Closing Time

A New Way to Map Sales Activities to Desired Outcomes: The Sales Success Calculator

Salespeople often operate like independent contractors in their organizations. They have their own book of business, are responsible for managing their own time, and track their own progress towards goals.

As a seller: you know when your pipeline is healthy and when it’s anemic… but have you ever quantified your personal efforts that drive your pipe?

In this episode of Closing Time, Dave talks with Luigi Prestinenzi about his Sales Success Calculator and why it should be a part of any rep’s toolbox.

Luigi’s not just presenting a calculator, he’s sharing a framework that encourages sales professionals to use their time wisely, focusing on tasks that truly lead to desired outcomes.

It emphasizes the importance of efficiency and effectiveness in managing one’s time, as every salesperson faces the same constraint: 24 hours in a day. The goal is to make the most of those hours with activities to drive success. 

Watch the video:
Key Moments:
The Sales Success Calculator & What Activities to Measure

Sales reps have lofty goals to hit. Monthly and quarterly revenue targets, new customer acquisition, retention and renewal, upsell and cross-sell… the list goes on and on. And it’s easy to lose motivation when it feels like you’re climbing a never-ending hill.

That’s why Luigi presents a new frame of thinking – rather than fixating on the outcomes (e.g. quota), he suggests reps focus on and measure their individual activity metrics that result in those outcomes (e.g. conversations, meetings, etc.).

The Sales Success Calculator enables reps to be proactive in their quota attainment by pinpointing and prioritizing the activities necessary for success. We’re no longer obsessing over final outcomes, whether attainable or unattainable. Instead, we’re strategizing on what is in our control – the day-to-day activities that will get us there.

The four primary activities Luigi measures are: conversations with prospects, the number of meetings held, opportunities generated, and proposals sent. 

Luigi also acknowledges that while consistent activity doesn’t always guarantee immediate results, it helps identify potential bottlenecks in the sales process. This, in turn, guides skill development and highlights areas that may need improvement.

For instance, if outreach efforts don’t yield appointments, it prompts a reevaluation of messaging strategies. If initial meetings don’t progress as expected, it signals the need for better questioning or positioning at the start of conversations.

The De-Risk Multiplier & Why it Matters

The De-Risk Multiplier

Luigi’s Sales Success Calculator incorporates a crucial concept he calls the “de-risking multiplier.” This concept is rooted in Luigi’s personal experience:

Back in 2010-2011, Luigi faced a challenging situation when his entire sales pipeline collapsed just before Christmas. Deals were falling through, and he contemplated leaving the sales profession. However, during the Christmas break, he had an epiphany.

He realized that the root cause of his predicament was a lack of sufficient pipeline. Instead of immediately seeking a new job, Luigi decided to invest in building a stronger pipeline. He became relentless in his prospecting efforts and created a pipeline that was significantly larger than his target, approximately five to six times larger.

This strategic move allowed him to de-risk his sales efforts. He no longer had to stress when a deal fell through because he had other opportunities waiting in the pipeline. It also gave him the freedom to give prospects the time they needed to make decisions without resorting to desperate tactics.

Luigi’s takeaway from this experience was the importance of having ample pipeline coverage. It became a game-changer in his career, leading to remarkable success. He realized that having a solid pipeline, with three to five times the coverage of his targets, made a significant difference in the quality of his sales efforts.

Won't Hit Quota? Here's What to do When Your Desired Outcomes are Unattainable

When sales reps find themselves in a situation where their desired outcomes seem unattainable due to challenging activity numbers, there are strategies they can employ to navigate this scenario effectively.

Firstly, it’s essential to recognize that there are factors beyond their control, such as sales cycle length or statistical challenges. Instead of fixating on unattainable final numbers, they should shift their focus to what they can achieve within the given time frame.

Rather than solely aiming to close a specific number of deals, they can concentrate on generating a certain amount of pipeline or creating a certain number of opportunities. It’s about setting achievable milestones that contribute to the larger goal.

Another crucial aspect is managing up, which involves open and constructive communication with their manager. Sales reps can use data and tools like Luigi’s Sales Success Calculator to have informed discussions with their leaders.

By presenting a well-thought-out plan that outlines what they can control and achieve in the upcoming period, even if it falls short of the ultimate quota, reps can demonstrate their commitment and proactive approach. This not only instills confidence in their manager but also ensures both parties are aligned on realistic expectations.

Measuring Sales Rep's Success & Overcoming Time Constraints

While working with a major telecommunications company in Australia, an intriguing issue arose regarding their sales metrics and ramp time. Luigi recognized that they had an extended sales cycle spanning about 12 months, yet their probation period for new reps concluded after just three months, with performance plans kicking in at six months. This misalignment essentially set their salespeople up for failure, as there were no clear success metrics beyond closing deals.

This situation highlights fundamental problems—short probation periods and a lack of clarity on what success should look like within the first nine months. It’s crucial for reps, especially those entering new roles, to ask pertinent questions about lead times and sales cycles. They should seek to understand what constitutes success in the short term and what metrics they must achieve to demonstrate progress.

The key lesson here is that focusing solely on final results can be counterproductive. Success should be viewed through the lens of controllable activities, not just outcomes. An effective salesperson needs to align their efforts with tasks that drive revenue and move them closer to their goals.

One common challenge arising from this framework is the perception of not having enough time for critical activities like prospecting. This often signals a red flag. Reps need to recognize that, in many cases, pipeline coverage is a KPI, and they must allocate time accordingly. It’s about making deliberate choices and prioritizing high-payoff activities that contribute to achieving their sales targets.



To learn more about Luigi’s calculator for B2B salespeople, visit Growth Forum’s website or message Luigi directly on LinkedIn


How are you quantifying your personal efforts that drive your pipeline?
We’re talking about the sales success calculator in this episode of Closing Time.
Hi, I’m Dave Osborne,
Chief Sales Officer at Insightly.
Thanks for tuning in to Closing Time, the show for go-to-market leaders.
I’m joined today by Luigi Prestinenzi,
sales coach, trainer and host of the Skalable Growth Podcast.
Welcome, Luigi.
Hey, Dave, thanks for having me on.
So Luigi, we’ve got about 70
plus people in our sales organization here at Insightly,
and keeping everyone motivated and moving forward is a constant challenge.
I’m sure a lot of CROs are dealing with that.
I saw your sales success calculator and it instantly resonated with me.
And I was curious to get a little more context.
What was the impetus behind you creating it?
I created it because I, in every sales role that I’ve ever worked in
and I’ve worked across both B2B and B2C, you know, channels,
I always,
before I started, spent time really understanding, well,
what are the activity metrics that I need to focus on
that’s going to lead me to the result.
I learned, early in my career, and when I say early,
it took me a couple of years to learn it.
But I learned that
focusing on the result is actually the wrong area of focus
when it comes to selling, because I can’t control the result, right?
I can’t control if I hit that number.
But what I can control are the activities
and the things that lead me to hitting that number.
So I designed the calculator with a whole bunch of, I got other calculators
as well that I’ve designed, that allow me to kind of break down
and know exactly what activities. I need to be doing.
That’s going to give me a better chance of hitting success.
There’s a caveat to it, right?
Because sometimes even if you do the activity, sometimes
you don’t get the result.
But at least then I can focus on
or you can focus on areas that might be bottlenecking.
And then that will give you an indication of what are the skill development areas
that you then need to focus on. Right.
So if I’m running a lot of outreach but not getting the appointment,
maybe my messaging framework needs to change.
If I’m getting that appointment, but it’s not progressing
from initial meeting to demo or discovery or qualified opp,
then maybe I’m not asking the right questions
or I’m not setting the right point of view at the start of the call.
So it just allows me to sort of assess where do I need to improve
in the sales process.
That makes sense.
So in a way, you’re instrumenting the sales cycle, right?
Like, what are the right inputs that are going to result in the outputs?
You know,
obviously revenue being one of them, but what are the right inputs
that are going to get the outputs that we’re predictably looking to drive?
I think it’s important, like especially if you’re selling in B2B sales,
it’s important to note that there are a couple of key milestones
that are going to occur during the sales process.
And one of the first key milestones is you need to be having conversations
with your prospects.
I think it’s important to, you know, let’s get the basics out the way.
So you’ve done your ICP, or your ideal customer profile,
you’ve got your persona mapped out.
So that should really help you when you’re building lists to have a
much tighter conversation with the right type of people.
But conversations is an
important metric or an important activity to
to measure. Making sure you’re having the right amount of conversations
that are going to turn eventually into some form of meeting.
You need to have a meeting, there needs to be a commitment
from the other side that they’re going to share
some information about their business, about their problem,
about the outcomes they’re seeking to achieve.
So that’s a pretty, pretty important step in the process, right?
Conversation leads to a meeting.
The meeting, you know, one would call it a discovery meeting,
but that just kind of validates that, yes, this is a problem that I’m having.
Yes, this is something that we should be progressing.
So that’s a key activity that we need to be measuring.
The next one is essentially around the opportunity, right?
Actually building out the business case for change, having something concrete
where the business actually says, you know what this does,
it’s now starting to make sense for us to look at investing this sort of money
into what you sell. Right.
So that’s you know, having an opportunity.. And then you propose something
against that opportunity that you’ve created.
So they’re kind of the key metrics that I always look to measure:
conversations, meetings, proposals.
Got it. That makes sense. So
one of the
one of the factors that you look at, you call it the de-risking multiplier.
Can you talk us through a little bit more about what
what that is referring to and what that manages?
Yeah, again, another story of experience.
I remember back in, it was probably 2011,
2010, 2011,
I had my pipeline just before Christmas.
The whole pipeline completely crashed.
I had deal after deal just fall over.
And I remember going into the Christmas break feeling really flat.
It was probably the first time in my career
I was really questioning, you know, is this a job?
I mean, I jumped on some job boards.
I started looking for another job.
I thought, you know what,
maybe, maybe the house of cards has completely fallen over.
Maybe my luck has run out.
You know,. I was having a number of great years
and I thought maybe this is it.
I’ve finally
realized that I’m not good for sales, and I started looking for a role.
But then over that Christmas period,. I realized something, I realized that
I just didn’t have enough pipeline.
And that was one of the issues that was affecting where I was at at the moment.
So I made a decision.
I said, look, before I go look for another job,
I need to go and see if I can sell myself out of this.
I need to just create more pipeline
As it turned out,. I had the best year ever and I ended up
winning world sales leader of the year for the company that I was working for,
and I rewrote the record books like 40 year record.
And that was because
I just I became relentless in how I prospected.
I also built a really good sized pipeline.
I think at the time. I might have had five times,
five or six times actually
the value of my pipeline, of my targeting in pipeline.
And that’s when I realized the importance of having enough coverage
so that if a deal did fall over,
I didn’t have to stress out because I had others sitting behind it.
And it also allowed me to give opportunities
the time that they needed to get to a point of decision,
because I think a lot of, if you think about some of the behaviors
and negative behaviors that some sales people exhibit,
it’s not because they’re bad people.
It’s because
they might not have enough opportunities and they’re trying to cut corners
and push people to a decision that aren’t ready to be to be pushed to that point.
And that’s because they’re desperate because they don’t have enough pipeline.
So, again, that’s something
that I learned and I had like a stellar couple of years after that.
And it completely changed my career.
So I learned early on, earlier sort of halfway through my career at the time.
But I learned that if I want to exhibit the right behaviors,
if I want to give opportunities
the time that they need to arrive at a point of decision and get consensus
and get, because I was selling enterprise,. I was selling large deals,
I needed to make sure. I had enough pipeline
so that my results weren’t dictating to me
what I needed to do with my prospects.
And that’s why. I was just always prospecting.
Pipeline will either make your life a living hell or life is good, right?
When life is real,
when you have a solid pipeline, like you said, 3x, 5x coverage,
life’s good.
You’re not making desperate decisions.
But when you’re pipeline’s bad, man, it’s stressful.
You know, coming back to the different inputs right.
Or the different variables or activity numbers
that are resulting from these calculations, right?
So let’s say activity numbers
and maybe it’s a new rep or underperforming rep.
Let’s say the activity numbers that they need to get to are unattainable.
Yeah, right.
Due to statistics or whatever.
Like what levers can a sales rep pull to work through that
and come out the other end
relatively unscathed.
Yeah, that’s a really good question.. And you know what?
This is an interesting one because I often get inquiries
or get calls from sellers that are saying, hey, I’ve just been put on a pip.
This is where I’m at.
I’m really struggling and they actually say, Hey, I checked out your calculator.
But because of the time to convert a deal, the sales cycle,
it looks like I’m not even going to hit that number in the period that I need to.
What do I do?
I bring it back to going back a step and saying, hang on a second,
we can’t control that number. Right.
But what is it that we can achieve in that period of time?
Maybe it’s not closing x deals.
Maybe it’s, I can actually create a certain amount of pipeline.
I can create a certain amount of opportunities.
And this is where I’d encourage a lot of salespeople that if they are
in that position, this is where they need to manage up.
This is where having this data and having this type of calculator
will help them with their conversations with their manager.
Because think about it, you as a as a chief sales officer, David,
if you have one of your team members that might not be performing,
but they come back to you and say, hey, understand I’m not performing.
Understand I’m not hitting my number, but. I’ve just gone through, I’ve done a sales
plan, and over the next 90 days, this is what I believe
I can create in pipeline
which might not my number, but at least it’ll give me the next three to six months
a better chance of hitting the number.. Then you as the leader,
you’ve got a lot more confidence in the rep.
Yeah, because they’ve got a plan, right?
And as we know, if like, the planning is critical, for me,
if you fail to plan, you’re basically planning to fail, right?
I mean, that’s a
great saying that we’ve heard
over the years, but that’s what I’d be doing if I was a rep.
If I was in a situation, needed to hit a number again,
I’d bring it back to what are the things that I can control in that period of time?
Because the worst thing that you can do is focus on the things
that you can’t control because this is where it creates stress.
And then you start to procrastinate.
I’m sure you’ve been there in the past in your career, right?
When you’re looking at it, you’re thinking,
you know what, this is getting too hard now.
What do I do? I might not do anything.
I stall, and then eventually just things completely fall over, right?
But that would be my biggest piece of advice
is just to go back a step,
think about what are the controllables, what can I control in this period of time?
And then if they are in a position with their manager, start to manage up,
like your ability to manage up is crucial in sales.
Luigi, that’s great feedback and I think it’s something
that, you know, reps especially maybe less experienced
or more junior reps struggle with is the concept of managing up. Yep.
Like obviously you have a manager or a leader
who’s trying to give you guidance and direction on how to best hit quotas.
But I mean I think with any relationship there’s going to be give and take, right?
So approaching that from,
you know, obviously hitting quota can be sometimes a really
a big hill to climb, but trying to break it down into
more compartmentalized wins and then kind of renegotiating kind of
what does success look like
as we’re trying to get ourselves there?
That’s a pretty interesting concept that you outlined there.
And it’s interesting, right, because I’m working with a large telco in Australia
and we were reviewing some of the metrics with the
with their sort of the key leadership team.
And what was interesting ramp time is like 12 months. They sell a
they sell a product, long lead, like long sales cycle
and they have a ramp time of it’s
usually nine to 12 months
but their probation period finished after three months.
And then a lot of them would be on performance plans after six months.
So they were basically setting their reps up to fail.
Instead of saying and they didn’t have any other metrics
that kind of decided, are they on the path to success?
So there’s a couple of fundamental issues there, right?
Like the probation period is probably too short,
and again they didn’t build out
what do they need to be doing in the first nine months,
that would mean, you know what, they’re on track for success.
And you’re absolutely right with that, David.
Like this is again why any rep if they’re taking a new role, for example,
because there’s a lot of change at the moment, especially in the tech sector.
These are some questions to be asking, right?
What’s the lead time?
What is the sales cycle?
If it is longer than my period of probation,
what does success look like in that short period of time?
What do I need to be attaining that’s going to give you the confidence
that I will be on the path to success.
And this is why I keep bringing it back to, the result
is the wrong focus it’s the wrong focus for, you know, sales leaders
and it’s the wrong focus for salespeople because we just can’t control that result.
So I mean, I love that example from the. Australian company.
And I agree like having a ramp that’s congruent to the cycle
and ensuring that people are getting up to speed or in a position to have long
term success is critical.
Would love to hear or if you have any other feedback
you received from this framework, either from team leaders or individual
contributors, would love to hear any sort of additional feedback
or anecdotes that you’ve had since rolling this out.
Yeah, the biggest
kind of, I suppose, challenge that we see with this.
And again, I’ve just said this with another client I’m working with
is that, based on the calculator,
based on how much time I’ve got to spend prospecting, et cetera, I don’t have time
I don’t have time to do this, you know, and that’s
it’s kind of a red flag as well,
like when you hear that.
But they’re saying, you know, I, for example,
in order to get pipeline coverage,. I don’t have time to do,
you know, 3 hours a week of prospecting 4 hours a week of prospecting.
But then you ask them what’s your pipeline coverage target?
Because a lot of companies especially big enterprise,
they’ve got a pipeline coverage target. Right?
They’ve actually got to have that.
It’s part of their KPIs.
And they say, well, X times and I’m like, well,
then you’ve got a challenge here, right?
If you haven’t got the time, then you need to find the time
so that then creates another conversation for them.
But that’s probably the biggest
the biggest aha moment that a lot of people have is
where do I find the time to do these things?
And this just brings it back again to the importance of sellers really
thinking about, you know, the high payoff activity or revenue raising activities.
And where they should be spending, you know, the principal 80% of their time.
Because the reality is in sales, there’s probably X
amount of tasks that we need to be spending our time
that’s going to help us achieve our number.
But yet when you talk to sellers, often they get distracted
and they’re doing a whole range of tasks that aren’t going to drive them
to achieve their number.
So this is also a great opportunity for salespeople and for sales leaders
to work with their teams to say you know, if you are struggling for time,
this is a great way to strip that out and focus on what matters.
Because at the end of the day, we’re judged in a sales role
based on the performance and the outcome, even though it’s
we shouldn’t be focusing on it.
That’s what we’re judged on.
So if we use the time, the precious time that we have on tasks
that don’t drive or lead us to that outcome, then
we’re causing ourself potential pain that we might not be able to overcome.
You’re right.. Everyone has the same 24 hours in a day.
We just got to be using it as effectively and efficiently as possible.
That’s great, Luigi.
That’s all the time we have today for this episode of Closing Time.
Thanks for joining, Luigi.
Thanks for having me on.
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