Category Archives: Sales Strategy And Planning

Maximizing Q1

Maximizing Q1

You’ve spent Q4 meticulously working through your sales plan. You’ve defined territories, segmented accounts, set targets, and planned roles. The plan is ready to go. Yet every first quarter, rep productivity is at its lowest. 

At the start of each fiscal year, the sales team is unsure of their patch and their quota. The team is so focused on determining their targets and territories, they don’t spend time selling. And as you hire new reps at the first of the year, ramp time and territory handoffs drain momentum

How can you solve this? 

1. Lock patches down a month before the fiscal year. This gives your reps a month to learn their new territory and prepare to jump into Q1. 

2. Use the balance of the month to fine-tune patch and quota for the year. Using current performance is a great way to determine future goals and ensure growth goals are attainable and easily understood. 

3. If you’re planning to hire more reps in the new year, over-carve territories in the planning phase. This ensures your new reps have a territory assigned when they onboard and you’re not removing accounts from existing reps in the first quarter.

4. To offset unproductivity while your new reps onboard, assign current reps as temporary owners to your over-carved territories. Specifying temporary territory ensures a smooth handoff to the new rep.

5. Define a holdout policy for reps covering patches temporarily.  This ensures reps will be credited for a deal if a new rep takes over an active opportunity, motivating reps to work their temporary territory. It also prevents turf wars and enables you to split opportunities.

6. Anticipate ramp for each role you’re hiring.  Knowing the productivity ramp of each role sets realistic goals to manage target versus attainment for the year. 

Sales planning is a stressful, complicated time. It’s easy to take shortcuts or ignore steps that save time in the long-run. Hopefully, these quick tips are easy to implement into your planning process and give your reps the boost they need to hit Q1 at full force. 

Read more of our tips for sales planning.

It’s 2019, Still Segmenting and Planning in Excel

This article was originally published on the Smart Selling Tools blog on August 27, 2019. You can read the original version of "It's 2019, Still Segmenting and Planning in Excel" here.

I shared an earlier post on LinkedIn about the necessity of fast-growing companies to switch their go to market (GTM) plans to stay in sync with their growth stage. What worked at one stage may not work at the next. The customers you served in the past may no longer be the right fit for you, or your product may have evolved to meet the needs of a different customer tier.

Customers or prospects come in all sizes. Depending on the nature of your business, not every customer is necessarily the right fit. In the initial days of building a company, the relentless focus is on the ICP. The team works together to refine the ICP and find fit. When things click, we find our growth spurt and focus on the repeatability of the sales process. Now everyone is focused on making the horses go faster and rarely do teams go back to revisit the ICP. Why is that? The product has probably evolved, your business model has evolved, and there is pressure to change segments. The effort is entirely focused on going upstream and most companies fail. The recent report from CNBC points to how recently publicly listed darlings have struggled to find fit.

Interestingly, these companies have grown, the fledgling sales team has grown, and so has the supporting ops team. They now have a dedicated sales strategy team, yet they struggle. They struggle because the sales strategy team is disconnected from the world in which the sales team operates. The sales team operates in CRM. But the sales strategy team is planning in Excel sheets with multiple copies and versions. The data in the Excel sheet is always out of sync.  You can no longer use the old ways of segmenting your customers once and allocating your best resources to a static set of accounts.

The current segmentation process in Excel sheets is rigid.

We take accounts, filter them against our current ICP hypothesis, add firmographic, demographic, or employee size segmentation, and put our best resources to go work against them. This happens in Excel and after multiple rounds of reviews, we finally update our CRM with the appropriate segmentation and assignment of ownership. In the time it took us to plan, segment, and deploy, the world changed. The salespeople we planned to have in a role or territory have left.  We've created new accounts. The leadership team has decided to find growth in an ICP not in your original plan, and the board is asking more “what if” questions. Your careful segmentation exercise is stale on day one.

This is 2019. You are still planning in Excel?

Instead, you should move accounts in and out of segments based on more granular data like usage, buying signals, content downloads, etc. You should track and weigh these factors to continuously evaluate the “fit” of an account in the segment.  The data should drive the business rules to recommend moving accounts in and out of segments. Maybe the hot logo account you had in your strategic list switched to the competition. That account should move out of the strategic account bucket, and another account with a higher propensity to close moved in. You may need to flag an existing account with low usage to have more account management love. Excel can't accomplish any of this. This requires us to think of automation.

In a world where we have more data than ever, fast-growing companies can’t afford to let their most critical tasks live in Excel. The horses may run fast with all the ops investment in tools to drive rep productivity, but they may be running in the wrong race or going fast in the wrong direction. It’s about time sales leaders looking to stay relevant stepped up and changed the status quo.

RevOps Metrics

Introducing a Balanced Scorecard for Aligning Toward Growth

This post was originally published by Forbes on August 27th. You can view the original article here.

Recently, I came across a post on LinkedIn from Dana Therrien, practice leader of sales operations strategies at Forrester. It highlighted the growth of the RevOps role with titles like director of RevOps, chief revenue officer and chief sales officer. The growth of these titles is aligned with a movement toward bringing disparate operational teams responsible for growth together, at least organizationally, under one leader -- the chief revenue officer (CRO).

The CRO is geared toward driving alignment across teams responsible for the customer life cycle experience: marketing, sales and customer success. The role has become prominent due to the shift toward the cloud in the tech sector, where winning the deal is only the start of the revenue cycle. After that, the real work starts. You have to earn revenue every day. Folks in traditional service industries like hospitality and retail have always understood this. Your customer wants to know "What did you do for me today?"

Typically, the RevOps leader is responsible for driving the alignment of the operations teams across silos to ensure all operations functions are orchestrated in line with the customer journey. The goal of the ops team is to smoothen the customer journey from the time they first became aware of the service to when they are serviced. I call it a journey from "education to wow."

To help with this transition, I created a framework to measure RevOps metrics. This framework drives alignment across every function in the company in support of the customer, from the traditional marketing/sales/customer teams to product/operations and partners in support of growth and revenue goals.

So, what are the RevOps metrics that indicate alignment is working and every single team is aligned toward the customer experience? Below is the breakdown for the first part of the balanced scorecard for the growth-focused RevOps organization.

1. Revenue Metrics

 Book of business by product/geography: What is the total dollar amount of all opportunities by weighted pipeline for all your products and geographies?

Revenue productivity (LTV /(CAC+CRC)): This will give you an insight into the dollar worth of a customer after adding costs for acquisition and retention

A company generating revenue but not growth is less than ideal. As such, I recommend teasing "growth metrics" separately.

2. Growth Metrics

 Net new revenue/Qtr- Excluding recurring revenue: What is the net new revenue earned or booked /quarter?

SaaS magic number tracking: This number reports what you get in customer acquisition for every dollar invested; for SaaS, if it is close to 75 cents on the dollar, invest in more sales resources

Quick ratio: The net revenue month over month, factoring in churn; the ratio is a better way to compare apples to apples

3. Customer Acquisition

Average contract value: This is your ARR or TCV value

The average revenue per user/customer: This identifies segments that are more attractive than others; it will allow us to invest our best resources in the segment that generates the highest revenue

• Average lifetime value: What is the average revenue if a customer is based on the anticipated length of the contract?

4. Top-Line Key Ops Metrics

Percent of market share gain: This is an important metric to track for more established firms; growing firms should ignore since taking market share from an incumbent is not a priority while in the growth stage; however, if you have multiple players and you are close to series C, then you need to start tracking this

Operating margin: Every founder should track it to find the right segment

 Customer acquisition cost (CAC): What is the total amount spent on all sales and marketing costs (people + tools)?

Every CRO is accountable to these RevOps metrics. In the next part of the balanced scorecard, we will look at the top-line metrics each team should track in support of corporate goals.

Traditionally, revenue metrics are tied to sales. More recently, organizations are looking to hold marketing accountable as well. However, I believe revenue is everyone's business. To that end, in the next part of the balanced scorecard for SaaS companies, we will review the set of metrics to be tracked for growth for marketing, sales and customer success, channel partners, product engineering, and operations.

Read more of Dharmesh Singh's Forbes articles here.

5 Considerations For Buying Sales Planning Tools

Buying sales software is challenging, and buying sales planning software is nearly impossible. Most products only offer one point solution and rarely integrate easily with your day to day tools like Salesforce and Slack.  This graphic from Smart Selling Tools paints the picture perfectly.


There are thousands of tools for sales teams, but very few tools that tackle all the complicated needs of end-to-end sales planning.  Which tool should you choose? We’re here to help you sift through all the tools on the market by offering our top considerations for buying sales planning tools. 

Let’s start by establishing your goals for the sales planning process. When it comes to sales planning, you have three basic goals:

  1. Designing a realistic and accurate plan that is both achievable and optimized for the opportunity you are chasing. To do this, you want to use as much accurate input data as possible
  2. Designing a plan that is understood and agreed on by everyone. You want both top-down and bottom-up analysis
  3. Designing a plan where assumptions are clearly understood and can be validated. You want a plan that is based on a realistic understanding of the sales environment, TAM opportunity, and recruiting market

Based on these goals, let’s dive into the five considerations that make choosing a sales planning tool easier.

1. Your Plan

Let’s begin by considering the process around your sales planning.  How big is your planning group? Is it one or two people reviewing a plan for a small company, or an entire planning team of stakeholders and departments? We’ll cover how to consider collaboration needs later, but begin by asking how many people will be involved in the planning process to give yourself scope.

Secondly, consider how you’ll build your plan. Are you building off an existing plan or creating from scratch? If the plan is existing, what data will you include? Financial, historical, and HR Data?

How sophisticated is your sales plan? Do you plan informally or do you have specific, detailed steps to work through? If you’re looking to move to a more formalized process, create your plan by setting segmentation, role assignment, territory carving, account balancing, ramp hiring plan, and target setting. You can learn more about the 8 steps in this video.

Finally, consider your reporting needs. Will your organization expect you to report on multiple elements of the plan, or simply the final revenue results? This impacts how to collect, aggregate, and display data so be sure to look for tools that report to the detail and metrics you need.

2. Growth and Scalability 

After considering your planning process, the most important consideration is the size, stage, and growth rate of your company and sales team. Growth impacts your plan constantly so you’ll want a tool that enables projections of team size. You’ll hire roles and expand territories throughout the year, so look for a tool that projects growth into your plan, and measures growth as the year progresses. You’ll also want a tool that grows with you as you scale. Any tool that can make planning more automated, repeatable, and measurable year over year will save your team from manual, repetitive tasks each planning cycle. 

Another question to ask around growth and scale is how much you anticipate your plan changing as you grow. What current stage of growth and competition do you operate in and do you anticipate that changing? Will you be doing quarterly or semi-annual adjustments to your plan, or does your plan cover year-round performance? Depending on the stage and size of your company, you may grow and change at a faster or slower rate so look for a tool that matches your rate of change. A more dynamic company will need a more dynamic tool.

3. Data Hygiene 

Bad data costs companies an average of $9.7 million a year - between 15 and 25 percent of revenue. With costs averaging $100 per out-of-date record, every data entry counts.  About 20 percent of every database is dirty, and with database growth around 40 percent each year, more growth results in more bad data. 

When looking for sales planning tools, it’s imperative to consider how that tool not only implements and measures clean data but preserves data hygiene and prevents bad records from growing with your database. This is much easier said than done. Tools used for routing, account hierarchy building, and data enhancement are great places to look when considering how data hygiene plays a role in your sales planning. 

4. Stakeholder Management

On average, 5 departments are involved in the sales planning process, resulting in multiple, individual stakeholders.  HR assists in planning how many sales reps and sales support staff will be hired. Finance sets financial targets. Marketing sets goals for market engagement, product features, and pricing. All these decisions are incorporated into the plan, reviewed, and revised before the plan goes to market. 

Sales planning tools must enable these stakeholders to see current numbers and data, review proposed plans in real-time, and offer feedback transparently. While email chains and collaborative documents are a starting point, next-level sales planning utilizes collaborative, transparent tools that give all stakeholders visibility into the plan before it’s launched. 

5. Segmentation

Each year, companies enter new markets. Those markets could be geographic, or expansions to Enterprise accounts, broader industries, different product lines, and tiered pricing structures. These market changes can be fast and sudden throughout the year, so sales planning tools should be equipped to handle changes with agility. Having a tool that can reassign reps based on account size or territory will save you hours of time and effort. Look for tools that enable you to customize deal size and product usage to better calculate ARR and customer segments, as well as tools that map out territories and assign reps.  This kind of customization and agility will ensure your sales plan stays accurate even as market changes force your plan to adapt.

A Final Word

Before we summarize, let’s talk about planning in Excel. While on the surface Excel planning appears straightforward, the reality is the spreadsheet format is two dimensional. It’s nearly impossible to organize and pivot view between your segments, territories, teams, and channels on a single page. At best, you can look at a matrix view of the information. A good, dedicated sales planning tool enables you to easily dissect your plan from all lenses that drive growth, which is needed when scenario building. Moreover, planning in Excel doesn’t allow you to improve your process and incorporate learnings each year. 

The best sales planning tool will improve your handle on data, collaboration, and execution agility. It’s important to consider your planning process, the growth and scale of your company, your data hygiene, stakeholders involved, and the markets and territories you’re operating in. These considerations will ensure the tool you choose meets the needs of an agile, collaborative sales planning process. 

Hopefully, these considerations have clarified your approach to choosing a sales planning tool.  If you haven’t seen the sales planning tool, contact us for a friendly, informative demo.

Read more tips for sales planning.

Rethinking Sales’ Go-to-Market Strategy

This article was originally published by Forbes on June 25th. You can view the original article here.

Building a company is akin to rock climbing.

Every growth spurt is an inflection point and, as in rock climbing or hiking, the time for switchbacks. For the uninitiated, a switchback is where a trail's steep inclines are too difficult to run directly up. Instead, back-and-forth trails are used to gradually lead a hiker up the trail. For a growing company, a switchback is where you must stop doing what you are doing and re-evaluate everything through the lens of your new desired endpoint or goal. What got you here may not get you to the next stage. As a fast-growing company, your execution mode switch keeps you glued to the surface. You are always analyzing how fast you are going, but you rarely check in to see if you are in the right race or, in the case of the hiking example, on the right trail. Being on the wrong trail can be fatal. Switchbacks allow you to create a path.

In tech, we use the phrase “go-to-market" (GTM) plan quite literally from the day we are ideating. It's supposed to be critical to our growth. It's our roadmap of sorts for getting our product-market-fit and beyond. In a fast-growth environment, though, we are so focused on the daily execution of sales that we are glued too close to the surface. We sometimes lose sight of the trail and miss our switchbacks. Continue reading Rethinking Sales’ Go-to-Market Strategy

Why You Should Stop Trying to Set “Accurate” Quota

The start of a new fiscal year brings excitement about the possibility of achieving the next scale of your organization, a fresh new operating model

…and quotas.

Behind compensation plans, sales targets are routinely the most difficult communications to the sales team – both impact reps pay, but targets are much more tangible. Reps understand how hard they worked last year to hit their quotas, and adding a growth target on top of that (however justified) is completely demoralizing to the sales team. They feel exhausted after achieving quota from last year, so their immediate reaction to increases is negative.

To combat this reaction, companies spend an inordinate amount of time double-checking their quota figures against historical account sales, pipeline figures, and whatever other metrics they can get their hands on in the interest of making quota more “accurate.”
I’m telling you right now – making “accurate” quotas is a waste of your time.

As I write this, I can hear the metaphorical crowds gathering: “if our quotas aren’t accurate, then reps won’t trust us! Who would possibly recommend such a thing?”

Hear me out – the reality is that there is no such thing as an “accurate” quota – at the end of the day, quota is an arbitrary production assignment to a rep; good reps will overachieve and the poor ones will underachieve. This is the way sales has always gone – so why is sales ops still focusing on this concept of quota accuracy?

Instead of putting their effort into calculating an “accurate” quota number, sales ops should focus on delivering fair
quotas – and communicating the quota determination process to reps so they understand where quotas were derived. This is done in two critical components:

1. Quota Setting: Quota setting is the process through which the total quota budget is calculated – the starting point for any company’s strategic plan. Generally, the formula starts with the company’s revenue target, which is then uplifted to account for profit margin, customer retention rates, partner margin, etc. This (often secretive) process is really the root of reps’ complaints – if the overall quota number is increased, then reps across the board will have to absorb that increase, which is where most number shock comes from. By showing reps why the overall quota number is what it is – and that the number being allocated is the best possible option – they will have the context to understand general increases in targets.

2. Quota Allocation: Allocation is the process through which companies take the number calculated during the quota setting process and distribute it to reps (more on that in a later blog post). Often overlooked, this is another critical piece of communication to reps – when they see their quota increase, they will naturally react, but by understanding how the company arrived at their quota – including all the key data points, process, and decisions required to determine final quota numbers – reps will quickly shift their mindset from mistrust to motivation. The end goal is that quotas are fair and logically derived – if your reps can’t follow the process then it raises the risk of unfair quotas.

Note that nowhere in this post do I advocate that companies should arbitrarily assign reps a number – and that “inaccurate” quotas are ok; instead, I argue that companies should stop searching for the elusive “accurate” quota because that accurate measure is meaningless. Try to define what an “accurate quota” is and how you can apply it to your quota process. You’ll quickly find that it’s nearly impossible to define and adds little to no value in the quota process. If anything, using the term “accurate quotas” gives reps ammunition to reject quotas, resulting in multiple review cycles that add to sales ops workload. The point here is that the accuracy of the individual quota is an elusive exercise – only transparency across the quota setting and allocation process really matters to your reps.

Matt Haller is the founder of The Startup Seller, a consulting firm specializing in go-to-market planning for early and mid-stage startups. Matt is a thought leader in sales communications and messaging, compensation and quota design, and designing sales teams to drive growth.  To learn more about his company, visit his website or connect with him on LinkedIn.

The Sales Ops Hierarchy of Needs

I was recently talking with a friend who runs Business Operations at a successful company in Boston about how large companies spend months on Sales Planning. To him, so much planning seemed unpractical – he fights so many fires daily in his 200-person business, that he can’t think regularly about the long term.

Really? I thought. Are you serious? If you are not thinking about the long term, how do you know what decisions to make today?

If you are not thinking about the long-term, how do you know what decisions to make today?

His is a common thought, though, and one we are seeing across the country at our Sales Ops events, in sales conversation, and in supporting our customers. Bottom line: Sales Operations is overwhelmed with day-to-day fires and unable to think strategically about the long term.

But why is this? Why do we regularly tie ourselves up in data weeds when there are important strategic things to consider?

One answer for this comes from a mid-century psychologist named Abraham Maslow.

Maslow’s Hierarchy of (Human) Needs

In 1943, Maslow created a framework that took over the psychology world, and which we still use today. His theory organizes human needs into a set of five progressive categories, often depicted as hierarchical levels within a pyramid. These categories are Physiological, Safety, Love/Belonging, Esteem, and Self-Actualization.

Maslow’s idea is that an individual or society’s lower level needs must be satisfied and fulfilled before they/it can move onto a higher need, and that moving up the hierarchy is a persistent goal for everyone. For instance, a person needs to attend their food and shelter before thinking about safety, which comes before love/belonging, esteem, and then self-actualization.

This theory makes a lot of sense (it has, after all, stood strong under more than six decades of scrutiny), and maps directly with a new theory from – the Sales Ops Hierarchy of Needs.’s Sales Ops Hierarchy of Needs

Similar to Maslow, a hierarchy of needs defines Sales Operations. These needs are: Data, Sales Software, Policies/Business Rules, Performance Analysis, and Strategy & Planning. As pictured below, these needs are progressive, with the foundations of each need dependent on those underneath.

Let’s dive deeper into each.


It’s safe to say that without data – accounts, contacts, firmographic information, news events  – sales  and sales operations teams would struggle. No one to call, nothing to analyze, nothing to organize – it’s impossible to succeed! For this reason, the foundation of any sales or sales operations team is data.

However, not just any data will do.

There’s a saying in the data science world of “garbage in, garbage out,” meaning that if you’re using bad data to make a decision (garbage in), you’ll make a bad decision (garbage out). Harvard Business Review wrote about this recently, sharing that 80% of a data scientist’s time goes to cleaning data in order to run an analysis. In sales and marketing, this is for good reason – SiriusDecisions estimates between 10 and 25% of marketing databases have critical errors, and that while it only takes $1 to verify a record as it’s entered, it costs a company $10 to cleanse and dedupe and $100 if nothing is done.  Their research shows that good data can mean as much as 70% higher revenue.

So, Sales Operations needs good data to start – accounts with correct firmographic information, contacts with phone numbers that actually work, emails and physical addresses for each. Without good data, a sales organization can’t function, but WITH it, that business can start working on where to put it – software.

Sales Software

With a strong foundation of data, needs turn to Sales Software. Software tools are a sales team’s workhorse for organizing data and logging tasks. They also standardize a team’s experience, allowing operational changes to happen at a large scale.

Sales Software is not simple. At our recent Sales Ops Summit, tech analyst Nancy Nardin from Smart Selling Tools put some data behind the adoption of CRM systems – 76% of companies use them, but satisfaction levels are below a 4/5. Similarly, there are over 600 different point solutions out there that help some part of the sales or sales operations job, but which come with their own challenges of enablement and integration.

And what happens when you don’t have your systems set up properly? Loss of productivity for sales, no process standardization for analyzing trends, and costly operations specialists to keep software running all put additional weight on your operating costs. This is the case regardless of whether you have good data or policies, but get increasingly worse if you don’t.

But a good software setup with good data? It allows for movement up the hierarchy, to Policies/Business Rules.


We’ve covered policies in past blog posts, defining why they are important and the general process for creating them. To summarize those posts, policies are the rules by which we run our business, set up our software, and manage day-to-day operations. In sales operations, policies include routing rules for new leads, account hierarchy logic, handoffs from marketing to sales to customer success, and many more. With these policies, individuals and teams run smoothly because they understand the rules of the road.

Policies, however, are not always good. A policy that requires an inordinate amount of data entry before a rep can create an account, for example, may lower the rep’s productivity below the value of actually having better information. Similarly, a sales process with  bad sales policies may lengthen the sales cycle and significantly increase the cost of sales! So, it’s extremely important to consider WHY you’re implementing a policy and specifically WHAT DATA you have to justify it. Again, as stated above, you need to have good data to make policy decisions.

Good policies, once created, allow you to properly organize your teams, systems, and processes. They allow you to take the next step up the Sales Hierarchy of Needs, to Performance Analysis.

Performance Analysis

Performance Analysis requires answering two questions for a company: “How did we do?” and “Why did it happen that way?” It’s the final part of the Sales Ops Job Cycle, the final step of Sales Planning for Growth, and provides the critical retrospection needed to make informed decisions. If a company performed poorly in a certain area, identify and eliminate the reasons it did poorly. For areas where there has been improvement, double down on the driving efforts.

Good performance analysis needs four things:

  • Subordinate Hierarchy Needs: Good Data, Software, and Policies to properly analyze performance (see sections above).
  • True North Metric: One specific metric that, at the end of the day, shows performance of the business. All other business metrics would role up under this one (e.g. “Attainment” consists of “Quota” and “Bookings,” which in turn consists of a host of underlying metrics).
  • Data-Driven Culture: A company that analyzes regularly, shares analysis regularly, and constantly asks “so what?” from that analysis.
  • Qualitative Input: Input from people out there in the front lines. Never make an assumption on a data point without the perspective from someone who created it.

Without these things, analysis is potentially biased or incomplete. With them, though, a business can step up to the “self-actualization” equivalent: Strategy & Planning.

Strategy & Planning

Similar to Policies, we have talked a lot about Strategy & Planning. For reference, here is a blog post breaking down who, what, when, and how, and a workshop presentation we put together with Salesforce’s Vice President of Strategy & Operations.

Strategy & Planning is the top of the Sales Operations Hierarchy of Needs. Here, Sales Operations drives a business’s strategy, identifying where the company is going in the long term and setting up steps to get there successfully. Strategy & Planning sits on top of Data, Policies, Systems, and Analysis, relying on properly addressing each subordinate hierarchy level. Skip one step, and your strategic vision is at best incomplete and at worst ineffective. But get everything right, and your sales team hums with efficiency and moves with agility in the right direction.

Similar to Maslow’s “self-actualization” summit, it is a constant struggle to spend time on Strategy & Planning, as my friend in Boston expressed at the beginning of this post. With all of the issues that exist in every subordinate hierarchy layer, upward mobility is a challenge! Even large successful companies like Salesforce struggle here,  if my experience says anything. Still, they and all companies strive to make it a constant thing.


Just like Maslow’s Hierarchy of Needs, the one for Sales Operations symbolizes a never-ending pursuit to  do more strategic work while regularly caught in painful operational minutia. As career Sales Operations professionals, we at have experienced this pain firsthand, and now spend our time creating solutions to help our customers move upwards.

Do you feel like your company is spending too much time in the lower levels of the Sales Ops Hierarchy, or are you interested in moving up? Reach out! We would love to talk to you.

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Linking Planning to Execution: The Challenges and the Solution

Ask anyone in sales strategy and operations, and they’ll tell you – one of the biggest challenges we have is connecting our strategy and planning with our execution. We come up with an effective plan, having considered all possible scenarios and identified all challenges before laying out the perfect go-to-market strategy, and then we struggle with actually implementing it! Or, we’re so busy tied up in executing and see planning as only adding more challenge, a challenge that we never actually get time to do the planning in the first place! This might show up in many different situations:

  1. Weeks or months of analysis to define segments, create territories, and design compensation plans are hamstrung when it comes to putting everything into systems.
  2. Management determines a strategic shift to align sales and marketing with the product, but company culture prevents that change from happening for months, even years.
  3. One group in a company decides to make a change to their team but other teams remain the same, creating misalignment and drops in handoffs and productivity.

It can be frustrating, but these are common scenarios across all types of companies. Why does this happen? Below we lay out some of the biggest culprits of planning and execution disintegration.

Problem 1: Increasing Go-to-Market Complexity

Companies have never had more information or technology than they do today, and their go-to-market complexities reflect this:

  • Focus on Account-Based Marketing means companies create unique plans for every single one of their prospects.
  • Machine Learning algorithms constantly update strategies as prospect and customer data changes the models
  • Today’s mobile and remote salesforces add additional levels of operational challenges since the workforce is rarely in the same place.

Each new layer of complexity adds exponential challenges to execution, requiring more time, effort, and resources than ever just to implement a strategy. Identify an opportunity that requires a new type of sales support role, or an underserved area that needs a unique team? These types of decisions (often valuable) create bespoke plans that slow down time to market and complicate everything in the  Sales Operations Job Cycle.

Problem 2: Tools

From our perspective, the single biggest problem preventing the integration of planning and strategy, especially as company plans get more complex, is software. While it’s never been easier to analyze, visualize, and access information to make decisions, at the same time there has been little effort to support sales operations as they try to put plans into action.

Consider the types of solutions that exist for strategy and those that exist for execution:

  • Strategy: Data Visualization (i.e., Tableau, Looker, Periscope, Excel), Predictive Analytics (Leadspace, Salesforce Analytics,, Price Optimization (Zuora), Forecasting, etc AND/OR Consultants
  • Execution: CRM, Consultants

Want to analyze your team, or think strategically? Use any of the hundreds of tools that can help you answer specific hypotheses you might have. Want to execute on that? Put it into your CRM.

For Sales Operations teams, the increased complexity that comes from the proliferation of tools means added complexity integrating all of these tools together as well as making sure that all of the right information is getting to the proper end users. When these tools DON’T integrate efficiently, as is very often the case, the burden on people to fix the problem drives the wedge between planning and execution even deeper.

Problem 3: Poorly-Scaling Processes

One of the more challenging, self-induced challenges of integrating planning and execution comes from processes that scale linearly while complexity grows exponentially. Today, companies solve their execution challenges by hiring additional people full-time, or by bringing in consultants. Teams get bigger, break up responsibilities between teams and people, and implement processes to share information. The intent of the processes is stronger integration.

The problem? It doesn’t scale fast enough and leads to breakdowns when handoffs don’t work and teams aren’t aligned.

At a small company with fewer stakeholders, the effects might be small because there is little complexity – a CRO or Sales Leader makes a strategic decision and passes on the information to one individual Systems Administrator who makes the changes in the system. A quick follow-up once the changes happen will confirm whether the changes are correct, or whether there needs to be rework. As long as this small planning<>execution link stays strong (i.e, good communication, both players stay at the company, etc), the company can be agile.

At a BIG company, things break down, and the process gets out of control. At one of our meetups, a senior executive at one of the fastest growing enterprise software companies explained how she spent eight months out of last year strictly working on planning – modeling capacity, creating segmentation, carving territories, designing quotas, and then working to input that into the system. Why? Well, according to her, much of it came from the sheer number of people that were involved in planning, who had to be in weekly meetings to maintain alignment and had to make sure their teams were represented and heard at all meetings. Unsurprisingly, this senior executive had hit their limit and left strategy and operations for a different role.

Problem 4: Bad Data and/or Lack of Transparency

Problem 4 is close to home for anyone in sales, operations, or business in general – bad data and lack of transparency are significant hindrances to making and executing on decisions.

Bad data comes in two forms – incomplete data, and incorrect data. Incomplete data comes through as accounts or leads that are missing important fields, and therefore provide an unfinished view on the market opportunity. Strategies built on incomplete data are at best incomplete, and at worst, when there is a pattern to the incompleteness, incorrect. Putting these strategies into execution is also challenging because processes like routing don’t work when they are based on data fields that are missing

Incorrect Data is data that is inaccurate – a data field has information, but that information is not true. Data can start inaccurate from the first time it goes into a system or it can become inaccurate over time (22.5% of data decays each year ), and in both instances causes issues when it comes to making decisions in planning and then putting that into execution. This is similar to incomplete data above, but the additional wrinkle is that planning usually happens in a static database, meaning that the people who are making changes doing it in one place while the database is changing in another place.

What’s the Issue?

Clearly, misalignment between planning and execution happens a lot and for a legitimate reason. The results, though, are unacceptable – companies diminish their planning efforts because of execution challenges or, even worse, they skip a formal planning process altogether. At one of our meetups in December, some of the companies even went so far as to call planning a “luxury” that they could not undertake because they were so focused on execution and didn’t have time to think about or execute on a plan. Let that sink in, and consider what would happen if YOUR company didn’t even have a plan to which you could track.

The Solution?

We’re working on that. Our software platform, which we’re calling Software Defined Sales Ops, integrates connects planning and execution into one platform, allowing all users to have visibility and plan collaboratively. With CRM integration and strong data visualization, we shorten our customers’ planning cycles by more than 25% and allow them to align their team to focus more quickly on what’s important – sales.

Want to learn more? Reach out here and we’ll get in touch. November 2018 Update

With a productive month of November, is starting off the holiday season strong! As mentioned in last month’s update, these months are high-stakes for many companies as they prepare for year-in-reviews while at the same time plan for their next fiscal year. This is certainly the case for our customers, and we’ve been right there with them.

In response to demand, we’ve developed several new features to expand our software offering. We also hit the road with a number of Sales Ops events, and a few webinars. Continue reading to learn more!

New Product Features

This month we’ve added several new features to improve our Planning App. Each of these updates helps make Sales Strategy & Planning more simple, flexible, and comprehensive:

  • Integrated Quota and Territory Review  – To support quota and target setting, we’ve developed review dashboards that bring all relevant data to one place for users to make more informed decisions about setting sales quotas and targets.
  • Expanded Disruption Report – We’ve expanded our Disruption Report (a view on the planned movement of accounts for each territory and person in the business) to include additional planning metrics and provide greater visibility.
  • Data Update Improvement – For customers who use our software through SFTP, rather than through Salesforce Integration, we’ve improved our ability to incorporate changes happening outside of the Planning App, bringing a more integrated planning process to those customers.
  • UI/UX Improvements:
    • Expanded Export Feature – For teams still using excel or a BI tool, we’ve expanded our export capability in the app to allow for a greater number of records.
    • Account Assignments – Users can now assign sales representatives at an account level, in addition to assigning by territory. For teams with complex sales organizations and a number of “exceptions” in their go-to-market strategy, this gives necessary flexibility.
    • Consolidated Grid Features – In our assignment grid, we’ve consolidated features and opened up visual space.

Interested in seeing everything in action? Reach out for a demo!

Community App

To give the Sales Operations community a place to connect and share best practices in an organized and simple way, we launched an app! Our GrowthOps Community App is where sales operations professionals can do the following:

  • Share Best Practices on topics ranging from Career Development to Compensation Design to Tools of the Trade
  • Post Open Jobs to recruit top Sales Operations talent
  • Connect with other professionals within the same field

Initial conversations on the app have been terrific, and we look forward to this becoming a great repository of Sales Operations information for all users.

Interested in joining the community? Fill out this form or email Katherine at and we’ll get you set up.

SalesOps Meetups

In November, we went on the road! We hosted meetups in Seattle, Los Angeles, and the Bay Area, to discuss Sales Operations career challenges and growth. It was tremendous to see the energy and excitement in the rooms, which reemphasized to us the great people who work in the profession. Up next, we have a few more meetups, with space remaining in each for those who can make it:

Keep checking our upcoming events if you’re interested in learning about future events in your area, or reach out to us and we’ll keep you posted.


We hosted two webinars this November. Thanks to everyone who participated! There were some great questions during the sessions and we’ve enjoyed the follow-up discussions since. Click either of the below links to hear a recording:

  • 10 Tips for  Sales Planning – We shared our top tips for managing a successful Sales Planning process, from using the right metrics to how to think about segmenting the market. With so much to discuss in Sales Planning, we look forward to future webinars about the topic!
  • Planning App Demo – We took a dive into our Planning App, highlighting a few of the features we think will change the way businesses do sales planning. Note that we continue to build features since, too, so get in touch to see the latest and greatest.

More webinars are on the way, so stay tuned!

What’s Next?

We’d love to share more with you about our future plans. To stay in touch, find us here at our blog, join our mailing list here, or send an email to

10 Tips For Sales Planning

Sales planning is one of the most important functions of sales operations, but it is often the most time consuming and frustrating. There are so many options and considerations in sales planning, how do you prioritize? And how do you make your sales plan scalable as you grow? We at put together 10 tips we think any sales operations professional should consider when planning for growth. To hear a discussion on these tips, watch this recorded webinar. We’d love to hear your thoughts!

1. Think “Customer First”

This is our first tip because it’s the most important to effective sales planning. It’s a mantra we hear often in sales organizations – think customer first, the customer is always right, and getting close to the customer is most important. But thinking customer first also prompts you to consider how your sales planning will impact your customer. For example, decisions on segmentation, resource ratios, and use of automation set the tone for how and when your customer is contacted. All your sales planning should be focused around improving your relationship with the customer, improving their experience, and shortening your sales cycle.

2. Use Metrics

Sales Planning can be a challenging process with a lot of ambiguity and emotional decisions. Setting metrics gives you an objective, clear path forward. Are you trying to figure out how to hit a certain growth target? Setting metrics around historical productivity, pipeline, and close rates makes it about the numbers instead of the people, which deescalates emotional situations and makes planning more productive. As an example, one of the biggest metrics Salesforce uses is Bookings Potential – an account score that estimates the amount a business spends on each of Salesforce’s products. Having this metric helped in territory creation, market opportunity, resourcing, and unifying stakeholders while maintaining objectivity.

3. Create a Timeline

A big part of planning is program management and meeting milestones. You need input from Finance, Marketing, and HR during planning, and then the planning outputs are fed back to Finance, Marketing, and HR. There are a lot of interdepartmental dependencies so giving a timeline with deliverables keeps everyone accountable. Work back from your ultimate deadline and deployment, considering all the processes that need to happen along the way.

This is an example of creating a timeline for one of our clients. In order to get to deployment, we need to conduct a performance review, market evaluation, capacity planning, and territory building. It’s a small part of overall sales planning, but it provides transparency and accountability across all stakeholders.

4. Think Ahead

This is best illustrated with an analogy from hockey – skate where the puck is going. Look to where the market is going, not where it is. Use forward-looking metrics instead of historical looking metrics. Past performance does not equal future performance, and past sales do not equal future sales, so look to where the market is going. This also applies to segmentation. You want to create your segmentation based on projected growth as you add sales staff, customer support, and customers. Staff your teams based on your plan, whether product-related or customer-service related.

5. Over-Carve Territories

Related to planning ahead, it’s important to think about ramifications for growing faster than you originally planned, and how you’ll manage that growth. This happens with so many companies – you grow faster than you plan and run out of territories as you bring in more headcount. A simple solution is to create more territories than you think you’ll need when planning. This is something Salesforce and many other high-growth companies do as general policy.

As an example, say you are planning to have 5 reps in a region, but you anticipate growing.  Carve out 6 territories so your new hire can hit the ground with a prepped territory.

This also sets the expectation with reps that they may lose some of their accounts. If you create extra territories, it becomes easier to share accounts when you continue to hire.

6. Create Balance

Sales Planning is about aligning resources across the company, and one of the most important things to do in this process is to create balance across all planning aspects. Balancing go-to-market efforts across resources prevents overextending one resource, and ensures all resources are fully optimized. It also allows you to balance risk across markets. Creating territories is really a way to balance market opportunity across your account executives so everyone feels empowered to meet quota. This creates a culture of accountability and everyone pulls their weight. Similarly, creating balance allows for easier performance analysis – if some territories outperform other territories, it’s easier to identify causes if you’ve made each territory equal.

7. Experiment

We discussed this in a recent blog post about optimizing processes. An important part of Sales Operations is conducting experiments in small parts of the business and taking those learning to the larger sales org. For example, experiment with a hunter/farmer strategy vs. account executives managing both customers and prospects. You could experiment with
SDR/BDR/AE ratios to optimize productivity and cost of acquisition. However, keep experiments small and scalable to reduce your risk.

8. Over-Communicate

There are a lot of people involved in and impacted by the sales planning process – sales, marketing, finance, HR, IT, just to name a few. These stakeholders have their own planning process congruent with sales planning. Not everyone needs to be involved every step of the way, but it’s important they know what is going on. This can be done by creating a timeline (per tip #3) and overcommunicating so everyone is aligned and understands planning goals.

Many of our clients have minimum weekly check-ins as a group to level set on priorities for the week. Smaller teams should meet and communicate daily. Things can get lost in translation or interpreted differently in each department, so having continual communication ensures everyone understands each department’s goals and planning method.

9. Document Everything

At, we take the view that if something isn’t written down, it doesn’t exist. On the topic of overcommunication, we recommend documenting everything – ultimate decisions, timelines, responsibilities, and ideas. This allows you to look back on past decisions when evaluating your plan or planning in the next year. It also gives you a roadmap when questions or disagreements arise. There could be disputes about account ownership, compensation policies, even overall planning processes. Documenting each of those things gives you a point of reference.

10. Stay Flexible

So far, we’ve talked a lot about specifics, being precise, and staying organized in your process. But this tip acknowledges the need to stay flexible. We’ve touched on this through a lot of our tips, but it’s important to recognize things rarely go perfectly to plan, especially as you’re scaling growth. Building in flexibility for contingencies and changes is important to save time and energy in the long run. Flexibility makes planning more fun and allows for unexpected growth and change. Here are some ideas on putting it into practice – over-carve territories, over-assign quota to create wiggle room, share resources, and create redundancy in workstreams. These are ways to de-risk the plan and make flexibility easier.

Bonus Tip! Revisit Often

No plan is perfect, and sometimes you need to make pivots. Revisit your plan often and evaluate whether you are meeting your expectations. Revisit quarterly, if not monthly, with your overall team. You’ll want to revisit with higherups and the board quarterly as well and check in weekly, if not daily, with your team. You don’t need to change the plan, but the more often you talk about it, reference it, and measure against it, the more successfully you’ll stay on track.

What are your thoughts? We’d love to know if these are helpful for you, and what other tips you might add. Shoot us an email at