Scaling Sales in Uncharted Markets: Lessons from the Trenches

Editor’s Note: At SuperOps, we’re not just rethinking how MSPs manage IT; we’re also redefining how we build and scale a modern sales engine. In this article, our VP of Sales, Javeeth Ahamed, shares hard-won lessons from scaling sales in two high-growth environments, and how those insights are shaping our go-to-market motion today.

Over the decade and more, I’ve had the privilege of helping scale two very different kinds of sales engines — from the rocketship growth days at Freshworks to now building a global motion at SuperOps, a challenger in the highly competitive MSP and IT management space.

And while no two journeys are the same, a few principles have consistently made the difference between good growth and great scale.

Here’s what I’ve learned — the hard way, and the rewarding way.

1. Outbound Isn’t Dead — It Just Needs to Grow Up

When outbound works, it compounds. When it doesn't, it burns cash.

What we’ve learned is: outbound needs to evolve from spray and pray to precision and patience. At SuperOps, we are building our outbound motion around:

• Segment-first thinking — Not all leads are created equal. We approach the SMB space with surgical clarity (Org sizes and IT Bands), and Mid-Market with geo- and intent-specific plays.

• Narrative > Messaging — Your SDR can follow a script, but if your product story doesn’t resonate, nothing will stick. The best outbound messages don’t sell features. They challenge assumptions.

• Multi-threaded outbound — Calls, emails, social, video — we use all of them, often together. And we’re not afraid to be human. Humor, honesty, and context still win.
  

2. You Don’t Need a Playbook. You Need a Play Factory

Playbooks are static. Markets are not.

Instead of creating a one-size-fits-all guide, I’ve found more success in building a play factory — a culture where AEs and SDRs regularly experiment, share, and scale micro-plays that work. A subject line that crushes it for certain MSPs in the UK? Document it. A unique objection handled by an AE in California? Turn it into a Slack thread.

Decentralized play creation leads to faster iteration — and faster wins.

3. Product-Market Fit Is a Moving Target

When we closed our first $100K deal at SuperOps, it wasn’t just a revenue win — it was a signal. That we could go upmarket. That our roadmap was resonating. That buyers were willing to bet big.

But here’s the kicker: product-market fit at $10K ARR is very different from product-market fit at $100K.

Which means sales needs to keep evolving with the product. Sales enablement isn’t a quarterly ritual — it’s a weekly recalibration. Especially in SaaS.

4. Partnerships Are Not a Shortcut. They’re a Long Game.

I’ve seen this mistake before — assuming partnerships will magically solve top-of-funnel challenges. They won’t.

But when done right, they become multipliers. Our early partnerships at SuperOps didn’t move the needle overnight. But six months in, we’re seeing in Europe and LATAM open up thanks to the right bets on people, not logos.

You don’t build partnerships with companies. You build them with committed individuals.

5. Good Sales Teams Close Deals. Great Ones Close Feedback Loops.

We obsess over ARR — but the most valuable currency in early-stage sales is feedback. Why did we win? Why did we lose? Why didn’t we hear back?

The best reps don’t just chase targets. They chase the truth. And when that gets looped back into product, marketing, and support — that’s when momentum kicks in.

Final Thoughts

We’re in the golden age of sales — where tools are plenty, but trust is scarce.

The companies that will win aren’t the ones with the biggest teams or budgets. They’ll be the ones with clarity, curiosity, and a willingness to adapt — fast.

If you're building in a noisy space, remember: your edge isn't just your product. It's your ability to learn faster, sell smarter, and listen better.

That’s exactly what we’re doing at SuperOps.