This Sales Plan Moves the Needle on Every Success Metric

This Sales Plan Moves the Needle on Every Success Metric

Derek Draper builds high-performance sales teams. His secret: a documented, bulletproof plan broken into stages and actions.

“Building a sales team is like running a kitchen that has to produce 100 chocolate cakes a week,” says Derek Draper, Co-founder and CEO of Pattern (as you'll find, he's a fan of analogies). “You hire a head or VP of sales to be your top chef, and they hire a bunch of reps to be your bakers. Only in sales, I feel like we're constantly sending people off to their work stations without a recipe or even a picture of what we want the cake to look like. If you ran a kitchen this way, it'd be a disaster. You'd end up with all kinds of inedible cakes that looked entirely different. This happens all the time on sales teams — deals fall apart, customers churn, targets get missed — all because there's no recipe.”

Formerly VP of Sales for Wildfire and an Ops Manager for Google[x], Draper has managed teams of hundreds of reps and seen the transformative power of an effective sales process firsthand. The recipe he suggests is backed up by real-world research from CSO Insights, showing that upleveling your sales process like this can have a significant positive impact on key sales metrics, including:

  • Reps’ understanding of your customer’s buying process (+24% on average)
  • Reps’ ability to focus on the right accounts (+10% avg)
  • Total sales rep turnover (-4% avg)
  • Percentage of reps beating quota (+13% avg)
  • Win rates on forecast deals (+11% avg)
  • Annual sales revenue (+12% avg)

In this exclusive interview, Draper shares exactly what this multi-stage plan looks like — and boy, does it get granular. It even includes questions that should be asked during each phase of a deal. You'll learn how to customize it to your own needs and train up reps as you bring them on. “After having  been both a VP of Sales and a founder, it's clear to me that it's never too early to think about sales process,” he says. “Things will change over time, but the minute you hire that first salesperson, you want them to know there's a recipe.”

Why You Need A New Plan

“By and large, no common language or standards exist for the way sales teams communicate,” says Draper. “You may have split your pipeline into different stages, but without firm definitions, those stages will mean different things to different people — which makes reporting, coaching and forecasting way more difficult.” An oft-used sales joke is that common process tends to be:

  • Show up
  • Throw up (just start talking about company and solution)
  • Demo (can’t wait to tell you about my product!)
  • Harass (are you going to buy or what?)
  • Close (offer a discount in order to get a deal done by EOQ)

When this is the case, performance becomes hard to measure and improve. “You grab onto the same old metrics like how many calls people are making and how many meetings they're taking. If people are working hard but you’re not seeing the results you want, it's impossible to know where to intervene. You end up giving people more time to figure things out, until it's too late.”

It doesn't help that new hire sales training is often done via “oral tradition” instead of clear documented instructions and expectations. In the early days of Wildfire, training consisted mostly of a first-day presentation and listening in on a couple calls with account executives. This is what he still sees at many tech companies, but it's a failure mode.

“Just because someone has past experience selling doesn't mean they'll know how to sell your product,” he says. “The process, the stories, the buyer personas, the questions you need to ask to qualify them — they're all different depending on what you're doing.

Too often, we expect people to learn by osmosis, hand them a phone and tell them to bring us some customers.

Buyers are less predictable than ever before. “In the not too recent past, salespeople were customers' main conduit for information about most enterprise products. They could pick and choose what to share,” says Draper. “Now with so much information at their fingertips, buyers are often well-informed about a given product before they ever engage with a salesperson. Consequently, sellers need to transition from being information providers to a new role of being value-added consultants in order to succeed. Demonstrating that your product can help solve critical problems for a given customer is vital.”

To adjust to this new reality, many reps end up following customers' leads rather than leading the process themselves. “They'll jump into a demo as soon as a customer requests one without understanding enough about the business,” he says. “More time should be spent on qualification and discovery — helping clients articulate their problems so we can craft the right solution for them. Otherwise, deals can look super promising and then evaporate at the very end.”

For all the reasons above, sales forecasts are seldom accurate. Pipeline visibility tends to be opaque at best, because without a rubric for standardization, it’s incredibly difficult to determine where each deal is in the process. One of the most common symptoms of this lack of visibility is the “hockey stick” — where some businesses close up to half of their revenue target in the final few days of the quarter.

When you’re the VP of sales and your team is 50% of their way to target with two days left, your ability to create leverage is limited. That's when less than ideal sales tactics prevail — offering massive discounts or pulling forward deals from the following quarter. If you’re lucky, you’ll hit your target and then wake up the next day realizing you just torched your pipeline and have to go through the same process all over again.

Diagnose Your Team’s Problems

If you answer 'yes' to any of the following questions in bold, you’re likely to benefit from developing a more granular sales process.

1. Does your sales “process” go no deeper than the names of opportunity stages in your CRM? Is there no common understanding of what those stages are and what reps should be doing during them? “If someone tells you their deal is in stage 3, is it the same as your stage 3? How do you know?”

2. Are you constantly trying to figure out where deals are in process? Are you always hounding your sales team to get this information? “Pipeline meetings can turn into interrogations and witch hunts — kind of like having your bunk inspected in the army. People feel like they need to put on a display for their manager. They fudge the details and present one-sided data. It's hard to know where to jump in and be helpful.”

3. Are a lot of prospects “going dark” and dropping off in later stages of a deal? Everything can seem promising and then suddenly implode. When this happens, it generally means really important steps were skipped early on in the sales process, typically relating to discovery. If you’re not doing a good job understanding your customer’s pain points, you’re missing a big opportunity to position your solution effectively.

Similarly, disqualifying is just as important as qualifying. If you don't have this attitude, you miss signals. Prospects fade away. You end up investing a lot of time with them for no real benefit.

Good sales people understand that the best performance and productivity come from accurately assessing who's willing or likely to buy.

4. Are your reps bad at estimating when a particular deal will close? Reps are overly optimistic and buyers often don’t think about all the steps involved to getting to a signed contract. Too often reps are accepting the overly-optimistic timelines they get from buyers and then deals don’t come through “on time.” Groups internal to your customers like legal, procurement, etc. pop up out of nowhere and drag the process out much longer than anticipated.

“Working with buyers to outline the entire buying process from the beginning will help illuminate the actual time and steps necessary to achieve a successful deal close. As a salesperson, you sell your product a lot more often than your customers buy, so your job is to help educate them on the most effective and efficient way to navigate the purchase process,” says Draper.

5. Is the process of sales forecasting a miserable experience? Does your sales forecast have you sweating bullets? “Most sales forecasts are based on really incomplete CRM data," says Draper. "So, as a VP of sales you’re in the position of spending a herculean amount of effort to track down every detail of every deal or you’re left with an incomplete untrustworthy picture of reality." Neither choice is palatable.

“More than once I’ve been through the miserable situation of staring at my sales forecast not really knowing what to believe and then having to walk into a board meeting to tell our investors that we’re confident we’re going to hit our number this quarter. After having lived through those moments, I can tell you there is a better way.”

Uplevel Your Process With This Stage Management Template

After working with the consultant, Draper and his team created the following sales Stage Management Guide for the Wildfire sales team:

You can download it as a PDF here. Implementing this process has proven impact — it leads to the positive changes enumerated above. Of course, this is not meant to be a one-size-fits-all solution for every startup. But it is a solid starting place that you can customize to fit your needs. Here are Draper's step-by-step recommendations for doing that.

1. Map out your customer journey as objectively and comprehensively as possible.

First, go back and dissect a few very successful sales you recently made. Identify the milestones and key turning points during that process. Who was involved on both sides? What was the timeline? They don't have to be your biggest deals. Your should also map out successful deals that came together quickly, or that left customers extremely happy.

“Cherry pick so you're looking at a combination of deals that fits what you want the future to look like,” says Draper. “Then reverse engineer the important moments: How did they find you? Who at their company was interested? Who did they need sign-off from? How many meetings did it take? Did you have to get IT involved? When did that happen?”

As you see commonalities between deals, you can start to pattern match and recognize how your product is likely to be bought, he says. Maybe it's clear a free trial helped. Maybe a demo earlier in the process made the difference. Note all this down to determine what your best progression of stages looks like. Using the milestones you identify, outline your ideal go-to-market and deal length (including the target length of each stage). Of course it will vary, but this will become your core recipe.

2. Define the key milestones of your process (and your customers’).

As sellers, we should never forget that buyers are going through their own process and we always need to be cognizant of that. It’s all too easy to create your ideal (likely over complicated) process and begin to push your buyers down that path which will result in a poor buying experience.

While it’s critical to define your key milestones (stages) for internal understanding and communication, it’s helpful to relate those stages to what your customers are going through.

For example, at Wildfire, Stage 1 internally was Qualify but from our customer’s perspective, it was “Initial Interest.” An eager seller following the process with gusto might be hungry to qualify a new prospect out of the pipeline without really realizing that prospect might be a really great customer if only they knew a bit more about how your solution might help them. Rather than trying to rush through the sales process, remember you’re there to help your customer through their buying journey, not to push them through your process.

The stages in your sales process are going to differ based on how your product is bought / sold but common stages look something like what you see in the Stage Management Template.

“There is an ideal process for your product to be bought just as there is an ideal process for it to be sold. Those two processes are going to be different but our job as sales leaders and salespeople is to align them as much as possible.”

3. Fill out your Stage Management Guide with questions, activities, gives and gets.

You can see how this looks in the chart above. For this step, it's very important to more members of your team involved to brainstorm the best approach to each stage.

“The best process will be the one your team believes in and actually uses,” says Draper. “Managers who come up with ideal process and push it out top-down are always met with skepticism or apathy. Your reps are the ones with actual front-line knowledge about how things should work.”

Assign each stage in your sales process to a small working group of 2-4 people led by someone with a proven successful track record. They should take a pass at fleshing it out. Depending on how big and stratified your sales team is, some people will be more responsible or active during different stages. For example, sales development reps (SDRs) are mostly involved in qualification. So you might want to put a junior SDR, an SDR manager, and an account executive (AE) on the team defining that stage.

For companies that are just getting started with sales, involve key stakeholders like the founders, the VP/Head of Sales and one or two front-line people (AEs, SDRs) if you’ve got them.

After these breakout groups have done their homework, get everyone together to evaluate the stages in sequence. You want to make sure the process seems continuous and smooth without overlap or too many handoffs to different people. Remove any duplicate questions or activities, and make sure it catches everything in the outline you created in step 1.

4. Make your plan core to your culture.

As a manager, take the final document coming out of this meeting and polish it up. Put it in a format that's clear, visual, and easy to reference. It's important that people see the plan as a method to discourage rushing and corner-cutting.

“This document should become the single most important resource for your sales team,” says Draper. “Make it clear this is the case, and suggest that people find a way to work the process into every sales conversation they have.” At Wildfire, Draper’s team created laminated copies that were handed out to each salesperson for quick reference.

Remember, it's very easy to over complicate this task. Less is more. If you feel like your plan is getting too extensive or cluttered, consider creating a pared down version with only the critical nuts and bolts that lives on people's desks, and a more detailed version that lives on your wiki or in some other central repository for use in training. For example, include the “questions to ask,” but maybe not all the “resources” you've devised.

The goal here is to have a map that your sellers can use to navigate through the jungle that is a sales deal. The map is also really helpful for managers to quickly jump in and assess where a given deal might be in process and how to help keep momentum going in the right direction.

In summary:

  • Map out your ideal timeline using past deals for pattern matching.
  • Create internal and external stages with concrete names and a sequence.
  • Break your sales team into small groups to devise the best approach to each stage; put the most talented or successful salespeople in charge.
  • Groups list all the questions that need to be answered before you can progress to the next stage.
  • Groups enumerate all actions/activities that should be done during a stage.
  • Groups inventory the resources they both need to give to and get from customers at each stage.
  • Meeting is called to de-dupe and smooth the full sequence of stages.
  • Manager or head of sales polishes up and creates a handy reference document for the entire team.
  • Leadership sets expectation that this document is the “gold standard” for selling your product and it should be consistently followed to give the team its best chance at success.

Needless to say, your plan should be open to iteration as you get feedback from more customers or learn from new experiences. Make the concept of the plan sacred while keeping the content flexible. Re-visiting your sales process every quarter or two to consider or make changes isn’t a bad idea.

Why This Plan Works

The key benefit of this sales process is that it creates a common language for your entire team around how you qualify, manage and close deals. When everyone in your pipeline meeting understands exactly what a stage 3 deal is, you can spend a lot more time ideating ways to move deals forward and less time hunting for clues to determine what’s actually going on. This makes it a lot easier for managers to ask about the progress and status of deals, and for managers or more experienced reps to jump in and help when needed. But there are a few other major advantages:

You enforce a much more consultative sales culture.

“Today, if you're going to succeed at sales, you have to invest the time understanding customers' problems and finding a way to map your solution to what they need,” says Draper. Rushing through the process simply because a buyer asks about pricing or wants to see a contract rarely works out well.

As he puts it, sales reps never see themselves cutting corners if they have no idea where the corners are. A solid sales plan establishes them. “It sets an expectation that certain milestones should be achieved before moving a deal forward. Reps like to take shortcuts or jump ahead because, generally speaking, they're optimists.” But this means they often don't do a thorough job in the early stages which means a deal is more likely to fall apart in the end.

Salespeople believe when someone tells us they want to buy, they're going to buy. A central process makes sure we don't skip the steps in between.

It's easier to train and coach your team — and assess their performance.

With a plan, you suddenly have the ability to 'coach to stages.'

“If I'm a manager in a pipeline meeting, I might say, 'Hey, Brenda, what's the status of the Acme deal?' She could respond, 'Okay, well I'm at the Validate stage and here's what I've done so far' while referring to the questions and activities on the Stage Management Guide,” says Draper. “If things aren't going well, it's much clearer why. I could ask her to back up to the Discovery stage to make sure everything went well there. I could ask her exactly how the client was responding to qualification questions — it gives a manager a lot more insight and latitude to reinforce best practices.”

This is much better than people touting the fact that a client already asked for a demo without any visibility into what got them there. If things go sideways after that, diagnosing the issue is much harder. Having a sense of what should and has happened during each stage also makes it clear where unsuccessful reps are falling short.

Forecasting becomes far more standardized.

Without a defined rubric, sales teams default to gut-based forecasting, Draper says.

Rather than trying to spend cycles to understand how each of your reps and managers calibrate deals, simplify things by establishing the “standard” (Stage Management Guide) and push reps to defend why deals are in a given stage. If they can’t justify why a deal is in a given stage, help them figure out which stage is appropriate and adjust your forecast accordingly.

If your reps are following your process correctly, they should also be mapping out the timeline for each deal with the customer so their forecasted close dates should be more accurate by default.

The qualification stage of your process is mission critical. When you have a complete and probing list of questions you have to answer in order to move a prospect past this stage, deals emerging on the other side are much more likely to close.

At the same time, if you've measured out how long each stage should take if steps are followed pretty closely, you can more consistently and accurately predict when deals will close.

Reps feel empowered and supported.

“Joining a company as a salesperson is always daunting no matter how experienced you are,” says Draper. “Learning from experience always feels too slow. Getting a process like this is like getting a map and a machete before heading into the jungle. You can make it through without those things, but it's a lot more painful.”

Having a defined plan is a distinct advantage for a young, less experienced team. It gives them the confidence that they're learning skills they'll use throughout their careers. For more seasoned salespeople, the exercise of breaking a process into manageable chunks has opened up new opportunities to be creative, leverage existing skills and learn new ones. They can also trust their less experienced colleagues more, which takes a weight off their shoulders.

Train Your Team to Internalize the Plan

At Wildfire, the sales plan became gospel largely because of the training program designed around it.

At onboarding, every new member of the sales team received their own laminated copy. Their first week was devoted to drilling them on the stages that had been hashed out, and what the ideal steps were within each stage. Examples were provided and lessons from failures discussed. But this was just the beginning.

The process was also front and center in all pipeline meetings and one-on-one coaching sessions. Managers were instructed to use the specific language on the document to coach their teams and assess deal progress. “It became very clear that if we didn't do this, people would quickly revert back to their old habits,” Draper says. “It was important for managers to carry the plan with them everywhere and use it in almost every deal conversation.”

Keep in mind that training doesn't work if it's super didactic, or if people are made to feel like they have to follow the map you've handed them 100% to the letter. In fact, Draper says, a lot of training should build in the concept of iteration and personal agency. There are two ways he's seen this work:

Put the top performers who helped define the stage of your plan run the training on that stage. That way they feel empowered to talk about why they came up with it the way they did based on experience, root causes for their recommendations, how it looks to execute on the plan in real life, and where there's room to improvise or break from the script. This also helps keep top performers continually bought into and excited about the plan.

When people break into the top performer bracket on your team, take them aside and say you want their help making sure the plan in place is the best one possible. If they see room for experimentation or a new approach, they should use their judgment and take it, as long as it remains customer-centric and thorough. When something different works, they should report back so the plan always keeps improving.

“As a manager, you actually don't want your process to be followed perfectly every time,” says Draper. “That's how you end up losing people because they're work feels stale, and it prevents you from evolving as your market or customers evolve.”

Deals are snowflakes. No two are the same. You have to trust your salespeople to adapt based on their familiarity with the terrain.

As a rule of thumb, be lenient with your top performers and stricter with new hires. You'll be surprised how grateful everyone will be for solid guidance, no matter how senior they are.

“Salespeople in this industry deserve better tools,” Draper says. “So many of them have this impressive raw, natural talent, but they're constrained by uncertainty, inexperienced teammates, lack of knowledge about a product or market. By putting in the effort, startups can easily do better by their people, unleash their capabilities, and profit at the same time.”

Art by John Shepherd/Getty Images Plus/Getty Images.