startup CEO here.

Maybe you can give us a bit. Of your background and how you ended up where you are today. My co founder and I both started our careers at Cutco. We were sales reps and sales managers there, and that's where we were first exposed to this world of offline sales. Now not everyone is on the phone or over zoo selling things, a ton of things that are sold in person, face to face.

Jake Cronin
When we were there, our entire process was driven by pencil and paper. We would write down leads and contact information on pencil and paper, track orders on pencil and paper, track the appointments that were scheduled on pencil and paper. So we actually independently both built tools to digitize that workflow. Fast forward like two years, we found each other on the App Store, merged, and turn that into a business that we thought, hey, this thing could go much beyond the single company. Cutco is the company we're building for.

We pivoted a lot, as many startups do. We first began as we're like a specialized CRM or lead management tool for a field sales company. So when we set out to build CRO, our understanding was there's a massive world of offline sales with just not enough tooling. When we went out, however, into the field sales world, we realized that there were a lot more tools than we had thought. And our idea of this very modular CRM lead management tool just wasn't ten x better than the next thing, we pivoted through several ideas.

We went about six months without doing any coding, trying to find an idea that was stick because we knew the this market was underserved. We just weren't quite sure what the product was to serve that need. And Joe and I both ended up reflecting on independent experiences where changed our lives involved hearing an example of someone else's sales pitch. Specifically, for me, it was learning to cold cold for the first time. Shortly after training at Cudco.

You schedule your appointments by just cold calling folks and trying to get them to sit down with you to hear sales pitch. And man, was I afraid of dialing a phone number. I called like my mom just to make it look like I was working. And then my sales manager saw that one of the other people in the room wasn't working, so went over to them and picked up their phone and called their lead for them, called this person's neighbor for them, and just did the pitch live and from the whole room. And that was completely mind shifting for me.

Yes, intellectually, I knew that you could call people and schedule a demo, but seeing him call someone right in front of me and schedule a demo that made it real. Every time I would do a sales demo, I was alone. There was no social proof that it would actually work. So the thought was, if we can record these conversations and somehow digest them so that it's worth a manager's while to listen in it, or worth your while to listen into a peers conversation, that would be career shifting for sales. Reps.

Maybe you can tell us, what can Siro do today? And what if things go well in five or ten years? What's the vision for that field sales rep on Ciro? What are they supposed to be able. To do that's different today?

Jake Cronin
Much of the value that comes from Siro is its ability to point out problems and then get your ear on the right content at the right time. So you've got dozens of sales reps, each recording hours of audio every day. It's a sea of data, it's a massive haystack, and people are trying to look for the needle. What's that nugget of information that I should actually listen to? I recorded 5 hours of audio today.

I really only want to listen to audio for like a minute, maybe two minutes. So what Siro is really good at is helping distill the signal from the noise and get that nugget of content that's worth you listening to. So if you're a sales rep, that's servicing to you that example of a top rep overcoming the objection that you failed at earlier today, or if you're a manager surfacing to you. The reps that were unusually bad today and the specific objections where they were messing up or having issues, that's the core of what Ciro is today. You can do some single player, but a lot of it is just facilitating the manager to do coaching and also facilitating information sharing between sales reps make it easier for reps to shadow each other virtually.

The future where we're going zero starts to behave a bit more like a personal trainer or an executive coach. You no longer need to have a manager in the loop to get good at your career. If you're a sales rep and you join a company and there is no great sales rep in your company, it's not a very big company. You have no world class talent to learn from. We don't want that to stifle people's growth.

Or if you have a manager who's excellent, but they don't match your style, like they're very aggressive, very loud, and maybe you're more introverted, shy and analytical. You might not be so up for success in that environment today, but in the future, Siro will be a personal trainer, an AI coach that's able to adapt to your sales style and your demographic. So you imagine it's an app that grabs your attention when it needs to. So it sends your notification throughout the day or at the end of the day with a digest of how you did, or in the morning with inspiration. And when you hit that notification or open up the app, it's able to communicate with you in a way that's both inspiring, but also pushes you to set more ambitious goals and supports you to hit those goals with one or two tactical piece of information.

In a similar way that like an awesome personal coach would drive you to hit your fitness goal, hold you accountable, prescribe for you your next workout, tell you what you need to do differently than what you did before. That is the direction that were moving. In, maybe shifting towards zeros. Mission Id say that maybe sales sometimes in certain circles, perhaps has a bad connotation. So wed love to get a sense of what you think sales is.

Why is it important? And specifically, why is it important for. You to serve the field sales population? Because I know you're very, very passionate about it. So we'd love for you to riff on that.

Jake Cronin
The first thing I'll say is everyone, if they reach the peak of their career, becomes a salesperson. If you are a partner at a law firm, you're selling the business. If you're a CEO of your company, you're selling to private investors, or you're selling to public investors, or you're selling division two or exactly hires they bring on. You're a senior XYZ company during XYZ. Function, involved in hiring.

While you are selling this role to this candidate, everyone is selling your dance to a certain level in your career. What separates the people who do well versus do poorly or. Just one of the qualities, I think. Is that some people embrace that and realize that they're in sales. Some people maintain that sales is dirty or not their job, or they're not a salesperson, and they suffer for that reason.

What do you think is the most misunderstood part about these folks and the way that they operate? Because, again, there is perhaps this connotation of a stranger shows up my door. I don't know who they are, but give us a window into what these folks are going through and why they matter. The world on residential sales is very large. There's people selling solar panels, people selling pest control, home security, people doing h vac installs, plumbing.

Jake Cronin
And what's important to know about them is, first of all, they're all people trying to make a living, and they're doing that with a valuable service. The reason these people are in business is because the things that they're selling are valuable. Solar panels save people tons of money. Having the proper pest control set up adds a lot of quality to your life. The reason that a lot of these folks are selling in person at your home is because they're not top of mind things that you might buy otherwise.

What would you say to folks that would say the world is moving online? People don't want to talk to a salesperson anymore. They want to be able to look. At the whole catalog, make their own decisions, and not get either someone showing up at their door or someone giving them a call. They don't want to talk to folks.

What do you have to say to them? A lot of folks don't want to talk to a salesperson, mostly because they've spoken with lots of bad sales people. Mislead that. Not letting you browse a proper catalog, not providing the full picture. A great salesperson is providing a service.

Jake Cronin
A great salesperson is building trust. What are some of the characteristics or the traits that you look for in hiring that you think maybe are specific. To ciro that not a lot of companies are looking at? Or it could just be something that, in general is valuable. Just curious about hiring, philosophy, and what.

You'Re really looking for first is alone. Go. This is something that's standing out as a defining trait of our culture, and it makes working really fun. Another thing that I look for, though, as an early stage fat mover, is autonomy. Or as Joe likes to point it, someone who's a barrel but not a cannonball.

You've had many stops on your career journey. How have you changed as a leader? And what were some of those key moments and key learning points that have really shaped how you lead zero today? Reflecting specifically on my time as a manager at Cutco, I'd say it showed me humility. It showed me the importance of authenticity and showed me the importance of a growth mindset.

Jake Cronin
I was constantly humbled in the sales career at just how tough the job is and how some people who you size them up to be like, perhaps not competition, completely surprised you. When I was a sales manager, I was 19 years old, and every single person in my office was older than me. I wouldn't tell people my age and tried to put on this big facade of being formal. I wear a suit every day. I tried to act like I was ten years older than I was.

One, it's exhausting to do that, but two, it made it hard to relate to the team in a way that drives them to do their best. I found towards the end of my time as a manager, when I was basically beaten down because it was so hard to keep up that facade. And I wake up at 06:00 a.m. And put the suit on every day. As I started becoming more authentic, it was getting easier and easier to relate to my team.

They would be more and more attentive to what I was saying, and it was easier to motivate me. So just being authentic, it's easier and more effective is something that I learned. The last thing, growth mindset. Kind of similar to the very first thing I said about being humbled by others. The office, the team that I recruited was extraordinarily diverse.

Folks from a year older than me to three decades older than me working on the office from every walk of life. I was absolutely ineffective at predicting who would be successful and who would not be successful. And by the end of the interview process, I can say I had zero confidence in my own ability to decide if someone would be successful at sales or not, because talent is useful, but way more important is someone's just ability to put in the work, and it's tough to pick that up in an interview process, which is part of what spiders to create. CiRO anyone can succeed in sales and have a life changing outcome if they're willing to put in the work and they have just the right enough support to steer them in the right direction. Unfortunately, today most people are not able to get that support, whether it's they don't have a manager who's able to give them the attention or they they don't have any role models or people they can look up to in their company.

And that's something that we're trying to change. Basero who have been sort of your role models throughout your career, and they. Could be people that you know intimately. Or people that you know from afar, but people that really inspire you on. The leadership level and why.

One example I'll mention which Edward and tech probably idolizing one way or another is Elon Musk for his boldness of decisions. Another role model of mine is my apartment. My girlfriend. She's a manager at McKinsey now and one thing that she does really well. Which I witnessed letting people show up with their full self and for you.

To be in the best shape you can be as a leader, what are some of the things that you're investing in for yourself? Either daily, monthly, annually, all the habits and or rituals that you subscribe to to make sure that you're in top shape? To lead this company, it's very important. To have stability outside of work, the social and the love life and the family. Spiritual.

Jake Cronin
Joe and I are now investing in an executive coach, both for us individually, but also it's the same person, so they'll be able to help us better collaborate. Our ability to continue leading this company and steer the right direction is super high leverage. This has been fantastic. Really appreciate you coming on this pod and so many fun nuggets and learnings from your very diverse past, your renaissance man through and through. So really appreciate you coming on and thank you so much again.

You've been listening to pour over presented by Fika Ventures. FICA is an LA based early stage venture fund investing in B two B companies across North America. If you enjoyed this podcast and have suggestions for future guests or general thoughts and feedback, feel free to email us at infoca BC thanks for listening.