Dear Prospect

During this crisis I will continue to serve my prospects by calling them.

I am calling you… because your livelihood depends on it


I will not stop.

I believe that I can help you.

I believe that my company can serve you.

I know you’ve got problems and pains in your current operations.

But I’m not blind or deaf, I know what’s going on.

I know people are scared.

I know your team is trying to figure things out.

I know that it’s not business as usual.

But I will not stop.

I will not stop calling you.

I will not stop emailing you.

I will not stop attempting to connect with you.

we’ve still got to do the work

Because when we get through this global incident, and we go back to our places of business will see that our real, longer-term problems still exist.

And that nothing has changed, accept the passage of time.

We’ve probably also learned how to balance our family and work lives a bit better.

But in the long term, we’ve still got to do the work.

We still need to make widgets, we still need to grow and process food, we still need services that make our lives more effective and easier.

because I still believe in the human spirit

So here’s what I will do:

  1. I will be respectful of your time.
  2. I will tell you how I can help you alleviate, mitigate or improve your current situation.
  3. I will be a human and ask about you, your families and your colleagues with genuine interest.
  4. And I will ask for a meeting, even if that meeting is in a few weeks or months

So when we eventually speak, all I ask is:

  1. Please be courteous.
  2. Please be honest.

And if I can’t help you, then I’d be happy to find someone who can or leave you to your own business.

because nothing can resist a human will

But I will not Stop.

Because our economy and way of life depends on it.

Thank you

Where have all the Sales Leaders Gone?

3 Crucial roles you need from your Sales Leaders even if you don’t have one.

Put me in Coach. Coach, where are you?

Over the last several weeks, I’ve held discussions with founders, CMOs and business operators about enhancing their revenue operations teams and one thing has struck me as very odd.  There is no real sales leadership resident to the current business. 

I mean none: no managers, no trainers, no recruiters, no leaders.

Now to be fair, in many of these organizations, there are less than twenty team members and thus the CEO or COO acts the revenue and sales leader.  Unfortunately, these CEOs and COOs appear to be delegating crucial sales management and leadership roles like recruiting, training, and retention to others in the organization who have little or no experience in any of these tasks.

As a result, the sales leader (ie. CEO, Founder, CMO, COO etc.) never really get the performance that they’re seeking from their sales team and they’re routinely disappointed. And welcome to churnsville… insert salesperson 1, 2 and 3 out comes sales person 1, 2 and 3….

So you might be asking yourself: why are they acting as the sales leader in the first place?

It seems that in Startup land and other smaller organizations that the hiring of sales leadership is considered a luxury.  So instead we get sales leaders who are either inexperienced and learning on the job or those that are filling the role of player-coaches.

For small businesses and start-ups sales leadership is treated as a luxury so there is no sales leadership

What’s a Player-Coach?

Let me explain.

Up until the “modern era” of most professional sports, it was common for there to be one seasoned or more experienced player who was near the end of their career to be on the team as an active player that would also act as an assistant or full coach.  For example, the most recent player-coach on a professional team occurred when the Chicago Cubs signed Manny Ramirez, a hall of fame player, to their Triple-A affiliate in Iowa to both play and mentor some of the “big club’s” younger players – a la Kevin Costner’s “Crash Davis” in the 1988 classic Bull Durham.  While in Iowa, Manny got the chance to continue to play baseball as his passion and also help out the Cubs organization.

Sounds like a great idea, no?  You get an All-Star caliber player who’ll help some of the younger experienced members of your team, put some numbers on the board – and all for a price that’s usually below the cost of both (a coach and a leader).

Let’s examine what’s happened to the player-coach role in professional sports over the last generation. 

The last player-coach in professional sports before Manny was Craig Berube who served as a player-coach for the AHL Philadelphia Phantoms in the 2003-04 season. And before Craig, Pete Rose worked as a player-coach for his hometown Cincinnati Reds from 1984 to 1986.  So Craig was 10 years before Manny and almost 20 years after Pete.  BTW, the last reported NFL player-coach was when Dan Reeves suited up for the Dallas Cowboys in the late 1960s.

In professional sports the role of the coach has become so extensive and all-encompassing that coaches can no longer play the game and keep coaching at the highest level. Craig Berube understood this and that’s the main reason he quit playing midway through the 2004 AHL season so that he could focus on being behind be bench instead of on the ice. 

Sean McVay, the Head Coach of the Los Angeles Rams was just shy of 31 years of age when he lead his team to Superbowl 53 this past February. While he might have been the youngest coach to do so, there is plenty of precedent for the venerable NFL hiring coaches that are just a few years older than many of their players. In fact, John Gruden, Bill Cowher, Don Shula, Al Davis, John Madden, Mike Tomlin and many others all started their head coaching careers in their early 30s.

To date, there are no more player-coaches in professional sports.

Revenue Operations needs Sales Leaders

While leadership is needed throughout your revenue operations team, it’s most appropriate for the sales operations team. 

In order for sales leaders to be most effective and operating a high velocity sales attack they should not be selling to prospects or managing accounts, they should be teaching and training others to do so.

If you’re asking your senior sales professionals to “help out” or “mentor” the younger professionals then you’re doing both groups a disservice.

What you need is a professional sales leader.

As goes the leader, so goes the sales organization

Mike Weinberg, Sales Management Simplified

But you’ll tell me that your small business or start-up can’t afford one.

The good news is that you can rent sales leadership. 

There are plenty of experienced sales leadership professionals who are prepared to act as consultants and coaches to your team.  They’ll charge you a modest retainer or fee to gain access to their experience and skils, run events and keep your team accountable to their mission.  They might even have organizations that focus on helping sales teams grow and become exceptional (for example Jeb Blount runs and Grant Cardone runs

Three Crucial Roles for your Sales Leader

Just so that you know what to expect from you sales leader, here’s the 3 crucial tasks of Sales Leadership:


For a variety of reasons, sales personnel are constantly changing roles;  a sales leader needs to understand the nature of the talent market at all times.  By having an active and robust candidate pipeline, the sales leader is going to have clarity on the market for sales talent.  If you’re handing this task off to HR or anyone else, then you’re likely not going to achieve the results you’re seeking from the team members you receive.

Culture & Accountability

The sales leader is the primary influencer in the creation and maintenance of the culture of the sales team.  This starts with setting objectives for activities, outcomes and behaviours and continues with recruiting the right people into the right positions.    In addition, sales leaders will make their team accountable for their results through the use of team and individual coaching.


Through one-to-one and team meetings, sales leaders should be interacting with ales team members almost daily.  These weekly or bi-weekly meetings should focus on reviewing activities, results and challenges that your team and members face with the intention of creating incremental improvements. 

General team meetings should focus on learning about elements of the sales process, market and product and celebrating all victories (large and small). Individual meetings should focus on removing obstacles to growth, encouraging hearts and, sometimes, providing the team member with a good nudge.  

The result of this coaching is incremental growth that’s both immediate and extensive.  As in sailing, a small course corrections can be as effective as full breakdown and analysis of an impending opportunity or process. 

If a sales leader is not coaching their team every day, then they’re quickly sliding off into irrelevance.  And the market will punish irrelevance with stagnant results.

Channel your Inner Sales Leader

So if your small organization is not ready to rent or hire a sales leader, are you doomed?  No, sales leaders are not born, they’re made. 

Fortunately, there are plenty of ways that you, your CEO, Founder or another leader can take over this role, but to truly drive revenues to new heights, they’ll need to dedicate sales leadership as their primary responsibility, and they’ll have to read and study a lot. 

To this end, I’ve got a number of great resources in the books section of my site that I’m constantly updating here.

Due Diligence For Sales Operations: 4 Areas of Focus

VC and PE Due Diligence is about more than the numbers

As an Angel, VC and Private Equity investor, I’ve conducted due diligence (DD) on over 100 + companies and given my skills I always examined the Sales Operations group as closely as the Financial Controls group. So why is it that almost every VC or Private Equity investor examines all facets of their target businesses with a microscope except for the sales function?

This is the full version of my thoughts.  A much shorter version of this article can be found on our LinkedIn page here

Due Diligence and Sales Operations

As part of Revenue Operations, the sales operation team is a key component in the future success of an organization.  When the sales engine is tuned up and performing well, profitable revenue is almost guaranteed.  However, during the initial due diligence process, the proficiency of the sales organization to drive future sales and the accuracy of sales projections are rarely, if at all, challenged or analyzed thoroughly.

In my due diligence work, the absence of a sales process is evident in almost every small to medium sized founder-based enterprise. These founders didn’t intentionally set out to ignore sales, they’re just so busy working IN the business, theyv’e forgotten or never really worked ON the business.  So with no metrics to guide them, there is limited accountability and a narrow or partial vision of future sales.

Dig Deep into the Data

Utilizing a metric-driven approach to a company’s entire sales operations is essential for Revenue Leaders and Investors. This part of the Revenue Operations strategy will provide the owners and investors with a complete and more accurate view of the business’ revenue-generating capabilities.  

According to the book The 4 Disciplines of Execution by Chris McChesney, Sean Covey, and Jim Huling, the authors discuss the difference between lag measures and lead measures, both of which are important metrics that are used in sales. The authors define a lag measure “is the measurement of a result you are trying to achieve”; while a lead measure “foretells the result.”  I find that many of today’s lag metrics are really just vanity metrics that have been used by teams forever. 

Don’t be Fooled by Vanity Metrics: Due Diligence is about finding drivers and leaders of revenue

An effective due diligence process needs to find the leading measures that drive performance. When executing due diligence on sales operations both lag and lead measures should be considered in the analysis. The data that comes mostly from lag measures, like the past financial performance of the company should be complemented by an analysis of the sales process that may reveal critical lead measures that are more indicative of future revenue performance. 

For example, in markets with complex sales, the sales team can’t generally control sales revenue volumes as these results or outcomes require decisions made outside of their span of control control; instead, the sales team can control their level and volume of inbound and outbound contact activities with prospective customers.  So while lag measures such as sales revenues are easily available during due diligence, leads measures such as sales activity levels are less so.

You may not know the leading indicators that drive revenues but you can find them in the data

DD Focused on 4 Areas

There are four elements of sales operations that are collectively critical factors in a company’s success. These four elements should undergo an in-depth analysis and benchmarked against other top sales organizations. These are infrastructure, organization, process, and support (collectively I call these the sales system).

1. Infrastructure

All highly-productive sales organizations should have a solid infrastructure in place. With the right infrastructure in place, your sales team can focus on the activities that will drive revenues.  In addition, with the tools and process from the infrastructure, your team will be able to execute faster with prospects.  The sales team will only reach its maximum potential and achieve consistent results if they have the infrastructure to support them.

A good sales infrastructure should include documented policies, procedures and activities related to sales performance, compensation, pipeline review, marketing collateral, payment policies and market/competitive review.  Not every sales team uses advanced technologies like local presence dialing or AI, but most, if not all, should have some core tools like CRM that are available to all team members.

2. Organization

When examining the organization you should be searching for these key elements as part of the sales culture: sales team structure, territory design, sales management, and sales personnel.

The sales team structure should be organized in such a way that will ensure maximum efficiency. The sales team structure should also be designed to look at each individual as a team member with a significant role to play, and it should be seen in the light of the rest of the organization – as an all-important cog in the machine.  This includes the sales team’s Sales Story (New Sales Simplified, Mike Weinberg) used in its messaging and methods of approaching new and existing accounts.

Territory design is not as straightforward as assigning geographical coverage to the sales team.  Apportioning territories requires an understanding of factors such as the approach to strategic accounts, competition, and expertise areas. Whatever the territory design, the main goal is always to find as much profitable business as possible.  Account-based Management has become a new “buzzword” in sales literature, but it’s just another way to discuss how accounts with multiple contact points should be managed within the organization.

Territory Design and Management is Crucial in Enterprise Sales.  Account Based Management (ABM) can help Revenue Leaders align sales teams.

An effective strategy for sales management involves setting goals for team members, providing sales support, training and monitoring the team’s results.  It also involves creating or updating the sales team culture and strategy.  Questions you should be considering include:

  • Do Account Executives (AEs) and Sales Managers have written and definable goals?  How are they held accountable?
  • How do Sales Managers interact with AEs, Sales Development (SDRs) and product specialists in aligning to the company’s vision and objectives?
  • How much time by the management team is spent “in the field” talking to customers?
  • How much time is spent on coaching, evaluating and praising team performance?
  • How are successes publicized and failures analyzed?

3. Processes

Processes that need to be evaluated include those relating to sales process, lead management, budget, customer success, and forecast management.

Building a sales process is absolutely necessary for the sales organization. Since the sales process is a set of repeatable steps, the team can easily map out each of the stages by identifying key activities at each stage. For example, at the qualifying stage, sales teams with good processes will know what information is required to determine if their prospect in is the buying window. 

A Sales Process is series of repeatable steps that helps the sales team execute the go to market strategy.

An organized and effective lead management process is designed to identify potential customers and engage them in meaningful channels and messages that resonate.  As a result, this lead management process, can ultimately contribute to more sales by creating more engaged prospect leads. A solid lead management process includes identifying and understanding needs, generating and collecting intelligence about leads, and scoring and nurturing leads.

The budget process includes all matters related to the expected volume of sales and selling expenses. A sales organization should have a certain procedure for the preparation of the sales budget. The process should include a review of past budget performance as well as the current and future factors of the marketing environment.

Customer Success is not created when a prospect gives you their credit card, signs an order form, contract or issues a purchase order.  Customer Success is created when that same customer orders again, refers you to a prospect or offers to be the subject of a case study.  This success only happens when there are documented processes that describe how the organization is going to act during the term of the relationship with that customer.  If the sales operation team doesn’t have a new and existing customer account management process, then they’re missing out on multiple revenue opportunities.

Customer Success happens when the same new prospect places another order, refers you to someone or acts as an advocate for you.  It must be built methodically and inculcated in your organization.

Lastly, good forecast management is also an essential part of sales operations.  The forecasting process allows the sales team to evaluate current market trends so that informed decisions can be made about sales operations, customer orders, delivery of goods, customer orders, budgets, and inventory.

4. Support

Support encompasses the following areas: sales operations, sales support, systems, and sales enablement. A solid support team will allow the sales team to just focus on the business of selling as they service new and existing clients.  

Some support functions include keeping track of sales targets, scheduling, monitoring customer accounts, monitoring new sales leads, and managing the correspondence between the sales force and clients.


While we’re always searching for the diamonds in the rough in our due diligence process, we’re likely to find some problem areas as well.  

Not suprisingly then, here are some of the red flags that I’ve found in a sales operation that imply a broken or non-existent sales system.

  1. When the sales team consistently does not achieve its desired outcomes.
  2. When sales projections are only upon the current book of business and do not consider historical data or activity
  3. When the sales pipeline is too optimistic (every deal is more than 70% of closing in the next 30 days)
  4. Despite an influx of qualified leads and prospects from marketing operations, the sales team does not seem to be able to scale
  5. When sales team members are operating with different platforms, messaging and processes.

Sales Operations is about Data AND People

It’s important for you to remember that Sales Operations is about People and Data working together towards a common objective.  When conducting DD, it’s easy to lose sight of this and just focus on the leading or lagging data.  

If you focus on both Data and People, you’ll likely open the door to opportunities for revenue growth or show that the current revenue projects are unlikely to materialize.  More importantly though, you’ll know WHY the these outcomes could occur.

It’s time to get serious about Revenue Operations

This is a 5 minute read.

Recently, I’ve seen a few articles, whitepapers and blog posts about the nature of Revenue Operations and the newly created executive role called the ‘Chief Revenue Officer’ or CRO.

I’m writing post to describe the framework from which I view the future of this emerging business unit. I intended to dig deep into my thoughts and research on the matter and will be sharing them with you over the next few months in the form of a weekly post.

While the role appears to be “new” it is in fact a mash-up of a bunch of functional responsibilities within organizations over the last two generations. That being said, the availability of sales, marketing, customer success and accounting data that, when combined, create an entire picture of an organization’s revenue cycle is completely new.

Revenue Operations. Really?

Despite what we read every day about successful capital raises, acquisitions or exits by start-up companies, Revenues are the life blood of the organization.  If companies cannot turn their ideas into revenues (that hit their bank account), then they’ll eventually die a slow, painful and ugly death.  The deal sheets and databases are littered with the carcasses of dead startups that were successful in achieve product market-fit, but failed to convert this to an ongoing business case.

In most corporations, traditional business functions (Marketing, Sales, HR, Accounting) are slotted into separate department Silos.  Inter-departmental communication only occurs between the most senior of the corporate leadership and it becomes the CEO’s role to align these functional teams around a common mission and purpose.

In reality, most CEOs spend most of their time fighting fires or attempting to mitigate internal and external matters and have little time to align their functional departments (which could be one or two people). So the coordinating job never really gets done.

In my view, any function that touches revenue is part of the Revenue Operations attack.

The Revenue Levers for any enterprise are found in Marketing, Sales, Customer Service/Success, and Accounting.  Each is, in some way or form, responsible for Revenue being converted into bank deposits.  To drive Revenue, your team needs to apply focus to the salient tasks, jobs and processes in each of these four levers.

This is a dramatically different thinking from the Sales-heavy method that has been predominant in the previous decades.  A company doesn’t need to just hire a “Rockstar” VP of Sales to drive revenue or a killer marketing campaign; they need a team of specialists with a highly skilled leader to focus on driving sustainable revenue.

Friction exists without a Revenue Operations Conductor

The existence of friction in any part of your business slows the ability to convert prospects and opportunities into deposits in your bank account.  I call the speed at which a prospective client converts into cash Revenue Velocity and the rate of change in speed Revenue Acceleration (I’ll discuss each in more detail in a future post).

In some cases, friction provides for checks and balance.  But from my experience, friction is created when you haven’t fully formulated what is required to make it easy for prospects to do business with you.

In today’s multi-channel, multi-media business environment, your prospects and customers are bombarded by messaging to entice them to allocate their budgets elsewhere, so if you make it hard to do business with your company (eg. friction), you can expect that someone who’s more been  frictionless  will be taking that customer’s budget from you (despite your hard work).

Processes, technology and people are the reason why friction continues to exist.  If you can’t convert new prospects into cash, you likely have misaligned processes, poor technology solutions or personnel challenges.

The purpose of a Revenue Operations team is to reduce the friction in your business and to increase Revenue Velocity and Acceleration.  So if you care about the amount and speed of which your bank account gets filled then you’ll care about Revenue Operations.

The Revenue Operations Business Levers

A lever is defined as “a rigid bar that pivots about one point and that is used to move an object at a second point by a force applied at a third” (

For Revenue Operations, the levers that are used to influence and build Revenues are the following:

  1. Marketing Operations
  2. Sales Operations
  3. Customer Success and Service Operations

While these appear to be straightforward, I’ll spend much of the next few months developing each of these in later posts, but in order to introduce the topics, I’ll summarize each below.

Marketing Operations

These tools, processes and programs will accurately describe and position your market offering, attract prospective customers to inquire and complete a purchase.  In general, marketing operations include market strategy and business analysis, demand generation, and message/brand management.

In describing your go to market strategy as warfare, marketing operations does the work that takes place before going to the market (Strategic battle preparations) and then iterates while you’re in the firefight (Tactical battle preparations).

Functionally, you’ll find brand and market analysts, graphic and web designers, strategists, writers and product specialists that will support Sales Operations.

Sales Operations

These tools, process and programs are used by your frontline team that interface directly with prospective customers.  This includes playbooks, scripts, cadences, dashboards and methods that your sales team will use in order to find, educate and convert prospects into first time customers.

Functionally, you’ll have business analysts, researchers, sales development reps, account executives, key account executives and data scientists in your Sales Operations team.

Customer Success and Service Operations

These are the tools, processes and programs that are used by your team with your new and existing customers.  Customer Success and Service relates directly to creating sustainable revenue.  Moreover, as the majority of the Customer Acquisition Costs are borne by the initial acquisition, the Customer Success team has the ability to create the most profitable Revenues in your Revenue Mix.  As such, the functional focus of these operations are on customer enablement, satisfaction and retention.

Functionally, you’ll have inside Customer Service Reps, Technical leaders, Onboarding Trainers and Product Support team members in your Customer Success team.

Data Drives Revenue Operations

During my time as an active investor in companies, I often heard that from the founders that they intended to hire a “Rockstar” VP of Sales to kickstart their nw market sales efforts.  Often these statements were met with skepticism because our investment committee felt that the hiring of one individual would not be the catalyst to launch an entire enterprise forward.  Rather it was a series of hires and execution of a business plan that would likely move the mountain.

The primary difference between how sales, marketing and customer service were run a decade ago and today is the availability of data.

In the same way that the marketing leader can determine which marketing campaigns are the most impact in developing business, today’s sales leader can pull statistical data from their Customer Relationship Management (“CRM”) or sales enablement system and easily understand the challenges that the sales team is having in their sales process.  Thus the prevalence of data creates a mosaic of insight that allows thoughtful and caring executives to move the business forward.

Unfortunately this abundance of data has left some leaders unclear of their focus.  It seems to me that the main challenge amongst today’s Sales, Marketing and Success leaders is that they are either measuring the wrong metrics or don’t know which measurements are meaningful to driving their revenues so they’re measuring everything.  Thus this ocean of data has created situation where leaders are drowning and they don’t even know how to catch the life preserver.

One way to ensure that data becomes a servant to the leader is to use a systematic approach.  For many, the scientific method of creating hypotheses, developing and executing tests for these hypotheses provides comfort to manage the reams of data that result from standard operations.  For others, the scientific approach seems cold and unkind and is inconsiderate of the human relations and reactions involved in a real person to person activity like sales.

Who will coordinate all of these efforts and manage this data?: the CRO

Today’s Chief Revenue Officer is more than just the Rockstar salesperson who closes big deals and inspires other to do the same.  Today’s CRO understands how to use data to advance the company’s interests via a coordinated attack from Sales, Marketing and Customer Success Operations.  The CRO is the master strategist who launches the campaigns and battle plans to drive the Revenue Attack.

In addition, the CRO is the internal leader who relentlessly reduces organization friction.  As a result, the CRO makes it easy for prospects to work with and buy from their organization at every step in the customer acquisition and success process.

In smaller companies (less than 30 employees), the CEO acts as the CRO, but as the business grows in either complexity or scope, someone must be tasked with the role of coordinating the go to market attack.

Today’s CRO

A quick search on LinkedIn Sales Navigator for the terms CRO or Chief Revenue Officer results in 17,996 names.  Drill down a bit by selecting for companies with more than 50 employees and seniority (Director, VP, CXO) and you find that throughout the globe there are 3,566 names.

What do most of these senior CROs have in common?  They’ve been in their role for less than 5 years (most less than 2 years) and that they’ve acquired experience in all forms of sales transactions and teams (SMB, Enterprise, Licensing, etc.) and they’ve got an analytical background (either Engineering, Economics or Finance).

Why is this?

As a CRO you need a combination of the social sciences of psychology and behavioural economics and the deep analytical framework to appreciate the power of data.  They are essentially a “people-person” who loves to spend time looking at puzzles in  numbers and figuring out what’s really going on.

In summary

There’s a lot to unpack here and I intend to do so over the ensuing few months.  I hope that you’ll join me on the journey through your comments, please follow me here and you’ll get all of my latest thoughts and ideas.

Blair Carey is passionate about using data to help companies meet their mission and purpose. He is the creator the new site where CROs can collaborate on anything they’re thinking about.  You can follow him here or find him on his LinkedIn profile here.