007: Learnings from Launching 60+ Tech Sales Careers with Lisa Plain
007: Learnings from Launching 60+ Tech Sales Careers with Lisa Plain
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[00:00:00] Intro
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Mike Bird: Hey there. It's Mike Bird here and welcome to Sales Seekers. I'm pumped to bring you this episode because it features a longtime friend, a former collaborator and fellow career coach, Lisa Plain. Lisa's been a full-time career coach for a number of years now and has helped over 60 clients enter tech sales. She also works more generally with job seekers who are bouncing back from a layoff, which has been unfortunately all too common in tech lately. So, this is a great conversation: it's very timely, very relevant.
Lisa and I are also collaborating on a free, two-part webinar series in early October, designed to help folks hone their networking skills. This is often one of the most valuable, yet most challenging career development skills a person can learn. So, whether you're looking for a new role right now or not, come and join us. I'll link in the show notes where you can learn more.
All right. Without further ado, let's get into the conversation.
Lisa Plain! Welcome to the Sales Seekers podcast, the show I decided to start without you. Sorry about that!
Lisa Plain: Thanks for having me. No, I'm really excited to be here. And this is actually the first podcast that I've been on since ours. It's a nice getting back into it.
Mike Bird: Yeah it totally is. Just for people who have never, for people who have not heard The Career Builders Podcast, which may be a lot of listeners to this show, Lisa and I ran a podcast for about two and a half years and about a hundred and I think 106 episodes in total, where we talked about how younger people in their twenties and thirties could build a better career. And that involved some one-on-one discussions, but also a lot of interviews with actually some pretty big names in the career development space. If you think about who's big on LinkedIn that was a really fun project that we wound down for a variety of reasons at the end of 2021.
But it's always fun to collaborate with you, Lisa, and I'm super curious. This is my ice breaker for everyone coming on the show, which is complete this sentence in one phrase or less. If you really know me, you know that I am blank.
Lisa Plain: I am a master of reinventing myself. I like to try a lot of different things and change things up and go in totally different directions just. Speaking to my career, that's been the way things have gone and it lends itself to the conversation that we're about to have too. I've been through it and I know that, starting over in something brand new can be an adventure and a lot of fun and also a little bit challenging.
Mike Bird: Yeah it sure can be. We've, we have both gone through some interesting career reinventions along the way. And the focus of today's talk is about how you've helped folks get into the world of sales and tech sales as a career coach, someone who has had a lot of reps at helping people make what can sometimes be a very unusual transition for a variety of reasons.
Jumping into that a little further, what would you say are the three big things that you coach on with your clients where you see them entering or they're trying to progress in their sales career? What are some of the things that you really tend to work on the most?
[00:03:10] 3 things Lisa coaches sales most
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Lisa Plain: Yeah, so the three most common things that I've seen are, first of all, working on self-awareness. self-awareness is such an important part of any career change or career progression, but particularly in sales, because there's so many different ways of coming at sales. And if you do it authentically, people can tell, and it makes a difference. So self-awareness is number one.
The second thing I work with people on is selling themselves. Salespeople are great at selling things, but when it comes to themselves, they tend to be a little bit shy to do it or feel a little bit awkward about it. So that's the second thing.
And then the third thing is really looking at the job search process as a sales process. And the biggest part of that being understanding your audience and solving problems for them. So a lot of times people look at a job search as a job search. And with that comes a lot of fear of judgment, a lot of worry about these people that you're going to be interviewing with, but when you break it down and look at it as a sales process, it's so much more manageable and it takes the emotion out of it a little bit too. You're not selling yourself in any situation, whether you're a salesperson or whether you're in a job search, but the way that you approach it as a salesperson, looking at it as a sales process can be really helpful for people.
Mike Bird: Yeah, absolutely. Certainly the mindset of, and what I think that implies when you think of anything as a sales process, is that there's going to be a percentage of times where you're not going to succeed, you're not going to get a job offer, or you're not going to get a callback on your résumé or on an application.
And that's totally okay. And it is part of the process, but the more you fill that funnel of opportunities, with that mindset, the more likely you are to find yourself in a favorable situation, maybe with multiple offers from different companies and the ability to have some options and real choices in your career, which is great.
Lisa Plain: Exactly.
[00:05:11] Unpacking job seeker discomfort
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Mike Bird: Can you unpack something that you alluded to? So the challenges that people experience around selling themselves and the discomfort that some people experience. What are some of the shades of discomfort that you've seen over the course of your coaching career?
Lisa Plain: I've had a lot of people, even people who have been a little bit later on in their career, come to me for interview coaching. And the, one of the first things that they say to me is I can sell anything to you, but I cannot sell myself to save my life. And it's all about mindset. It really is. Because they're looking at it as: I'm going into this, I have one shot at this interview, but it's really, it's a whole process from the second you send in your résumé to the follow-up emails that you send to, if it's an in person interview, as soon as you walk in the room, those are all part of your reputation, your first impression.
So yes, it is about the interview, but it's more than that. And if you say something wrong in the interview, we're all human beings. So a lot of people worry about that. They worry, I'm going to say something wrong and I'm going to completely mess up the whole thing. Another thing that a lot of people worry about is just telling their story.
If I've had a career, that's maybe a little bit unorthodox. Or doesn't follow the linear path. I haven't worked in this industry. How do I explain my story in a way that they care about, or that is going to show them that I can do this job? Because most of the time people come to me and say, I can do this job. And I believe them. I a hundred percent believe that they can do the jobs that they're applying for. That's really just building their confidence in the problem solving piece.
So not looking at it as you need to go and sell yourself, but looking at it as this company has a problem. They have a hole. They're trying to get something done. You are able to do this job and you're probably a really great fit. So how can you explain that or show them proof in a way that feels non-salesy and feels authentic to you?
Mike Bird: Yeah. Yeah. It's about helping them, the employer get what they want out of this posting that they have created. They are looking, they're looking to make a change and to do something. And if you can map your skills and your background, your experiences to that better than anybody else. That usually means you're going to get the offer.
I think when you boil it down to something like problem solving or you frame it that way. It can definitely relieve some of the discomfort that people might feel about it being a process that's more about them when it's really not, actually, it's much more about how you can help the employer.
Lisa Plain: For sure. And there is that cultural fit piece too that a lot of people take personally, but it really isn't. If you think about friends that you have or even people that you've bought things from, there's multiple products that you can buy for anything.
I'm in the market for doors right now for our house. I know, exciting. But we've had a couple of people come and quote and. The one company just was a better fit. We just felt better when we were chatting with them, we hit it off. It was really easy to ask questions and there was a fit there. Whereas, one of the other companies that came, it's a huge company in this area so obviously a lot of people like them. So there's nothing wrong with them. It's just that it didn't fit with us and our needs. So that's another thing to remember in both sales and in job seeking is that it's rarely personal. Even though it feels personal.
Mike Bird: Yeah. That's so true. And it's very hard oftentimes to overcome that mindset of, "yeah, this is not really them rejecting me," if I'm the candidate. It's about them selecting someone else who was a better fit.
And I do hope you've got a good situation with your doors. Cause we all need a door somewhere in our lives.
Lisa Plain: Totally.
Mike Bird: I love that. Great analogy. What else? So what are some of the other common challenges that you see job seekers encounter? Whether it's related to getting into sales or not, just other things that you have seen folks struggle with?
Lisa Plain: This is a funny one that is unique to salespeople. And I'm going to say this as a generalization, not every sales person that I've met is like this, but I do find that they tend to be a little bit overconfident about their résumé. And what I mean by that is they've maybe done some research online. They've asked their friends. So they will come to me and say, "Oh, I don't really need you to look at my résumé."
Can I just take a peek? Cause there might just be a couple of things. And again, they're not looking at their résumé in a sales lens. They're looking at it as a static document that says what they've done in their past, but you need to apply that sales lens to your résumé to look at it as a marketing document. And once you do, that's when it starts having an impact. The other piece of it is thinking that their résumé is going to get them the job and in the market that we're in right now, it's just not realistic.
The résumé alone, I have had clients who have gotten jobs just from online applications, so it does happen. But the majority of people that I work with get jobs through networking. And over-reliance on your résumé. It's not going to get you as far as you think. And there needs to be other strategies that you're utilizing.
Mike Bird: You make a couple of great points around some of these challenges and it's interesting hearing the tendency for sellers to sometimes be a little overly confident in their résumé.
Oftentimes salespeople are not always the greatest marketers, and they're used to always being in the room with people having a discussion. The résumé is separate from them. They are usually not accompanying the résumé when an employer is first looking at it. So it totally makes sense that there is that disconnect.
In this market right now where there's actually a lot of tech sales talent that's available and it's not like there is sort of this out-of-control hiring spree that we saw a few years ago as there were tech companies just accelerating their hiring and taking kind of anybody almost, it seemed like, into their sales organizations.
The résumé doesn't always carry the day. And you talked about networking: what sort of process do you see folks taking to make networking an effective approach to make their job search better?
[00:11:49] Leveraging networking in a job search
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Lisa Plain: It really depends on the person and their network. I find that people who have a wide, warm network are great going out and reaching out to people that they already know, particularly if they're in an industry that, it's a bit of a close knit industry. You get to know other people pretty well, it's easy to then transition in between companies.
People who don't have a big warm network, it's really important for them to start going out and reaching out to people cold. And it can feel really uncomfortable. And, shameless plug, we have a webinar coming up on this that you can join, but, it's really important to put yourself out there, in the same kind of cold calling way. Like you're cold calling, but doing it without having to sell anything it's really a win situation because if you have some way to help somebody, people always feel good about helping other people.
So if you have a contact that you reach out to cold. They're like, "no, I don't have anybody, but I know this company that's hiring. It sounds like you would be a great fit." They then feel good about passing you forward as long as they get to know you a little bit and build that relationship.
But that's the way that I see people usually doing it. I like to call it snowball networking. You reach out to one person, you ask if they know anybody else and you go from there. But, talk to as many people as you possibly can, that's the best way to network in this market.
Mike Bird: Yeah. Conversations over applications. I feel like I am maybe quoting Dominic Imwalle, but yeah, it is selling without the stakes of a typical sale. And I don't think personally I've ever rejected the opportunity when someone reaches out to me for a conversation, especially if they do it through the context of, "Hey, like I, I saw that post you had on LinkedIn, or I heard you on that podcast" or something like that.
It can be really easy to say yes to those kinds of things. Those people care about you. It's neat, actually.
Lisa Plain: That's so true. Yeah, and it's fun. It is. Once you start doing it, it becomes a fun, uplifting conversation. It's not something that's as draining as sending out hundreds of résumés.
Mike Bird: Exactly. Nobody likes that.
[00:13:57] The wildest transition to sales Lisa's seen
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Mike Bird: What's the wildest career transition you've seen someone make in order to enter sales?
Lisa Plain: I used to work with a company called SV Academy out of Silicon Valley in San Francisco. And the program was centered around bringing people with non-traditional backgrounds and training them to become tech salespeople. And so I've worked with a lot of people who have gone through a pretty life change at various stages, whether they were younger, whether they were halfway through or even later in their career.
So some of the biggest that I saw were going from military service into sales. Somebody was a baker and decided to go into sales. Tech support, teacher, property management, finance, a warehouse worker. You name it really it's more about your desire to be in sales than it is about your past experience.
Anybody can be a salesperson if you have the right mindset and also will to do it.
Mike Bird: That's a powerful message for people who are listening. Part of the goal of this podcast is to show that there are a lot of different ways into the world of sales, and you can come from just about any background to do it. And just in your experience alone, that's a huge variety of backgrounds and walks of life that people can come from, into this space.
That's really neat. I feel like it's hard to pick one that's like the wildest transition when you hear that.
Lisa Plain: Yeah, all of them were challenging in one way or another. I think one of the biggest things that people really struggle with when they're switching from something very different is just the new feeling. Because a lot of times if you've been doing something for a little while and now you're switching into something new, you were an expert maybe at the last thing, and now you're not. That can be tough. Any of these things it's just getting into the sales mindset and perspective and, then taking action and going out there and not letting the doubts or fears get in the way.
Mike Bird: Yeah beginners mindset, right? Doing something for the first time and being okay with that. It's not something everyone is a natural at, but it is definitely a helpful skill if you can employ that when you're making any kind of transition, really.
[00:16:11] Job searching if you've been laid off
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Mike Bird: As we were preparing for this recording, you mentioned how you often support folks who have just been laid off. And that this is something that can really have an impact on a job seeker. There have been a lot of layoffs in tech as of late. So, can you expand on what makes this circumstance so unique and/or challenging?
Lisa Plain: Yeah, absolutely. So I've been working with a lot of people who have been laid off in a lot of different industries. And one of the big challenges that come with a layoff is the surprise, the element of surprise, but also the feeling of rejection or just being blindsided or somebody that you thought you trusted not being able to be trustworthy. It's a really challenging thing.
And a lot of times people try to jump into a job search right after, which is totally understandable. You need to work, you need to pay your bills. It's tough because you want to get right back into it.
You want to start sending out résumés, but there is at least a couple of weeks that need to be taken to reset, really process the layoff. Sometimes there's anger. Sometimes there's burnout. There's a lot of things that come up when you've been laid off that you need to deal with, whether it's with a coach, whether it's with a therapist, whether it's with a friend or a family member, writing in your journal, there's lots of different ways to do it.
Working through some of those feelings and thoughts are really important because if you go into a job search and you're angry or you're feeling deflated or rejected, that's going to show up in the way that you go into an interview or even the way you approach your networking or sending out résumés. I've seen a lot of people who haven't done the work initially, who then go out and they start applying and the burnout of the job search happens even faster.
Job search burnout is real, but if you haven't processed your layoff, it can happen much sooner. And so it's so important to manage that and deal with that before you go out. And it doesn't even have to be like really deep soul searching. It could be something as simple as writing a letter to your old boss, just getting all your thoughts out and never sending it. Throw it into the fire, burn it, get rid of it in some way. Just getting it off your chest can help to release some of those feelings.
So that's the first part, but then going off of that, going into the action piece, because a job search is largely about action. And so after a layoff, it can be really tempting to take longer periods of time off in between, and it's funny because I have two thoughts on this.
On the one hand, take advantage of the time that you have, go for coffee at 10 am. with a friend, sleep in, take advantage of the time. Cause it doesn't always come around.
But at the same time, try to be taking action consistently, because the job search right now is taking about 4 to 6 months for people. Depending on your network, depending on the amount of action that you're taking, there's a lot of variables. But start by taking that consistent action. And it can be really hard to do that after a layoff. Be gentle with yourself. Do take advantage of it as much as possible, but try to create some sort of schedule.
Mike Bird: Wow, that was an amazing pile of different golden nuggets. Job search burnout. I had not really thought of it in that way, but it makes total sense. And the sort of almost grief cycle that is happening to someone as they are let go from a job that they depended on or that they trusted.
And now you're dealing with can I trust the next employer who hires me? I could see that being very demoralizing as you think about, wow, I have this life as an employee, but look where it's gotten me to.
Then you talked about the fact that processing of the transition, if not done to a degree of thoroughness, can really impact how quickly you might hit a level of fatigue or burnout, right? And balancing self-care sharpening the saw, not letting yourself run out of steam. And going back to the idea that a job search is a sales process, you're trying to build a flywheel of momentum.
Different leads, different opportunities, interview cycles, and things like that. And that only comes from stacking action on top of itself.
I appreciate you sharing all of that. And I think for anyone who is in a situation where they've been laid off, dealing with all of those different kinds of forces on you can be super draining and overwhelming. And yeah, just that's totally normal, I would say is if that's you and you're hearing this and you're feeling this now.
Lisa Plain: Absolutely. It's totally normal and it's totally possible to get past it. And even though it might feel like really far away, that your next opportunity is eons away, it'll come around faster than you think. And It'll be better than you expect.
Mike Bird: Love that. Yes. We always want to leave folks here with some encouragement and that is exactly a great note to hit that on.
[00:21:22] What should people jumping to tech sales know in advance?
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Mike Bird: I'm curious from what you have seen from folks who have gone into a career in tech sales, what's one thing that people who have made this jump, or are thinking about it, what should they know in advance before they actually make the jump?
Lisa Plain: I think that there's a lot of different types of companies and a lot of different types of roles in sales. So, be really clear on what type of role is going to fit best for you and make sure that you're making decisions about the type of company and the type of clients that will work best for your personality, going back to the self-awareness piece.
You can work for a company that has really high volume sales, and you can work with a company that has low volume, high value sales. And that's going to be better for different people. So play up your strengths, pay attention to what type of companies are out there.
And when you're choosing, companies to go and network with or to apply to, as much as you can, try to focus on the ones that are really going to work for your personality and your goals.
Mike Bird: Yeah, that's a great point. And I believe when you work with folks that you're coaching, self-awareness is one of the first things you try and coach people on to help them become more self-aware, but also functionally to help them not end up in a situation where they're suddenly in a role that really doesn't align with them at all. Am I right in that guess?
Lisa Plain: Yeah, exactly. There's a bunch of things that you can think about in terms of personality, learning style, introversion, extroversion, interests, skills that really, it doesn't need to all exactly align, but you want to try to find the best mix of things for yourself so that you're not getting into an environment that you're not going to thrive in.
Mike Bird: Cause then you're back looking for another job!
Lisa Plain: Exactly. Exactly.
Mike Bird: Doing it all over again.
Lisa Plain: Yeah
[00:23:19] How job seekers hinder their own efforts
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Mike Bird: Yikes. Okay. What is one thing that you have seen sales job seekers do maybe aside from what you just shared that usually hinders their transition efforts in some way?
Lisa Plain: I'm going to sound like a bit of a broken record, but just not treating the job search as a sale. Not applying whatever process you use in your sales, and people do different processes so that's why I say using yours, whatever you are comfortable with, create a plan for yourself, put it down on paper, be really clear on what your goals are, be really clear on who your audience is, and then go out and take action towards that. But, people who avoid, that's really going to hinder their job search.
Mike Bird: Yeah, that's something that I coach people on a lot in terms of gaining as much clarity as possible on what they are pursuing. Sometimes people seem very, I'm not sure if unconfident or uncertain... what the right word is, but people often just don't want to make a decision when it comes to where they want to go.
Some people do. And they're very clear and that's a different kind of person to work with, but there are lots of folks that I come across where they just don't want to make the decision. That's been true for you too?
Lisa Plain: Yeah, absolutely. And how do you work with clients on that? What's one piece of advice that you would give them?
Mike Bird: Yeah. I think using a sales mindset again, here, a product cannot be a great fit for everybody. Unless you're toilet paper. I've always said that, unless you are a toilet paper, there are very few products that are made for everybody on the planet. And you as a job seeker really are only made for certain folks, certain companies, certain roles, certain environments.
And, the job search gets easier, the more you figure out who you're really made for. And that does involve to your point earlier, all this introspection, like you need to know yourself as a product. And from there, it becomes easier to figure out, okay, what's the market that I want to play in as a job seeker?
But I think it's coaching around that mindset of, " we're not made for everybody, but we are made for someone." And if we are clearer on that, we will just be sharper in terms of how we think about who to reach out to and what to apply to. We're going to be more confident in mapping our fit to an organization when we're in an interview. And it's just going to be hopefully a more fun process in that way too.
Lisa Plain: Yeah, absolutely. Yeah, totally agree. And it's funny. I can just picture people going, "ew, introspection? Ew, that sounds gross." I don't want to do that. And it's not that bad, really. It's probably stuff you've already done. You just didn't realize it.
Mike Bird: Exactly. Yeah. It becomes a habit for sure. If you get started and coaches are often very good at helping people develop that introspection habit if they've never had it before. Very cool.
[00:26:14] Where to connect with Lisa
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Mike Bird: Okay. This has been a great conversation. We're coming up on time. I feel like we could have gone 60 more minutes here...
Lisa Plain: As usual.
Mike Bird: As usual.
It feels just like the old days of TCBP, on our old show. Where can people go to connect with and learn more about the work that you're doing?
Lisa Plain: I'm most active on LinkedIn, so you can find me, Lisa Plain, on LinkedIn. And you can also check out my website, careerbalancecoaching. com.
Mike Bird: Super. Okay. Links will go out to both of those things. Yes. I will follow up in terms of our cool webinar collaboration that we've got coming up at the beginning of October. But Lisa, thank you again for coming on. I appreciate it.
Lisa Plain: Thanks so much for having me. This has been so much fun.
Mike Bird: Likewise.
[00:26:59] Outro
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Mike Bird: Hello again. Hope you enjoyed this amazing chat, Lisa and I just had hard to believe. It's been almost three years since we last recorded a show together. I'll drop a link in the show notes if you want check out our old podcast: The Career Builder's Podcast.
And if you want to learn more from both of us, again, we have an upcoming couple of events. The first of which is on October 9th at 8:00 PM Eastern Time. Link for that will be in the show notes as well. If you have any questions, ping me on LinkedIn.
Lastly, if you're liking this show and think it could help other sales job seekers out, then why not leave a review? Reviews are a great tool for helping more people in need of this content, discover conversations like this one.
I appreciate the help. Thanks so much for tuning in, and I'll see you in a couple of weeks. Bye for now.
