From startup to scale-up: Sales enablement growth strategies

This article comes from Chuck Marcouiller’s insightful talk at our Las Vegas 2024 Sales Enablement Summit. Check out his full presentation and our wealth of OnDemand resources.

Let me start with a confession: I’ve built my career by tumbling backward. Most people start small and work their way up to bigger companies. I did the opposite. I spent 20 years at ADP, working in sales and sales leadership. Then, I discovered this thing called sales enablement, and my career took a turn.

Working at a massive organization like ADP has its perks. You get to dive deep into processes and learn how things work at scale. But at the 20-year mark, one of my mentors gave me a nudge: “Chuck, you’ve already proven yourself here. If you’re ever going to try your hand at a pre-IPO company, now’s the time.”

So I made the leap. I joined Avalara, a startup aiming to bring sexy back to sales tax (yes, sexy sales tax—it’s possible!). We grew from 40 to 500 salespeople, went public, and kept scaling.

From there, I moved to other startups, taking on the challenge of being the first enablement leader through the door. Let me tell you, that first-person-in role? It’s no joke. Another enablement leader once called it a “woodchipper” job, and she wasn’t wrong.

Today, I work as a fractional enablement leader, helping startups navigate the transition to scale-up. If you’re considering taking the plunge into a startup, buckle up—it’s a rocky ride but it’s also incredibly rewarding if you know how to tackle the challenges head-on.

Here’s what I’ve learned along the way.

The startup reality check

Let me paint you a picture of what typically happens when you join a startup. The founders will tell you, "Hey, join the rocket ship! We're taking off! This is phenomenal! We've got the next big thing!" They'll probably even compare themselves to Elon Musk.

But when you get there, reality hits – often in the form of unrealistic growth targets (anyone else been handed that casual 97% year-over-year growth expectation?) and minimal infrastructure.

So, why do it? Because the chaos is also an opportunity. You get to build something from scratch, define how things should work, and make an impact that would be impossible in a more structured, established organization. If you’re the kind of person who thrives in that environment, it can be a career-defining experience.

This is where the Revenue Triangle Framework comes in – an approach I've developed through years of hands-on experience in building revenue engines from scratch.

The Revenue Triangle Framework: Raw materials, operators, and the machine

Think of building a revenue engine like constructing a factory. Everyone wants to build the Tesla Gigafactory, but you need to start with the basics. I break this down into three critical components: Raw Materials, Operators, and The Machine. Each plays a crucial role in creating a sustainable revenue engine.

1. Raw Materials: The foundation of success

The first thing I always assess when entering a startup is the raw materials – what does the team actually have to work with?

Here are the key questions I ask:

How baked is the product? Is it truly ready for implementation, or are we selling vapor?
Is there a clear Ideal Customer Profile (ICP)?
Do we have clean data to work with?
Is there documented evidence of pain points and impact?

Let me share a real example. When I joined FreightWaves, they were pivoting from a media company to selling data as a service. They had brokers who were great at selling truckloads of SaaS solutions.

The product was new, the target market was undefined, and the sales team had zero experience in the new space. Classic startup scenario.

💡

Pro tip: One of the best investments I've made across multiple employers is hiring a market research assistant to clean data. This allows our sales team to focus on selling rather than data mining.

2. Operators: Building your dream team

When it comes to talent in startups, I've learned to look beyond the obvious. Most startups hire for industry experience rather than sales skills – a classic mistake that leaves you with operators who know the market but "couldn't sell their way out of a paper bag."

Here's how to fix this:

Assess whether current team skills match future needs
Rewrite job descriptions (HR will love you for this)
Help leaders develop talent assessment and coaching skills
Have frank conversations with the CEO about talent investment

One of the biggest challenges is getting founders to understand they either need to invest in experienced (expensive) talent or build a robust development program. Both are costly, but not doing either is a recipe for disaster.

3. The Machine: Creating scalable processes

This is where the rubber meets the road. The machine is your operating system, and it needs several key components to function effectively:

🗣️ A common language

It doesn't matter which sales methodology you choose – what matters is that everyone from marketing to customer success speaks it fluently.

📋 Clear processes

I once walked into a situation with 400 deals sitting in the MQL stage for over 300 days. Why? Because reps were treating it as their personal lead parking lot "just in case" prospects responded later. You need clear processes and ownership guidelines.

📊 Meaningful metrics

As a wise CFO once told me, "A number has no meaning unless it's compared to another number." Focus on comparing metrics across teams, stages, and periods to identify patterns and problems.

🎯 Leadership alignment

Work with your CRO to identify one key metric to move each quarter. Don't try to boil the ocean – focus on specific, measurable improvements that align with leadership objectives.

Your role as the architect

As an enablement professional, your job is to be the architect of the revenue engine. That means having an opinion, creating a blueprint, and driving the organization toward scalable success.

After years of being the "first enablement person in," here are my key takeaways:

Have an opinion: You were hired to draw the blueprint. It doesn't have to be perfect – any structured approach is better than chaos.
Focus on numbers: Learn to speak the language of metrics. It's your most powerful tool for diagnosis and improvement.
Think sustainable: Don't just focus on immediate wins. Build systems that can scale.
Document everything: Create clear processes, playbooks, and measurement frameworks.
Get early wins: Build credibility before tackling the major tasks.
Know your real team: This was a hard lesson for me – while you serve the sales team, your true stakeholders are the CRO and VPs. Make them successful, and you'll be successful.

Remember, our job is to pave the road so others can travel it repeatedly, efficiently, and successfully.

Final thoughts

Starting as an enablement leader in a startup can feel like being handed a cardboard rocket and asked to fly to Mars.

But with the right framework, sustainable processes, and a clear understanding of what success looks like, you can build something truly remarkable. Just remember to pack plenty of coffee – you're going to need it.

So roll up your sleeves, embrace the chaos, and start building.

From startup to scale-up: Sales enablement strategies that drive growth