I’ve been the founding sales hire in startups a bunch of times now.
The first time, I sold to the Defense and Police forces in India. This is where I cut my teeth, leading complex deals that took upto 4-6 quarters to close.
The second stint, albeit short, was selling a software solution in the micro-mobility space. Again, I learned a lot within a packed couple months.
My 3rd gig, which has just started, is possibly the most challenging yet.
Over the rest of this year, I need to:
- Hit my own revenue targets
- Support the wider team in hitting their number
- Build a Go-To-Market motion and a sales playbook
That’s why I’m writing this (hopefully) weekly series- where I journal what experiments I’m running on the way to reaching these goals, and sharing my learnings.
I read somewhere that plans aren’t important but planning is everything.
The aim is to think clearer through writing these, and hopefully get feedback from people who might have something to add.
so…. how do we start?
By becoming someone else.
I’m a believer of adopting a certain mindset in a certain phase of life.
And right now- I need to be Indiana Jones (this will make sense soon, I promise)
You see, in a startup, how to sell is not clear.
Sometimes, what to sell isn’t clear either.
To uncover ‘how to sell’, you need to be a detective and an archeologist.
To actually sell– you need to be a cowboy.
Which is why Indiana Jones is the perfect archetype.
Last week, I started interviewing the current team who has sold deals previously and asking them tons questions to understand:
- The buyers’ pain
- Why they couldn’t solve it before us
- What was the impact of the pain on their organisation
- How we solved that and generated impact
I’ve been doing this for clients we’ve landed in the past couple years- the challenge is that I’m building my own sales enablement as I go along.
I’ve been digging up the past (CRM, case studies etc) filtering through 99% of the information to retain the 1% that is gold-dust for building a Go-To-Market strategy.
I’ve basically monopolised my boss’s time all of last week just going through previous and current clients, understanding the context of those deals, sales cycles etc and building a rolodex of case studies, talk tracks and uncovering non-obvious ‘pain’ that we’ve solved for our clients previously.
This is a common challenge in startups- where a lot of the data one typically needs for sales enablement is just in the heads of people in the company- so, as a Founding Account Executive, you need to be a detective and archeologist to uncover the true picture that informs your next steps.
Once you’ve done that- you need to start selling.
That’s when you go into Cowboy mode.
That’s when you become Indiana Jones.
The strategy is to prioritise ruthlessly. Find the 80/20, build a basic plan and start executing.
Test hypotheses rapidly, iterate and move on till you know what works.
This need thinking in a contrarian fashion, asking ‘why’ when it comes to the status quo.
Hence the cowboy analogy- I’m not trying to force fit something here just because it sounds cool – okay well maybe I am, but hopefully you get the point.
I could spend weeks doing the archaeologist and detective work methodically- but I need to start building pipeline yesterday.
So this is what I did last week:
- Listing our previous clients and reaching out to them to see if we can re-initiate few opportunities
- Finding our best clients and case studies
- Finding lookalike accounts of clients listed at pt. 2
- I know our buyer persona well and have started building a list of ‘change agents’ who are new to their roles
- Looking for LinkedIn connections of our current clients in my overall list of target accounts (shoutout to Andrew Kobylarz for this tip)
As of Day 10 into my job- this is V1 of my Go-to-Market strategy, which I’ll only refine further as the weeks go along.
What’s coming up this week:
- I’ll interview the founders, and exec team in my company to get their inputs on my Go-To-Market
- I’ll start prospecting and outbounding to my book of business
Wish me luck!
PS: Read so far? I’d love to hear if you found this piece useful.
PPS: Work in sales? I’d really love to hear how you might adjust my Go-To-Market strategy.