Something happened this last week that made me the happiest man this side of Thames. It gave me the kind of feeling you get when you just know that the stars have aligned and things are finally in place (you ever get that lately?)
And no, this isn’t about a girl. This is about 4 middle manager and VP types that I’ll be meeting with over the next 15 days, and honestly… I am stoked.
This may seem like a very inconsequential thing, but it is in fact, very consequential, my friend. Allow me to tell you why it is so, before I tell you how I did it:
You see, I have a really ambitious sales target this year- one I’ve never hit and frankly…I don’t even know if it is in my capability to achieve it.
Back in March, I spent the first 30 days on this job agonising over how things could go wrong. I’d feel really anxious outside of work hours. Mostly, I was generating doomsday scenarios of how this startup sales role would blow up in my face. Like my last one did. But, a funny thing happened around day 30.
I realised that the only time I didn’t feel anxiety was when I was at work. When I was there, I was focused on execution, and the outside world didn’t matter. I also reminded myself that while I may not have done this before, it wasn’t rocket science either, and that I could figure it out.
Experiments I did to book meetings and their results so far
So…I got to it. The first thing I did was set a north star metric to track progress. Something I could control. I did a bit of sales maths to reverse engineer how many intro meetings I should be booking with new prospects to be able to hit my target.
That number was 4 meetings a week and for the past 3 months, that’s the number I’ve been chasing.
In this time, I’ve sent nearly 2000 cold emails, ~200 LinkedIn DMs, made ~100 cold calls and attended two networking events.
I realised cold emails are a long game and that I’ll have to continuously refine my messaging and list of people I reach out to before I hit message-market-timing fit. All in all, I haven’t booked a single meeting off of cold email, only had a few responses that wanted a look at the lead magnet I offered.
LinkedIn DMs are a more recent thing I’ve started doing in May- they generally have a higher response rate but I’m trying to refine my approach to not sound salesy and get them to engage even further by offering more info, insights etc without making asks at all.
Cold calls- are pretty decent but the number of people that go straight to voicemail (I do leave voicemails) makes me unsure if it’s worth it. I need a better strategy there I think.
Networking events are great- I generated 8 leads from a single event over 4 hours, and will be going to more this year.
However- all of the above are very much a work in progress. None of them helped me hit my target of 4 meetings/wk.
And then, finally, one experiment I did last week blew that number out of the water.
What finally worked
I studied our CRM. And it gave me the idea to start reaching out to a sizeable number of prospects we had engaged but never sold to since 2020 (logged as ‘closed-lost’ in the CRM)
I started looking at our past interactions logged in the CRM, looked them up on LinkedIn and spent 2 hours first thing every morning last week to send them customised emails.
Some of them- I made asks from my executive team to reach out. For everyone I emailed, I sent a LinkedIn connect to show I was a real person.
And guess what- I booked 4 meetings this week, and have a few others that should get booked next week!
I think I have enough juice from this list of closed lost accounts to last another few weeks so I’m going to be milking this strategy and hoping I can book as many meetings, create as many qualified opportunities as I can.
I figure that the best chance to hit my target is by engaging prospects that already know us. Starting cold opportunities is important, but at this stage of the year, that’s likely pipeline for next year (my sales cycle is pretty long).
So, I’m shifting focus to these accounts for the next 20-30 days while simultaneously trying to book meetings with some of the larger, high impact accounts for us.
Let’s see where things go.
If I succeed this year, it’ll be amazing. If I don’t I would have learned a lot. And that, I’ll continue sharing on this newsletter.
Have a great week ahead,
Shubhankar