Category Archives: Sales

Using This/Next/All-Quarter Analysis To Understand Your Pipeline

This is the third in a three-post series focused on forecasting and pipeline.  Part I examined triangulation forecasts to improve forecast accuracy and enable better conversations about the forecast.  After a review of pipeline management fundamentals, part II discussed the use of to-go pipeline coverage to provide clarity on how your pipeline is evolving across the weeks of the quarter.  In this, part III, we’ll introduce what I call this/next/all-quarter pipeline analysis as a way of looking at the entire pipeline that is superior to annual or rolling four-quarter pipeline analysis.

Let’s start by unveiling the last block on the sheet we’ve been using the previous two posts.  Here’s the whole thing:

You’ll see two new sections added:  next-quarter pipeline and all-quarters [1] pipeline.  Here’s what we can do when we see all three of them, taken together:

  • We can see slips.  For example, in week 3 while this-quarter pipeline dropped by $3,275K, next-quarter pipeline increased by $2,000K and all-quarters only dropped by $500K.  While there are many moving parts [2], this says to me that pipeline is likely sloshing around between quarters and not being lost.
  • We can see losses.  Similarly, when this-quarter drops, next-quarter is flat, and all-quarters drop, we are probably looking at deals lost from the pipeline [3].
  • We can see wins.  When you add a row at the bottom with quarter-to-date booked new ARR, if that increases, this-quarter pipeline decreases, next-quarter pipeline stays flat, and all-quarters pipeline decreases, we are likely looking at the best way of reducing pipeline:  by winning deals!
  • We can see how we’re building next-quarter’s pipeline.  This keeps us focused on what matters [4].  If you start every quarter with 3.0x coverage you will be fine in the long run without the risk of a tantalizing four-quarter rolling pipeline where overall coverage looks sufficient, but all the closeable deals are always two to four quarters out [5].

Tantalus and his pipeline where all the closeable deals are always two quarters out

  • We can develop a sense how next-quarter pipeline coverage develops over time and get better at forecasting day-1 next-quarter pipeline coverage, which I believe marketing should habitually do [6].
  • We can look at whether we have enough total pipeline to keep our salesreps busy by not just looking at the total dollar volume, but the total count of oppties.  I think this is the simplest and most intuitive way to answer that question.  Typically 15 to 20 all-quarters oppties is the maximum any salesrep can possibly juggle.
  • Finally, there’s nowhere to hide.  Companies that only examine annual or rolling four-quarter pipeline inadvertently turn their 5+ quarter pipeline into a dumping ground full of fake deals, losses positioned as slips, long-term rolling hairballs [7], and oppties used for account squatting.

I hope you’ve enjoyed this three-part series on forecasting and pipeline.  The spreadsheet used in the examples is available here.

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[1] Apologies for inconsistences in calling this all-quarter vs. all-quarters pipeline.  I may fix it at some point, but first things first.  Ditto for the inconsistency on this-quarter vs. current-quarter.

[2] You can and should have your salesops leader do the deeper analysis of inflows (including new pipegen) and outflows, but I love the first-order simplicity of saying, “this-quarter dropped by $800K, next-quarter increased by $800K and all-quarters was flat, ergo we are probably sloshing” or “this-quarter dropped by $1M, next-quarter was flat, and all-quarters dropped by $1M, so we probably lost $1M worth of deals.”

[3] Lost here in the broad sense meaning deal lost or no decision (aka, derail).  In the former case, someone else wins the deal; in the latter case, no one does.

[4] How do you make 32 quarters in row?  One at a time.

[5] Tantalus was a figure in Greek mythology, famous for his punishment:  standing for eternity in a pool of water below a fruit tree where each time he ducked to drink the water it would recede and each time he reached for a fruit it was just beyond his grasp.

[6] Even though most companies have four different pipeline sources (marketing/inbound, SDR/outbound, sales/outbound, and partners), marketing should, by default, consider themselves the quarterback of the pipeline as they are usually the majority pipeline source and the most able to take corrective actions.

[7] By my definition a normal rolling hairball always sits in this quarter’s pipeline and slips one quarter every quarter.  A long-term rolling hairball is thus one that sits just beyond your pipeline opportunity scrutiny window (e.g., 5 quarters out) and slips one quarter every quarter.


Using To-Go Coverage to Better Understand Pipeline and Improve Forecasting

This is the second in a three-part series focused on forecasting and pipeline.  In part I, we examined triangulation forecasts with a detailed example.  In this, part II, we’ll discuss to-go pipeline coverage, specifically using it in conjunction with what we covered in part I.  In part III, we’ll look at this/next/all-quarter pipeline analysis as a simple way to see what’s happening overall with your pipeline.

Pipeline coverage is a simple enough notion:  take the pipeline in play and divide it by the target and get a coverage ratio.  Most folks say it should be around 3.0, which isn’t a bad rule of thumb.

Before diving in further, let’s quickly remind ourselves of the definition of pipeline:

Pipeline for a period is the sum of the value of all opportunities with a close date in that period.

This begs questions around definitions for opportunity, value, and close date which I won’t review here, but you can find discussed here.  The most common mistakes I see thinking about the pipeline are:

  • Turning 3.0x into a self-fulfilling prophecy by bludgeoning reps until they have 3.0x coverage, instead of using coverage as an unmanaged indicator
  • Not periodically scrubbing the pipeline according to a defined process and rules, deluding yourself into thinking “we’re always scrubbing the pipeline” (which usually means you never are).
  • Applying hidden filters to the pipeline, such as “oh, sorry, when we say pipeline around here we mean stage-4+ pipeline.”  Thus executives often don’t even understand what they’re analyzing and upstream stages turn into pipeline landfills full of junk opportunities that are left unmanaged.
  • Pausing sales hiring until the pipeline builds, effectively confusing cause and effect in how the pipeline gets built [1].
  • Creating opportunities with placeholder values that pollute the pipeline with fake news [1A], instead of creating them with $0 value until a salesrep socializes price with the customer [2].
  • Conflating milestone-based and cohort-based conversion rates in analyzing the pipeline.
  • Doing analysis primarily on either an annual or rolling four-quarter pipeline, instead of focusing first on this-quarter and next-quarter pipeline.
  • Judging the size of the all-quarter pipeline by looking at dollar value instead of opportunity count and the distribution of oppties across reps [2A].

In this post, I’ll discuss another common mistake, which is not analyzing pipeline on a to-go basis within a quarter.

The idea is simple:

  • Many folks run around thinking, “we need 3.0x pipeline coverage at all times!”  This is ambiguous and begs the questions “of what?” and “when?” [3]
  • With a bit more rigor you can get people thinking, “we need to start the quarter with 3.0x pipeline coverage” which is not a bad rule of thumb.
  • With even a bit more rigor that you can get people thinking, “at all times during the quarter I’d like to have 3.0x coverage of what I have left to sell to hit plan.” [4]

And that is the concept of to-go pipeline coverage [5].  Let’s look at the spreadsheet in the prior post with a new to-go coverage block and see what else we can glean.

Looking at this, I observe:

  • We started this quarter with $12,500 in pipeline and a pretty healthy 3.2x coverage ratio.
  • We started last quarter in a tighter position at 2.8x and we are running behind plan on the year [6].
  • We have been bleeding off pipeline faster than we have been closing business.  To-go coverage has dropped from 3.2x to 2.2x during the first 9 weeks of the quarter.  Not good.  [7]
  • I can easily reverse engineer that we’ve sold only $750K in New ARR to date [8], which is also not good.
  • There was a big drop in the pipeline in week 3 which makes me start to wonder what the gray shading means.

The gray shading is there to remind us that sales management is supposed to scrub the pipeline in weeks 2, 5, and 8 so that the pipeline data presented in weeks 3, 6, and 9 is scrubbed.  The benefits of this are:

  • It eliminates the “always scrubbing means never scrubbing” problem.
  • It draws a deadline for how long sales has to clean up after the end of a quarter:  the end of week 2.  That’s enough time to close out the quarter, take a few days rest, and then get back at it.
  • It provides a basis for snapshotting analytics.  Because pipeline conversion rates vary by week things can get confusing fast.  Thus, to keep it simple I base a lot of my pipeline metrics on week 3 snapshots (e.g., week 3 pipeline conversion rate) [9]
  • It provides an easy way to see if the scrub was actually done.  If the pipeline is flat in weeks 3, 6, and 9, I’m wondering if anyone is scrubbing anything.
  • It lets you see how dirty things got.  In this example, things were pretty dirty:  we bled off $3,275K in pipeline during the week 2 scrub which I would not be happy about.

Thus far, while this quarter is not looking good for SaaSCo, I can’t tell what happened to all that pipeline and what that means for the future.  That’s the subject of the last post in this three-part series.

A link to the spreadsheet I used in the example is here.

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[1]  In enterprise SaaS at least, you should look at it the other way around:  you don’t build pipeline and then hire reps to sell it, you hire reps and then they build the pipeline, as the linked post discusses.

[1A]  The same is true of close dates.  For example, if you create opportunities with a close date that is 18+ months out, they can always be moved into the more current pipeline.  If you create them 9 months out and automatically assign a $150K value to each, you can end up with a lot air (or fake news/data) in your pipeline.

[2]  For benchmarking purposes, this creates the need for “implied pipeline” which replaces the $0 with a segment-appropriate average sales price (ASP) as most people tend to create oppties with placeholder values.  I’d rather see the “real” pipeline and then inflate it to “implied pipeline” — plus it’s hard to know if $150K is assigned to an oppty as a placeholder that hasn’t been changed or if that’s the real value assigned by the salesrep.

[2A] If you create oppties with a placeholder value then dollar pipeline is a proxy for the oppty count, but a far less intuitive one — e.g., how much dollar volume of pipeline can a rep handle?  Dunno.  How many oppties can they work on effectively at one time?  Maybe 15-20, tops.

[3] “Of what” meaning of what number?  If you’re looking at all-quarters pipeline you may have oppties that are 4, 6, or 8+ quarters out (depending on your rules) and you most certainly don’t have an operating plan number that you’re trying to cover, nor is coverage even meaningful so far in advance.  “When” means when in the quarter?  3.0x plan coverage makes sense on day 1; it makes no sense on day 50.

[4] As it turns out, 3.0x to-go coverage is likely an excessively high bar as you get further into the quarter.  For example, by week 12, the only deals still forecast within the quarter should be very high quality.  So the rule of thumb is always 3.0x, but you can and should watch how it evolves at your firm as you get close to quarter’s end.

[5]  In times when the forecast is materially different from the plan, separating the concepts of to-go to forecast and to-go to plan can be useful.  But, by default, to-go should mean to-go to plan.

[6] I know this from the extra columns presented in the screenshot from the same sheet in the previous post.  We started this quarter at 96% of the ARR plan and while the never explicitly lists our prior-quarter plan performance, it seems a safe guess.

[7]  If to-go coverage increases, we are closing business faster than we are losing it.  If to-go coverage decreases we are “losing” (broadly defined as slip, lost, no decision) business faster than we are closing it.  If the ratio remains constant we are closing business at the same ratio as we started the quarter at.

[8]  A good sheet will list this explicitly, but you can calculate it pretty fast.  If you have a pipeline of $7,000, a plan of $3,900, and coverage of 2.2x then:  7,000/2.2 (rounded) = 3,150 to go, with a plan of 3,900 means you have sold 750.

[9] An important metric that can be used as an additional triangulation forecast and is New ARR / Week 3 Pipeline.


Using Triangulation Forecasts For Improved Forecast Accuracy and Better Conversations

Ever been in this meeting?

CEO:  What’s the forecast?
CRO:  Same as before, $3,400K.
Director 1:  How do you feel about it?
CRO:  Good.
Director 2:  Where will we really land?
CRO:  $3,400K.  That’s why that’s the forecast.
Director 1:  But best case, where do we land?
CRO:  Best case, $3,800K.
Director 2:  How do you define best case?
CRO:  If the stars align.

Not very productive, is it?

I’ve already blogged about one way to solve this problem:  encouraging your CRO think probabilistically about the forecast.  But that’s a big ask.  It’s not easy to change how sales leaders think, and it’s not always the right time to ask.  So, somewhat independent of that, in this series I’ll introduce three concepts that help ensure that we have better conversations about the forecast and ultimately forecast better as a result:  triangulation forecasts, to-go pipeline coverage, and this/next/all-quarter pipeline analysis.  In this post, we’ll cover triangulation forecasts.

Triangulation Forecasts

The simplest way to have better conversations about the forecast is to have more than one forecast to discuss.  Towards that end, much as we might take three or four bearings to triangulate our position when we’re lost in the backcountry, let’s look at three or four bearings to triangulate our position on the new annual recurring revenue (ARR) forecast for the quarter.

In this example [1] we track the forecast and its evolution along with some important context such as the plan and our actuals from the previous and year-ago quarters.  We’ve placed the New ARR forecast in its leaky bucket context [2], in bold so it stands out.  Just scanning across the New ARR row, we can see a few things:

  • We sold $3,000K in New ARR last quarter, $2,850K last year, and the plan for this quarter is $3,900K.
  • The CRO is currently forecasting $3,400K, or 87% of the New ARR plan.  This is not great.
  • The CRO’s forecast has been on a steady decline since week 3, from its high of $3,800K.  This makes me nervous.
  • The CRO is likely pressuring the VP of Customer Success to cut the churn forecast to protect Net New ARR [3].
  • Our growth is well below planned growth of 37% and decelerating [4].

I’m always impressed with how much information you can extract from that top block alone if you’re used to looking at it.  But can we make it better?  Can we enable much more interesting conversations?  Yes.  Look at the second block, which includes four rows:

  • The sum of the sales reps’ forecasts [5]
  • The sum of the sales managers’ forecasts [6]
  • The stage-weighted expected value (EV) of the pipeline [7] [8]
  • The forecast category-weighted expected value of the pipeline [9]

Each of these tells you something different.

  • The rep-level forecast tells you what you’d sell if every rep hit their current forecast.  It tends to be optimistic, as reps tend to be optimistic.
  • The manager-level forecast tells you how much we’d sell if every CRO direct report hit their forecast.  This tends to be the most accurate [10] in my experience.
  • The stage-weighted expected value tells you the value of pipeline when weighted by probabilities assigned to each stage. A $1M pipeline consisting of 10 stage 2 $100K oppties has a much lower EV than a $1M pipeline with 10 stage 5 $100K oppties — even though they are both “$1M pipelines.”
  • The forecast category-weighted expected value tells you the value of pipeline when weighted by probabilities assigned to each forecast category, such as commit, forecast, or upside.

These triangulation forecasts provide different bearings that can help you understand your pipeline better, know where to focus your efforts, and improve the accuracy of predicting where you’ll land.

For example, if the rep- and manager-level forecasts are well below the CRO’s, it’s often because the CRO knows about some big deal they can pull forward to make up any gap.  Or, more sinisterly, because the CRO’s expense budget is automatically cut to preserve a target operating margin and thus they are choosing to be “upside down” rather face an immediate expense cut [11].

If the stage-weighted forecast is much lower than the others, it indicates that while we may have the right volume of pipeline that it’s not far enough along in its evolution, and ergo we should focus on velocity.

Now, looking at our sample data, let’s make some observations about the state of the quarter at SaaSCo.

  • The reps are calling $3,400K vs. a $3,900K plan and their aggregate forecast has been fairly consistently deteriorating.  Not good.
  • The managers, who we might notice called last quarter nearly perfectly ($2,975K vs. $3,000K) have pretty consistently been calling $3,000K, or $900K below plan.  Worrisome.
  • The stage-weighted EV was pessimistic last quarter ($2,500K vs. $3,000K) and may need updated probabilities.  That said, it’s been consistently predicting around $2,600K which, if it’s 20% low (like it was last quarter), it suggests a result of $3,240K [12].
  • The forecast category-weighted expected value, which was a perfect predictor last quarter, is calling $2,950K.  Note that it’s jumped up from earlier in the quarter, which we’ll get to later.

Just by these numbers, if I were running SaaSCo I’d be thinking that we’re going to land between $2,800K and $3,200K [13].  But remember our goal here:  to have better conversations about the forecast.  What questions might I ask the CRO looking at this data?

  • Why are you upside-down relative to your manager’s forecast?
  • In other quarters was the manager-level forecast the most accurate, and if so, why you are not heeding it better now?
  • Why is the stage-weighted forecast calling such a low number?
  • What’s happened since week 5 such that the reps have dropped their aggregate forecast by over $600K?
  • Why is the churn forecast going down?  Was it too high to begin with, are we getting positive information on deals, or are we pressuring Customer Success to help close the gap?
  • What big/lumpy deals are in these numbers that could lead to large positive or negative surprises?
  • Why has your forecast been moving so much across the quarter?  Just 5 weeks ago you were calling $3,800K and how you’re calling $3,400K and headed in the wrong direction?
  • Have you cut your forecast sufficiently to handle additional bad news, or should I expect it to go down again next week?
  • If so, why are you not following the fairly standard rule that when you must cut your forecast you cut it deeply enough so your next move is up?  You’ve broken that rule four times this quarter.

In our next post in the series we’ll discuss to-go pipeline coverage.  A link to the spreadsheet used to the example is here.

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[1] This is the top of the weekly sheet I recommend CEOs to start their weekly staff meeting.

[2] A SaaS company is conceptualized as a leaky bucket of ARR.

[3] I cheated and look one row down to see the churn forecast was $500K in weeks 1-6 and only started coming down (i.e., improving) as the CRO continued to cut their New ARR forecast.  This makes me suspicious, particularly if the VP of Customer Success reports to the CRO.

[4] I cheated and looked one row up to see starting ARR growing at 58% which is not going to sustain if New ARR is only growing at ~20%.  I also had to calculate planned growth (3900/2850 = 1.37) as it’s not done for me on the sheet.

[5] Assumes a world where managers do not forecast for their reps and/or otherwise cajole reps into forecasting what the manager thinks is appropriate, instead preferring for managers to make their own forecast, loosely coupling rep-level and the manager-level forecasts.

[6]  Typically, the sum of the forecasts from the CRO’s direct reports.  An equally, if perhaps not more, interesting measure would be the sum of the first-line managers’ forecasts.

[7] Expected value is math-speak for probability * value.  For example, if we had one $100K oppty with a 20% close probability, then its expected value would be $100K * 0.2 = $20K.

[8] A stage-weighted expected value of the (current quarter) pipeline is calculated by summing the expected value of each opportunity in the pipeline, using probabilities assigned to each stage.  For example, if we had only three stages (e.g., prospect, short-list, and vendor of choice) and assigned a probability to each (e.g., 10%, 30%, 70%) and then multiplied the new ARR value of each oppty by its corresponding probability and summed them, then we would have the stage-weighted expected value of the pipeline.  Note that in a more advanced world those probabilities are week-specific (and, due to quarterly seasonality, maybe week-within-quarter specific) but we’ll ignore that here for now.  Typically, one way I sidestep some of that hassle is to focus my quarterly analytics by snapshotting week 3, creating in effect week 3 conversion rates which I know will work better earlier in the quarter than later.  In the real world, these are often eyeballed initially and then calculated from regressions later on — i.e., in the last 8 quarters, what % of week 3, stage 2 oppties closed?

[9]  The forecast category-weighted expected value of the pipeline is the same the stage-weighted one, except instead of using stage we use forecast category as the basis for the calculation.  For example, if we have forecast categories of upside, forecast, commit we might assign probabilities of 0.3, 0.7, and 0.9 to each oppty in that respective category.

[10] Sometimes embarrassingly so for the CRO whose forecast thus ends up a mathematical negative value-add!

[11] This is not a great practice IMHO and thus CEOs should not inadvertently incent inflated forecasts by hard-coding expense cuts to the forecast.

[12] The point being there are two ways to fix this problem.  One is to revise the probabilities via regression.  The other is to apply a correction factor to the calculated result.  (Methods with consistent errors are good predictors that are just miscalibrated.)

[13]  In what I’d consider a 80% confidence interval — i.e., 10% chance we’re below $2,800K and 10% chance we’re above $3,200K.

What a Pipeline Coverage Target of >3x Says To Me

I’m working with a lot of different companies these days and one of the perennial topics is pipeline.

One pattern I’m seeing is CROs increasingly saying that they need more than the proverbial 3x pipeline coverage ratio to hit their numbers [2] [3].  I’m hearing 3.5x, 4x, or even 5x.  Heck — and I’m not exaggerating here — I even met one company that said they needed 100x.  Proof that once you start down the >3x slippery slope that you can slide all the way into patent absurdity.

Here’s what I think when a company tells me they need >3x pipeline coverage [4]:

  • The pipeline isn’t scrubbed.  If you can’t convert 33% of your week 3 pipeline, you likely have a pipeline that’s full of junk opportunities (oppties). Rough math, if 1/3rd slips or derails [5] [6] and you go 50-50 on the remaining 2/3rds, you convert 33%.
  • You lose too much.  If you need 5x pipeline coverage because you convert only 20% of it, maybe the problem isn’t lack of pipeline but lack of winning [7].  Perhaps you are better off investing in sales training, improved messaging, win/loss research, and competitive analysis than simply generating more pipeline, only to have it leak out of the funnel.
  • The pipeline is of low quality.  If the pipeline is scrubbed and your deal execution is good, then perhaps the problem is the quality of pipeline itself.  Maybe you’re better off rethinking your ideal customer profile and/or better targeting your marketing programs than simply generating more bad pipeline [8].
  • Sales is more powerful than marketing.  By (usually arbitrarily) setting an unusually high bar on required coverage, sales tees up lack-of-pipeline as an excuse for missing numbers.  Since marketing is commonly the majority pipeline source, this often puts the problem squarely on the back of marketing.
  • There’s no nurture program.  Particularly when you’re looking at annual pipeline (which I generally don’t recommend), if you’re looking three or four quarters out, you’ll often find “fake opportunities” that aren’t actually sales opportunities, but are really just attractive prospects who said they might start an evaluation later.  Are these valid sales opportunities?  No.  Should they be in the pipeline?  No.  Do they warrant special treatment?  Yes.   That should ideally be accomplished by a sophisticated nurture program. But lacking that, reps can and should nurture accounts.  But they shouldn’t use the opportunity management system to do so; it creates “rolling hairballs” in the pipeline.
  • Salesreps are squatting.  The less altruistic interpretation of fake long-term oppties is squatting.  In this case, a rep does not create a fake Q+3 opportunity as a self-reminder to nurture, but instead to stake a claim on the account to protect against its loss in a territory reorganization [9].   In reality, this is simply a sub-case of the first bullet (the pipeline isn’t scrubbed), but I break it out both to highlight it as a frequent problem and to emphasize that pipeline scrubbing shouldn’t just mean this- and next-quarter pipeline, but all-quarter pipeline as well [10].

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[1] e.g., from marketing, sales, SDRs, alliances.  I haven’t yet blogged on this, and I really need to.  It’s on the list!

[2] Pipeline coverage is ARR pipeline divided by the new ARR target.  For example, if your new ARR target for a given quarter is $3,000K and you have $9,000K in that-quarter pipeline covering it, then you have a 3x pipeline coverage ratio.  My primary coverage metric is snapshotted in week 3, so week 3 pipeline coverage of 3x implies a 33% week three pipeline conversion rate.

[3] Note that it’s often useful to segment pipeline coverage.  For example, new logo pipeline tends to convert at a lower rate (and require higher coverage) than expansion pipeline which often converts at a rate near or even over 100% (as the reps sometimes don’t enter the oppties until the close date — an atrocious habit!)  So when you’re looking at aggregate pipeline coverage, as I often do, you must remember that it works best when the mix of pipeline by segment and the conversion rate of each segment is relatively stable.  The more that’s not true, the more you must do segmented pipeline analysis.

[4] See note 2.  Note also the ambiguity in simply saying “pipeline coverage” as I’m not sure when you snapshotted it (it’s constantly changing) or what time period it’s covering.  Hence, my tendency is to say “week 3 current-quarter pipeline coverage” in order to be precise.  In this case, I’m being a little vague on purpose because that’s how most folks express it to me.

[5] In my parlance, slip means the close date changes and derail means the project was cancelled (or delayed outside your valid opportunity timeframe).  In a win, we win; in a loss, someone else wins; in a derail, no one wins.  Note that — pet peeve alert — not making the short list is not a derail, but a loss to as-yet-known (so don’t require losses to fill in a single competitor and ensure missed-short-list is a possible lost-to selection).

[6] Where sales management should be scrubbing the close date as well as other fields like stage, forecast category, and value.

[7] To paraphrase James Mason in The Verdict, salesreps “aren’t paid to do their best, they’re paid to win.”  Not just to have a 33% odds of winning a deal with a three-vendor short list.  If we’re really good we’re winning half or more of those.

[8] The nuance here is that sales did accept the pipeline so it’s presumably objectively always above some quality standard.  The reality is that pipeline acceptance bar is not fixed but floating and the more / better quality oppties a rep has the higher the acceptance bar.  And conversely:  even junk oppties look great to a starving rep who’s being flogged by their manager to increase their pipeline.  This is one reason why clear written definitions are so important:  the bar will always float around somewhat, but you can get some control with clear definitions.

[9] In such cases, companies will often “grandfather” the oppty into the rep’s new territory even if it ordinarily would not have been included.

[10] Which it all too often doesn’t.

What Are The Units On Your Lead SaaS Metric — And What Does That Say About Your Culture


  • How big is the Acme deal?  $250K.
  • What’s Joe’s forecast for the quarter?  $500K
  • What’s the number this year?  Duh.  $7,500K.

Awesome.  By the way:  $250K what?  $500K what?  $7,500K what?  ARR, ACV, bookings, TCV, new ARR, net new ARR, committed ARR, contracted ARR, terminal ARR, or something else?

Defining those terms isn’t the point of this post, so see note [1] below if interested.

The point is that these ambiguous, unitless conversations happen all the time in enterprise software companies.  This isn’t a post about confusion; the vast majority of the time, everyone understands exactly what is being said.  What those implicit units really tell you about is culture.

Since there can be only one lead metric, every company, typically silently, decides what it is.  And what you pick says a lot about what you’re focused on.

  • New ARR means you’re focused on sales adding water to the SaaS leaky bucket — regardless of whether it’s from new or existing customers.
  • Net New ARR means you’re focused the change in water level in the SaaS leaky bucket — balancing new sales and churn — and presumably means you hold AEs accountable for both sales and renewals within their patch.
  • New Logo ARR means you’re focused on new ARR from new customers.  That is, you’re focused on “lands” [2].
  • Bookings means you’re focused on cash [3], bringing in dollars regardless of whether they’re from subscription or services, or potentially something else [4].
  • TCV, which became a four-letter word after management teams too often conflated it with ARR, is probably still best avoided in polite company.  Use RPO for a similar, if not identical, concept.
  • Committed ARR usually means somebody important is a fan of Bessemer metrics, and means the company is (as with Net New ARR) focused on new ARR net of actual and projected churn.
  • Terminal ARR means you’re focused on the final-year ARR of multi-year contracts, implying you sign contracts with built-in expansion, not a bad idea in an NDR-focused world, I might add.
  • Contracted ARR can be a synonym for either committed or terminal ARR, so I’d refer to the appropriate bullet above as the case may be.

While your choice of lead metric certainly affects the calculations of other metrics (a bookings CAC or a terminal-ARR CAC) that’s not today’s point, either.  Today’s point is simple.  What you pick says a lot about you and what you want your organization focused on.

  • What number do you celebrate at the all hands meeting?
  • What number do you tell employees is “the number” for the year?

For example, in my opinion:

  • A strong sales culture should focus on New ARR.  Yes, the CFO and CEO care about Ending ARR and thus Net New ARR, but the job of sales is to fill the bucket.  Someone else typically worries about what leaks out.
  • A shareholder value culture would focus on Ending ARR, and ergo Net New ARR.  After all, the company’s value is typically a linear function of its Ending ARR (with slope determined by growth).
  • A strong land-and-expand culture might focus on Terminal ARR, thinking, regardless of precisely when they come in, we have contracts that converge to a given total ARR value over time [5].
  • Conversely, a strong land and expand-through-usage culture might focus on New Logo ARR (i.e., “land”), especially if the downstream, usage-based expansion is seen as somewhat automatic [6].
  • A cash-focused culture (and I hope you’re bootstrapped) would focus on bookings.  Think:  we eat what we kill.

This isn’t about a right or wrong answer [7].  It’s about a choice for your organization, and one that likely changes as you scale.  It’s about mindfulness in making a subtle choice that actually makes a big statement about what you value.

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[1] For clarity’s sake, ARR is annual recurring revenue, the annual subscription value.  ACV is annual contract value which, while some treat as identical to ARR, others treat as first-year total contract value, i.e., first-year ARR plus year-one services.  Bookings is usually used as a proxy for cash and ergo would include any effects of multi-year prepayments, e.g., a two-year, prepaid, $100K/year ARR contract would be $200K in bookings.  TCV is total contract value which is typically the total (subscription) value of the contract, e.g., a 3-year deal with an ARR stream of $100K, $200K, $300K would have a $600K, regardless of when the cash payments occurred.  New ARR is new ARR from either new customers (often called New Logo ARR) or existing customers (often called Upsell ARR).  Net New ARR is new ARR minus churn ARR, e.g., if a regional manager starts with $10,000K in their region, adds $2,000K in new ARR and churns $500K, then net new ARR is $1,500K.  Committed ARR (as defined by Bessemer who defined the term) is “contracted, but not yet live ARR, plus live ARR netted against known projected ARR churn” (e.g., if a regional manager starts with $10,000K in their region, has signed contracts that start within an acceptable time period of $2,000K, takes $200K of expected churn in the period, and knows of $500K of new projected churn upcoming, then their ending committed is ARR is $11,500K.  (Why not $11,300K?  Because the $200K of expected churn was presumably already in the starting figure.)  Terminal ARR the ARR in the last year of the contract, e.g., say a contract has an ARR stream of $100K, $200K, $300K, the terminal ARR is $300K [1A].  Contracted ARR is for companies that have hybrid models (e.g., annual subscription plus usage fee) and includes only the contractually committed recurring revenues and not usage fees.

[1A] Note that it’s not yet clear to me how far Bessemer goes out with “contracted” ARR in their committed ARR definition, but I’m currently guessing they don’t mean three years.  Watch this space as I get clarification from them on this issue.

[2] In the sense of land-and-expand.

[3] On the assumptions that bookings is being used as a proxy for cash, which I recommend, but which is not always the case.

[4] e.g., non-recurring engineering; a bad thing to be focused on.

[5] Although if they all do so in different timeframes it becomes less meaningful.  Also unless the company has a track record of actually achieving the contractually committed growth figures, it becomes less credible.

[6] Which it never actually is in my experience, but it is a matter of degree.

[7] Though your investors will definitely like some of these choices better than others.


Thoughts on Hiring Your First VP of Sales

There’s some great content out there on the subject of hiring your first VP of sales at a startup, so in this post I’m going to do some quick thoughts on the subject in an effort to complement the existing corpus.

In other words, this is not your classic TLDR Kelloggian essay, but some quick tips.

  • Hire them first.  That is, before hiring any salesreps.  The first VP of Sales should be your first salesrep.  Hire someone who wants to walk (and even discover) the path before leading others.  Hire someone who enjoys the fight.
  • Hire them hopelessly early.  Don’t wait for product availability.  Don’t wait until you’ve hired 3-4 reps and they need a manager.  Don’t wait until you have a bookings plan that needs hitting. Hire them as early as possible.
  • Glue yourselves together for 6-12 months.  You want to spend 6-12 months as Frick and Frack.  Why?  Most founders can sell their idea and their software.  The real question is:  can anyone else?  By gluing yourselves together you will transfer a huge amount of critical knowledge to the sales VP.  That, or you’ll drive each other crazy and discover you can’t work together.  Either way, it’s good to succeed or fail fast.  And the goal is total alignment.  [1]
  • Hire them before the VP of marketing.  I know some very smart people who disagree with me on this question, but as a three-time enterprise software CMO (and two-time CEO) I take no shame in saying that marketing is a support function.  We’re here to help.  Hire us after hiring sales.  Let the VP of Sales have a big vote in choosing who supports them [2].
  • Hire someone who is a first-line manager today.  Their title might be district manager or regional vice president, but you want someone close to the action, but who also is experienced in building and managing a team.  Why?  Because you want them to be successful as your first salesrep for 6-12 months and then build up a team that they can manage.  In a perfect world, they’d have prior experience managing up to 10 reps, but even 4-6 will do [3].  You want to avoid like the plague a big-company, second- or third-line manager who, while undoubtedly carrying a large number, likely spends more time in spreadsheets and internal reviews than in customer meetings.

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[1] Hat tip to Bhavin Shah for this idea.

[2] A wise VP of Marketing often won’t join before of the VP of Sales anyway.

[3] On the theory that someone’s forward potential is not limited to their prior experience.  Someone who’s successfully managed 4-6 reps can likely manage 10-12 with one extra first-line manager.  Managing 36 through a full layer of first-line managers is a different story.  That’s not to say they can’t do it, but it is a different job.  In any case, the thing to absolutely avoid is the RVP who can only manage through a layer of managers and views the sales trenches as a distant and potentially unpleasant memory.