Learn to Fly

Setting up Revenue Enablement

Same Old Song and Dance

One area that early stage Revenue leaders know is important but typically falls down the list is enablement.  When faced with sky-high priorities, like closing deals and managing pipeline, it feels like enablement can wait one night.  And defining it adds another complication: what is enablement?  The word gets tossed around but not everyone’s sure what it includes or where to start.

So, what is enablement?  It flies well beyond training alone, although training and resources are the most common focus areas.  Lesser known are the processes that facilitate sales—like lead conversion handoffs—and systems—such as your CRM.  The devil’s in the details, but here are the basics:

  • Training: onboarding plus ongoing training, weekly, monthly, quarterly, and annual training is needed.  Add in one-offs, like when your company introduces a new product.
  • Resources: like sales decks, reference materials (ex. product info), one-pagers and other leave-behinds for prospects. 
  • Systems: your CRM and other tools in your tech stack, most frequently used areas or functions, system updates, and internal changes to systems (like custom fields or automation).
  • Processes: the most common steps that tie everything together across the Revenue team.

Your entire Revenue team benefits from getting a solid system in place.  They’re out there fighting to grow the company, but they can’t quite make it alone.  Skills atrophy over time – for example, studies show that trained sales reps behave like untrained reps after 90 days if not retrained.  In other words, your team will burn out bright if you don’t have a comprehensive enablement program.

A Change Would Do You Good

No need to look to the sky to save you.  Here are some ways to get your enablement program to take off:

  • Training: Determine the most important competencies for each role within your Revenue team.  Be specific and set a timeline for achieving it.  An example for new sales reps is to be able to do a 30-second pitch on your company within the first 30 days of hire.  Remember to add in a skills progression that leads the learner to the goal in a smooth way.
  • Resources: Put them in one place, like a shared folder.  Make sure everyone can access them and knows where they are.  Bonus points for working with your Marketing content manager, if your company has one, to ensure that your resources feature the company’s latest branded assets.
  • Systems: Review your most common motions, like moving deals through the pipeline stages.  Check that everything works the way you’ve asked your team to do it, and that it’s getting done correctly across the team.  There might be easy disconnects to fix.
  • Processes: Getting started with process documentation
  • Tip: Don’t forget to set up a cadence for reviewing your training, materials, and processes at least once a year – many will get outdated before you know it.

What’s My Age Again?

Why Deal Aging is Important

Same Old Song and Dance

Few things worry B2B revenue leaders more than pipeline management.  Of the 182 things leaders need to do each week, it’s one of the more difficult: dozens of deals, all with varying amounts and in different stages, all sitting at future dates on the calendar.  Collectively, it’s supposed to represent the Revenue team’s ability to hit their sales number that year.  But when looked at more closely, what’s in the CRM might not be as mature as it appears.

Sadly, many of those deals could be as phony as prank phone calls.  Savvy leaders know that a good portion of what’s in the CRM can and will disappear in the blink of an eye. True, there are many things that can affect a B2B deal as it moves through pipeline stages.  So which deals are here to stay, and which are about to walk away from you? 

One of the best ways to tell is to check the deal’s age.  Older deals aren’t necessarily better.  The reason comes down to simple human psychology: loss aversion.  Sales reps tend to hold onto deals too long because the thought of “losing” them—closing them out and letting go of the possibility and the pipeline they represent—is more painful than just leaving them there.  For reps, it’s better to push the deal out to a future parking lot date and hope that it doesn’t come up in the weekly pipe meeting.  Maybe the extra time will help it close, right?  Actually, time works against deals closing past a certain point.  This is why when companies get around to doing loss analysis, it’s common to discover that the average age of their Closed Lost deals is 1.5x-2x longer than for Closed Won.  

A Change Would Do You Good

Nobody likes it when the pipeline is aging out.  Here’s how to check the expiration date:

  • Calculate age: if you have a RevOps or SalesOps team, have them determine your average deal cycle length.  Bonus points if they can tell you the average time in stage for each of your deal stages.    
  • Estimate age: if there aren’t enough deals to calculate an average, estimate the length by talking to your more experienced sales reps (get a directional idea based on specific deals) and then validate how long those deals took by checking the CRM.
  • Check age against stage: a deal should progress through the stages over time.  Stuck deals are typically a yellow flag, if not a red one.  Deals that sit in your first or second stage of a multi-stage deal cycle are almost surely a sign of bad pipe.
  • Set up an aging deals report.  Most CRMs have this out-of-box.  You can regularly check to see which deals are past or approaching your average Closed Won deal age.
  • Set time limits: since time kills deals, put a time limit on prospect responsiveness.  If they don’t reply or signal that they want to move the deal forward within the timeframe you’ve set (say, 30 days), move the deal to Closed Lost. 
  • Bring it back: after you’ve closed out that old deal, set up a nurture track to check in with the prospect at a better future time (like in 90-180 days).  You can always reopen the deal later if it makes sense.
  • Tip: As a leader, make it ok for your team to move deals to Closed Lost.  Put the word out to your reps that you’d rather have them get the aging deals out and focus on the deals that can close.  Reinforce this by recommending that they close out deals that pop up on the aging deals report.   

Feels Like the First Time

Getting Started with Process Documentation

Same Old Song and Dance

One of the core functions of RevOps is to streamline processes and drive efficiency across all groups in the Revenue organization.  For early-stage companies, this means establishing a baseline of operations and more importantly, getting the steps on paper.  As unsexy as the idea of documenting processes is, you can’t wait a lifetime to do it.

If documenting processes seems like a foreign concept, you’re not alone: many revenue leaders of early-stage companies believe that processes are for big companies.  Putting processes in place now will slow things down, making the company less flexible.  It’s a common enough myth that it often prevents leaders from documenting even basic processes. 

Ironically, the truth is the opposite: not putting processes into place causes more problems than doing so.  For example, having recurring issues with key areas, like communicating across departments.  Until you establish a baseline process, you’ll repeat the same mistakes or reinvent the steps each time you do it.  For core processes—those activities across the business that must be done consistently for the business to succeed—having to come up with new ways daily, weekly, or monthly will exhaust your team.  It might also lead to preventable and potentially disastrous results with morale and customers.

A Change Would Do You Good

If it feels like the first time you’re doing it, here are some ways to approach documenting processes:

  • Create a template: include the basics that will be a part of every process, regardless of how complicated it is or which department owns it.  General go-tos are Who, What, When, and How (the steps).  Include an example or two.  Share the template in an accessible place, and make sure everyone knows that it’s there and the expectations around using it.
  • Create a repeatable process: yes, even processes need a basic process for doing correctly.  Outside of the basic template, offer a structure for making sure that the How section is simple to create.  This is especially important for those who are new to documenting processes.
  • Document the first process: your first process should always be how to document processes.  This sets the tone for what right looks like and makes the exercise scalable across your teams.  RevOps can open up the door for Revenue and then assist others as needed. 
  • Provide training and support: offer some initial training and support from your RevOps team to other departments.  While outside the scope of Revenue’s need to document its own processes, it’ll help create consistency across the company, including the processes that overlap with Revenue’s.  It’s also good for inter-departmental relations, meaning that it could help your company work together like it never did before if done right.
  • Tip: The best process structures have a validation framework that verifies the process is complete.  Typically, these frameworks follow a “Do, Document, Communicate” loop format.  See if you can come up with one to validate your processes as you build them.

Who Can It Be Now?

Finding Your First RevOps Hire

Same Old Song and Dance

Revenue leaders who are lucky enough to set up a RevOps team often don’t know who to bring on as the first hire.  Whether hearing about RevOps for the first time from a board member or having worked with RevOps teams in prior roles, the leader might not be sure where to start. 

It’s no surprise: women and men at work in RevOps today were most likely doing other things even recently.  The concept evolved over the past decade or so.  It started out with a much smaller scope, often sitting within Marketing or Sales groups and focusing only on external customer behavior and insights.  Those groups then gradually added internal elements, such as process improvements, training and enablement of the team, and analytics in key areas like deal movement.  From there, it was easy to expand to all groups within a company’s revenue team.

Now, RevOps often spans diverse areas like data analysis, KPI tracking, process improvement, CRM and tech stack ownership, and team enablement across many connected but different groups.  Just thinking about covering all of that can leave leaders very tired and not feeling right.

A Change Would Do You Good

Before those feelings come again, here are some ways to think about getting started:

  • Follow the trend: now that RevOps roles have become mainstream, there are a couple of more common paths:  sales or marketing analysts and FP&A analysts appear to be the most frequent.  Project managers are also joining the mix due to the process portion of the job.
  • When those candidates start knocking at your door, here are a few vital qualities and skills to uncover with behavioral interview questions:  
    • Analytical: anyone in RevOps must be able to make sense of the data, get answers that lead to good decisions, and advocate for change based on facts
    • Driven: along with analysis, RevOps team members must drive for results and get things done, both alone and collaboratively
    • Service Mindset: all of the work RevOps does is in support of others; their customers are inside the company, essentially everyone whose work improves because of the analysis RevOps does, the systems RevOps helps put in place, and the processes and improvements RevOps makes
  • What to focus on first? At its core, RevOps will always need to track KPIs, do data analysis, and improve processes.  Look for those abilities in your candidates first.  You can always bring on specialists for CRM administration and enablement once you’ve established a solid foundation. 
  • Tip: Don’t forget about fractional options.  There are experts out there who have skills across all of the areas you need, but who will cost you less because they accomplish your initial needs in less time.  These are great bridge resources to get you started.

Even Flow (Part II)

Pipeline Flow Across Deal Stages

Same Old Song and Dance

Sales leaders in complex B2B selling environments know that it’s not enough to know how much pipeline they’ve got. They also need to know how the pipeline got to that point. What changed in the last week, month, quarter, etc? Which deals increased or decreased? Which ones pushed? How about stage changes?

Having these pearls of knowledge at their fingertips will make managing pipeline much easier for sales leaders. Not knowing will put them in a jam. Fortunately, the changes are straightforward and limited in number, making them easier to deal with than, say, a pillow made of concrete.

There are eight things that can affect a deal’s amount and timing as it flows across deal stages between two calendar dates (ex. last Friday to this Friday). I call these the Eight Deal Stage Changes (DSCs). The Eight DSCs are similar to the Seven RPCs, but with one addition:

  1. Created: The deal was created.
  2. Moved to a later stage: The deal stage changed to a stage further along in the deal cycle.
  3. Moved to an earlier stage: The deal stage changed to a prior stage earlier in the deal cycle.
  4. Increased in amount: The deal went up in value.
  5. Decreased in amount: The deal went down in value.
  6. Closed Won: The deal was won.
  7. Closed Lost: The deal was lost.
  8. Pushed beyond the current FY: The deal remained in the same stage and at the same amount, but the close date moved outside of the current FY. Note: for those reporting in a rolling 4-quarter basis, this may have less of an impact than for those reporting strict FY results.

Tracking each of the Eight DSCs gives tremendous visibility into how the pipeline changes across stages.  And it will give a rolling summary view of when leaders can expect their team’s deals to land during the year.  The sum of the changes in each DSC is the net gain or loss to the pipeline.

A Change Would Do You Good

Here’s how to make sure you’re seeing an even flow of pipeline:

  • Reporting cadence: Determine which time period makes the most sense for you to track.  For example, if you’ve got a fair amount of change in a short time period, like a fast deal cycle or deal amounts that change drastically as deals advance, maybe tracking weekly makes the most sense for you.  One benefit of tracking weekly is that you can cover the largest movements during your weekly pipeline review. Tip: Unlike the the RPCs, tracking DSCs is bit trickier for those with out-of-the-box CRM setups. The reason is that seeing changes in deal stages in CRMs requires automating date/time stamps when deals enter a given stage. Most CRMs hold out this functionality for more advanced (and expensive) enterprise versions. For those not able to make the upgrade in the short term, you’ll need to set it up in a spreadsheet. Either way, set up a Pipeline Flow dashboard that shows all eight DSCs and compare changes between time periods. To see the changes in one consolidated view, create custom fields in your CRM or set up a spreadsheet report that summarizes across the eight (Note: use the spreadsheet as a supplement to your CRM dashboard, which should always come first).
  • Other views: Combine the DSC view with other views, like RPCs, and your weekly pipeline review sessions will have life again.

Even Flow (Part I)

Pipeline Flow Across Reporting Periods

Same Old Song and Dance

Sales leaders in complex B2B selling environments know that it’s not enough to know how much pipeline they’ve got. They also need to know how the pipeline got to that point. What changed in the last week, month, quarter, etc? Which deals increased or decreased? Which ones pushed? How about stage changes?

Having these pearls of knowledge at their fingertips will make managing pipeline much easier for sales leaders. Not knowing will put them in a jam. Fortunately, the changes are straightforward and limited in number, making them easier to chase down than, say, butterflies.

There are seven things that can affect a deal’s amount and timing as it flows across major reporting periods (ex. months or quarters) between two calendar dates (ex. last Friday to this Friday). I call these the Seven Reporting Period Changes (RPCs):

  1. Created: The deal was created.
  2. Moved out to a future reporting period: The close date changed to a later date in a different reporting period.
  3. Moved in from a future reporting period: The close date changed to an earlier date in a different reporting period.
  4. Increased in amount: The deal went up in value.
  5. Decreased in amount: The deal went down in value.
  6. Closed Won: The deal was won.
  7. Closed Lost: The deal was lost.

Tracking each of the Seven RPCs gives tremendous visibility into how the pipeline changes between dates.  And it will give a rolling summary view of when leaders can expect their team’s deals to land during the year.  The sum of the changes in each RPC is the net gain or loss to the pipeline. Note that this is different from tracking pipeline flow across deal stages.

A Change Would Do You Good

Here’s how to make sure you’re seeing an even flow of pipeline:

  • Reporting cadence: Determine which time period makes the most sense for you to track.  For example, if you’ve got a fair amount of change in a short time period, like a fast deal cycle or deal amounts that change drastically as deals advance, maybe tracking weekly makes the most sense for you.  One benefit of tracking weekly is that you can cover the largest movements during your weekly pipeline review. Tip: Each one of the seven can be tracked and reported on via any standard CRM.  Set up a Pipeline Flow dashboard that shows all seven and compare changes between time periods. To see the changes in one consolidated view, create custom fields in your CRM or set up a spreadsheet report that summarizes across the seven RPCs (Note: use the spreadsheet as a supplement to your CRM dashboard, which should always come first).
  • Other views: Combine the RPCs view with other views, like DSCs, and your weekly pipeline review sessions will have life again.

867-5309

Know your industry benchmark numbers

Same Old Song and Dance

As sales leaders in complex B2B selling environments, it’s easy to get caught up in the numbers: revenue closed, revenue to-go, closed lost, pipeline created, pipeline coverage multiples, pipeline per stage and per rep, leads created, monthly, quarterly, etc. Keeping track of it all is hardly a good time.

Luckily, there are reports, dashboards, and (ahem) sales ops gurus to help with that. Gaining visibility into your most important metrics is a great start. But what happens when the new board member, Jenny, asks that all-too-common question: “what’s normal for our industry?” Who can you turn to?

A Change Would Do You Good

Here are a couple of practical ways to make sure you’ve got your number:

  • Experience: For each of your key metrics, think through what you’ve experienced as normal in your industry. What’s the typical ACV? How many months does a deal take to close? How many leads does it take to close one deal? Ask your team or peers if needed. Record industry benchmarks for each metric. Tip: Add benchmarks directly to your CRM dashboards, just like you do with goals. This will keep these important numbers on the wall so everyone can see them.
  • Data: If you have enough historical data, pull this, too. Compare your company to the industry data. Note where you’re ahead and where you’re not, and have honest internal discussions around the impacts of both.

I Can See Clearly Now

Forecasting Your Sales Pipeline

Same Old Song and Dance

Forecasting sales pipeline accurately in a complex B2B environment is challenging: deciding when to start counting deals as pipeline, selecting the correct deal valuation, determining your weighting methodology, sorting through unclear deal stages, and knowing when you have enough forecasted pipeline to hit your number are typical hurdles sales leaders face. Any one of them can be enough to cause your crystal ball to cloud up.

Sales leaders use many methods to cut through the murkiness. One common way is to ask AEs to provide insight. They rate each of their deals according to established criteria, and these forecast categories act like an additional layer on top of deal stages. An example is any deal that the AE believes has a 90% chance of closing in the current month would have a forecast of Commit. That same deal would likely be in a later deal stage, too. The main benefit of this approach is that it allows sales reps to weigh in on how likely they feel the deal is to close. Two clear drawbacks are that a) it can become a highly subjective exercise, even with defined rules, and b) it’s one more field for your sales reps to fill in and update.

Another way is to apply deal amount weighing by stage. This means setting percentages based on actual or estimated close rates (ex. 10% once a deal is qualified, 25% after completing the first demo, etc.), and applying those percentages to each deal by stage. Although it seems like a straightforward way to decrease the value of early-stage deals, the practice isn’t always understood or supported by AEs. Some prefer to change the deal value itself as it progresses through stages. Set weight percentages can also get complicated if there are drastically different close rates for certain products or business segments that require a variety of weights to be applied.

A Change Would Do You Good

Here’s a practical way to help see the future:

  • Look to the past to get more accurate weights: Using a historical measure, such as trailing twelve-month rolling average conversion rates by stage, takes the guesswork out of it. This method relies on actual data, instead of requiring constant input from your reps, or forcing you to choose what would likely end up being arbitrary weights. The best part? Your fortune-telling abilities improve over time: weights will stay up-to-date automatically as you go and better reflect your actual close rates by stage. Bonus points for having your AEs enter a standardized dollar amount for each based on average closed won deal amounts. The removes another layer of subjectivity from the process. Tip: Make sure you have enough data points to calculate a correct average. Too few could cause wild swings in the average.

You Spin Me Right Round

Stop Playing Reporting Roulette

Same Old Song and Dance

It’s not easy to lead an enterprise B2B sales team. In addition to being responsible for hitting the number, there’s pipeline management, forecasting, process improvements, people issues, and a dozen other things to consider. There’s also tremendous pressure to show that things are going “up and to the right” at all times.

Sales leaders often respond by playing “reporting roulette”: they change what’s reported each period based on what makes them look good, instead of what’s really happening with the key drivers of the business. Spinning that wheel like a record may work in the short term, but it’s bound to cause some major skips in performance sooner rather than later.

Here’s why: business is rarely all positive, and the fundamentals of growth don’t change that much. Pretending that you’re in the groove, and showing supporting evidence via dashboards and other reports, might save you today. But savvy senior leaders and board members will soon catch on. Tomorrow, they’ll ask the smart yet simple questions that always cut through the spin, and you’ll still have to answer why your team fell short. Do this enough times and they’ll find someone who will play a more consistent note.

A Change Would Do You Good

Here’s a practical way to keep from spinning out of control:

  • Key metrics: Once you set your annual goals, take some time to lay out the specific, actionable activities that will drive performance. Start with the typical top hits, like pipeline coverage multiples, new deal creation, and deal ACV. Layer in the relevant time periods based on your sales cycle, plus your major products, geographies, and/or business segments. Create a CRM dashboard that shows total performance and as many key metrics combinations (metric plus time/product/etc.) as makes sense to know if you’re on track. Review the dashboards frequently with your team, again as often as makes sense for your deal cycle. Be honest about how you’re doing against your overall goals and the benchmarks for each metric. Finally, spend your time fixing shortcomings in each area instead of coming up with new and clever ways to look at the data. Tip: Review your key metrics every 3-6 months. It’s possible that one or more need to be tweaked slightly or replaced altogether to drive growth more effectively. An example could be realizing that later-stage pipeline is a better predictor of closed won deals than overall pipeline. Make the change, and be sure to communicate the reasoning and analysis behind it.

How Will I Know?

Creating Verifiable Outcomes for Each Deal Stage

Same Old Song and Dance

Complex B2B selling is hard. Multiple decision-makers, weeks or months of conversations, competitive offerings to overcome, several contract terms to negotiate…. So many things can go wrong along the way, even for the most experienced sellers. Keeping it all straight requires designing a sales process with several stages that reflect your internal selling steps and the customer’s buying journey.

But even with a well-laid plan, all of the moving pieces can cause confusion for account execs and sales leaders alike. Which deal stage is correct based on the latest phone exchange, virtual demo, or onsite meeting that the rep did in Houston? When’s the correct time to move something forward in the process, without jumping the gun? How long should a deal stay in the same stage before it’s officially considered stalled (or sings its swan song as closed lost)?

A Change Would Do You Good

Here’s a practical way to confirm an opp’s deal stage:

  • So, how will you know when a deal truly belongs in a given deal stage? Don’t just trust your feelings. Create verifiable outcomes for each stage. A verifiable outcome is exactly what it sounds like: a result that can be validated objectively. A basic example is confirming the next meeting on both sides’ calendars as an indicator of interest following the initial discovery call. Think through the key events that need to take place to move your deals forward, and then align them to your deal stages. Don’t move deals forward to the next stage until you complete the verifiable outcome(s) for the current stage. Tip: Try to define one key verifiable outcome for each stage. That will allow you to align each stage with a single event from your selling process, with the added bonus of being able to automate or semi-automate each stage in your CRM.