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.