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Ali Rastiello has seen just about every side of RevOps.

Starting in sales, she made her name in marketing ops, became one of Marketo’s earliest customers, and today—as VP of Revenue Operations at Health Catalyst—she’s running full-spectrum GTM strategy in one of the most operationally complex industries out there: healthcare technology.

Thanks to breadth and depth of experience, Ali's remit spans the entire revenue lifecycle. And her lens on RevOps is unusually holistic because she’s been the one growing the funnel and holding everyone accountable.

In this episode of The Sales Compensation Show, Ali joins ˮ��ֱ��.ai CEO Nabeil Alazzam to share how she operationalizes RevOps in HealthTech—where sales teams face limited TAMs, and mission-critical buyer journeys.

Whether you’re wrangling data chaos, navigating global scale or niche markets, or even making the case for a new tool in a skeptical org, this episode delivers a rare look at what it really takes to make RevOps work across the entire customer lifecycle.

Episode resources

• Connect with Ali on ��

Data discipline is your advantage

For Ali Rastiello, data quality isn’t merely a minor hygiene issue—it’s the very infrastructure that makes GTM strategy executable.

As she shares, in HeathTech, where you're selling to a limited number of highly regulated buyers—often across sprawling health systems with complex parent-child hierarchies—there’s no margin for data mess. A misrouted email or duplicate contact record can damage a first impression or relationship with one of your few prospective buyers.

Which is why, no matter the company, Ali treats data quality as a front-end, always-on priority. At Health Catalyst, every new contact—regardless of source—is pushed through an automated normalization process. Within 10 minutes, the record is cleaned, deduplicated, segmented by job function and seniority, and enriched with buying role context. This enables better segmentation, cleaner attribution, and faster sales outreach.

As Ali explained, without this underlying infrastructure, it’s too difficult to ensure the customer is getting serviced properly. That data layer is tantamount to where you can even start with further automation.

If you’re operating in a low-volume, high-value industry like HealthTech, where buyer attention is scarce and brand reputation is everything, the takeaway is clear: if you’re not proactively operationalizing data cleanliness, you’re creating downstream friction for sellers, marketers, and comp plans alike.

What does Ali recommend you do to ensure a solid data infrastructure at your org?

• Implement a “data washing machine”: Use a tool like or comparable orchestration platforms to automatically clean and normalize incoming data—especially in industries with layered buyer committees and account hierarchies.

• Standardize buyer roles: Define clear job function and seniority tiers in your system so you can consistently segment personas and tailor messaging.

• Think depth over breadth: In limited-TAM environments, focus on the completeness and accuracy of known accounts rather than net-new acquisition volume.

Ultimately, sometimes—given the market you operate in—the goal isn’t always velocity. It’s precision. And precision starts with clean, structured, deeply integrated data.

Compensation complexity often signals a structural problem—not always a comp problem

When sellers miss quota or confusion arises around crediting, the default reaction is often to tweak the comp plan. But Ali sees something else afoot...

In her experience, comp breakdowns are often symptoms—not root causes. At her current organization, overlapping regional responsibilities and enterprise customer hierarchies sometimes made it unclear who should get credit for deals spanning multiple geographies. The result? Sales leaders pushing for regional overrides, dashboards struggling to reconcile conflicting logic, and a ton of manual intervention.

Ali’s team stepped back and asked a bigger question: Do we really need this much complexity in the sales comp plan? Or are we compensating for a structural issue in how we assign accounts and organize the team?

The fix wasn’t a more granular comp model—it was a new GTM structure:

• Clearer delineation between new business and expansion roles

• Simplified regional accountability

• A comp plan built around this streamlined structure—not fighting against it

The takeaway here? Before adding edge cases to your plan, pressure-test whether the underlying structure itself is broken. I.e.:

• Are multiple people claiming credit for the same revenue?

• Are dashboards forcing logic that feels more like a workaround than a reflection of strategy?

• Are your comp rules doing the job that territory design or role clarity should be doing?

Ali’s rule of thumb: when building your eventual sales comp plan mapped onto the GTM strategy, start with standardized “table stakes” components—elements that apply universally. Then isolate true outliers and ask whether the plan needs to accommodate them… or if the org needs to address the root cause elsewhere.

In healthcare technology, where deals can range from high-touch enterprise contracts to quick-turn point solutions, this discipline is especially critical. Not every seller—and not every sale—should be treated the same. But that doesn’t mean every team needs a bespoke plan.

Executive buy-in starts with solving their problems

Something else Ali hit upon was that RevOps doesn’t just run the systems—it often must sell them internally for initial investment.

When Ali Rastiello arrived at Health Catalyst, the company didn’t have CPQ, for example. The prevailing belief was that their high-touch, highly customized sales model simply didn’t need it. But as the business matured and added point solutions with faster sales cycles, the cracks started to show.

Rather than lead with features or operational pain points, Ali repositioned the investment around something executives couldn’t ignore: renewal visibility. Without CPQ, there was no centralized record of contract values or timelines. Forecasting was fuzzy. Retention planning was guesswork.

Ali effectively reframed CPQ from a “RevOps tool” to a strategic unlock for growth and risk management.

The takeaway: When selling systems internally, don’t lead with efficiency or automation. Lead with executive pain:

• What can't they see?

• What can't they predict?

• What risk are they exposed to without this system?

Then map your recommendation directly to those outcomes. A dashboard is good. A multi-million-dollar risk exposure found early is better.

Ultimately, across industries, execs need clarity on renewals, upsell opportunity, and account health. RevOps can deliver that clarity—but only if you frame up investment asks in terms of business visibility and financial leverage, not just operational pain.

Want more insights like this?

Listen to the full episode to hear Ali’s candid takes on:

• Right-sizing your tech stack to your company’s maturity

• How to challenge complexity bias in comp plans

• Why long-term success in RevOps depends on the strength of your peer network

Subscribe to The Sales Compensation Show on Spotify or Apple Podcasts for bi-weekly episodes featuring the revenue leaders behind today’s fastest-growing companies.