One of the major decisions I made last year to leave my previous job at a great company only after a few months to join Spot.io
Spot.io is an israeli tech startup which has a cloud infrastructure optimization and automation SaaS platform. We were recently acquired by a bigger tech company from the USA.
Making this move to leave a great company like Workato after only 10 months was a difficult one for me and what I would describe as a calculated risk.
When it comes to taking risks and making important decisions, I will write an entire thesis to make sure my thinking is thorough and clear. Ultimately, our quality of life is also determined by the quality of our decisions as well.
This doesn’t apply to my work but also in my personal life.
Since I’ve completed an FY at Spot.io, I decided to reflect and also share my thesis on why I joined this company and took up this role last year.
For context: I sell software for a living and more than 50% of my income depends on my performance which is ultimately also influenced by factors outside my control like macroeconomic conditions.
The situation in Jan 2022
One year ago, in early 2022, I chanced upon a deck by a growth stage founder.
He shared that “There has been > 50% compression in public SaaS multiples since Nov 2021. This will persist so long as inflation and interest rates remain high. It is prudent for the company to have a longer horizon for the use of our funds.”
At the same time, I was asked to share about inflation on CNA (Video above).
This got me interested in the topic of inflation, rising interest rates and the tech sector. I studied more about this topic and felt like a drop in valuations and massive cost cutting was coming.
Logically, this made sense. However, at that time, I was not super sure. This is because reality on the ground was different in February 2022.
Startup leaders in Southeast Asia were telling me that their focus was all on growth and not reducing costs.
I was also still receiving multiple recruiter messages on a weekly basis and it did not seem like people were focusing on saving money at all.
However, during this time, I also got to know a founder who raised a $xxx million growth stage round. I told him about the differences I saw between what I analysed versus what I am hearing from other leaders I was speaking to. Despite not having to worry about runway then, he validated my hypothesis.
I kept my eyes on the news in USA, stayed on top of it and slowly observed more startups doing layoffs there.
At the same time, one of the recruiters that reached out hiring for Spot.io
What were the risks of leaving?
There were a lot of reasons against taking the offer which made this a risky one
Firstly, I did not feel comfortable with leaving a job in less than one year. I was worried to be seen as a quitter and job hopper. I had a reliable track record in staying in companies for a long time. In my previous two roles before Workato, I was there for almost 3 years and got promoted in both stints. Throughout my life, I think I have stayed longer in jobs and relationships than I should.
Furthermore, I had a good team. I felt excited to come to work every day. I love working with my SDRs and superstar solution engineer. We also hired a super experienced GTM leader and a new sales director who I felt I respected a lot and could learn from.
One year has passed since and there is nothing I miss more than working with a bunch of young, super driven, hungry and innovative young people. We went through a lot of crap together and built a strong bond.
There were also several risks about joining Spot.io for me:
- Spot.io was not known in the market. We were not on any Cloud100 list, G2 Crowd or Gartner MQ. There is still no local marketing in APAC.
- The parent company was already publicly listed: This means no potential for life-changing money in the form of stock options, only ESPP. An ESPP only allows you to purchase company stock at a discounted price at 15% off the fair market value.
- Joining in May means I would have to give up my Workato stocks. While the sign on bonus offered was greater than the stocks value, I felt that the stocks had a bigger chance of appreciation in the long run.
- I never heard of the parent company in my life until 2022. I was worried about being a cultural fit in this older company given that I have been in fast paced high growth cloud companies my entire life.
Why I took this risk
1. In 2022, this is an opportunity of a lifetime
I am Taoist. The core philosophy of Taoism is to live in harmony with the world.
A key principle we believe in is effortless action (無為). To put simply, this means we act in harmony with the way of what is happening externally; ride the wave of change; move together with it and not against it.
Some practical applications of this in our daily lives is like joining a high growth company and rising along with it; choosing to date guys who are initiating and excited to meet you or following a great leader who will remove obstacles for you.
If tech winter was here, I wanted to “借东风”/”borrow the east wind”, to turn a crisis into an opportunity.
This was an opportunity of my life time to:
🚀 Help as many people with cost savings and also to find jobs so I can to build strong lasting relationships that will compound over time
🚀 Make as much money from work by leveraging the market conditions that was in my favour (Selling cost optimization platform when everyone is caring about cost savings)
🚀 Deploy the capital I’ve earned to buy shares of great businesses at low valuations
While I did not have much clarity into how the organization was run back then, I knew that in the short run, major market forces will always be more powerful than the quality of leadership, strategy and execution.
I knew that this opportunity won’t wait for me and I only had one year to maximize every dollar that I could from it.
I worked my ass off to make that possible and basically had no life at all besides swimming and work for my first few months at Spot.io to make that happen.
The world will do most of the work for you, provided you cooperate with it by identifying how it really works and aligning with those realities. If we do not let the world teach us, it teaches us a lesson.Joseph Tussman
2. Build a wider set of skills
When it comes to my career, I want to be a Generalized Specialist.
What is the difference between a Generalized Specialist and a Generalist?
A generalized specialist has a core competency which they know a lot about. At the same time, they are always learning and have a working knowledge of other areas.
While a generalist has roughly the same knowledge of multiple areas, a generalising specialist has one deep area of expertise and a few shallow ones.
For me, I’ve chosen SaaS sales as a specialisation. Specialising in this has given me a lot of options, mobility and bargaining power.
However, if I want to lead teams in the future, one area of expertise is not sufficient. So, it was also important for me to get exposed to areas outside of deal making.
The opportunity at Spot.io gave me a chance to develop more generalist skills which I picked up over the past year:
- Partnerships: Engaging VCs and Growth Equity firms to build our pipeline of opportunities
- Organize events
- Alliances: working with cloud providers like AWS
3. A good manager
A 100% non-negotiable factor for me to stay in a role or accept a role is the quality of the person I’d be reporting to.
A good manager in a bad company can shield you from a lot of crap.
A good manager in a good company can help push you upwards for good opportunities.
As a guiding principle, I want to play long term games with long term people who I can help and work with for years. The idea is really for both parties to earn compound interest from the relationship we have. I have done so for my past three hiring managers at Salesforce, Workato and Spot.io
I like working with my manager (who recently left) because I felt he was action oriented and shielded us from drama.
Two interview questions I like to ask to evaluate a manager is “Why do you want to lead a team?” and “How do you see your role as a manager?”
I asked my then manager this question and watched his expressions closely to determine his sincerity in his answers.
He shared that he had been in situations when others do not perform and suffered a lot when there was no accountability and ownership. He did not want others to experience the same.
He also felt that the role of a manager is about removing obstacles, leverage and support.
These answers gave me a lot of conviction to move forward.
It’s been 12 months with several key achievements:
- Grew Spot.io‘s revenue in Southeast Asia by 50.5% despite not having any SDR or local marketing
- Contributed 56.8% of total revenue in entire APAC in FY 2023
- Q3 FY 2023 Attainment: 190.5%, First place in International Team (despite target increasing by more than 60% from Q2)
- Q2 FY 2023 Attainment: 192%, Top 2 in the International Team
- Won 16 new logos in 11 months of which, two were the largest deal in Indonesia and Malaysia in Spot’s history
If I evaluate this based on financial returns; accomplishments; network I’ve built; skills I’ve learned and relationship with my hiring manager, I feel that taking up this role is one of the great decisions I’ve made.
The world is constantly changing. When we write thesis about our decisions in life, it is unwise to never look at them again. When facts change and circumstances change, we have to reflect and adjust too.
I would encourage everyone to think about why you took a job and whether you can reap the same benefits ahead. Some questions you can ask yourself:
⭐ 1. Non-negotiable: How is my direct manager like? Can he remove obstacles for the team? Do I trust and respect him?
⭐ 2. What am I optimizing for at this point in my life? For me, it is growth.
⭐ 3. How is the company doing? In high growth companies, your career will soar as the companies grow. In slow growth companies with a lot of fat, you carry the company and suffer from the mistakes the people on top make
⭐ 4. Is there money still to be made in the long term? This is based on various factors including product innovations; competitors; the quality of leaders and supporting team they will bring onboard
⭐ 5. What are your career goals? Does staying here bring you there? If not, where?
The answers to these questions will tell you if you should stay put or part ways.