Emily Racioppi – Sales Account Executive

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Starting in traditional, door-to-door sales to breaking into startups, Emily Racioppi is a true testament to her belief that while you can be taught how to be successful, the ultimate secret to success is really just you. Emily Racioppi is an Account Executive at Cisco WebEx. Prior to her current job, Emily was a Sales Development Representative at an infrastructure startup called Instart Logic. Getting much inspiration and guidance from her father, Emily is following her dad’s footsteps as she continues to make her mark in the world of sales.


Years in Tech 3
Grew Up Santa Cruz
Current Job Sales
Date Recorded 8/10/2016

Key Points:

  • When you’re in sales, you’ve got to be confident and competitive. Startups are pickier in terms of hiring people so there is no room for slacking.
  • In sales, you have to be a team player. There are times when you close deals on your own but there may also be other times that you need to work with different people such as engineers to get those deals done.
  • If you’re considering breaking into a sales role at a startup, do enough research about the company, their product, and their competitors. Ask questions about your role and how quickly that role progresses within the company.
  • As an inside sales representative, you have to be a closer. Take all the knowledge you have with you as a sales development rep, learn how to manage your time, and be able to qualify your deals.

Show Notes (focus on the Stepping Stones):

[1:05]  Growing up in Santa Cruz, California, Emily knew she wanted to come in the Bay Area due to its proximity to her family. She also draws major inspiration from her dad.

[2:04]  Being more artistic most of her life growing up and her dream of becoming a curator in The Louvre in France.

[2:27]  Taking up International Economics, minoring in International Business and how this has opened doors for her in terms of internships through her college career.

[2:51] The power of asking questions – Emily’s dad has been a big influence professionally as she moved throughout her career. She started her sales journey looking for sales jobs right out of college and she asked her dad questions about the different types of sales roles.

[4:13]  Emily’s experience of taking an outside sales role as an account executive at Worldwide Express that had heavy sales conservative traditional atmosphere. Emily shared her struggles of doing door-to-door sales and what she learned from them.

[6:19]  Factors for choosing the jobs she applied for: Location + Opportunities

[6:48] How to handle interview questions – Confidence and the ability to sell yourself

[7:48]  Qualities of a good candidate – Experience, competitiveness, the natural ability to work with people and work on teams, success-driven

[9:04]  Emily’s advice on how to break in – Develop your skill sets around strangers so you can be the best friend with the person you’re selling to which is what sales is about

[9:42] Getting promoted from a sales development rep to an inside sales role: You have to be a closer!

[11:37] What motivated Emily to switch over to a smaller company: An opportunity to climb the career ladder more quickly.

[13:55] How Emily prepared for her interview process at the startup company: Personal contributions to her previous company, technical knowledge, doing enough research about the company and the product. They want to see your effort: How badly do you want the job?

[15:37] How Emily dealt with frustrations and turning them into best practices: Writing the formula for success as a startup as a major frustration and using the things they’ve done right as best practices.

[17:34]  Crafting your pitch – Sounding confident in your pitches as a critical element of success in sales, self-teaching, and asking for help from the technical people in your team to answer questions for you

[19:36] Tonality is key: Articulate what your thoughts are. Believe that you know what you’re talking about.

[22:45]  How to handle the interview process at a startup – Find a common ground with the engineer because maybe you need those engineers to get the deal done. Also, you’ve got to be a team player. You’ve got to be hungry.

[24:25]  Resources to help you get ready for these types of interviews – Research about the interviewer. Find a common ground. Reach out to the person with a role you’re interviewing for to learn more. Know the

[25:01]  Knowledge is Power: Get as much knowledge on the product, the company, and their competitors so you can differentiate yourself from them. For startups, find out who’s funding them and what other companies the VC is funding. Read blogs and news about them like TechCrunch.

[26:28]  How the salary/commission scheme works at a startup versus a corporate environment (On Target Earnings of $40-$60k for beginning sales role)

[30:47]  Key questions to ask as you try to break into a sales role – Timeline of the progression of reps, what successful reps are doing, what they do differently (Progression of reps is quicker at startups versus bigger companies)

[32:17]  What metrics are you evaluated on: Activity levels (calls per day, number of bookings, size of deals, big accounts brought in)

[33:37] The next steps as you get promoted from a sales development rep (SDR) to an inside sales rep: Knowledge application, time management, qualifying deals, asking for help

[35:10] Emily’s plans for the future: Combining sales and art (Going back to her creative roots and trying to break into the art world )

[39:14] The Lightning Round

Imagine if you had to start over again and you had a $100. You get dropped in a completely new city, what would you do and where would you start?

  • Invest in a company where you like the product. Take a little risk.

Was there any music or movies or blogs that you read or someone that you talked to that you inspired to get through that frustration?

  • Emily’s father was her biggest source of leverage, inspiration, and guidance being one of the “best of the best” in the sales industry

What is the one advice that you would give our listeners?

  • Just act like you know what you’re doing and believe in yourself because if you trust yourself then whoever it is that you’re working with, even if you’re not in sales, just in life, those people are going to trust you too.  And as soon as you can learn to just trust yourself and go with whatever flow it is, even if it sucks, even if that flow pulls you in completely opposite direction, trust that it’s going to work out because you know that you can figure it out.

What is one thing that you fundamentally believed in that you changed your mind on after this process?

  • Emily fundamentally believed that “you could just be taught how to be successful.” Now, she believes that the secret to success is just really you. Just figure out what you want to do and then go after it. Find a direction. Find a path. And even if you don’t have a clear path, walk in that direction. The path will find you. You will only be successful if it comes from within.

But is there any books that you’d be like, this is the best sales book I’ve ever read?

  • The Psychology of Selling
  • Solution Selling
  • Books on Mindfulness (Find a book that settles your mind.)

Articles Mentioned & Resources:

Learning Resources
Cisco WebEx
Instart Logic
Worldwide Express
Andreessen Horowitz, Tenaya, Greylock

The $12 Million Stuffed Shark
The Psychology of Selling
Solution Selling
The Power of Now

Contact Information:

Emily Racioppi

Full Transcript: 

Intro: Growing up we’re told that in order to be successful, you have to be a banker, a doctor, or a lawyer. That’s what the gatekeepers want us to think. But we’re a part of something bigger. We’re part of a technological revolution. Either you’re at the table or on the table. Getting eaten. 10X.

Ruben:Yo, yo, yo, this is Ruben here so I’m here with the homies Artur and Timur Meyster and this is the Breaking Into Startups Podcast. Timur, can you please tell the people what we’re doing today?

Timur: Yeah, we’re here with a very special guest. We’re sitting at Hack Reactor’s alumni lounge on a Tuesday at 7:30, just talking about Breaking Into Startups. Artur, take it away.

Artur: Yeah, so today we have Emily Racioppi, who is an Account Executive at Cisco WebEx and before that she was a Sales Development Representative at an infrastructure startup called Instart Logic. We’re going to talk with her about her sales journey and then some advice for how to break into a sales role at a startup. Emily, before we begin, can you tell us a little bit about where you’re from and what were you interested in, in your early years?

Emily: Cool. Well first of all, thanks guys for having me. I’m really excited to work with you and talk to you guys. This is an awesome project you have going on. A little bit about me and my background, I am from Santa Cruz, California, NorCal girl through and through, happy to be in San Francisco, perfect match if you ask me. Going back, I went to school in California, always been in California. I knew I wanted to come to the Bay Area. It’s close to my family, close to home, and it’s where my dad kind of launched his career and seeing the success he’s had over the years and the life that he has been able to provide for my family and myself is what’s inspiring me to create that life for myself here as well. There’s a ton of opportunity in San Francisco so I think it was a good choice for me and it continues to show that I’ve made the right decision.

Starting kind of where my personality is not traditional, I guess, sales, I’ve been a little bit more artistic most of my life growing up. If I could have gone to school for anything, I would have gone to school for art history. And I wanted to be a curator in the Louvre in France right now with some Parisian boyfriend eating a baguette. That was kind of a dream.

But I talked to my dad a lot more and I ended up going to school for International Economics and International Business, that’s what I minored in. Definitely, a little bit more of a traditional route. I think it opened a lot of doors for me in terms of internships going through my education in college career. My dad has been a big influence both professionally and as I moved throughout my career. Ultimately, after school, just knowing that I had a natural act and ability to do sales, that’s what started my journey looking for jobs right out of college in sales.

Ruben: I completely understand as an artist myself. You know how much I listened in my childhood, you’re also advised that you should go the business route first. Maintain the music along the way and then eventually you could be a supporter of the artist and fund it and have it invested in yourself as well. Tell us a little bit more about what your sales journey was or what you were doing after listening to your father? What led you to that path?

Emily: The sales journey was pretty much asking because I didn’t really know the different types of roles that you can do in sales. I was still very much holding on to the idea that I could be creative and maybe doing a marketing type of route. Just the beginning of the journey was really asking my dad all kinds of questions like what type of company should I be looking to work at? What’s an account executive? What’s outside sales? What’s headhunting? What’s prospecting? Because as a college student that’s ready to graduate, you’re looking at these descriptions and these roles and you have no idea what they really mean. And I think that’s actually what ended up starting the journey in a little bit of a backwards way.

I ended up taking an outside sales role as an account executive for a company called Worldwide Express. They’re third party resellers so it’s an entire organization of just salespeople. They don’t actually have a new type of product that they sell. They resell UPS. So going into a very heavy sales conservative traditional atmosphere right out of college was a big eye-opener. They are the type of sales organization that trains 50 new graduates at a time. Take no prisoners. You would always hear these horror stories of really traditional sales roles where you’re in training and people are crying and you’re doing your pitch and that’s pretty much exactly how it was. We got to do pitches in front of the VP of Sales, his entire company, and he would just rip kids apart. Recent grads, in the middle of all your peers, and if you can’t hack that or stomach that, the role that we were going into was an outside sales role so customer facing.

My job was essentially to go knock on people’s doors, try to convince the gatekeeper that I was there to see the owner or the CEO or the executive in the company, convince them to then have a meeting with me on the spot and then try to buy business in person. It’s called cold close. So that, as a 23-year old, was rattling because you don’t have time to second guess yourself. You don’t have time to stand there and say “um.” You’re in front of the owner of a business. You need to be professional and keep it together. On top of that, just the very “stick to the numbers, stick to the script” type of sales. It’s good to get a thick skin that way. It’s good to get rejection. It’s good to learn if you can handle it and how to handle it.

Ruben: Got it. So you got that job just by asking questions to your dad and understanding what the terminology was and just applying and you got the job?

Emily: Yeah, I was interviewing at a couple different sales roles. I also looked into technical recruiting. It’s got similar sales echelon/type to it, but ultimately. I just went for the traditional sales route and then really I chose the role because it was in San Francisco and I knew that’s where I wanted to be. The other ones, I was looking at were down in LA in Southern California and to me in the long run like, okay what if this doesn’t work out, where am I going to go next? And there wasn’t as much opportunity.

Ruben: What was the interview process like?

Emily: The interview process for recent grads is I think is all the same especially because I’ve been on the other end of the interview process where I’ve been interviewing recent grads. It’s a lot of, “Tell me about your internships.” “Tell me about what you learned from your classes.” And then it’s more of a test of can you handle not knowing? Can we teach you what we need to teach you? As a company, we don’t expect the person to come in and know how to pitch the product that they’re selling. They just want to see if you’re the type of person that’s going to be able to listen to a pitch and then recite it back and be confident. Say it in your own way. Be convincing and ultimately, is this the type of person that is selling themselves because if you can sell yourself then you could probably sell the product that they want you to sell.

Artur: So being on the other side of the interview table, what kind of soft and hard skills are you looking for? What are some of the things that send out about a candidate that immediately let you know that they’ll be a good candidate?

Emily: Yeah, absolutely. The traditional things that most companies look for is the experience, like what type of internships that they do. If it’s a kid that did an internship with HP or Dell or any type of big company obviously shows that that kid’s got hustle, right? They’re going to make it into… because those are very competitive internships. So knowing that that person is competitive, that’s great. A big thing that everyone always looked for was fit in terms of, you’re an athlete. You’re probably going to be competitive.

I was an athlete growing up. A lot of the people on my teams athletes. A lot of the people, they’re in clubs. They’re in social settings. They already have that natural ability to want to work with people, to be on teams, to find ways as a whole to be successful. Those are the types of people that fit well into a sales org.

Timur: Cool. So I guess looking back, and I’m sure you’ve interviewed, you’ve worked with a ton of people. For our listeners, what kind of personalities would you say don’t succeed in sales? I know you have to kind of stereotype. But just for our listeners, if someone was asking you for advice on how to break in, what would you watch out for? Or how would you advise them?

Emily: I think that what I would advise them is what makes you feel comfortable? Who are you around that make you laugh, that make you funny, that make you personable? Find those traits and how you develop them and then learn to develop them with strangers because every can be funny and their group of friends. Everyone can be outgoing. But if you can’t develop those skill sets with a group of strangers then that’s going to be the hardest part because that’s essentially what sales is, is being best friends with the person you’re selling to.

Ruben: Got it. So you started in this lower level role, grinding it out. Walk us through the next steps in your sales journey.

Emily: Yeah, absolutely. I think that most people start up in sales as a sales development rep or a business development rep. There’s different terms for it but essentially, all means the same thing. You are doing the outreach. You are headhunting. You’re finding the business. You’re booking the meetings. You’re building pipeline. And essentially, you’re probably supporting a higher level salesperson. Once you prove yourself in that role, you hit your quota of meetings booked, you contribute X amount of dollars to new pipeline, you’ve maybe assisted in closing a deal in some way for your account executive, you’ll most likely get promoted to an inside sales role. That’s a role where you’re going to be closing over the phone. So it’s a first closing role. And every company is going to ask you when you’re interviewing for your first sales role, do you want to close? Do you want to be in sales? You have to say yes. You have to be a closer. You have to want to bring a new business and you can’t be afraid to do that because those people are going to be people that are going to make that company money. So that’s the people that they want on their teams.

Essentially, once you’ve booked meetings then it’s your chance. You’re going to close business. You’re probably going to close smaller sized deals. It’s going to be over the phone. It’s going to be high transaction most of the time, just closing as many deals as you can because that’s what your job is now is to close deals over the phone. They probably have the money to send you out into the field or you’re not at that role yet where you’re customer-facing. So after my sales development role, that’s what I did. I moved into an inside sales role. I was working with customers. My territory was New York so I was working with customers on the east coast and trying to close business with people in New York. I would go out every once in awhile and work with my extended team. That’s where I went next.

Artur: So it sounds like you’ve got to experience several different roles, like kind of right out of school. What actually motivated you to consider switching over to a smaller company?

Emily: Right out of school, I went for a bigger corporate company because I wanted that training and I wanted the ability to be taught the basics. You need the foundation. Sales 101. How to handle objections. How to properly conduct meetings. That kind of stuff is what you need to learn – how to prospect, how to cold call. And ultimately, this opportunity came along at my last company Instart Logic and I was one of the first five people on the sales team, one of the first 50 people in the company. I was so confused by the technology. I tried to go on their website and figure out what they were doing but still very early stages. So they didn’t have their focus or their marketing necessarily narrowed down either. I remember working a lot with my dad trying to prepare for the interview because it was relatively rigorous interview process.

I think that startups tend to be a little bit pickier with who they add to their teams both on the technical side and the marketing side and the business side because one weak wheel in the entire thing and it’s noticeable. If you go into a 50-person team on a bit huge corporate company and you’re slacking, people might not notice. If you’re going to a five-person team and you can’t get the job done, people will know right away because everyone is giving everything they have to make it work.

So the opportunity came along. They offered me shares in the company and just ultimately an opportunity to grow really quickly in my career and that’s what I think a lot of the people for to start up is how am I going to climb the corporate ladder if that’s a 50-person team in a corporate company versus a five-person team. So it was a chance for me to get to an account executive role or a closing role faster.

Timur: It sounds like throughout your career, you’ve been taking chances. You weren’t afraid to deal with rejection and then after you had your few years of experience under your belt, you decide to move over to startups. When you were going through the interview process, just to take a step back, how would you say… you mentioned it was more rigorous, more intense. What sort of questions were they asking you? Maybe you can give some examples and how did you prepare for that?

Emily: Yeah, they asked me a lot more about personal contributions like the corporate company before, it was like, why are you a good team player? Stuff like that, more generic stuff. And the startup, if they’re looking to add a six-person to a five-person team, they’re going to want to make sure that person fits on that team. What are you bringing to the table? I had only been at my previous company a couple of months so I was still young. I think I was 23 or 24. I had to figure out really quickly what are my strengths. How can I take my sales experience which isn’t very much and make it into this big picture that’s going to show them I’m going to be the sales person on their team that’s going to take their sales team to the next level. So it’s a lot more, what can you add to the team and individual accomplishments. Where do you see yourself? Bigger picture types of questions.

And then of course, they want to see that you can actually do the sales job so I had to learn the pitch or give a mock pitch in my best ability because I didn’t know the product yet sot that was a bit more kind of scary because my previous company didn’t really ask me to do the pitch or anything, They’re like, “We’ll teach you that. You’ll learn that.” This one was like, “Hey, do a research on our product and you pitch us.” So I had to be prepared to know some technical questions and prove that I could do research on my own time. So really they’re just looking for effort. How badly do I want that role?

Ruben: Got it. What were some of the most frustrating things that you had to deal with on the job? So far, it sounds like everything was kind of a breeze even though the questions were harder but a lot of people deal with frustrations. So I love to hear a little bit about that.

Emily: Every single day was a frustration. You’re going into an environment, especially for me, where before, I had a script where it told me exactly what to say. They had the formula to success. “We’ve been doing this for 10 years. These are what the sales reps do. They’re successful. You do that.” Going into a role where like, “Alright, so we’re trying to build pipeline. These are the types of verticals you want to go after. These are the size of companies we want to go after. Go find the people that we need to get in front of.” And so the frustration was I’m not very far long in my sales career. I don’t necessarily know what I’m doing but neither do the people that I’m working with because we’re a startup and they don’t have the formula for success.

So writing the formula for success, that’s frustrating because in order to be successful, you have to do a lot of things wrong. And when you’re young, especially thinking this generation, the instant gratification and having a lot of praise and that kind of stuff, you’re not necessarily prepared all the time for failure. And knowing that your failures shape that formula. So knowing that I had to go in everyday and do 10 things wrong just to get one thing right, that’s definitely frustrating. But once you get that one thing right then you get to tell everyone in your team, I figured this out. We’re going to use this best practice. And that’s what everyone was doing, just trying to figure out what’s the right way to do things, what’s the fastest way to do things, what’s the most efficient way to do things.

Artur: Sounds like experimentation is really important like rapid prototyping and things like that, right?

Emily: Yeah.

Artur: Nice. So Instart Logic is a pretty technical company. They’re selling infrastructure to enterprises. What do you do to get to up the speed on their technology and sound confident in your pitches with people you’re selling to?

Emily:  Sounding confident on the pitches was probably the hardest part of it because I’m on the phone with CTO’s because that’s who are buying this offer that we were selling. And essentially, trying to convince them that I knew what I was talking about enough to scratch the surface, I think a lot of it was how badly do you want to know it? How badly do you want to feel confident on the phone? Because there’s always a threshold. There’s always the minimum amount of work that you can do to sound convincing. I mean that’s with any type of sales. You can practice a script a thousand times or you cannot and just sound confident.

So for me and most people in the team, it was getting any and all material that the company had on the product and then of course working with the different teams. This was the first time I’ve ever been in the same company with a lot of really technical engineers, a lot of really technical product people. The company itself recruited people with computer science PhD’s, like the top tier talent in Silicon Valley that are working on their product. They have funding from Andreessen Horowitz, Tenaya, Greylock, the top tier venture capitalists. They were recruiting the best engineers. So really being able to go to the engineers at their computer and being like, “I don’t understand what this part does to the product.” And having to figure out a way how do I communicate? How do I learn from them when I’ve never been exposed to this stuff before. So definitely, a lot of self-teaching, a lot of asking questions,19:06 a course on the fly, having solutions engineers on the call with me so that when I don’t know a question, they answer it. I learn from that and maybe next time I’ll answer that question differently.

Ruben: Got it. And then also working in sales, at least for me, I know tonality is something that we talk about a lot. I know that with a female voice is a little bit easier just because it sounds more pleasant to the ear. But was that something that was coached to you or did you just learn it on your own?

Emily: You know what, it’s so interesting that you asked that question because I have never thought of that until the other day when I was talking to a good friend of mine. He works at Salesforce. We were both talking about these deals that we’re trying to get closed and he was like, “Yeah, sometimes I got to pump the brakes.” and “I can’t call them as much and leave as many voice mails.” I was like, “That’s so weird. I literally call them every single day and leave a thousand voice mails.” When I get them on the phone, they’re like, “Hey, I’m really sorry about that. Let’s get this done now, Emily.” They’re always like really accommodating and he was like, “Well, yeah because it’s easier to listen to a woman’s voice. They’re not going to get pissed off if they hear five voice mails from a woman’s voice every single day.” And I was like I never thought of that. I definitely think that I sound very crass and annoying but I guess that’s not the case. So definitely, it wasn’t taught to me and it wasn’t even brought to my attention until recently. I think it’s just confidence and the ability to slow down. Articulate what your thoughts are. Believe that you know what you’re talking about.

Ruben: Is your team a good balance of male and female?

Emily: No. It is not. I’m on a team right now of 8 guys. On my team before, it was mostly men and then 2 women. And the office as a whole though on my sales floor, much better balance but then again, we just have more people so by default, there’s going to be more women. On my startup team, there’s only 8 of us and 3 of us are women.

Ruben: Got it. And how does that affect your day-to-day work life?

Emily: I don’t realize it during the day-to-day because it’s been like that for so long. My first job right out of college was a team of four and all three guys and then me. Much smaller environment. So that was like close quarters. It’s just been that way for so long that I don’t know any different. It gets a little difficult because it’s a big boy’s club sometimes. I know I hate to say that and feed the stereotype but it’s true. It’s a lot of talking about sports. It’s a lot of… I can’t say that though. It’s really inappropriate. It’s a big ego competition sometimes like, “Yo bro, we closed this deal. I got this one coming in.” And I kind of liked that. I’ve always been a tomboy. I live with four guys right before I graduated from college. I grew up with having guys as my best friends. So I think that I don’t feel uncomfortable about it. I don’t feel like the minority. I don’t feel like I’m getting any type of short one of the stick. It just makes it that much better when I beat all the boys.

Timur: For our listeners, some of them might not necessarily start out in sales and they want to break into startups, I can imagine you be the person probably sitting at the table, doing the interview. For people who want to break into the sales roles, what advice would you give them? Also, what are those things that you look for and how would you advise them to approach this type of interview?

Emily: Yeah, absolutely, First and foremost, we’re looking for outgoing confident people. People that when they show up to the interview, they are ready to look you in the eye, shake your hand, and answer your questions directly, truthfully. You’re looking for someone that’s the type of person that other people are going to want to work with because first of all, they have to be able to sell to the customers. Second of all, they have to be able to work on a team. For the startup I was at, you got to be able to walk down to the engineers and find a common ground with the engineer because maybe you need those engineers to get the deal done. You never know it. So you need someone that’s going to be able to work with other people because sometimes you might be the type of salesperson that’s just closing deals on your own but there is going to be the day that comes when you’re going to have to work with either different people on the customer side or different people internally and you’ve got to be able to work with everyone. You’ve got to be a team player.

I personally look for someone that was really hungry. That’s something that people say all the time but they’re not just looking to have job security. Everyone looks for that but sometimes, going to a startup is a risk. You’re not guaranteed your role. Especially in sales, if you don’t hit your number, you might get fired. So if that isn’t something that scares you because you’re so confident that you are going to hit your number, that’s the type of salesperson that people want.

Ruben: Got it. Related to Timur’s question about getting prepared for these types of interviews, I know you had your dad to help you answer the questions. Are there any resources or books or movies that people could watch to understand the terminology, the sales cycle, and just different things like that to get ready for these types of interviews?

Emily: Yeah, absolutely. First and foremost, if I’m interviewing for a role this is what I do. I find the people that I’m going to be interviewing with. I look at them on LinkedIn. I might look where they went to school. I try to find common ground. I try to understand who they might be, which is kind of hard to do but you just try. You get a good sense of the type of people that they might be hiring. One thing I learned recently was reach out to the person in that role that you’re interviewing for. Ask them what they like about it, what they don’t like about it, how their interview went. Most people are going to be more than willing to answer your questions.

Second thing I do is cram. You try to get as much knowledge on whether it’s a product that they’re selling, their competitors. Huge. Know the competitors in your space because you know your competitors, you know what to look for, you know how to differentiate. And that’s what the company wants to do is differentiate themselves. So research the company. Research the product. Find out who’s on the team. Find out where the executives came from. If it’s a startup, who’s funding them? What other companies is that VC funding? And then try to read the blogs or the press about the company. So then you get a better understanding of the outside. What are people saying about this company? On any given website, they’re going to say they’re the best company ever. But if you read the blogs and the post or you go to TechCrunch and you find out more information about it then I think you’ll get a better understanding of what are other people saying.

Ruben: Got it. Related to career path, a lot of people talk about what’s the upside in these types of roles, how does it compare to engineering or design or marketing? And a lot of it is hazy for a lot of people I know in terms of the salary plus commission. Sometimes it’s commission just on an individual contributor basis and then there’s sometimes this commission based off of a region basis or it’s a hybrid model. Can you talk a little bit about that, how it’s different between startup and corporate environment and shed some light there.

Emily: That’s a great question because it differentiates quite a bit. First and foremost, at the startup that I was at, quota changed every quarter. What we were measured on in our parameters of success changed every quarter. And that’s ultimately because they don’t know what to gauge or what the range is going to be because no one’s done it before. So I would definitely say that at the startup, I know that for the account executives in that role, it was a higher payoff. We’re not going to be able to give you maybe as high as a base, but you’re the only person with a territory of Europe. So you have the chance and the opportunity to go make a lot more money. Just the guarantee that you’re going to make that money is not as much there because they don’t know. They don’t know how much you’re going to make in one month versus how much you’re going to make in a year whereas at the corporate company, when I was working on my recruiter, she was like, “This will be your OTE.”

Ruben: What’s OTE?

Emily: Sorry. On Target Earnings. So one things I’ve also learned as I progressed and developed in my sales roles is don’t be fooled by the fancy terminologies because a recruiter could tell you, “Yeah, you’re On Target Earnings versus… is going to be 200,000.” Great. How many of your reps are hitting their OTE and how many of your reps are hitting quota? What does your quota look like? How many consistent quarters has that been the quota? What are reps doing differently at this company to hit their quota versus other companies? Really being prepared to call their BS. That’s what I’ve learned definitely throughout this because necessarily at a startup, I wasn’t hitting the OTE that was promised. That wasn’t anything on the company. It’s unpredictable. They don’t know what the sales cycles are going to look like how each deal is going to turn out whereas at the company I’m now at, Cisco, there’s no room for negotiations. This is the base and that’s because we have thousands of people that are on the same base and this is what you get. However, our OTE is this amount and we can tell you exactly how many people are hitting OTE, how many people are accelerators, and that’s enticing.

Ruben: Got it. You broke down the different roles like SDR and the AE, etc. Can you give a range for what that looks like from a salary and comp perspective for a lot of people?

Emily: It’s going to be different especially as companies get more money. It might even be slowing down now. From what I’ve recently been reading about is that funding is becoming a little bit more scarce. The new economy is going to change but I think that anywhere from 40K to 60K for a beginning sales role, sales development, business development rep, it’s probably around average, obviously 40 being on the lower side. But then they might offer you a better comp plan or more commission or X amount of accelerators. They’ll make it enticing in some sort of way. And then some of the best account executives in Silicon Valley, they’re making 300,000+ OTE.

When I was looking for account executive roles, I was OTE, On Target Earnings of a hundred more. It could be split right now. I have a 50 split. I have 50% of that salary base and 50% of that, that’s my commission-based. How obtainable is my commission going to be? As of the startup before, I had 70/30 where I have a lot higher base but not necessarily a better commission structure after that. And that’s probably come from the uncertainty of not knowing.

Ruben: So you typically eat what you’re telling 30:17  So like if your base is 50/50 split, started 40/60, probably making between 80K-100K, first year.

Artur: Great. So I love the fact that you brought up the OTE. Every company is different so make sure to ask those questions. Also, what other pitfalls would you say people looking to break into this role should watch out for? If someone hasn’t done sales before and they’re trying to break into a startup, what are those red flags that they should watch out for?

Emily: I would definitely ask for timeline. Ask how long their current reps are in this role that they’re currently interviewing for. What’s the progression like? How do they get promoted? What are the key parameters for success? What are the most successful reps doing? What are they doing differently? Definitely, ask about that because the last thing that you want to do is accept the job as a sales development rep where you’re cold calling and you’re prospecting and you’re doing outreach because that’s hard. Cold calling is super hard. No one likes it unless you do which is super weird but it’s so hard. So the last thing you want to do is get into a role where you’re cold calling for a year or plus. You probably shouldn’t be doing that. I think sales progresses pretty quickly so you want to look for how quickly they can progress. I think bigger companies will make you stay in the roles a little bit longer and that’s just because they have a lot more people. They have a lot more protocol. They have a lot more hoops to jump through. A startup, you could be in a sales development role and kill it and be promoted to the next big thing in three months or more. So it’s really what you make it.

Ruben: And related to some roles like the things you mentioned a lot about metrics and you evaluate it and I know that on that startups especially, those metrics change a lot but what are some of the most common like no cold calls, maybe like email sent. How do they evaluate it?

Emily: A lot of the lower levels sales, like sales development reps and business development reps are measured on their activity levels – a hundred cold calls a day, 300 emails sent, LinkedIn messages, Twitter. I’ve booked a meeting over Twitter. So get creative. And then of course, how many meetings have you booked? Or maybe how many demos have you booked depending on what type of company, I guess you could potentially run in your own demos as a sales development rep. What size deals are those? Are you bringing really big what of accounts? Are you breaking into really big accounts? That’s impressive for a sales executive, especially an account executive. You want your SDR to be booking you meetings with the CTO of a huge account that you’ve been trying to get into. That’s what you want. If you can do that, then your metrics are going to be measured on exactly what I just said that those metrics and then of course how successful you are breaking into accounts.

Timur: Cool. You kind of described the more earlier stages as a sales rep and then once you become an account executive, how does your mindset change and then how do you evaluate which opportunity to go after because you have the experience? You’ve proven yourself as a sales rep. What is the next thing? Do you decide basic compensation, career progression, or anything else?

Emily: As a sales development rep and let’s assume that you then get promoted into an inside sales rep with the same company. So you take all that knowledge of who are you going to be booking the meetings with? Who are the people that are actually buying? How long is the sales cycle? What are the big objections that you see within the sales cycle? And who are your champions? Who are the people both internally and on the other side externally, in the other company that are the people that helped push that deal through?

So you take all that knowledge as a sales development rep and then you apply it to yourself. Because now, there’s this fear of, okay I’m not just handing this deal off for someone else to take control of. I’m running with this deal so time management is big because you can be wasting a ton of time breaking into accounts that are never going to buy. You can’t be wasting your time having conversations, week-long conversations with people that aren’t the decision makers.

Ruben: That’s qualifying, right? Is that what they call it?

Emily: Yeah. Qualifying. So qualifying the deals and making sure that you have everyone on the same page. So if it’s a deal that is going to require multiple people from the technical side, make sure you find out who the people are and bringing them into the deal early on and often. So I guess I’d say time management, qualifying, and then being able to ask for help because most likely, you haven’t closed before if you’ve just been promoted into an inside sales rep. Ask for help from anyone and everyone that will help you close this deal.

Ruben: So what are you up to now? What are your plans for the future?

Emily: Right now, I’m an account executive at Cisco WebEx. I’ve been closing a ton more business which is great. I think that any sales rep feeds off of success and closing deals, just fire going. But I think that going back to my creative roots is somewhere where I see myself going. I was recently talking to a good friend of mine who works in HR at Google. Her entire job is to help people figure out where they want to move within the company, where they see themselves. And Google is a huge company. They have tons of different types of roles. So she just asked me, what are you really good at? I’m pretty good at sales. I can do it. It’s in my blood. It’s been passed down from my dad to me. And that’s natural. It feels natural when I’m doing it. I feel good when I’m doing it. I’m seeing success. I’m good at sales. And she’s like, what do you love? Well, I do love technology but there are so many different types of products and it’s so changing that do I see myself being in the world where I’m going to be tied down to a product that I didn’t create my own? I’m a creator. I’m an artist. I want to have that. So maybe not. I love art. And she’s like, have you ever considered selling art? I’m like, how have I not considered this? So I actually see myself, as of right now, a lot of my free time I spend, I go to galleries in the city. I got to art openings. I go to exhibits. I go to museums. And a lot of that time is by myself. That’s what I do to unwind and I’ve found that I might not be technically trained in the arts but for as long as I can remember, my first time in Europe seeing the Mona Lisa and Meunier’s pieces. Those are the things I can spend hours doing with nobody around at all and still be completely happy and satisfied. I think trying to break into that art world potentially and maybe being a private seller for investors or art collectors or working for a museum, or even just to get started is working part time at a museum and seeing what that’s like.

Timur: Have you ever considered partnering out maybe with an engineer and then coming with some sort of product idea or related sales idea to promote it?

Emily: Potentially. I’ve definitely thought in terms of doing a creative side of like a design team almost. How do we want to make our website look? How do we want to market our brand? Doing more of like the visual design aspect of that and painting the picture of a company. But then I think that that would mean that I would have to break into graphic design, which I’m not opposed to. I’m open to that as well but I think that I’m also really good doing sales and doing the face-to-face interaction, the people aspect of that. So I think that at the end of the day, I’d still want to get in front of that person and close deals.

Ruben: That’s like how Artur and Timur and I met each other. When he was in college, he used to run the website buying and selling art. And it’s so interesting that we have the same similarity.

Emily: I do remember that.

Timur: It’s definitely a tough business but if you could position yourself and you’re good at selling then hell yeah.

Emily: Yeah. Well, I can imagine. Because when I’m selling the best and I’m most invested in a sale is when I’m really interested with the company that I’m working with or the person that I’m working with or selling to. So I can imagine if I was selling art, which is something I’m so extremely passionate about. How much better of a salesperson I would become?

Timur: I heard the commissions are pretty good too in art.

Emily: I guess it just depends on what part of it. I think that it will be a lot about who I know and how to even make money selling art, where I need to go. I need to rub shoulders with the right people.

Ruben: There’s a book called The $4 Million Stuffed Shark that talks a lot about the economics and art. That’s interesting.

Emily: Oh really? I would have to have you write that down for me afterwards.

Ruben: We’ll put it in the show notes.

Timur: Great. So with that said, we’re going to move onto the final part of our podcast and that’s the Lightning Round. Artur, Ruben, and I, we’re basically going to ask you several questions. Try to give us short responses but at the same time, including your tactics, strategies, or resources that you’ve used to become good at sales and just be successful at what you do.

Emily: Cool.

Timur: Nice. Imagine if you had to start over again and you had a $100. You get dropped in a completely new city, what would you do and where would you start?

Emily: That’s tough. I would probably invest. I would probably start investing more. I bought my first stock shares this year so that was exciting for me. And I don’t think I ever would have done that before but knowing that when you’re young, $100, you’re holding onto that $100. I would invest. I would just try to find a company that I think is cool, that I like the product, and then just invest my money. Take a little risk.

Ruben: Yeah, financial literacy is important. So related to frustrations and things like that. Throughout the process, we talked a little bit about that but was there any music or movies or blogs that you read or someone that you talked to that you inspired to get through that frustration?

Emily: Honestly, my dad. I keep going back to him but at any given time, I always find it funny. I’ll go to his LinkedIn and I’ll just see what he’s up to because he’s so humble about it. He would never be like, “I’m currently on the board of xyz companies.” and “I have this investment in this company.” and he’s been the CEO of a couple of different companies, the VP of Sales, and he’s a private consultant now so people come to him. He does joke sometimes when I was at my company before at my startup. He’d be like, “Just have them pay me $300 and I’ll come fix your shit.” “I’ll come fix stuff for you.” So just knowing that he has that reputation and has been there and has been successful, I know that I can do that. I know that I have that guidance because he’s one of the best of the best. And it’s good for me to have that just in my back pocket.

Ruben:  It’s interesting you say that about your father because a lot of people talk about sales as a quick path of CEO’s. Even like presidential roles, the talk about a lot of that type of stuff too so trajectory is interesting.

Artur: But it sounds like you’ve found someone in your life whom you can learn a lot from or you’re leveraging their experience and their advice and it could be your parent or it could be your best friend or your relative. Just find someone who inspires you, right?

Emily: Yeah, I definitely leverage my dad whenever I start a new job or if I’m doing interviews whether it’s me venting to him about the struggles that I’m having in this process and having him be like, “Take a step back. This is what you need to do. These are the things you need to look at.” And as hard as he is on himself, he’s never been hard on me. He’s never made me feel like, “This is it. Get this job.” or anything else. He’s just like, “If this doesn’t work out, this wasn’t the job for you. You’re smart. You’re capable. You’re hardworking. You’re going to find another job.”

Ruben: That’s beautiful.

Timur: So the next question. We typically like to ask what is the one advice that you would give our listeners? You can either answer that or maybe share some advice that your dad has given you that has had a huge impact on your life?

Emily: 100%. And I think about this all the time. Both my mom and my dad. My mom first and foremost, because she sees how hard I can be on myself sometimes where I feel the need to be perfect or to know everything and to have it all figured out. And she said that, “You know, your father might not be the smartest man in the room or know all the answers, but he sure acts like he is.” So I’ve kind of kept that with me and I feel it all the time. I feel it when I get scared on a call. I feel it when I’m in front of a customer and I don’t know the answer. Just act like you do. Just act like you know what you’re doing and believe in yourself because if you trust yourself then whoever it is that you’re working with, even if you’re not in sales, just in life, those people are going to trust you too. And as soon as you can learn to just trust yourself and go with whatever flow it is, even if it sucks, even if that flow pulls you in completely opposite direction, trust that it’s going to work out because you know that you can figure it out.

Ruben: That’s great advice. It reminds me of that Dilbert quote that says, “You can get anywhere in life if you look serious and carry a clipboard.”

Emily: That’s so good.

Timur: Awesome. What is one thing that you fundamentally believed in that you changed your mind on after this process?

Emily: Yeah, I think it goes back a little bit to what I was touching on earlier. I think I fundamentally believed that you could just be taught how to be successful. And this is going to be very contradictory and very controversial I think because there are people that spent their life trying to replicate Steve Jobs and try to find the secret of success. This is so difficult to say but I think that I believe now that the secret to success is just really you, figuring out how you’re going to do exactly it is what you want to do. If you don’t know what you want to do, you might not be that successful right now. Just figure out what you want to do and then go after it. Find a direction. Find a path. And even if you don’t have a clear path, walk in that direction. The path will find you.

So the one thing I believed before and especially when you’re fresh out of college and you’re reading a bunch of books when you’re trying to find out the best places to go and the best degree to have is that you can be taught how to be successful. And there is a degree to that that’s truth. But you will only be successful if it comes from within.

Ruben:  Yeah, and also being willing to learn like that quality that you’re talking about and 44:58 about friends and family that could guide you in the right way.

Timur: Approach yourself as a product. We wrote a blog post a couple of months ago about how the first product you build is yourself. If you know how to sell yourself then you’ll be able to sell anybody else.

Emily: Sell yourself.

Ruben: The last question. I know we talked about it a little bit and things that you can learn like was there any books that you’ve read about sales or any online resources. I mean I mentioned a book before that was related to art. It was actually The $12 Million Stuffed Shark, not the $4 Million one. But is there any books that you’d be like, this is the best sales book I’ve ever read?

Emily: I do have sales books. There’s The Psychology of Selling. That’s really interesting for me because I like the dynamics of knowing exactly the personal interaction, maybe less of “understand the product” and go from objection handling to cold call closing and all the steps and more of like the persona. Find out the personas of the people you’re selling to. So The Psychology of Selling. I know I’ve heard it before. You guys have probably heard it, Solution Selling and those are my two favorite ones. This is kind of out of the box. I read a lot of books that don’t have anything to do with selling. In terms of, I read a lot of books about mindfulness and I know that you asked for a sales book but this honestly helps me with my sales because it helps me to have a balanced and even-keeled mind. Because in sales, it is up and down. I know that I can go from having the best week that I’ve had all quarter to the very next week having not close a single deal. How do I not let that stress me out? How do I come into the next call that I have that could potentially be the biggest deal and not already being upset or worried about whatever else that happens? So find a book that settles your mind. It doesn’t need to be religious or anything like that or spiritual but that’s what worked for me.

Timur: Awesome.

Ruben: That kind of goes to us, the athlete type of thing too where you might be the best three-point shooter and you shoot at air ball. And if you dwell on that, you might have the bad rest of the game but you’ve got to keep moving forward because the game is not over until it’s over.

Emily: Exactly.

Artur: And there’s another, my other topic of awareness, mindfulness, I think The Power of Now is a great book where he talks about the ego and then how you disconnect yourself from being attached to certain things that make you feel like that’s what success is. And then once you’re able to detach yourself then you’re actually focusing on what’s important. In any job in sales or engineering or anything else, if you’re always going after what everyone else praises then when you don’t accomplish it then you feel like you’re a failure but if you know for yourself what’s important and what you’re going to define as success then you’re most likely you want to be as important. It sounds like you’ve been able to internalize it i some ways.

Emily:  Yeah, I think I have a little bit figured it out. I sure have a long way to go.

Timur: For sure. What is the best way for our listeners to get in touch with you? Are you on any social media or email?

Emily: I am on social media. A lot of my Twitter was highly connected to my startup because you’ve got to get the word out. I would say email though because you never know what company I’m going to be at in the next couple of months. My email is great. I always answer my personal email as well.

Ruben: So what’s the email address?

Emily: It is eraciopp@gmail.com.

Timur: Nice. We’ll include it in the show notes.

Ruben: Thank you for spending time with us and we’ll keep in touch.

Artur: Thanks Emily.

Timur: It’s super interesting and we hope that it encourages people to get into sales.

Ruben: Thank you guys so much. This was so much fun.

Timur: For sure. Thanks.

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Episode 1