How the Best Companies Design and Deploy a Scalable Sales Engine

In this episode of The Private Equity Podcast, Alex Rawlings speaks with Bill Bell, Fractional Chief Revenue Officer at Chief Outsiders, about building a repeatable sales engine that drives organic growth across private equity portfolio companies.

Bill explains why commercial due diligence is often far less rigorous than financial, legal, and operational diligence—and how this leads firms to underwrite ambitious growth plans against sales organisations that were never designed to deliver them. He shares why hiring more salespeople rarely fixes a broken system, what strong sales leadership looks like, and how documented processes, CRM governance, pipeline discipline, and structured onboarding create scalable performance.

The conversation also explores the risks of hiring competitors solely for their “black book”, the value of stage-gated sales processes in long-cycle industrial markets, and Bill’s experience growing a PE-backed North American business from $180 million to $325 million in revenue while more than doubling its EBIT margin.

Key Takeaways

• Diagnose the commercial engine before adding sales headcount.
• Assess whether sales managers are truly managing, coaching, and forecasting—not simply carrying major accounts.
• Build systems that make capable salespeople productive rather than relying on individual heroics.
• Use clear stage gates to qualify opportunities early and avoid wasting months on deals that will never close.
• Professionalising the leadership team and commercial function can unlock organic growth and support M&A integration.

Timestamps

00:00 – Introduction to Bill Bell and Chief Outsiders
00:52 – The biggest commercial mistake private equity firms make
02:17 – Why hiring more salespeople can increase cost, not revenue
02:46 – Diagnose, fix the infrastructure, then add capacity
03:17 – Four areas of commercial maturity to assess
04:46 – What makes an effective sales manager
07:03 – How manufacturing companies typically hire sales talent
08:00 – The danger of relying on a salesperson’s “black book”
08:56 – Building a sales system instead of hiring your way to growth
09:56 – Four foundations to establish before recruiting sales reps
11:24 – What a documented sales process should look like
11:53 – Using stage gates in an 18-month industrial sales cycle
13:43 – The hidden cost of pursuing customers who will not buy
15:40 – Bill’s biggest PE-backed growth success story
17:34 – Recommended books, masterclasses, and podcasts
18:58 – How to contact Bill
19:27 – Closing remarks

Raw Selection partners with Private Equity firms and their portfolio companies to secure exceptional executive talent. We focus on de-risking executive recruitment through meticulous search and selection processes, ensuring top-tier performance and long-term success.

🔗 Connect with Alex Rawlings on LinkedIn https://www.linkedin.com/in/alexrawlings/
🌐 Visit Raw Selection www.raw-selection.com

Transcript

00:00
Joining us today is Bill Bell, CRO at Chief Outsiders.

Today, we’re going to dive into one of my favourite topics: building the sales engine and driving the organic growth of a business. Let’s dive in.

00:23

Alex:
Bill, could you share a brief insight into your background?

Bill:
Sure. I currently work as a fractional Chief Revenue Officer for a company called Chief Outsiders. We’re a large consulting firm that works mostly with middle-market and private equity-backed companies ranging from $50 million to $500 million in revenue. I primarily work on top-line revenue structure.

I’ve spent about 40 years in industrial manufacturing, run five different companies both domestically and globally, and started doing this work around 2019.

00:52

Alex:
Marvellous. What is one mistake you see private equity firms or portfolio companies making, and what would you suggest they do to correct it?

Bill:
The most common mistake I see private equity firms make is conducting rigorous financial, legal and operational due diligence before a deal, while their commercial due diligence is surprisingly thin.

01:22

They usually conduct a market-sizing exercise that confirms the addressable market and some management reviews that confirm the CEO is optimistic. However, they almost never examine the revenue engine with the same rigour as the balance sheet.

That includes things such as the sales process, pipeline discipline, CRM and pricing governance.

01:49

They also need to determine whether the sales leader is truly leading or simply carrying the biggest accounts.

Typically, they underwrite an aggressive growth thesis based on a commercial organisation that was never designed to deliver it. Then, around 12 months later, revenue is lagging and the reflexive response is always, “Let’s hire more salespeople.”

02:17

That mistake compounds the first one. When you add headcount to broken infrastructure, you don’t add revenue; you simply add more cost.

New representatives enter an environment with no onboarding, no defined sales stages and no coaching cadence. In a complex industrial sale with a 12-to-18-month ramp, those salespeople often flame out or quietly underperform.

02:46

You then spend around $150,000 to $200,000 per person with nothing to show for it.

The solution is to do things in reverse: diagnose first, fix the infrastructure second and add capacity third.

Before closing—or at least within the first 100 days—you need to conduct a commercial maturity diagnostic. That is something I normally do with the private equity firms I work with.

03:17

There are four basic areas to assess:

First, is there a documented sales process that people actually follow?

Second, is the pipeline governed through honest forecasting?

Third, is the compensation plan designed to generate new business rather than simply maintain existing accounts?

Fourth, is the sales manager actually managing rather than just selling?

That is the mistake I see private equity firms make, probably 70% of the time.

03:46

Alex:
I think you’re being kind with 70%. A lot of firms have this problem, and sales leadership is one of the positions that is not replaced as effectively as it should be.

I don’t think private equity firms always understand the competencies that make a good sales leader. I also think they are often terrified of making a change because they believe companies only trade with people because of personal relationships.

04:16

However, as you know, changing suppliers can be extremely complex, especially in an industrial production environment. A customer is not buying from the business simply because the sales manager is their good friend and brings custard creams every time they visit.

I would love to explore every area you mentioned, but we don’t have time, so I want to focus on one. When you assess a company’s sales manager, what are you looking for from a sales-leadership perspective?

04:46

There will be a lot of factors, but imagine you only had 15 minutes. What are the three fundamental things you would want to see so that people can apply the same thinking in their private equity portfolio companies?

Bill:
From a sales-management standpoint?

Alex:
Yes.

Bill:
The first thing to understand is that many companies promote someone from the sales team into sales management, but those are two completely different skill sets.

05:14

A good salesperson does not always make a good sales manager.

A good sales manager is highly analytical. They understand sales processes, sales structures, compensation plans that drive results and sales leadership. It is a completely different skill set from that of an individual salesperson.

05:43

I see this mistake all the time.

A strong sales manager is almost more like an engineer than a salesperson. They are an analytical individual who can examine a pipeline, understand where opportunities are moving and structure a process that moves deals forward.

06:11

They can analyse whether those deals are likely to close and understand the different situations affecting them. It is a unique skill set that is not normally present in an individual salesperson.

Alex:
I agree. You’re looking for people who can dive into the details and coach the sales team.

06:36

I don’t know whether you’ve used Insights or similar assessments, but they are often high blue: very detailed, process-oriented and capable of building and implementing systems.

That can be the opposite of a very strong individual salesperson from a speed-to-competency perspective. They may want too much detail before jumping onto a call or entering a sales process, so they can sometimes freeze.

However, when it comes to holding people accountable and building an engine that is replicable across the whole sales team, those are often the strongest people. As you said, they are not usually the strongest individual salespeople.

07:03

Moving from sales managers to sales teams, many manufacturing companies we work with follow a typical playbook: they hire external sales representatives from their competitors, hoping those people will bring a black book of contacts.

They then hope those representatives will be able to sell because the company has no reliable way of measuring their sales competency.

What is your view on how manufacturing companies should structure their sales engine?

07:31

Bill:
I see that all the time.

When I was a sales manager, my CEO used to say, “Go and hire someone from your biggest competitor.”

My response was, “Here’s the problem with that.”

08:00

That black book walks through the door, and it walks back out again. You haven’t built anything. You have simply rented someone’s relationships for as long as they remain with the company.

Your growth becomes completely dependent on one person, which creates the same fragility as a founder who keeps the entire pipeline in their head. I see that all the time as well.

08:28

You are not building sales capability; you are building individual heroics, and hope is not a strategy.

Most of the time, it doesn’t work because the representative enters an environment with no process, no support and no system to plug into. The company then concludes that it hired the wrong person, lets them go and moves on, but the underlying problem remains: there is no system.

08:56

Manufacturing companies should stop trying to hire their way to growth and start building a system.

The goal should be to create a sales engine that makes ordinary, good salespeople productive rather than betting everything on finding one extraordinary salesperson.

I put it to boards this way: revenue growth is an outcome, but sales-organisation maturity is the input. You do not get the output without first building the input.

09:26

There is a sequence. As I said before, you diagnose the system first, build the infrastructure second and add headcount last.

If you do it the other way around and add headcount first, you are simply adding cost.

Before I hire a new sales representative, I make sure four things are in place.

09:56

First, a documented sales process.

Second, good CRM governance—not simply CRM software, but proper governance.

Third, a consistent pipeline-review cadence.

Fourth, an onboarding and ramp programme that allows the person to become productive quickly.

When you have those four things, you do not need to hire someone purely for their black book. You need a good system, and then you can hire good people.

10:26

Alex:
That aligns with our experience. We spend a lot of time developing our sales process and making sure it is effective.

We have found that when we hire people directly from competitors or from the executive-search and recruitment industry, they often cannot operate at the level we require. We therefore look outside the industry and assess specific competencies.

10:55

I often talk about high industriousness, high orderliness, low neuroticism and a high speed of learning, which can generally be seen as intellect.

I’d like to get your view on the documented sales process. From our perspective, every interaction with a client has a scripted process around it.

Not everything can be scripted or documented, but we have a process for around 80% of the conversations that arise.

11:24

Whether we are taking on a search, pitching for business or assessing a client’s pains, problems and challenges, we follow a documented sales process.

Is that what good looks like to you? Is there anything you would add?

Bill:
Yes, absolutely.

When I was managing salespeople in industrial sales, our sales process was around 18 months because we were selling highly specialised robotic industrial assembly lines.

11:53

With an 18-month sales cycle, you need a highly structured process. We used stage gates and had a nine-stage process.

The first stage involved identifying the customer. There was a defined method for doing that and a specific set of questions to ask.

The next step was qualification: determining whether the customer had a problem we could solve.

12:21

Once you had established that, you moved to the second stage gate. You confirmed that the customer had a problem you could solve and enough money to buy the product you sold.

You then continued through each stage gate until you reached stage nine. That process could take 18 months, so it needed to be extremely methodical.

12:49

As in your process, every stage gate had specific questions, qualifications, processes and systems. You could not move forward until the previous stage had been completed.

What used to frustrate me was reaching stage nine and hearing the salesperson say, “We lost the order.”

I would ask, “Why did you lose the order?”

They would reply, “The customer went in a different direction.”

13:13

We had been working on the opportunity for 18 months and reached stage nine, only to discover that the customer had gone in a different direction.

That is why I became so methodical. You cannot move to stage three unless you have completed everything required in stage two. Otherwise, you reach stage nine and discover something you should have known much earlier.

13:43

The biggest expense in sales is selling to a customer who is never going to buy from you.

If you spend 18 months selling to a customer and then discover they will not buy, that is an enormous expense. You want to identify that as early as possible and move on.

Alex:
Absolutely. We take accountability throughout the entire process. There is a great book by Jocko Willink called Extreme Ownership, and we apply that principle all the way through.

14:12

Obviously, when we introduce people to businesses, there are variables. There are not many products that can decide they do not like your company and no longer want to work for you. Perhaps software will do that in the future, but it does not happen yet.

It is about managing the entire process. If we reach the end and an offer is not accepted, we have made a mistake. The offer should never have been extended, and we should never have reached the final interview if the candidate was not interested.

Everything should be prepared and aligned, and we should have pulled every available lever.

14:42

That creates a clean process.

A lot of salespeople hide behind the idea that they cannot control everything. You cannot control every outcome, but you can understand the risks throughout the process.

For example, someone might ask, “What is the likelihood of this closing this month?”

We may have a candidate at the final-interview stage, but I have already told the client that I do not think the candidate will accept.

We use a likelihood score of one to four, with four meaning the deal is effectively done and one meaning it is very unlikely. That opportunity would be scored as a one, so it would not go into the forecast.

15:11

It may still happen, but we are not forecasting it, and we can clearly explain the issues we are trying to resolve. For example, the candidate may be well outside the compensation range and the client may be unable to move. They still want to conduct the final interview, and what happens after that is up to them.

That type of structured sales process makes sense.

Bill, tell me about your previous experience. You have not been at Chief Outsiders throughout your whole career. You previously served as President and CEO across five different companies.

What was your biggest success story, and what journey did you go on to achieve it?

15:40

Bill:
My biggest success was probably with a company called Leadec, which was the last company I worked for.

It was a private equity-owned company backed by Triton Partners. I stepped in as President and CEO of the North American operations.

It was roughly a $180 million company with an EBIT margin of about 3%, which is very low.

16:06

For a private equity-backed business, it occupied an uncomfortable middle ground. It was too big to be nimble but not profitable enough to be safe. It had a growth thesis, but the commercial organisation was not built to deliver it.

I had to work through a specific sequence. The first thing I did was avoid chasing revenue. I needed to build the executive leadership team, put a proper corporate infrastructure in place and then begin scaling the company.

16:35

We introduced a lot of discipline and professionalised the commercial function.

We then layered in some M&A and completed the integration work, adding roughly $45 million in revenue through acquisitions and around $5 million in EBITDA.

I did not blow up the operating teams. I retained the people I had and focused on developing the talent already in the organisation.

17:06

By the end, I had grown the business from $180 million to $325 million in roughly three and a half years. We more than doubled the EBIT margin from 3% to 7%, which was difficult in that type of business.

We were then positioned to sell the company. Unfortunately, I was only running the North American operation, and the global organisation was not positioned for a liquidity event at that point.

Fortunately, I had negotiated my exit before the private equity firm bought the business.

17:34

I told them I would only stay for three years, so I was able to realise my equity position after three years and exited in 2019.

Alex:
Congratulations on that journey.

What do you read, watch or listen to that you would recommend others check out?

Bill:
I’m a big reader of business books about founders and entrepreneurs.

18:01

I like books such as Shoe Dog, about Phil Knight, and Zero to One by Peter Thiel. I am also a big fan of Elon Musk, as everyone is.

I recently read The Thinking Machine by Stephen Witt, which is about Jensen Huang and Nvidia.

My wife thinks it is strange and it drives her crazy, but I am also really into MasterClass. The last one I watched was Sales and Persuasion with Daniel Pink.

18:31

I have also watched Business Leadership with Howard Schultz and The Power of Mindset with Carol Dweck and Steve Young.

I do have a favourite podcast. I have to admit it is not yours, but have you ever listened to Founders by David Senra?

Alex:
Yes, it’s great.

Bill:
He reads these huge books about founders and then summarises them in a one-hour podcast. It is a very good podcast.

18:58

Alex:
Absolutely. If anybody would like to contact you or Chief Outsiders after listening to this podcast, what is the best way to get in touch?

Bill:
My email address is wbell@chiefoutsiders.com. You can also reach me on my mobile at 248-982-6459.

Alex:
Bill, thank you very much for coming onto the podcast and giving us an insight into the sales process and how to build a sales engine.

19:27

Bill:
All right. It was great talking to you, Alex.

Alex:
As always, thank you very much to everybody for tuning into the Private Equity Podcast. Until next time, keep smashing it.