In part 1, I wrote about the early days of my career – starting at BMO and then at TD.
In Part 2, I wrote about finding out what was next and reaching my immediate financial
In this post I’ll describe the steps I took to leave the corporate world and join a start-up and end with my evaluation process.
By the end of 2021, I had set up a secondary revenue stream via my condo and bought the house I planned to live in for at least the next decade. I also sold my old house for more than expected and used the extra money to set up an emergency fund and improve my savings.
I was ready to focus on my career and take some risks.
In part 2, I wrote about exploring consulting to earn extra income and expand my skillset. During that exploration period, I became deeply familiar with two companies.
The first company provided recreation services to children, looking to spin up a tech arm to rebuild their software. And the second company was a fintech start up with a payment and communication platform, branching out to work with larger NFPs.
Both companies had innovative, hardworking founders with an interesting vision for the future and a history of success. However, it was clear to me that I was a better “fit” for the fintech company – even compared to what I was doing at the Bank.
That fintech company was Pllenty, where I currently work!
I had access to inner workings of both companies through my personal network. And the more I learned about Pllenty, the more I felt this COULD be the place for me!
So, at a 1-1 with my contact at Pllenty, I expressed my interest in working with them “one day”. I didn’t know exactly when that “one day” would be. But I followed up regularly with my contact throughout the next months to keep my interest top of mind.
The more I learned about Pllenty and the payments, the more I liked what I was learning and wanted to learn more. For example, after having an in-depth conversation with my contact about the payments space, I joined a Fintech book club online and bought my first book on payments (Anatomy of the Swipe).
However, when I received the call from my Pllenty contact winter of 2022 for a potential job opportunity, I totally wasn’t ready!
At TD, I had an awesome salary, a fabulous boss, a leadership position in an interesting and career defining program rolling out Salesforce. While I wanted to take a career risk, I didn’t expect to cross that bridge for at least another 18 months!
I had been gathering intel on Pllenty for over three years, so I HAD to explore this opportunity now that it had presented itself.
I kicked off the exploration process with some real talk with my Pllenty contact. I asked probing questions about what was working and what was not working. I asked about the team and who they were. I asked about the history of the company and the vision for the future.
Then, I put myself forward for a conversation with the President & COO of Pllenty. He was an acquaintance and already a person I admired and respected. But in our 1-1 I was blown away by how he was able to walk me through the past, present and future of the company in a 45-minute conversation. For me, this was a sign of a leader who wanted to go somewhere, and I felt excited to be part of the journey.
After I felt “the feeling”, the rest was an exercise in satisfying the rational parts of me and identifying blind spots.
I had a solid career trajectory at TD but at Pllenty I had a tremendous chance to grow as a leader more immediately.
TD provided me with stability and predictability, but Pllenty will provide exposure to all parts of a business – from the early sales calls to discussions on infrastructure.
I would be more vulnerable at a start-up if things didn’t work-out, but I also had a chance to be participate in tremendous upsides if they did.
As part of the blind spot evaluation, I had an hour-long conversation with my smartest and most brutally honest friend with a tech background and whatever downsides they could come up with didn’t sound all that bad.
I am not privy to what the conversations were like on the Pllenty side. But both parties saw a fit, took a chance, and I was offered a job!
I gave my start date as April 18th to allow me 3 weeks of notice at TD, plus two weeks off to decompress.
That was now 3.5 months ago, and I haven’t looked back! It has been an intense ride so far and I enjoyed almost every moment of it.
Looking back, I can summarize my evaluation process (whether to stay at TD or join Pllenty) from three angles:
My medium-term financial goals such as buying real estate and a substantial emergency fund were all met before leaving the Bank. If I still had such financial goals, I may have tried deferring the move for 1 or 2 more years.
I also focused on adequate cash-flow vs total compensation to ensure we could maintain our current lifestyle (e.g., equity vs salary). Taking a big pay cut in exchange for more equity, for example, would not have worked for me.
Finally, I looked 5-10 years ahead and saw which would bring me more upsides. I felt that while steady ladder climbing at the bank would be great, I had a higher chance of being part of something more rewarding in the long term by joining Pllenty.
Pllenty offered more flexibility of working hours compared to the bank.
Most of my meetings at Pllenty are concentrated between the hours of 10am and 4pm, Tuesday to Thursday. So, by working a few hours on the weekend, I can significantly improve the flexibility of my days outside of those core hours.
I also influence the efficiency at Pllenty, as we are a small team. So I feel more confident that I can continually improve efficiency over time in ways impossible within a complex corporation.
Finally, the nature of a start-up offers tremendous opportunity for growth. Any problem that occurs in the company, we need to solve ourselves – there is no X department (looking at you TRMIS) we can do an intake with. Additionally, origin of every mistake is painfully obvious – so there is no where to hide either.
I find that I have learned something new literally every day since I started, and I have not scratched the surface of all there is to learn.
That’s it! I hope you enjoyed my three part journey from a Corporate lifer to a start-up “newb”.
Thanks so much for reading, please keep reaching out with your comments and questions.