A SaaSBoomi Fellow’s perspective working on the Annual ‘24
In a nutshell, program managing SaaSBoomi Annual ‘24 gave me a renewed, possibly lifelong, faith in surrounding myself with people incredibly talented than myself.
As a SaaSBoomi Fellow, and on my own parallel journey of building, I’ve been getting a peek into how founders shoulder massive responsibilities, think, and execute in their daily lives.
On execution though, to be honest, these founders have become incredible at the art of delegation and keeping the house in order, more than execution.
That said, when situations demanded getting hands dirty, execution for them was like riding a bicycle after years – you pretty much don’t forget the basics.
Here’s how all of this went.
Curiosity
The Program team was responsible for all things agenda. Every single thing you saw as part of sessions was our doing. I know you didn’t like everything, and that’s expected. Some of you gave us incredibly helpful feedback – having too many parallel sessions causing analysis paralysis, session audio cross-wires (IYKYK), need more juicy (read “startle the founder back to reality”) content. Point noted and thank you for sharing!
The Program Team – Avinash Raghava, Ashwin Ramasamy, Krish Subramanian, Shruti Kapoor, Varun Shoor, Prasanna Krishnamoorthy, Sparsh Gupta, Anand Jain, Raviteja Dodda, Vivek Khandelwal, Sridhar Ranganathan, Dhruvil Sanghvi, and several others who attended whenever we requested them to.
We met every Saturday from 10:00 am to 12:30 pm which almost never ended on time, and often went to 3 hours at a stretch. No one complained, except when we asked Krish, who was already joining us at his 6 am, to come earlier ?
For the first couple of weeks, I bombarded them with questions, and Googled/ChatGPT’ed incessantly as the meeting went on, to figure out the company, founder names, concepts, and principles of building a business, flying around the Zoom room.
And I took notes. To be precise I have 15465 words of notes, that’s almost 4 short stories worth. Sure, some of it I didn’t go back to (you gotta admit, no one really does ?), however, a meeting with over 10 incredibly accomplished founders meant that they are throwing names, topics, statistics, frameworks of education, top-notch parent jokes, literally every minute of the 90-180 minute meeting.
I started with curiosity.
I started sharing my perspectives.
Even if I was told that would not work.
Over, and over again, until I started adding value.
A Founder community enabled by founders
The beauty of SaaSBoomi in general is watching these experienced founders enter a different world. A world they want to create, the one they did not have.
You may not believe me but during several meetings, I took notes while having the chills hearing how far and how hard they were willing to work to bring something truly valuable to the community.
Founders cold-emailed potential speakers, asked for introductions from people in their network they perhaps haven’t spoken to in a while (it can be a bit awkward but they did not care), in some situations they reached out to someone so many times that the speakers finally gave up and gave in!
Delegation reverse uno
Technically, this group was reporting to Ashwin and I. Wild! But 10+ smart, experienced, kind people in a meeting means that they have ?? SO ?? MANY ?? GREAT ?? IDEAS ?? and simply not enough time.
I had to constantly find new ways to keep us on track
→ Share my screen with the Program Agenda Draft sheet and talked through each section
→ Politely interrupt someone mid-sentence to say we’re digressing
→ Create and populate sheets on the fly as we started a new dimension of planning a session
→ Share agenda before every call
→ Make real-time edits to the agenda to “seal the plan”
→ Send an elaborate email with action items for each person (at its peak, there were over 30 action items among 10-15 founders)
→ Email, WhatsApp, Phone Calls, get Ashwin to send an email, CC Avinash on emails
…and several other methods that I tried once and dumped immediately
But this is where I learned most about how effectively work with extremely busy individuals. Trust me, they would LOVE to give you all the mindspace in the world, but they physically and mentally cannot. There have been times when I felt frustrated because I wasn’t able to get someone to give us updates on their action items.
However, this is where I leaned heavily on my Support experience, to empathize with my users, in this the volunteers, who are either running or until recently ran multi-million $ companies.
And empathizing also means that sometimes we have to be tough, but never without kindness.
No longer a fly on the wall but an active contributor
Past me would have wished to be a fly on the wall while these conversations happened. Let me preface this by saying that this is not some weird flex or power play or ego, but founders who already work with some of the best people in the industry pay attention only if someone’s adding value.
When one has a wealth of experience, it’s painful to sit through monologues or low-effort questions.
You don’t have to be a founder to know this. We’ve been those people and have been told to make concerted efforts, and/or have been in situations to enable someone to contribute more meaningfully.
Becoming (sort of) indispensable
Everytime I worked in a Support team, I would dream of doing proactive support. When a user runs into a known error, how cool would it be to send them a proactive email explaining the error and how to fix it!
Applying that very principle here, I raised my hand up for almost every single task that came to me or Ashwin. I always took a shot at V1, asked for feedback to improve.
This was a deliberate effort to immerse myself into the team as deeply as possible, setting a high bar of expectation, because several parallel tasks means higher chances of dropping the ball.
This lead me to uncover higher thresholds of what is possible to achieve.
Finally, when push came to shove, tasks fell on my plate. While it was overwhelming at times, I knew that my mission to execute high quality work was achieved.
When others took a chance with me, it was only fair that I took that chance too.
Working with Ashwin, my mentor
This was a special one. All thanks to Avinash, I met Ashwin Ramasamy a few months prior to having any indications of working on programming the Annual. He was always a text away and I got a lot of my valuable early startup advice from him. He built and sold two SaaS products – ContractIQ and PipeCandy, an embodiment of humble yet unabashedly smart.
Ashwin ran the Programming for Annual in 2023 and I had absolutely NO idea what I was getting myself into. ?
Thankfully, I didn’t have to do all the heavy-lifting myself. We had 1:1’s almost every day, barring holidays and vacations, where I gave updates, brought up concerns, deliberated on red zones, and he would share updates on all his action items.
I kept a to-do list only from these 1:1’s which came up to 131, not including the dozens of ad-hoc tasks.
We were on the same page 99% of the time because I documented everything, leaving almost nothing up to memory, and Ashwin was incredibly quick at finding workarounds and “how to handle a situation like this” sitch (cause I can’t say situation twice in one sentence, and now I’ve said it thrice).
An ever-evolving community
I’m giving you these behind-the-scenes perspectives because some of us can tend to jump straight to harsh criticisms. While criticisms are literally what helps us deliver better and truer value to the community, all of our volunteers pour their heart & soul into this because…
…there’s no one who knows your journey as a founder better than those who have lived or continue to live in those shoes.
This was a long one, but I could have written at least 4 more pages about the incredible ride I had playing a little part in possibly one of the best SaaS conferences in the world!
If you attended SaaSBoomi Annual ‘24 and want to share feedback with us, please fill out this form!
Here’s an overview of the Annual ’24 – a snapshot of the numbers, the feedback, and the impact:
