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The Road from $0 to $20 Million: What Breaks Along the Way & What to Do about It

10 June 2021

Ricky Cookson

In every business narrative, growing pains and bottlenecks are familiar characters that direct how companies think they should be growing.

They’re “familiar” because these pains and bottlenecks are the same across businesses and industries.

When it comes to how to grow the business, whether you find yourself in the $0-5 million, $5-10 million, or $10-20 million range, inevitable but quite specific disruptions start to occur.

The Road from $0 to $20 Million resource hub was created to help you accelerate growth and forgo these disruptions by arming you with the resources you need to scale.

But before you start downloading the templates, playbooks, calculators, job descriptions, tech hit list, digital selling best practices, etc… the short webinar What Breaks Along The Way & What to Do About It highlights how to grow a business by seeing around the corner at what’s next when it comes to your people, process, and technology.

Documentation of the sales process and different portions of the process that become more complicated as you grow
Your people / support roles / and leadership
Technology and sales operations

From $0-5 million, $5-10 million, or $10-20 million range, we’ll cover what breaks along the way so you know what you should be pulling out of The Road from $0-$20 Million.

Or if you’re pressed for time – here’s the deck.

What Breaks When Growing from $0-5 Million

People: Lack of Direction for Hiring

Hiring can be one of the most disruptive and ill-defined aspects of growth. For companies at the $0-5 million stage, the ability to hire the right people is stunted by ill-defined needs and unrecognized bottlenecks. As a result, they rush to hire outside sales leadership without sales processes, and they turn to expanding their AE team without understanding where exactly their constraints are.

“We have this idea in sales that salespeople just magically sit down and produce sales… It doesn’t work that way… If you’re going to hire and scale your sales team, you have to set them up for success.” – Jake Dunlap

Process: Unrealistic Buyer Personas

Do you really know your buyer? When you built your buyer personas, were you just checking a box?

Too often, growing sales organizations skimp on the buyer personas — they aim high with unfounded market targets, and they fly too close to the sun. Yet, understanding your buyers is central to understanding how to grow the business’s sales.

Accurate buyer personas give you an accurate depiction of who you should be selling to and if the market you are going after is realistic.

Technology: Poor Implementation

Without a doubt, some technologies are absolutely essential to scaling to $5 million and beyond: a customer relationship management (CRM) platform, sales engagement tools, contact database, and the newcomer in sales essentials: LinkedIn Sales Navigator. Without those, scaling in today’s market is just an idea.

But the real loss happens in the gaps between these technologies. When set-up and integrations are omitted from the equation, the system breaks down (and the benefits along with it).

What Breaks When Growing from $5-10 Million

People: The Onboarding Problem & Sales Leadership

While you may have a clear idea of where help is needed, many companies lack clear expectations and onboarding processes for new hires. They also struggle with the question of promoting from within or going with an outside hire.

They struggle with the option to hire someone with potential who’s been with the company or look for an experienced leader who’s done it 2-3 times before. (Hint: the latter is probably what you want to go with.)

Process: Disparate Sales Strategies and Minimal Account Planning

Your sales team should start considering the best way to synthesize practices and implement account segmentation at this stage. Companies will often have more sales reps at the $5-10 million stage, but different pockets are doing different things, and the new people can’t follow along. You have to have everyone on the same page and enable them from the get-go.

“If you don’t have a process, if you don’t have a playbook for the way that you do things, you’re going to have reps that take 2-3 times longer to ramp and a lot more churn over.” – Jake Dunlap

Technology: Unimplemented Sales Operations

Sales Operations is one of the most under-acknowledged parts of a sales organization but one of the most valuable teams in a sales arsenal. If you have 10 salespeople, you need sales ops. If you have 20-30, you need a few people in ops.

Many organizations don’t readily see the ROI of Sales Operations, but investing in support can improve performance metrics and drive revenue for your business.

What Breaks When Growing from $10-20 Million

People: Inaccurate Hiring Forecasts

Projections and forecasting tend to deviate from reality when companies are figuring out how to grow the business from $10-20 million. They either over hire or under hire, resulting in higher churn and missed quotas instead of retention and employee success. At this stage, it is finally the time to start considering hiring for sales leadership to guide the sales team from point A to point B.

“This is about the time you want to be considering a VP of Sales. … Now is the time to get that person who’s done this once or twice, the person who can see around corners, and help get you from $10 to $20, and $20 to $50.” – Jake Dunlap

Process: Playbook Paralysis and Ineffective Communication

Now is the time to revisit your sales methodology, establish more effective onboarding, solidify repeatable processes, and invest in a tight timeline and playbook. Succinct sales processes and refined playbooks will further your growth through the $20 million mark and beyond.

Communication also starts to break down as you onboard more team members and add new departments. The natural base erodes, and sales, marketing, and customer success stop having the conversations they did before because of changing priorities and more complicated processes.

Technology: Tech Hoarder Mentality

“Companies are only using 20–30% of what’s possible with their technology.” – Jake Dunlap

At this stage, the technology issue is that companies are trying to augment their digital capabilities with any “shiny new toy” they can. It’s important to onboard tools like revenue intelligence and maybe partner relationship management, but adding to the collection isn’t as effective as connecting the collection.

The overarching goal is to visualize and plan how you’ll integrate (how data should be transferred and collected) every new tool you include in your stack.

How to Grow the Business at Every Stage

As you scale – whether it’s in your people, process, or technology – you’ll face the same milestones and hurdles as many companies before you. The great thing about that is we’ve learned from these companies how to grow the business and sales, and The Road from $0 to $20 Million resources tackle these scalability challenges head-on so you can accelerate growth.

>> Access your guide to accelerated growth.