Leaving my job in big tech to start my own business

N.B. Some background. I worked at Salesforce for over 6 years before stepping away to start Shuttle with my best mate. I wrote this piece about my time there and all the moments that ultimately led to my decision to leave. With all the change and shifting in the tech space over the past year - companies faltering and masses of people being made redundant from jobs they thought were secure and companies they had a sense of loyalty to - I thought this might resonate with people who now find themselves in a state of flux or unsure of their next move.

February 1st 2022. The alarm on my phone startled me but I was already awake. Yesterday I closed my biggest deal ever at Salesforce and today I no longer work at the company. January 31st 2022 was my last day after six and a half years. It was a weird feeling and one I hadn’t experienced before. It’s not the first time I’ve moved company but this time I had no one to report to.

I owe Salesforce a lot. The company gave me a career and helped me build a lot of confidence in my ability and what I have to offer. It was exciting but I couldn’t get away from the anxious feeling in the pit of my stomach! Have I made a mistake?

I run back through what I’ve left behind. A regular salary, a role I was comfortable in; wrapped in all the perks and benefits a big company like Salesforce provides. It’s also full of great people so I was saying goodbye to friends I had been working with for years. Some I’d been working with since day one. And the reality is, it was probably the last time I'd see a lot of them. I remind myself I’ve gone through this 100 times and roll out of bed.?

Despite the uneasy feeling, I was incredibly excited. We had been working on this in our spare time for the last 6 months but it felt like the first truly big step. We were going all-in.

I didn’t realise it then, but starting a business was a culmination of a number of micro-moments that started when I joined Salesforce. All coming together to prepare me for this step.

After limping through my business degree I ended up working in recruitment. It didn’t interest me and I wasn’t good at it. I had no idea what I wanted to do leaving college but a friend's sister had given me a job. I told myself to just stick with it for now and I’d pick up some transferable skills I could bring elsewhere. Turns out that when you’re not interested in something and don’t really want to be there, you’re unlikely to do very well. Who’d have guessed?? After two stagnant years, it was finally time to move on. But where to?

I’m sitting at the kitchen table in the house I grew up in staring at a job site on my laptop. I’m looking for a new role but I don’t even know what to search for. Two uneventful years haven’t left me feeling particularly confident or helped me uncover what I’m good at. All I know is whatever's next needs to be vastly different to what I’ve spent the last two years doing.

Dublin had attracted some big names in tech and I had friends working in the industry. I still had no idea what I wanted to do with my life but big tech seemed like the place to be. I wasn’t feeling particularly sure of myself though. I hadn’t learned a great deal in my last role. Plus I had no experience in the tech industry. I remember literally Googling 'Best tech companies in Dublin'. “There’s Salesforce again”. It featured heavily. Lots of talk about culture (whatever that was), perks and benefits. Sounds nice. I decided that was my target and it turned out I knew someone working there who was happy to refer me for an interview.?

I let out a sigh of relief as I hung up the phone. A sense of calmness came over me as I sat on the edge of the bed. I had been offered a job. The tension I’d been feeling started to melt away as my future became a little clearer. A new start.

Salesforce was a different world from where I had come from. I had no idea what to expect but I loved it. The best part was realising I had a natural talent for the job. It was competitive and I did well. My confidence was back. I was working with smart people and learning a lot. The training and resources they offered were excellent. Life was good! After a year as an SDR (Sales Development Rep), I was promoted to a BDR (Business Development Rep) role where I worked with large Enterprise businesses. It was a challenging new opportunity. Once again, I was pushed out of my comfort zone. It felt like progress and after another year I was once again building towards a promotion.

The goal of the SDR/BDR role is to prepare you for a move into a closing role as an Account Executive. That was always the path and it’s the same in pretty much any sales organisation. Regardless, It’s easy to internalise your shortcomings when you’re facing a change. Most who go for it get the role but some colleagues who interviewed recently weren’t successful and it made me question my own ability.

I speak to as many people as I can who are already in the role. It's somewhat helpful but I know they’re all maintaining the bluff. No one wants to give away that they find it tough. I make note of what's useful and hope it comes in handy. I interview for the role and get the job. Another challenge.

Something you hear a lot when you’re in sales is that the rep is the CEO of their own territory. Treat it like you would your own business. It’s cliche but it's not untrue. It’s actually a good mindset to have and probably laid some foundations for stepping out and starting a company of my own.

Being an Account Executive came with a new pressure. As an SDR/BDR you’re kind of wrapped in cotton wool. You play in a bit of a grey zone and the rules can be bent to suit you if needed. Now I was out in the open with a big fat quota over my head. The learning quickened and the competition jumped several levels. I enjoyed the change and the competitiveness but it wasn’t easy.

All 4 years as an AE I sold into tech companies in the UK. Many of these were VC-funded at various stages of growth and included a number of Unicorns. It was fascinating. I was always super interested in companies that were raising capital. More funding meant new objectives to reach; new revenue targets, new hires, new territories and new products. I got to spend time with these companies and learn about what their leaders care about; what challenges they face and how they overcome them. The variety of companies and people I dealt with meant I spent much of my time outside my comfort zone. Something I appreciate more in hindsight. It trumped my business degree 1000-fold but a lot of those learnings are only coming to light now.?

I specifically remember one moment which helped form some of our thinking around what we’re building at PitchedIt. It was year-end (Jan 2021). The busiest time of the year at Salesforce. The office was heaving with activity as every rep made their last roll of the dice to reach their target and earn as much commission as possible. I’m looking at my accounts and I’m frustrated as I pass one name. Peakon. They were one of my more active clients but had gone cold a few months back. “What the hell happened there?” I do some digging and up pops some news on Techcrunch. Announced that day - Peakon acquired by Workday for $700m.

No wonder they aren’t speaking to me.

I immediately started thinking about the founders. Six years and they exit for almost a billion dollars. Impressive. I start trying to calculate how much they made.

Then a question forms in my head.

“How can someone like me invest in a company like that?”.

And without realising it, that moment was a catalyst that helped form some of the thinking for what we’re working on now.

Salesforce felt like a real career and built me up to be a valuable contributor. It helped me realise where my strengths lie and gave me confidence in how I can add value to a team and company. And despite it all, I started feeling unhappy towards the end of 2019. I had been in the company for over 4 years and my first two years as an AE were a bit of a slog. That first year in particular was a big learning curve. Then, I was unexpectedly given the opportunity to interview for a move up. I got the job which was great but I was once again the least tenured on the team. I was progressing but still hadn't found my feet and everything felt like it was losing its shine. A change of scenery might be a good idea but my wife and I were also thinking about having kids. Not an ideal time to step away from a steady salary and a company that offers 3 months of paternity leave! I decided to see out the financial year while I kept thinking about a move elsewhere.

At the end of Jan 2020, just as Covid was rearing its head, we found out we were expecting a baby. We couldn’t have been happier and work issues no longer seemed important. Thoughts of a move were put to bed along with any feelings of discontent.?

That year was pretty bizarre. My wife and I closed on our first home in February. A few weeks later I was sent home from the office indefinitely. We had planned to move out of our apartment and into my mum's house to save money. That ended up happening the same week the first lockdown kicked off! Not ideal but truth be told it was nice to be back home and I spent most of my free time that summer working on the house as we prepared for the arrival of my son, Jack.?

Summer is also the time at Salesforce when everyone first starts thinking about promotions. Interviews are usually held in November/December but there’s a lot of politicking and preparation that happens in the lead-up. With everything I had going on I decided against going for a move I was eligible for.?

Since joining Salesforce, my thought process was to always take every opportunity put in front of me even if I felt unsure. But this time around I just really wasn’t feeling it. I was still adapting to WFH and had a baby on the way. We were moving into our first home and I was going to be taking two months of paternity leave. I didn’t want to be thinking about interviewing while I was off. That's probably a good enough excuse as it is but adding to that, internal moves require a lot of “brand-building” with hiring managers. Something I always detested and found exhausting. I also hadn’t been feeling as excited and confident in the career path in front of me lately. Another year on this team was looking like a good call and without the added stress of interviews, I enjoyed the rest of the FY and exceeded my quota.

I didn’t know it then but February 2021 was the start of my last year in the business. And coming into the summer of that year, I was once again facing the possibility of a move internally. I was coming off a good year and was now the most tenured on the team. But it didn’t matter. One way or another it was time to move on. But where to? Move internally or move company.

I’m leaning on my kitchen counter with my head in my hands, agonising about what to do. For some reason, the decision felt debilitating and I struggled to figure out what to do. Uncertainty had crept in. I was trying to work through this internal conflict but kept hitting a wall. I was completely incapable of making a decision. It felt like a test where the question offered two possible answers and you know both of them are wrong but you're forced to pick one regardless.

Salesforce always laid everything out for you in terms of career progression. It was something I appreciated about the company. You knew from day one what your next step was and what you needed to do to get it. It was now the summer and the chatter about interviews had come around again. I needed to move on to the next chapter of my career but wasn’t confident about what that should be. I started meeting hiring managers and their teams but my head just wasn’t in it. I didn’t want the job and even the thought of asking someone for a coffee to discuss the role was exhausting and I avoided it. I started researching other companies and even spoke with a few. I wasn’t sold. Selling software here vs. selling it there. I just wasn’t excited by the idea. I was resisting the internal move and resisting a move to a new company. I was at a loss.

Don’t get me wrong, I’m under no illusions I was in a pretty fortunate position. I also look back on my time at Salesforce with great memories and appreciation. But over time, the path in front of me began to erode little by little and eventually broke apart. It became clear that wasn’t what I wanted and all the conflict I was feeling was my body’s way of telling myself I needed a change. I wanted off the conveyor belt.

Most of my time at Salesforce I was happy to be on the path I was on. There was a clear road in front of me. And when you’re in a company that’s always pushing employees to move to the next rung on the ladder, progression becomes a pretty central element in your thinking. But was it really what I wanted or did I just get swept up with the corporate propaganda I was spoon-fed. I didn’t know what I wanted to do before I joined the company so how could I expect that to change so quickly? Maybe I was just happy that I found a company where I was doing well. And it was easier to let them pick the route for me. A prefabricated career handed to me on my first day.?

“How can someone like me invest in a company like this?”

I’m sitting on the kitchen counter in Scott's house, laughing with friends. It’s the end of July and a summer BBQ brings some welcome respite from the thought of work and “what next?”. Someone asks Scott about his “business”. I perk up. Business? Scott takes out his phone and starts showing us the early stages of a platform he was building. The idea was to connect startups with service providers. Think developers/designers/illustrators etc. and people who could help them finance these projects. He had recognised how some startups he worked with often struggled to pay for high-quality work which ultimately sparked this idea. Hearing he wanted to start something of his own impressed me. I was proud of him but also pretty envious. A feeling that was magnified by my own situation. I always wanted to start my own company but the moment hadn’t found me yet. Not until I listened to Scott speak and it triggered something in me.

It took a couple of weeks for me to successfully broach the idea with him but after two poor (and slightly inebriated) attempts to explain I wanted to build a company with him, he got where I was going. In hindsight, it’s clear that my avoidance to get to the point was a fear he would say no. But it turned out he loved the idea and had been looking for a co-founder… so why not his best mate who he trusts completely?

That was August 2021. Lots has happened with the company since then but that's for another post. We worked at our respective jobs for another 6 months and focused on PitchedIt in the evenings and weekends before making the jump to full-time in Feb 2022. I still remember preparing to tell my manager I was going to be leaving at the end of the year. Doubt creeping in, making me question myself again. Was this the right decision? My son, Jack, had just turned 1 and at the same time, I found out we had another on the way. There were some nights spent tossing and turning as I wrestled with my own uncertainty. Was it reckless to leave a secure job in pursuit of a dream??

“If you don’t do it you’ll always regret it and I’ll never hear the end of it”. My wife always had a way of cutting through the noise. That was the final push over the edge.

Since then my second son, George, was born and even with the huge stresses, pressure and knowing the business hasn’t even gotten to the starting line yet, I’m happy and feel like I am accomplishing something important to me. This is what I was looking for.

I’ll finish with this. It’s been pointed out to me many times that my decision was incredibly risky and to those people I say this. I was in a job that I was no longer enjoying, at risk of stagnating and no longer happy. I wasn’t motivated by the option to stay in the company or to move to a similar role in another company. I’ve learned more since Scott and I decided to go on this journey than I have in my whole career up until that point and I’m far more valuable to any company or team now than I was before this. Yes, I have big priorities that come first but when your opportunity shows itself you either grab it with two hands or get comfortable living with the regret that you let it slip past you. I’d rather avoid the latter.

If you're facing similar feelings in your own job or have recently started thinking about starting something of your own, I'm always open to a chat. Don't hesitate to reach out.

And for anyone interested in what we’re building, you can join our waitlist at PitchedIt.co .?