# Tag Archives: sales

## How to Train Your VP of Sales to Think About the Forecast

Imagine a board meeting.

Director:  What’s the forecast for new ARR this quarter?

Sales VP:  \$4.3M, with a best case of \$5.0M.

Director:  So what’s the most likely outcome?

Sales VP:  \$4.3M.

Director:  What are you really going to do?  (The classic newb trap question.)

Sales VP:  I think we can come in North of that.

Director:  What’s the worst case?

Sales VP:  \$3.5M.

Director:  What are the odds of coming in at or above the forecast?

Sales VP:  I always make my forecast.

Director:   What do you mean by worst case?

Sales VP:  You know, well, if the stars align in a bad way – a lot of stuff would have to go wrong – but if that happened, then we could end up at \$3.5M.

Director:  So, let’s say a 10% chance of being at/below the worst case?

Sales VP:  I’d say more like 5%.

Director:  What do you mean by best case?

Sales VP:  Well, if we really struck it rich and everything lined up just the way I wanted, that would be best case.

Director:  You mean if all the deals came in — so best case basically equals pipeline?

Sales VP:  No, that never happens, I’ve made about 10 scenarios of different deal closing combinations and in 2 of them I can get to the best case.

You see the problem?  Does it sound familiar?  Do you realize how much time we spend talking in board meetings about “forecast,” “best case,” and “worst case” without every discussing what we mean by those terms?

Do you see how this is compounded by the sales VP’s natural, intuitive view of the outcomes?  Do you see the obvious mathematical contradictions?  “I always make my forecast” says it’s a 100% number, but then the VP says it’s the “most likely” number which implies 50%.  Then the VP says there’s a 5% chance of coming in at/less than worst case (which is much lower) and then kind of implies that there’s a 20% chance of beating best case – but the 2 out of 10 is meaningless because it’s not a probability, it’s just a count of scenarios.  Nothing adds up.

The result is, if you’re not careful, the board ends up counting angels on pinheads.  What can we do to fix this?  It’s simple:  teach (and if need be, force) your sales VP to think probabilistically.  Ask him/her how often:

• It is reasonable to miss the forecast.  A typical answer might be 10%.
• It is likely to come in at/below the worst case? Typical answer, 5%.
• It is likely to meet/beat the best case? Typical answer, 20%.

So, with those three questions, we’ve now established that we want the sales VP to give us:

• A 90% number on being at/above the forecast
• A 20% number on being at/above the best case
• A 5% number on being at/below the worst case

Put differently, when the sales VP decides what number to forecast that they should be thinking:

• I should come in under my forecast once every 2.5 years (10 quarters).
• I should hit/beat the best case about once every 5 quarters (a bit less than once a year).
• I should come in/under the worst case once every 20 quarters (once every 5 years, or for most minds, basically never).

The beauty here is that when you work at a company a long time you can get enough quarters under your belt, to start really seeing how you’re doing relative to these frequencies.  What’s more, by converting the probabilities into frequencies (e.g., once every 10 quarters) you make it more intuitive for the sales VP and the organization to think this way.

In addition, you have a basis for conversations like this one which, among other things, is about overconfidence:

CEO:  You need to work on your forecasting.

Sales VP:  You know it’s hard out there, very competitive, and we don’t have much deal flow.  Back when I was at { Salesforce | Oracle | SAP }, I was much better at forecasting because we had more volume.

CEO:  But we agreed your forecast should be a 90% number and you’ve missed it 2 out of the past 4 quarters.

Sales VP:  Yes, but as I’ve said it’s tough to forecast in this market.

CEO:  Then forecast a lower number so you can beat it 90% of the time.  I’m asking you for a 90% number and empirically you’re giving me a 50% number.

Sales VP:  OK.

CEO:  Plus, when those two big deals slipped last quarter you didn’t drop your forecast, why?

Sales VP:  Because where I grew up, you don’t cut the forecast.  You try like crazy to hold it.  Do you know the morale problems it causes when I cut the forecast – especially if it’s below plan? So, yes, when those two deals slipped it added more risk to the forecast – and I told you and the board that — but I didn’t cut forecast, no.

CEO:  But “adding risk” here is meaningless.  In reality, “adding risk” means it’s not a 90% number anymore.  You’ve taken what was a 90% number and it’s now more like a 60% or 70% number.  So I want you to forget what they taught you growing up in sales and always – every week – give me a number that based on all available information you are 90% sure you can beat.  If that means dropping the forecast so be it.

This also helps with the board and the inevitable sandbagger issue.  In my experience (and with a bit of exaggeration) you always seem to be in one of two situations:  (1) intermittently missing plan and in trouble or (2) consistently making plan and a “sandbagger” – it feels like there’s nothing in between.

Well, if you establish with the board that your company forecast is a 90% number it means you are supposed to beat it 9 times out of 10 so you can only really be labelled a sandbagger when you’re 15 for 15 or 20 for 20.  It also reminds them that you’re supposed to arrive at the forecast so that you miss once every 10 quarters so they shouldn’t freak out if once every 2.5 years if that happens — it’s supposed to happen in this system.  (Just don’t let a once-in-ten-quarter event happen twice in a row.)

I like this quantitative basis for sales forecasting and I carry it down to the salesrep and pipeline level.  I believe that each “forecast category” should have a probability associated with it.  For example, at the opportunity level, you should link probabilities to categories, such as:

• Commit = 90%
• Forecast = 70%
• Upside = 30%

This, in turn, means that over time, a given salesrep should close 90% of their committed deals, 70% of their forecast deals, and 30% of their upside.  Deviations from this over time indicate that the rep is mis-categorizing the deals because the probability should be the basis for the forecast category assignment [1].

Finally, I do believe that salesreps should give quarterly forecasts [2] that reflect their sense for how things will come in given all the odd things that can happen to deals (e.g., size changes, acceleration, slippage).  I believe those forecasts should be a 70% number because the sales manager will be managing across a  portfolio of them and while there is little room for a company to miss at the VP of Sales level, there is more room for and more variance in performance across salesreps.

While I know this will not necessarily come naturally to all sales VPs — and some may push-back hard — this is a simple, practical, and rigorous way to think about the forecast.

# # #

[1] Some people do this through an independent (orthogonal) field in the CRM system called probability.  I think that’s unnecessary because in my mind forecast category should effectively equal probability and your options for picking a probability should be bucketed.  No one can say a deal is 43% vs. 52% and forecast category doesn’t indicate some probability of closing, then … what use is it and on what basis should you classify something as forecast vs. upside?

[2] Some people believe that only managers should make forecasts, but I believe both reps and managers should forecast for two reasons:  (1) provided it’s left independent and not “managed” by the managers, the aggregated salesrep-level forecast provides another, Wisdom of Crowds-y, view into the sales forecast and (2) it’s never too early to teach salesreps how to forecast which is best learned through the experience of trial and error over many quarters.

## How to Manage Your First Sales VP at a Startup

One of the hardest hires — and one of the hardest jobs — is to be the first VP of sales at a startup.  Why?

• There is no history / experience
• Nobody knows what works and what doesn’t work
• The company may not have a well defined strategy so it’s hard to make a go-to-market strategy that maps to it
• Any strategy you choose is somewhat complex because it needs to leave room for experimentation
• If things don’t work the strong default tendency is to blame the VP of sales and sales execution, and not strategy or product.  (Your second VP of sales gets to blame product or strategy — but never your first.)

It’s a tough job, no doubt.  But it’s also tough for a founder or new CEO to manage the first sales VP.

• The people who sign up for this high-risk duty are often cocksure and difficult to manage
• They tend to dismiss questions with experienced-based answers (i.e., well we did thing X at company Y and it worked) that make everything sound easy.
• They tend to smokescreen issues with such dismissals in order to give themselves maximum flexibility.
• Most founders know little about sales; they’ve typically never worked in sales and it’s not taught in (business) school.

I think the best thing a founder can do to manage this is to conceptually separate two things:

• How well the sales VP implements the sales model agreed to with the CEO and the board.
• Whether that model works.

For example, if your team agrees that it wants to focus on Defense as its beachhead market, but still opportunistically experiment horizontally, then you might agree with the sales VP to build a model that creates a focused team on Department of Defense (DoD) and covers the rest of the country horizontally with a enterprise/corporate split.  More specifically, you might decide to:

• Create a team of 3 quota carrying reps (QCRs) selling to the DoD who each have 10+ years experience selling to the DoD, ideally holding top secret clearances, supported by 2 sales consultants (SCs) and 2 business development reps (BDRs) with the entire team located in a Regus office in McLean, VA and everyone living with a one-hour commute of that office.
• Hire 2 enterprise QCRs, one for the East and one for the West, the former in McLean and the latter in SF, each calling only on \$1B+ revenue companies, each supported by 1 local SC, and 2 BDRs, where the BDRs are located at corporate (in SF).  Each enterprise QCR must have 10+ years experience selling software in the company’s category.
• Hire 2 corporate reps in SF, each sharing 1 SC, and supported by 2 BDRs calling on sub \$1B revenue companies.  Each corporate rep must have 5+ years experience selling software in the category.

In addition, you would create specific hiring profiles for each role ideally expressed with perhaps 5-10 must-have and 3-5 nice-to-have criteria.

Two key questions:

• Do we know if this is going to work?  No, of course not.  It’s a startup.  We have no customers, data, or history.  We’ve taken our best guess based on understanding the market and the customers.  But we can’t possibly know if this is going to work.
• Can we tell if the sales VP is executing it?  Yes.  And you can hold him/her accountable for so doing.  That’s the point.

At far too many startups, the problem is not decomposed in this manner, the specifics are not spelled out, and here’s what happens instead.  The sales VP says:

The plan?  Yes, let me tell you the plan.  I’m going to put boots down in several NFL cities, real sales athletes mind you, the best.  People I’ve worked with who made \$500K, \$750K, or even \$1M in commissions back at Siebel or Salesforce or Oracle.  The best.  We’re going to support those athletes with the best SCs we can find, and we’re going to create an inside sales and SDR team that is bar none, world-class.  We’re going to set standard quotas and ramps and knock this sonofabitch out of the park.  I’ve done this before, I’m matching the patterns, trust me, this is going to be great.

Translation:  we’re going to hire somewhere between 4 and 8 salespeople who I have worked with in the past and who were successful in other companies regardless of whether they have expertise in our space, the skills required in our space, are located where out strategy indicates they should be.  Oh, and since I know a great pharma rep, we’re going to make pharma a territory  and even though he moved to Denver after living in New Jersey, we’ll just fly him out when we need to.  Oh, and the SDRs, I know a great one in Boise and one in Austin.  Yes, and the inside reps, Joe, Joey, Joey-The-Hacksaw was a killer back in the day and even though he’s always on his bass boat and living in Michigan now, we’re going to hire him even though technically speaking our inside reps are supposed to be in SF.

This, as they say in England, is a “dog’s breakfast” of  a sales model.  And when it doesn’t work — and the question is when, not if — what has the company learned?  Precisely and absolutely zero.

If you’re a true optimist, you might say we’ve learned that a bunch of random decisions to hire old cronies scattered across the country with no regard for strategy, models, or hiring profiles, doesn’t work.  But wait a minute — you knew that already; you didn’t need to spend \$10M in VC to find out.  (See my post, If We Can’t Have Repeatable Success Can We At Least Have Repeatable Failure?)

By making the model clear — and quite specific as in my example above — you can not only flush out any disagreements in advance, but you can also hold the sales VP accountable for building the model they say they are going to build.  With a squishy model, as my other example shows, you can never actually know because it’s so vague you can’t tell.

This approach actually benefits both sides

• The CEO benefits because he/she doesn’t get pushed around into agreeing to a vague model that he/she doesn’t understand.  By focusing on specifics the CEO gets to think through the proposed model and decide whether he/she likes it.
• The Sales VP benefits as well.  While he/she loses some flexibility because hiring can’t be totally opportunistic, on the flip side, if the Sales VP implements the agreed-to model and it doesn’t work, he/she is not totally alone and to blame.  It’s “we failed,” not “you failed.”  Which might lead to a second chance for the sales VP to implement a new model.

## Book Review:  From Impossible to Inevitable

This post reviews Aaron Ross and Jason Lemkin’s new book, From Impossible to Inevitable, which is being launched at the SaaStr Conference this week.  The book is a sequel of sorts to Ross’s first book, Predictable Revenue, published in 2011, and which was loaded with great ideas about how to build out your sales machine.

From Impossible to Inevitable is built around what they call The Seven Ingredients of Hypergrowth:

1. Nail a niche, which is about defining your focus and ensuring you are ready to grow. (Or, as some say “nail it, then scale it.)  Far too many companies try to scale it without first nailing it, and that typically results in frustration and wasted capital.
2. Create predictable pipeline, which about “seeds” (using existing successful customers), “nets” (classical inbound marketing programs), and “spears” (targeted outbound prospecting) campaigns to create the opportunities sales needs to drive growth.
3. Make sales scalable, which argues convincingly that specialization is the key to scalable sales. Separate these four functions into discrete jobs:  inbound lead handing, outbound prospecting, selling (i.e., closing new business), and post-sales roles (e.g., customer success manager).  In this section they include a nice headcount analysis of a typical 100-person SaaS company.
4. Double your deal size, which discusses your customer mix and how to build a balanced business built off a run-rate business of average deals topped up with a lumpier enterprise business of larger deals, along with specific tactics for increasing deal sizes.
5. Do the time, which provides a nice reality check on just how long it takes to create a \$100M ARR SaaS company (e.g., in a great case, 8 years, and often longer), along with the wise expectations management that somewhere along the way you’ll encounter a “Year of Hell.”
6. Embrace employee ownership, which reminds founders and executives that employees are “renting, not owning, their jobs” and how to treat them accordingly so they can act more like owners than renters.
7. Define your destiny, which concludes the book with thoughts for employees on how to take responsibility for managing their careers and maximizing the opportunities in front of them.

The book is chock full of practice advice and real-world stories.  What it’s not is theoretical.  If Crossing the Chasm offered a new way of thinking about product lifecycle strategy that earned it a place on the top shelf of the strategy bookcase, From Impossible to Inevitable is a cookbook that you keep in the middle of the kitchen prep table, with Post-It’s sticking out the pages and oil stains on the cover.  This is not a book that offers one big idea with a handful of chapters on how to apply it.  It’s a book full of recipes and tactics for how to improve each piece of your go-to-market machine.

This book — like Predictable Revenue, The Lean Startup, Zero to One, and SalesHood — belongs on your startup executive’s bookshelf.  Read it!  And keep up with Jason’s and Aaron’s great tweetstreams and the awesome SaaStr blog.

## Stop Making the #1 Mistake in Presentations

Ever hear this story?

VP of Sales:  “Hey, how did the sales training on the new presentation go?”

VP of Marketing:  “OK, well, you know, pretty good.”

VP of Sales:  “Why are you hemming and hawing?”

VP of Marketing:  “Well, I could tell they didn’t love it.”

VP of Sales:  “Do you know why?  I do.  They told me it was a great looking set of slides, but it felt more like an analyst pitch than a customer presentation.”

What’s gone wrong here?
It’s simple.  Marketing made the #1 mistake that managers of all ilks make when it comes to creating presentations:  they start with what they have — instead of starting with what’s needed.

What does that mean?
Marketing probably just came back from a few days of analyst briefings and when they needed to make a revision to sales presentation, they re-used a bunch of the slides from the analyst deck.  Those slides, created for analysts, talked about company strategy, positioning, and messaging.  Customer slides need to talk capabilities, benefits, and customer testimonials.

The slides, never designed to be used with customers, are thrown into a deck, and marketing feels great and super-efficient because they’ve re-used materials and presumably even increased message consistency in the process.  #wow

But it’s a #fail.  They broke the first rule of presentations:  it’s all about the audience.

Know thy audience
Presentations are all about the audience.  The first step in creating any presentation should be asking:  who I am speaking to and what do I want to tell them.

It’s not about you; it’s about them.  Which brings to mind one of my favorite quotes from Frank Capra, director of It’s a Wonderful Life.

“I made mistakes in drama. I thought drama was when actors cried. But drama is when the audience cries.”  — Frank Capra

While I started with a marketing example, this isn’t just a marketing problem.  Here are some other favorite examples:

• Making a board presentation from an operations review deck.  Yes, they both have a lot of data and analysis about the business, but the ops review deck is created for an audience of your peers, for people who want more detail and who are far closer to the daily operations of the business.  One great way to hang yourself in a board meeting is to paste a bunch of slides from your ops review deck “to save time.”
• Making one sales presentation from another.  This might work if the two customers have a lot in common, but if they don’t it will be a disaster.  My favorite quote here comes for a story about an Atlanta-based salesrep who kept referencing Coca Cola to Delta Airlines.  “Stop telling us about Coke.  We are Delta.  We fly airplanes.”
• Making a product introduction presentation from a product management presentation.  You instantly doom yourself to feature-itis.
• Making a vision presentation from a sales presentation.  Sales presentations about motivating benefits and differentiation.  Vision presentations are about what’s wrong with the status quo and how to fix it.
• Making a roadmap presentation from a product planning deck.  Not only will you forget to pad the dates, but you will likely end up turning your product vision into a laundry list.

I could go on and on.  But the key mistake here is simple.  Instead of starting blank-slate with what’s needed based upon the audience, you start with leftovers.  What you have lying around from a prior presentation or meeting.