How My Sales Playbook is Evolving

I wrote my first update about a month ago on how I'm building the Go-To-Market motion at my latest role- and here's what's happening now.

Over the last 2 weeks, I’ve started ramping up activity on outbounding to my book of business -which as of now consists of past clients we’ve shortlisted for re-engagement.

I don’t know if that’s the right strategy though- and I want to diversify my bets.

You see, my main challenge is top of funnel right now, i.e: booking meetings- and I can't afford to put all my eggs in one basket (or a single strategy).

Last week, I started brainstorming ways to find low hanging fruit - and tried the following:

1. Made a list of 10 past clients that engaged heavily with us and reached out to them. Result- nothing so far.
2. Made a list of ex-Bainees (I’m an alumni) that fit the description of our Ideal Client Profile- and emailed them all. Result- booked one meeting.
3. Reached out to past employees of clients that have moved to new companies. Result- TBD. Need to see it out this week and next.

What I’m doing on the execution side of things this week

To be fair, I’ve only really been able to focus on pipeline building in the last week- so I was happy to get started and follow a methodology of email + LinkedIN + cold calling in my outreach to prospects.

I want to ramp up my activity this week. I want at least 2× 1hour blocks for outbounding to prospects daily - and believe cold calling should be my focus to complement the email and LinkedIn outreach.

This week is about gathering data and sending 20-30 emails/daily and similar amount of cold calls.

I’ll review progress at the end of the week.

What I’m doing on the strategy side this week

1. CRM Insights.

Looking at our CRM, we have a few really strong clients and one strategy I want to follow this week is build a list of lookalikes of that client- and go after those accounts.

I already have a rough list ready. I’ll refine it over the course of the week, tier the accounts and plan to focus 80% of my time on the top 15-20 accounts- the rest going into an automated sequence.

2. Sales Tech Stack

I realised that we have thousands of data points in our CRM that we’re not leveraging- from past clients that are still active in the Industry.

Also- we have a huge company. 70 odd employees, few investors- why shouldn’t I be leveraging everyone’s networks?

So, this week, I’m drafting a memo for my boss to get sign off on us using Sales Nav Advanced to integrate with our CRM.

That should unlock the ability for us to solve for both the above blockers.

It’s really easy to get caught up in the execution (which is why I haven’t actioned this already).

That’s why I like writing this newsletter.

It forces me to think strategically- to figure out what the highest levers are for me to pull in order to get results I want.

I see the Sales Nav-CRM integration as the highest RoI thing I might do this week- so this will be probably the first thing I work on Monday am (in a few hours).

That’s all for today- see you in a week’s time.

PS: The meeting I booked with my Bain campaign? It’s in a few hours- wish me luck!

Oh and by the way- a podcast recommendation if you’re interested in early stage startup sales, or going 0→1 in any B2B sales motion is this one on Harry Stebbings ’ 20 VC