Sales
Data
Account Executive
Pipeline

All hail the data nerd

10 mins

|
15.04.2025
woman

Written By Michael Whittaker,

Senior AE at Trumpet

There is one trait in sales I rank so highly, that I would consider it more important than being a stone cold cold caller, a certified hostage negotiator (sorry Chris), more valuable than running elite discoveries, or being the most all round charming salesperson anyone has ever met.

And you’re not going to like it.

The best salespeople I know are all nerds about the data.

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No, no, don’t leave! Bear with me -

In sales, for good or bad, we chose a career with a binary output. Come month, quarter, year end we are either at target or we’ve missed. And that feeling when that signed contract drops is chefs kiss. Equally, we’ve all felt that gut punch, stomach churning moment a deal falls through days or weeks before the end of quarter and we look at the pipeline to realise we no longer have the coverage.

We grieve, we bargain, we try and pull deals forward from next quarter, offering discounts and burning up great sales rigour in the process. Then we go through the old closed lost lists, praying someone is now miraculously ready to move forward, and finally all we have left to do is pray for a bluebird to drop in our lap.

All of these are shortcuts, attempts to cut corners, to bypass the typical sales cycle, because ultimately, that signed contract is not the result of today's work, it’s the graft and effort we put in over the last 2, 6, 12 months and if the contract doesn’t come in as expected, we can’t fix it today, we needed to have fixed it 2, 6, 12 months ago.


So, what stops us from building enough coverage ahead of time?

When presented with competing demands on our time each day, two factors play against us. Firstly we suffer from delay discounting (not that kind of discounting), the tendency to value immediate rewards more than future ones, so even though the pay check and the buzz are greater for a closed won contract it loses its value to us when we have to wait months for the pay off from the activities that drive it.

Secondly, we are all at the mercy of “The Whirlwind”. The Whirlwind is all the urgent activities necessary to sustain your business day to day. It’s the standing meetings, customer calls, emails, slacks, all high priority, all demanding we drop what we’re doing and give them our attention. If we aren’t careful we’ll spend all day in The Whirlwind. I’m sure we’ve all had those days where we get home exhausted. We know we’ve been busy, but we don’t necessarily know what we’ve accomplished. All we’ve done is battled The Whirlwind.

So how do we ensure we carve out enough time each day for the non urgent, high value, activities that will drive real revenue success in the future whilst still satisfying The Whirlwind?


The problem with company-wide activity targets


Companies’ regularly try to support reps in this. Every single one of us will have worked in a sales organisation with set activity metrics, calls to make, emails to send, meetings to book, that are tracked every week, so why don’t these always work?

Well, firstly, there’s two different types of metric. Lead and Lag. Lag metrics are the results of other behaviours and can not be influenced immediately. Revenue is one, but so is meetings booked, an activity metric standard. Tracking these is important, but it is effectively tracking a symptom not a primary indicator.

Then we have the lead indicators, the behaviours we can impact right this second, how many calls we make, how many new contacts we identify and add to sequences. These are the very first step in a long chain of events that lead to closed revenue. But is 50 calls enough or does it need to be 10?. What impact will 105 calls have over 95 in the long run?

This is my big gripe with metrics and goals based on analysis of the company’s global data sets; they feel impersonal and detached from my own success. I know making 100 cold calls is a good thing but I’m unclear on its inherent value, on a call by call basis, how it moves the needle against my overarching goal, closed won revenue.

If I don’t make enough calls today will I miss? If I make them up tomorrow surely that’s fine?

This makes sense when we consider one of the primary techniques psychologists use to reduce the impact of delay discounting; choice bundling 3.

When we are presented with a single, one off, choice between a long term greater reward and a short term smaller reward, we’re more likely to choose the smaller short term reward. Comparatively when we bundle multiple choices together that sequentially lead to a long term, greater reward, we are far more likely to consistently make the long term, greater reward, choice each time.

In application, when asked to make 100 calls each week by the business, this is an isolated decision and you’ll see greater instances of reps choosing to solve urgent, low reward tasks from the Whirlwind instead.

If we know 100 cold calls each week for the next 6 weeks, will deliver 3 meetings a week; that 2 in 3 of these meetings will lead to opportunities, and our average deal size is £50,000; then in 6 weeks time we’ll likely have £600,000 in new pipeline.

When broken down like this it’s far easier each week to make time for those calls.

Knowing our average sales cycle lengths, we can ensure we have enough pipeline, months ahead, so that on the day we lose that opportunity we have our pipeline already built to cover us.

It can never be an exact science, we can always keep refining our models, factoring for likely inbound leads, holiday in quarter, how cycle lengths vary in different verticals or segments. But it will always be more powerful than a company wide activity target, where the personal repercussions are less visible and we tend toward the short term, smaller rewards of checking off tasks from The Whirlwind.


The Path to Consistency


So why do I value this level of focus on data more so than those incredibly powerful sales skills I was so flippantly dismissing at the start of this article?

Each of those skills are vital across the sales cycle. If you’re a student of “Never Split the Difference” you will likely have a higher close rate than me, or perhaps you discount far less often and to a lesser degree.

If you’ve had the pleasure of training with Benjamin Dennehey, you might book a meeting every second or third connection in a power dialling hour; whilst I’m only seeing success on my ninth or tenth call.

But if I understand my data correctly, I’ve already accounted for these variables, and my top of funnel activity metrics are higher to accommodate. My path to 100% is my own. In fact if you understand your conversion points you can spend time upskilling and refining your implementation of MEDDICC, or your 10 minute product demo, in order to increase your win rates, or how many meetings convert to opportunities. These will inevitably reduce the top of funnel activities you need to hit the target next quarter or the quarter after.

Without fail, I’ve seen average sellers consistently hit target quarter over quarter, provided they get obsessive over their data. Sure the most natural, or the most talented sellers will be more likely to have a history making quarter but in the same vein if they’ve dropped the ball on input for a couple of weeks or months during that time, they’re also more prone to barren spells and missed quarters they put down to bad luck.

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In fact when I interviewed with Rory (trumpet 🎺 Co-founder and CEO) at the end of last year, it wasn’t proof of my largest ever quarter I was sharing with him.

It was my spreadsheets. The ones I’ve used for 8 years to not only calculate on a day by day basis how many new contacts and accounts I need to add to my sequences, but how they in turn tell me how I’m pacing next quarter, and the adjustments I need to make to stop gaps appearing 2 months ahead of time.

I firmly believe the most coveted ability in sales is not the mammoth quarters or the flash logos, it’s the consistency with which you come back month on month, quarter on quarter, and deliver as close as possible to quota. If you reliably hit 3 out of 4 quarters a year, and when you do miss you miss by 4-5% not 20-40% you’ll quickly become an indispensable asset.

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If you want to become a consistent, top-performing, data nerd, there are two places I’d recommend starting:

  1. Read the 4 disciplines of execution. This is where I first learned about The Whirlwind, and understood the applications of lead indicator tracking. I still revisit it every couple of years and it is a fantastic resource for creating accountability over your business.
  2. Deep dive the data. For some people this can be daunting, there’s lots to factor in, and learning excel formulas can be many rep’s idea of hell. If a template to start from would be of value feel free to connect with me on LinkedIn and I would be happy to share mine.



1. Delay discounting of different outcomes: Review and theory: Odum. A, Becker. R, Haynes. J, Galizio. A, Frye. C, Downey. H, Friedel. J, Perez. D. M. 2020

2. The 4 Disciplines of Execution: McChesney. C, Covey. S, Huling. J, 2012

3. A brief review of choice bundling: A strategy to reduce delay discounting and bolster self-control: Ashe. M, Wilson. S. 2020

Thank you for reading

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