E46: $5M to $55M: Craig Harris’ ScaleUp Journey at Deputy

Timestamps:

02:57 From $5 Million to $55 Million: The Growth That Nearly Broke Us

03: 48 The AAA Framework: Assess, Architect, Accelerate

16:51 What Founders Need to Know About Hiring Leaders

19: 43 What Leaders Need to Know About Choosing Founders

26:31 The CCC Framework: Confront, Control, Commit

About Craig Harris:

Here’s Craig’s story ….

For 25 years, I’ve helped tech companies build at pace. But one journey that stands out—because of what it gave me, taught me, and broke in me—was Deputy.

In four years, we scaled from $5M to $55M. We didn’t do it with smoke and mirrors. We did it with systems, sweat, and a few very sore lessons. I’ll walk you through the path we took to scale, the frameworks that held under pressure, and how we pivoted when COVID sideswiped the entire business.

Not the “forgot your keys again” kind of chaos—but the high-octane, VUCA-drenched kind where companies grow fast, systems break, and you have to lead anyway.

Let’s get into it.

From $5 Million to $55 Million: The Growth That Nearly Broke Us

When I joined Deputy, the company had a great product. The founders had nailed a solution that genuinely helped frontline teams manage shifts and rosters, and they had paying customers to prove it.

They had reached $5 million in ARR, which is no easy feat.

But like a lot of early-stage rocket ships, the growth was inconsistent. No two quarters looked alike. There was no reliable operating rhythm, no structured way to accelerate globally. They needed a scale engine—and that’s where I came in.

We didn’t have some magical go-to-market trick. What we did have was relentless focus.

We expanded into the US and UK. We hired local leadership. We obsessively studied the buying journey, identifying every leak in the funnel—from trial signup to paid conversion. At the start, only about 6% of people who trialled the product ever became customers. That number wasn’t going to cut it.

So we rebuilt the journey—aligned product, sales, marketing, and customer success. We redesigned onboarding, added trial incentives, gave prospects more guidance, and followed up with high-quality, well-timed outreach. We tracked every change, every iteration, every micro-improvement.

By the end of my time there, we’d reached a 15% conversion rate. We were growing at 100% YoY. We tripled our global footprint. And the most important thing? We built something sustainable. Something that didn’t depend on any one individual doing heroics.

But we didn’t start there.

We started with a framework I now live by.

The AAA Framework: Assess, Architect, Accelerate

Whenever I walk into a new business, I bring the same approach. I call it the AAA framework—and it’s saved me from more false starts than I can count.

First: Assess.

You can’t fix what you don’t understand. And you definitely can’t scale chaos. The assess phase is about brutal honesty. What’s working? What’s broken? What’s limiting growth? Not just in the product or sales process—but in the team, the culture, the structure, the rhythms of execution.

At Deputy, we found gaps everywhere. The product was strong but under-optimised. The sales motion was reactive. The handoffs between teams were clunky. And most importantly, the team didn’t have a shared view of what great execution looked like.

Second: Architect.

This is the design phase. We reimagined the customer journey, built a cross-functional growth team that spanned product, sales, engineering, and marketing. We aligned everything around one thing: improving the buying experience.

Product wasn’t built in a silo. We made sure prospects experienced the value fast. We shortened time-to-value, redesigned onboarding flows, and used incentives to guide behaviour—more free trial days if you completed key steps. It sounds small, but these changes stacked up.

We also architected the organisational design. We set up decentralised leadership in the US and UK. We knew we couldn’t scale internationally from Sydney. And we baked in flexibility, because startups need room to pivot as markets change.

Finally: Accelerate.

This is where things get spicy. Acceleration doesn’t mean chaos. It means operational rhythm.

We rolled out OKRs to align the business. We embedded execution cadences that created forward momentum. And we kept iterating on our GTM motion monthly—optimising conversion, tightening loops between product and sales, and hiring for critical roles just before we needed them.

We didn’t always get it right. We made some poor bets, chased opportunities we shouldn’t have. But we learned. And we stayed nimble.

That’s AAA: Assess. Architect. Accelerate. It’s how you scale anything without burning it down.

The CCC Framework: Confront, Control, Commit

If AAA is what I use to build, CCC is what I use when everything hits the fan.

March 2020. COVID arrived. And Deputy was vulnerable. Our core customer base? Hospitality and retail SMBs. Most of them on month-to-month subscriptions. Suddenly, the revenue we thought was secure became optional.

The music stopped.

So we turned to crisis mode: CCC—Confront, Control, Commit.

First: Confront.

No sugar-coating. No waiting for “more clarity.” You have to call reality early. We asked ourselves: What is really happening? How far could this drop go? What happens if 40% of customers cancel?

Pretending we’d be fine wasn’t an option. Confronting the brutal facts allowed us to act early—and with intention.

Second: Control.

Our burn rate was high. We were built for growth, not survival. So we cut. Hard. One-third of the workforce. Projects shelved. Hiring frozen.

We didn’t just cut—we also controlled the experience for customers. We let them pause subscriptions rather than cancel, so when they reopened, they could resume with one click. We preserved goodwill, relationships, and platform data. That mattered when the recovery began.

Third: Commit.

We told the team the plan. We didn’t pretend things were fine. But we showed them what we were building toward. That the rebound would come. That if we stuck together, we’d be ready.

And we were.

By early 2021, revenue was back at pre-COVID levels. Because we didn’t flinch. We acted fast. And we stuck to the plan.

What Founders Need to Know About Hiring Leaders

Founders wear all the hats in the early days. But eventually, if you want to scale, you’ve got to build a team around you.

Here’s what I tell every founder I work with:

Be brutally honest about what you’re not good at.

Not just what you don’t like—what you shouldn’t be doing. Hire leaders to complement you, not replicate you. If you’re visionary but messy, get someone methodical. If you’re great with product but not people, bring in a culture-builder.

Let go—properly.

This is the hard bit. You’ve built the baby. But once you’ve hired someone good, give them space. Define the outcomes, align on success, then back off. You don’t get to micromanage and delegate at the same time.

Create an environment they can win in.

Executives don’t just need trust—they need scope. Give them a clear runway and enough latitude to make it their own. If they feel like passengers instead of co-pilots, they’ll bail.

Great execs can scale a company. But only if the founder lets them.

What Leaders Need to Know About Choosing Founders

This goes both ways.

If you’re a sales leader, COO, or GTM pro thinking of joining a startup, choose your founder carefully. Skills matter, but fit is everything.

Choose someone you actually want to work with.

You’re going to be in the trenches, day after day. If you don’t like the founder’s style—or worse, if you don’t trust it—it’s going to unravel fast.

Get clear on expectations.

Before you join, align on what success looks like. What are you responsible for? What does the founder still own? What does “good” look like at 90 days, 6 months, a year?

Know how to manage the spark without snuffing it out.

Founders are idea machines. That’s a gift—and a risk. Your job is to protect the plan without killing their magic. You’ve got to balance creative energy with operational focus. That tension is part of the job.

If you nail it, you’ll help build something extraordinary. If not, it’ll be chaos—and not the fun kind.

Summary

Building is hard. Scaling is harder. Surviving when the world tilts on its axis? That’s elite-level hard.

But it can be done. You just need frameworks that hold under pressure—and the humility to adapt as you go.

AAA when you build: Assess. Architect. Accelerate.

CCC when you’re punched in the face: Confront. Control. Commit.

They’re not perfect. But they’ve worked for me—from $5M to $55M, from tailwinds to tornadoes.

And if you’re building something bold, they might just work for you too.

Hiring or replacing someone in the next 90 days?

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