001: How I Broke into Tech Sales
[SS Podcast] 001 - How I Broke into Tech Sales
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[00:00:00] Intro
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Mike Bird: Hello and welcome to Sales Seekers. You're listening to the first full length episode of the show, where I interview people who transitioned into individual contributor roles in B2B tech sales- sales development reps, account executives, account managers- as well as people who have recruited and hired for these kinds of roles and other coaches like me.
You'll also hear some solo episodes like today's where I'll share either my own take or my own experience on something related to making the jump to B2B tech sales or working in the world of tech sales.
My name is Mike Bird and I'm a career coach and the founder of Sales Seekers, a coaching company, helping people break into and up through B2B tech sales as individual contributors. I create actionable content like this and other places like my biweekly newsletter which you can subscribe to, by going to Salesseekers.ca/tips, that's sales with an S seekers, all one word, .ca/tips.
If you ever have questions for me, I invite you to write back to my emails. I'll always do my best to reply to everyone, who does write in.
[00:01:04] What my life was like before switching to tech sales
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Mike Bird: Today's episode is a dive into my own career transition, which I'll break down into three parts. Number one, where I was in my career and life when I started to transition to B2B tech sales. Two. What the transition looked like for me mechanically, what actually happened. And number three, what I learned in my first full year of B2B tech sales, which is probably not super typical of many people who've maybe worked for larger B2B tech organizations, but I'll give you what I have experienced. Maybe it is relevant to what you may experience one day.
Let's get going into this deep dive on my own experience. Going back to 2020. Everyone's favorite year in this millennium. I was becoming a pretty uncomfortable in my job at the time. I was almost eight years into my career. But I was only making about $44,000 Canadian a year. That was roughly my salary at the time. I was so blatantly uncomfortable and ready to leave, that I still remember taking a phone screen from a recruiter. Taking a phone call in the hallway of where I was working, which was a school at the time. And. I ended up leaving that environment for another education setting.
.So for the first eight years of my career, I was working in education. I was actually working in athletics. I have a background in coaching and I took another role, going to a local IT- focused college working in career services.
How I got, there is really not an overly fancy story. I ended up leaving a copy of my resume and on indeed and someone who just happened to be looking for an unusual type of role an internship placement advisor. Came by and gave me a call. And that was a lot of fun. But it's ultimately not how I got into tech sales.
At the time that I was making that transition. A former colleague of mine, her name is Jess, introduced me to a guy named Scott and Jess had been my colleague and had moved into an EdTech company. And she connected me with Scott who was running the sales organization at this small startup. . Jess knew that I was building at the time, a coaching business, on the side of my nine to five job and she knew that I was interested in business development and sales just as a set of concepts. And so she put me in touch and Scott was great. He and I connected over to Zoom. And he at the time was looking to actually hire a more experienced Account Executive, to come into his organization. And I certainly wasn't going to be that guy I had, I had no, no previous experience formally in sales. But we had a great conversation and we agreed to stay in touch.
Pressing pause on the tech sales transition for just a moment. So I took that new job right at the start of what was our COVID lockdown here in Quebec? I literally went into my new employer for a day. Did some onboarding and then the next day everyone was told to stay home. I'll still remember that transition. It was very coincidental. And ultimately I did a lot of what Daniel Pink calls "non-sales selling" in that role.
If you ever read his book... one of his books is called _To Sell Is Human_. And in that he talks about the fact that about, 10% of the workforce, in North America is working formally in sales, but up to 90% of it does some form of what's called non-sales selling. Where we have to, as people, we have to convince others to follow our ideas or our prescriptions or our guidance and that's actually really helpful, I think for anyone who's trying to transfer into the world of sales, but we'll come back to that, in another episode.
So I started this new job and I was still working on building a coaching business on the side at the time. And that involved me selling to coaching clients. And that gave me some experience in some simple transactional sales environments. And eventually when I hit a ceiling in that new nine- to- five role in the IT school, in career services. I came to realize that my income was going to cap out somewhere in the mid- to- high $50,000 range, which was more than I was making at the previous school. But I could see that growth was going to be tough to come by and that I wasn't really going to make a meaningful jump in my income by staying in this place. So I, again, started to open myself up to making a move. Scott in the time that I'd been working in this new role, joined a company at the start of 2021.
He moved from one EdTech company to another. And we'd been having calls probably about once a quarter, just trying to stay in touch and I, I just brought curiosity to those calls. I was super interested in knowing, from Scott, how does he think about prospecting and how does he think about, handling challenges in terms of building pipeline or closing deals. I was trying to, with my side business, figure these things out on my own and just having access to someone who had spent most of his career doing some of these things, albeit in in a slightly different context, it was a real joy. And I think that ultimately the curiosity that I showed for the work, stayed with Scott, which was great.
Scott came back to me in April or so of 2021. So if you're doing the math, this is Yeah, this is close to 14, 15 months. Of time between when I first met Scott. To when he came back to me. Asking to interview for a position in his new EdTech startup that he had joined earlier in that year.
[00:07:13] Does it really take this long to switch?
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Mike Bird: Maybe you're thinking right now, Mike. Wow. That's a lot of time between when you started to consider the idea of going into tech sales, and when you actually ended up with an opportunity to enter that space. And I agree that that over a year, almost a year and a half is a pretty long period for a career transition. Generally, what I would say is most people could probably have done this, in a fraction of the time, if they had been a little bit more intentional about making this kind of a jump. I just was kind of going with the flow a little bit, which is frankly, kind of how my career had been to date and not putting the kind of intentionality into what I wanted to do, what kind of money I wanted to make things like that. I had had some direction previously in my life, wanting to be a full-time football coach, but in the wrong country. And ultimately there wasn't necessarily going to be the potential for the career I wanted in that space.
So. I say all that to say for the people who want to, who are listening right now and thinking, Hey, I'd love to go into B2B tech sales tomorrow. I don't think it's going to take most people a year to a year and a half to do that. Especially if you have some guidance on how to do it. I just happened to be the guy who relied on one relationship, which I got fairly randomly. And that carried itself into an opportunity, which I'm going to get into now.
So. That's where I was when I was coming into the scene. Very frustrated and ready to move on. And when Scott came to me in April of 2021. He said, Hey, I've got this new role that we're opening up. You've been interested in sales for a long time. I know we've been in touch. And I think you would really appreciate having a shot at this.
I think you could do well. And that sort of vote of confidence led to me saying "sure". Yeah, I'll, I'll take a look at this. And I ended up getting into a series of interviews with folks from this 25 person startup.
[00:09:15] Interview #1 w/future sales colleague
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Mike Bird: Scott handed me off to the founding Account Executive of the company. So this is someone who had been with the startup pretty much since Day One.
He'd closed all of the business and the organization up until that point. And so he was someone who was going to have a lot of influence in terms of whether or not I was going to be seriously considered for the role.
Really really great guy. He remains a colleague to this day. And is someone who during our interview together really probed me to understand, had I received any kind of training? What was my background really? Like what had I done? And I confessed that I didn't really have formal sales training or experience other than what I was doing in my coaching business. Closing the odd client in a one-on-one sales setting. And then doing the non-sales selling activity of my current job in career services where I was often talking to employers, trying to get them to take on our students as interns or possibly even entry-level employees.
I was trying to map out the experiences that I had to. The role that they were hiring for. And that that's another topic for another day. I think the skill of being able to map what you have done and what you can do to what an employer is looking for in the present is such a critical component of being able to sell yourself, let alone selling anything else to anyone.
The Account Executive and I had a great conversation. And he gave me an opportunity to throw some questions his way to better understand some of the challenges that, that he was facing or that the sales organization was facing. And I think he appreciated that.
One of the things that is really critical in a sales interview is that when you are asked to bring questions to an employer, that's a great opportunity as a candidate to display your ability to do sales discovery. And that's something we'll definitely cover in future episodes as well, but long story short, your ability to understand the problems that an employer is experiencing, that they're ideally trying to solve for, by hiring someone like you. The more you can do that, the more effectively you can do that the more effectively you can understand the pain points that they are experiencing. Not only is it easier for them to see, oh, this is someone who actually can do a very important functional skill of sales, which is understanding prospective client's issues. But it also helps you the, the more clarity that you have over the things that you'll be asked to do, the easier it is for you to bring about stories from your own career and life that demonstrate how you might address the challenges and the problems that they are facing.
So all that to say Had a great first interview and did receive the green light to go ahead to a second round.
[00:12:18] Interview #2 w/company CEO
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Mike Bird: That second round interview happened to be with the company's CEO which was a pretty scary moment, honestly, for me. The CEO of this company is a pretty unusual individual. They are someone who has had a very long successful corporate career in the world of technology super uncommon, especially for a female leader. And so I just sort of walked into that second interview feeling pretty nervous, feeling a bit intimidated. Like, kind of "who was I to actually talk to this person."
Some of the fears that I had about being in front of someone who seemed in some ways, so much "higher" I'm going to say, quote unquote, than me in the corporate pecking order. That's actually another challenge that I would say most salespeople deal with worth exploring as we talk about what it means to get better and better as a salesperson, learning to actually speak to executives as though you are a peer and what it means to actually be in that position as a sales rep.
So that second interview with the CEO was a rapid 30 minute back and forth where she spent some time trying to figure out why the heck I had been brought forward for consideration. She was looking at my LinkedIn profile and trying to get a grasp on my experience and really just trying to put the pieces together. And eventually there was a breakthrough moment or what felt like a breakthrough moment in the call for me, where I basically connected the dots.
I realized that, "Hey, you're looking to sell to academics, to coaches, to people who work on the front lines of academia and education settings." And those are the people that I have been surrounded by throughout my whole career to date. Like I have been a frontline person in education settings for years and years.
I know what teachers experience. I understand what, what frontline, what I'll call frontline managers in education deal with. I can speak to these people and that is ultimately where the conversation started to shift from where she was thinking. Hmm. I'm not sure I'm understanding the fit here to her saying, oh, maybe you could also, given your background, try helping us with this priority over here that's different from the one that I had originally intended.
There started to be a new level of engagement in that 30 minute interview. And ended with her basically saying, Hey, I'm going to have to think this over.
This is pretty interesting. I'll get back to you. You'll hear from Scott on whether we go with some next steps here or not, but appreciate the time. I thought, okay, that's interesting. I've got like a 50/50 shot here at getting onto a next step. And. I thought, Hey, the hardest part, may be over right now.
Now I've got a CEO thinking about whether or not she wants me to join the company. Even if this doesn't go my way, I'm going to be really, really happy that I've put myself forward. That I've had this conversation with someone whom I think otherwise I felt very scared of before that call.
[00:15:43] Interview #3 for final executive alignment
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Mike Bird: So. Good news! I did get the opportunity to go to a next step. The CEO was willing to move me forward in the process. And I think part of that might actually, if I'm being really honest, is because I displayed a real openness to, to do something that was brand new and I wasn't going to necessarily cost a ton of money to do it. But. The next step for me was a third and final interview. With the company's Head of Client Success.
And in case you're like what is client success, client success is sort of a proactive form of customer support. It's the easiest way I can put it. Client success teams are responsible for usually helping to implement, train, onboard new clients, support them in an ongoing basis. And are ultimately measured based on client retention metrics.
So. Keeping people that the salesfolk have brought into the company happy is a big part of their role. And the reason I was being interviewed by our Head of CS was because, at the time, it was drawn up that my role would have me doing my own client onboarding. So I was going to be this full, full, full cycle position. A mix of a sales development rep (SDR), an account executive (an AE) and CSM (Client Success Manager) all in one bundled position, which yeah, that's a pretty intense kind of role by the way. We'll come back to that another day.
But because I was going to be doing some post-sales work, some CS work, the company wanted me to sort of be tested by the CS team lead. And that was a really fun conversation, frankly, kicked off by the mutual appreciation that we have for Elton John's music.
And that was just sort of this great icebreaker that turned into a discussion where we just really learned about one another learned about what we were looking for in this role, learned about what I was looking for in this career move. And we left that call on a great note. I was pretty certain that I'd done everything that I could at that point to position myself for an offer. Which was really exciting.
Fast forward a few weeks, took a little while for a letter of employment to come, but it did come. I will skip the part where there was a bit of a negotiation that happened, that didn't go too far, but ultimately I did accept the role and I started working in what I would now describe as an SMB Account Executive role, a small to mid-sized business Account Exec role. Someone who is responsible primarily for closing new business. Usually in the three figure four figure contract range. So this is someone who in a perfect world is closing certainly a bunch of deals every quarter, a bunch of deals every month, sometimes multiple deals in a week. And this is supposed to be one of the more transactional structures within a tech sales org. But what that actually was for me, I'll get into a little later.
[00:18:58] What I was initially tasked with in my new role
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Mike Bird: I was selling our product, which was normally being sold into the leadership levels of various university departments. So not, not the very top of an institution and its leadership, but sort of the top of various departments and, and colleges and universities are very complex organizations most of the time.
So there are a lot of different people that we could involve, but I was looking to in my role, trying to get around that very busy, sometimes very drawn out sales cycle and put us in a position where we could sell directly to university professors who would then initiate a sell-through. So we would get them to agree to present our product to students. Students would pay for access to our product on a per user basis. And that was going to be a new model for us as a company.
We gave it a shot. Didn't really amount to anything in the end, although I did try and I did close some business. This is what I did initially for the first several months at this startup.
[00:20:04] Major pivot in my role as our company changed focus
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Mike Bird: So just stepping back for a second and recapping what I've covered so far. Number one, where I was at before I joined this EdTech startup back in 2021. The 18-month transition window that it took for me to go from a K-to-11 education setting, to a higher ed, education setting, finally landing in B2B tech sales and the process that it took for me to actually get to that.
And now we're going to just chat through quickly what I learned back in the first full year so if you think of, summer 2021 to summer fall 2022. This is what I experienced in my new role, my first role in B2B tech sales. Again, not saying that this is everyone's experience, but this was how it turned out for me.
So after going out and selling our product direct-to-professors or attempting to do so and I did some very fun and creative things to try and do that. A lot of Twitter prospecting. It was called Twitter at the time. And finding kind of interesting professors who might be open to technology a little bit, oftentimes a little bit younger.
Bringing new things into a higher ed environment can be tough in the best of circumstances. But this was an opportunity for me to try and find people who'd be a little bit more open to making a change.
One thing that I hadn't really mastered at this early stage of my career was understanding what the real pain points that these folks were experiencing. And since I didn't do a great job of uncovering the pain that these professors were living through, I didn't really sell a ton of our product. But I did manage to sell something that no one else managed to sell in our company.
And I think that that persistence and that creativity gave me an opportunity to have my role shifted in November 2021. I was asked following a company offsite to lead our work in expanding into some new markets. As a company, we wanted to broaden our reach and go beyond just having a single market of operation. I worked with our new Demand Gen Manager at the time of marketing person. And worked to create campaigns that would allow us to generate some awareness in new verticals.
And we, in January of 2022, got that really underway, got into the market. Created a little bit of noise and started to take some discovery calls from folks who were essentially early early adopter type folks, people who are willing to try out something new in these new markets that we had targeted. We weren't sure which of these markets was going to be our main area of focus moving forward, but it was one of these really neat experiments that we were able to conduct that can be sometimes it's really, really hard to execute in a larger organization. There just isn't the same amount of agility, or speed. And so I was very excited to be doing this work. I was now selling to all of these different kinds of organizations that I didn't fully understand yet.
I didn't fully understand what our value proposition was going to be to them, but it gave me a tremendous opportunity to hone my skills. And continue to just lean into my adaptability. It's probably one of the things that I have been able to lean on as an attribute in my career.
The company was pretty happy with the work that I was doing in terms of generating new pipeline in these new markets. Which was going to be really, really key for us, not only from a, just a, a revenue generating standpoint, but also from a, an investor marketing standpoint, in order to raise more money for our company. Any company that can prove that it's able to serve a larger addressable market or multiple markets is going to be one that can be valued at a higher level. And therefore it becomes easier to raise more and more capital for that business.
[00:24:17] Getting promoted and the life impact this made!
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Mike Bird: But in February of that year, February, 2022, I was promoted. So about seven or so months after I started. And that was really eye-opening for me. I had never been promoted that quickly for anything in my career. My compensation jumped quite significantly. At that point, my base pay went into the high $80,000 Canadian a year. Which was about a 60% increase over the job that I had right before I got into tech sales.
So that was, that was a really life-changing moment. And my appreciation for that recognition made me even more engaged as an employee. There was commission income that came in that year, which can be something we talk about later, but I was able to cross into the six figures in 2022 by the end of that full year.
And I just couldn't believe the difference that it made in my life, I didn't think quite as hard about where my money went to. I was able to actually accumulate some meaningful savings for the first time in my life. Just again, for context, I was entering my mid-thirties at this point. And to sort of not really have the financial foundation that I wanted to knowing that my career wasn't going to last forever. This was something that really just changed what I felt I could do in my life, but my partner and I started to go out to the odd, nicer restaurant a little bit more often, or just buy a higher quality food. I'm a relatively frugal person. But these increased means really allowed for a solid impact on, on my life and my wellbeing.
[00:26:01] 3 things to think about or do if you're considering the jump to tech sales
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Mike Bird: And so I'm going to pause here because there's some more stories that I could tell about this first full year that probably belong in their own episode. I know I've said that a few different times here, and you're getting sort of a preview of what's to come in the programming of the show. But what I want you, dear listener, to take away is that if you are considering a transition into B2B tech sales I want you to realize the great potential there is to have an engaging and well-compensated career where there can often be significant room for growth. Particularly if you enter into an earlier stage company, like I did.
My experience isn't everyone's experience. But with guidance, I do believe that a lot of people can shape an experience that would be meaningful for them, whatever that means. Sometimes money isn't the most important thing to pull out of a career. Sometimes it is feeling like you have the flexibility to maybe take care of things on the side of work, maybe children or a family. Aging folks. All of these things that happen in life that demand our ability to be present. There can be a lot of things that come out of having a tech sales career. That enable that kind of flexibility.
There are three things that I think anyone could probably do. Right now if they wanted to make a transition and were looking for ways to make it easier. One is to reach out to the salespeople in your life and start to make connections to them, understand their work, make connections to people in their network and really start to grow the relationships that you have with people who work already in the B2B tech sales world.
I'm sure someone out there that you know, friend of a friend, could be your door into the space, much as it was for me. If you're doing that with a regular consistency and you have a growing network of people who could lead you to an opportunity, you're going to land in the space a lot faster than I did. I only had one connection that I was really doing anything with. And again, I just didn't bring the kind of intentionality that you need to have to have an efficient career transition.
The second thing that I would recommend is to go out and work on your own sales skills. And that means, it mean a lot of things, it could be having a side hustle where you're selling something. Whether it's a service, something you're doing on the side. Maybe you have a, an arts and crafts side to you. You want to sell something that you've made, getting experience being in front of people who are going through a buying journey is so priceless. Maybe you work as a fundraiser or a door knocker, someone who is looking for donations for a nonprofit organization, or is looking to sign people up for a petition. All of these are types of sales activities.
Maybe you work in athletics and you can recruit people to join your team. Recruit athletes. Recruiting is a great sales domain. If there are partnerships aspects to your workplace, maybe you work with community groups around your organization. And some people on your team are carrying out activities where they're building these partnerships. Maybe you can try and get involved with some of that work as well.
My third recommendation here is to start to think about what you actually want your professional life to look like and why you might want to be a salesperson. Not everyone feels great about the idea of going into sales and that's okay. If that's you, I would say it's helpful to interrogate this.
So you might ask questions, like, what are my underlying beliefs of sales and salespeople? What experiences or people have shaped by own view of sales? What are some of the poor sales experiences I've lived through in my life? What are some of the great experiences I've lived through? It's really helpful to unpack how you really feel about this kind of a career, because if there's hesitation in your approach, it's going to show up in how you sell yourself throughout a job search process, an interview process, a hiring cycle, et cetera.
So having belief that this is what you really want to do is important. And if you feel hesitation around that belief, then it's a great opportunity for you to explore. What could strengthen that belief or make you feel more confident based off of where you're at right now?
It takes a lot of fortitude and conviction to stick it out in sales. Perhaps from the story that I've shared so far, it sounds like I had a very rosy, easy pathway through sales and my first year. And that's very far from the truth. I still battle a lot of the emotional rollercoaster that comes with a life in sales. But I do believe that for folks who want to take this seriously and make the jump and grow their skills as salespeople, this is an amazing career path. I couldn't recommend it enough.
I do really enjoy the work that I do. Even though sometimes it comes with some difficult moments, it's made me a better person, someone who's a lot more resilient. Someone who is better at understanding relationships and, and running the relationships in my own personal life a lot more effectively and meaningfully, so.
I'm going to pause there. That is my story of how I made the jump into tech sales. I will continue to unpack some of the things that I've learned in my first three years in B2B tech sales, mainly as an Account Executive.
And if you enjoyed this episode you'll probably enjoy my biweekly writing. Again, go to salesseekers.ca/tips.
If you liked this episode, I'd love for you to subscribe, leave a review of the show or share it with someone who would appreciate hearing this. I'd certainly appreciate your support. And I'll be back in a couple of weeks.
Thanks so much for tuning in. Bye for now.
