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January 28, 2019

While it is a market behemoth today, Salesforce.com in 2003 found itself in a very different place. We had a product considered a toy by enterprises, an enemy by IT, and more expensive by CIOs and industry pundits than on-premise. We had less than 15 account executives with 90% of them focused on the inbound SMB free trial mode that we had pioneered and has just hired our first field sales “experiments”.
As the first head of field operations and strategy, it was my job to partner with amazing people like David Rudnitsky, Brian Millham, Kendall Collins, and Mike Rosenbaum and the broader sales and finance leadership to help define and execute the very first SAAS playbook — ie how do we take roughly the same product to market in every segment of the market effectively (which in the on-premise world had never been done before), albeit with different pricing, packaging, and sales and marketing motions and resources.
To do so we were essentially answering the same question constantly — in what segment/location do we add the next five salespeople to generate the most success. Furthermore, which segments did it make sense to pause on and if so, what was the underlying issue for us to solve? As you flash the movie forward, it turns out in retrospect we were pretty good at doing just that. To do so, we had to become masters in not just defining and understanding our sales process and sales pipeline but also forecasting future performance.
Now almost two decades later, I work across our portfolio companies to implement the very same concepts. My end goal is always the same: for them to develop mastery and be able to not only effectively predict their future sales achievement but also diagnose past performance to help guide their team to identify the key areas to focus on for improvement.
For the myriad of software companies out there, this need is especially critical before you are in mega product fit/growth stage (even more so for the tech product founder) where you are still not comfortable yet in just regularly adding account execs for fear that you may have an underperforming group of people down the road who aren’t hitting their number and resort to saying not so lovely things about you on Glassdoor :)
While there are of course thousands of books you can read, and thousands of podcasts you can listen to, and thousands you can spend on industry/saas gurus, I will attempt to demystify all this as concisely and simply as possible. The good news is that it’s not that complicated and if your organization follows the steps/approaches I will describe, I am confident you will be more successful and more calm in discussing sales with your team and your investors.
For your stages - use your customer's buying stages rather than your team's selling stages.
I can’t tell you the number of organizations that I have worked with who come to me frustrated that their sales forecasting is all over the place. Worse, when I dig in, we find out that there is a completely inconsistent application of whatever sales stages they use by their sales teams.
9 out of 10 times the problem is that the organization has defined their pipeline stages by actions their team has done — ala “gave demo”, “sent proposal”, “provided reference check” and so on. The problem with this approach is I truly don’t care what you have done as an organization to properly codify a deal — I care where the buyer is within their evaluation mindset of your product.
To that end, look to redefine the name of your sales stages as buying stages — ie, understanding offerings, building business cases, running an evaluation process, comparing shortlisted vendors, negotiating a price with the selected vendor, confirming deployment specifics, redlining documents, etc — ie steps your buyer is taking. You should use the appropriate terminology for your buyer and their process. When you start to codify your pipeline this way, you can consistently:
If you do not have a clear definition of a qualified pipeline, your metrics won’t tell you much.
Time and time again, a company’s ability to answer the basic sales performance question (do you not have enough pipeline or do you need to be better at closing it) is a well-educated guess at best because they have yet to define what it is a qualified opportunity and what is not.
It’s understandable — fifteen years ago, we could insist on approaches like BANT ( Buyer, Authority, Need, Timing) or MEDDIC (Metrics, Economic Buyer, Decision Criteria, Decision Process, Identify Pain, Champ) as a justification for whether or not a deal was qualified. But with the rise of the Internet and all the research many people who are way down the totem ladder of responsibility will do, you rarely will find the Glengarry lead — ie someone early in your discussion who has all the money, all the power, and all the pain and resources available to make a decision and move forward quickly.
As such, how do we start to think about what should be a qualified opportunity — ie what I call a SAL — or sales accepted lead. This SAL is the holy grail of qualified pipeline and is the end of the hot lead journey as follows:
From my perspective, if you believe there is a path to an appropriately funded project within the next 12 months for which you are a good fit and the organization does have a compelling event / real pain you address, it’s a qualified opportunity. If you are not talking to someone with purchasing or decision-making power that is fine as long as the person you are talking to has committed to connect you with power during the process.
Your entire organization should understand well what qualified pipeline is and is not and you should be measuring your demand generation engines on this and not leads, especially your marketing organization. There are not many more important metrics to track in your business regularly than the net qualified pipeline you have created within a quarter.
Making the power of Salesforce Forecast Categories Work for You.
With your sales stages now well defined (i.e. mapped to buyer behaviors) and a clear definition of a truly qualified pipeline, you can leverage the true power of Salesforce.com Pipeline Forecast Categories to grok the health and maturity of your pipeline.
There are 100’s of different terms and methodologies used by software companies to define their definition of what is Pipeline, Best Case, Commit, and Closed. In my opinion, it’s best to keep it simple and agree that a sales process is really about moving from Conversations to Funded Projects to VOC Negotiations to Closed Contracts:
From a mapping perspective, I recommend that you map your pipeline forecast categories as follows: all stages that fall within the conversations phase = Pipeline, all those that fall within the Funded Projects Phase = Best Case, and all those that fall within the VOC negotiation phase = Commit. Closed is self-explanatory :)
While allowing you simply to understand at a high level where all your qualified pipeline sits from your buyers perspective (Are they considering, are they selecting, are they negotiating, etc.), it also helps to guide you on where you should focus your sales enablement and sales product marketing/content.
If deals seem to take forever to get from the Pipeline to Best Case (ie funded projects), then you have a top of funnel persuasion problem. If deals stay forever in Commit and you always have slipped commit deals that break your heart, it’s clear you need to look at how to remove all the obstacles you need to overcome to cross the finish line (a quick tip: look at your MSAs, SLAs and PS organizations and offerings first here).
Truly understanding if you have enough pipeline coverage to hit your targets.
If you have followed the instructions I have provided and you now have a well-defined sales process, a well-defined definition of a SAL, and proper usage of the Pipeline Forecast categories, then congratulations! It will be simple to understand if you have or don’t have enough pipeline to make your target for any given period.
If you are an enterprise sales oriented company (ie > 4 to 5-month sales cycle and larger average sales prices), DO NOT add up all of your pipeline in the Pipeline, Best Case and Commit categories. Why? Because very little if any of your deals in the Pipeline Category will close — unless you have tripped the light fantastic and it takes less than 90 days for your buyer to decide to fund a project, run a selection process, negotiate a proposal, agree on an implementation plan, run a marathon backward while wearing a blindfold, and get legal and finance to agree quickly to a contract for an enterprise deal.
Instead, add up all your deals in Best Case and Commit and Closed with close dates in the quarter and that is your enterprise pipeline coverage for that quarter.
My general rule of thumb is that you want that coverage at a minimum to be 3x your financial plan number for that period (kudos for the overachieving rate-busters out there who prefer to use ramped quota capacity instead). Anything less than 3x your target means hitting your number for the period is going to be a struggle unless for some reason most of that pipeline is already in the Commit category.
I will cover this deeper (along with a helpful downloadable template) in another guide but if you find yourself consistently below 3x (Best Case + Commit) , then you need as an organization to elevate the following metric to a top 3 metric for the entire organization — which is amount of qualified pipeline that needs to be created in a given quarter for future quarter sales success.
Leveraging two simple but oh so powerful calculations to understand where best to focus on your sales process.
With a true understanding of both what qualified pipeline is and if you have enough pipeline or not, it’s time to now focus on the second key question on understanding sales performance — how good are you as an organization in closing the qualified pipeline you do have? For that, you just need to calculate and understand two calculations. For each of these calculations, you exclude any deals that have yet to make it to the stage that is your proxy for a SAL — ie I only care about performing the math below on real qualified pipeline.
Close Rate or how good are your teams at converting qualified pipeline to revenue. This is defined as:
Sum of Won Deals / (Sum of Won Deals + Sum of Lost to Competition Deals + Sum of Lost to No Decision Deals).
Generally, as a rule of thumb you want to achieve a minimum of 33% here as out of 3 deals, 1 goes away, 1 you win and 1 you lose. Anything less than 33% means that your organization needs to deliver more than 3x qualified pipeline which can be unhealthy and expensive long term.
It also important to track the two lost categories — if your close rate is being dragged down by Lost to No Decision — this means your org is either doing poor discovery/qualification (i.e. wasn’t really a SAL) or is ineffective at convincing prospects the value as to why they should move forward on a new initiative in which your product will be considered.
If you see a much higher percentage tied to Lost to Competition, then you need to focus your org on driving differentiation and validation more effectively versus your competition. Perhaps identify your top two competitors and make it an organization-wide effort to crush them.
To identify this better, I like to see organizations calculate Win Rate which measures how good you are at beating the competition when a prospect actually buys something. This is calculated as:
Sum of Won Deals / (Sum of Won Deals + Sum of Lost to Competition Deals)
You should look to achieve a minimum of 50% Win Rate across competitors and market segments. Ideally, you would target 66% Win Rate or you winning 2 out of 3 deals that go final. I like to track win rate by market segment, by competitor, and by sales teams.
It goes without saying that for both of these calculations, you should be tracking them by both the sum of deal amounts and the count of deals. The former is the most important. However, calculating deal count ensures you don’t ignore the possibility that you may be losing many smaller deals.
These two metrics are, in my view, corporate-wide top ten metrics to track. Additionally, they are the primary measurements you should use to evaluate the quality and performance of your product marketing output and teams. PMM’s job is to provide the content and messaging to ensure customers want to fund the projects in your category (“If I don’t invest here, I will fall behind”) and when they do, they pick you (“my highest chances of success are with this vendor”). The former is defined by Close Rate (and the minimization of Lost to No Decision) and the latter by Win Rate.
Leverage all we have learned and implemented to forecast like a pro.
I worked for 17 years at Siebel Systems and salesforce.com. I promise I had nothing to do with implementing the concept of a percentage tied to a given sales stage. I had nothing to do with the crazy notion that you then calculate your pipeline by multiplying the sum of the amount of all deals within a stage by a given percentage per stage.
This approach might make sense for a high volume inbound business when you have historically accurate data to apply such math, but for enterprise forecasting, this is pure silliness. You never win 25% of a deal — you either get it or you don’t. When organizations do implement this silly applied math approach, I often see sales leaders often changing the sales stage of a deal backward (even if that’s not where the deal and buyer mindset naturally lies) to exclude the higher calculated amount from the sales forecast — which of course isn’t helping anyone.
So instead, just follow the steps below, and you and your organization will be quickly on its way to forecasting mastery:
Aside from coming up with a more accurate forecast number, you can also create a common language and understanding to the specific paths to increasing that number to do better. For each deal in your given category that isn’t in your forecast number, do the following to try to move them over the finish line as well:
In addition to a more accurate forecast number, you can also provide a rational justification for an upside range by speaking to the excluded from your forecast deals that are in the Best Case and Commit Category.
How to leverage all of this work into effective management and board discussions.
It goes without saying, but if you can forecast accurately and explain concisely where your teams need to focus more going forward, you may be beyond the “hard things about hard things” phase. Go forth and prosper and:
Forecast Well. There is no better contributor to an effective and positive board meeting than forecasting accurately (actually you don’t get credit for forecasting you will do terrible and then actually doing terribly) and explaining with confidence which specific deals are required to hit that number and the upside potential. It also allows you to manage your cash burn better as you can tie your expense and hiring plans to that forecast.
Diagnose Well. Become a professional in calmly explaining whether or not you have a pipeline challenge, a sales conversion problem, or if you actually have neither but just not enough sales capacity. Even better, orient your team’s focus with your “Eye of Sauron” on the biggest needs (pipeline, close rate, and/or capacity). If close rates are good and qualified pipe is good, never be shy to add more AE capacity.
Focus Well. Go deeper in orienting your marketing, product marketing, and enablement on where best to apply resources and money. If your close rates are low, don’t just spray your efforts — understand where in the sales funnel the conversion issues lie. If its top of the funnel — work on business value justification. For the middle of the funnel, improve differentiation and validation. For the bottom of the funnel, improve your ability to negotiate and remove your buyer’s roadblocks.
Many people reached out to really bare their soul around those darn deals that always slip and how best to decide what is truly “Lost to No Decision” versus still alive. Instead of calling them dead, why not just push the close dates farther out in the pipeline as that 1) sure feels better psychically and 2) makes your close rates (as I previously defined them) look better to your board as they are excluded from your denominator. As Chuck put it best, especially for new category creation companies:
“You’ll see deals sit around and move from quarter to quarter in best case. Yes — one should be rigorous about closing them out, but hope (or fear) keep them lingering. And as we know hope (or fear) is not a strategy.”
Here is how I would address slippage:
Understand it - Go look at your deals that seem to consistently slip and ensure that all the deals have been properly codified against the new more rigorous buyer-oriented stages. I tend to see slippage more often in companies that have poorly defined their sales stages and processes because they mistake the actions that their sales team are doing for confirmation of buyer intent and commitment. You should also be rigorous in defining what “Closed-Lost to Decision” means to your company and avoid just pushing the ‘dead” forward quarter after quarter unless you for some reason want an improperly inflated future pipeline. If you have confirmed from a buyer that they are not moving forward with anything (which includes not replacing what they have if you are a swap-out sale), mark it as “Closed-Lost to Decision” and be consistent with the close date you use (either the date you have this information or when it was targeted to close — one could argue that neither of these approaches is precise but whatever path you choose, just be consistent in your approach). For those prospects that just go silent and never respond to tell you if they picked someone or did nothing or fell off a cliff or joined a monastery and took a vow of silence, I don’t know what to tell you — make your best judgment.
Address it — As I have previously discussed, you need to dig into what is driving a lower conversion rate from the VOC Negotiations phase (Commit Forecast Pipeline Category) to signed in-hand contracts and properly prioritize removing the friction and obstacles to the final stages of the buying cycle. For example, I met with a portfolio company this week with this problem. It is a pre-Series A company that sells to large enterprises who, regardless of the company’s size, has a hard time buying products that have not yet solved for GDPR, SOC2, Info Security, etc. My guidance was, other than “fake it until you make it”, was that they had to properly commit to solving for those requirements in their roadmap over the next 12–18 months. For other companies that do not have clear compelling events (i.e. replacing an existing solution whose renewal date is X), I spend time with their sales enablement and product marketing teams to improve sales’ ability to create artificial compelling events often tied to the buyer’s fear of missing out on all the amazing kudos and fame they will get from deploying your solution :)
Account for it — if, despite all your efforts in the two points above, you continue to have significant slippage then I recommend that companies start to calculate an additional form of the close rate calculation that incorporates slippage as follows:
Close Rate = Closed Won / (Closed Won + Closed Lost to Competition + Closed Lost to Decision + Deals that Slipped out of the period).
The difference between this close rate and my original definition will allow you to understand the scope of how big your slippage problem actually is. It will also allow you to understand, especially if slippage is a consistent problem, how much pipeline coverage you would actually need entering a quarter to hit your targets. For example, if your slippage adjusted close rate = 25%, then you would need 4X coverage rather than the traditional 3X coverage most companies shoot for.
That being said, in general, I do not hold marketing and the demand generation engines accountable for adjusting the amount of pipeline they need to create to cover this slippage — in my mind that is on sales to go and clean up. There is one exception — for certain companies, their buyer persona (who looks very much like power and the ultimate decision maker) simply doesn’t have the power to jam deals through procurement and legal. Therefore, instead of shaving your head with a cheese grater and dipping it into ghost pepper oil or questioning the meaning of life and your small infinitesimal role within it (because that is what it feels like when your two big deals that were supposed to close just didn’t because the CXRO or EVP actually have no juice), just recognize that 1/4 of your deals will always slip and as such, you need more pipeline coverage as a company.
While it should have been clear that I was speaking to primarily an enterprise sales cycle, I received questions on what people should use versus discard from my advice for high-volume inside sales organizations. These organizations tend to have sales cycles that are less than 90 days and are more transactional in nature.
What Stays the Same (More or Less)
What Changes (But not Dramatically)
I received some comments that my advice did not apply to those companies that were able to leverage low-friction initial product consumption to drive their success (i.e. think open-source like elastic, freemium like slack, etc). While there are differences, unless these organizations never have account executives (like Atlassian) who at some point do engage to sell something, I would somewhat disagree. I believe that my advice is still relevant, especially for the “go-back and sell something” phase that most of these companies enter into with customers (i.e., the “mium”).
Those business models have replaced the traditional B2B demand generation engines and initial ‘customer’ acquisition cycles with their model of software distribution and consumption.
For companies that are successful at doing this (WARNING: there are many buyers and markets where this doesn’t work), it can be an amazing result: it dramatically reduces your initial CAC, simplifies corporate focus (buzz + strong inbound + amazing product + self-serve experience), and makes your “sales” approach clear — which is to inject people (hopefully at lower costs) appropriately to support the install and initial usage.
The magic continues when you decide to move beyond in-product self-serve purchase and upgrades. There is no mystery on where to direct the army you have hired to go back and upsell the client — you just focus on those accounts that are using the hell out of your product! When that occurs, I believe that if you apply my guidelines to that sales process, most still applies. You are just applying it after the initial customer acquisition cycle. The language that you use to call the buyer stages may differ and your pipe coverage ratios may differ from traditional B2B sales processes, but the music remains the same.