Revenue forecasting has become a high-stakes challenge for most businesses.  

Today, predicting an end state for revenue with any sort of precision is tougher as market conditions shift faster, customer behaviors are more unpredictable, internal priorities pivot without warning, and data streams are often fragmented and unreliable.  

This is when all eyes in an org turn to Revenue Operations—to align teams, clean up data, and deliver forecasts guiding critical decisions.

The pressure to adapt is immense, but, for Tana Jackson, VP of Operations at Upright Labs, it’s just another day in the role. Recognized as a “RevOps Leader to Watch”, Tana has earned her reputation as a trailblazer having transformed go-to-market strategies and revenue growth.

As our first guest of season three of the Sales Compensation Show, Tana shared her perspective on everything from ensuring clean sales data to fostering collaboration and embracing AI.  

Check out some of the highlights below.

‍Episode resources

• Connect with Tana Jackson on LinkedIn

• Book recommendation: The Qualified Sales Leader by John McMahon

When it comes to data, gatekeeping's good: protect your data hygiene at all costs

Throughout our conversation, Tana emphasized good business decisions start and end with good data as an absolute non-negotiable.

Left unchecked and unclean you'll only end up with sales forecasts built on shaky foundations:

"If you're operating without transparency into what's happening it's really hard to make your best guest [when] everything's hypothetical....[sales] need to know what's happening in the pipeline...

How much we think we'll have in bookings coming in for the year...[so that] you know how much overhead you need to bring in, if you'll have bandwidth to take on more customers. If you don't have that data correct, you're going to make very poor decisions."

Whether it's close dates off by months, duplicate accounts muddying CRM pipelines, or customer information riddled with gaps, these are tiny cracks that sink ships.

Here's how Tana thinks about enriching your data and, critically, the ownership over data hygiene within an org:

Ultimately Tana stresses the importance of sales process discipline. You can’t just throw tech at the problem. You need validation rules, audits, and accountability.  

This vigilance ensures that no rogue entries or sloppy integrations pollute the pristine data pipeline you've worked so hard to build.  

And while it's RevOp's job to guard fiercely, Tana insists everyone plays a role in this:

"It's everybody's data and everybody's responsibility. You have to have that ownership and who is responsible for making sure it stays clean...Rev OPS, sales OPS, whoever that is that's owning the customer relationship upfront should have some kind of responsibility with that.

[And] if you don't have a business analyst or a data analyst...then you're the person that owns it upfront."  

Especially for those in legacy industries where sellers aren’t living in the CRM, you need to watch for red flags like inaccurate close dates, how long something sits without activity, missing fields, incorrect validation rules and the granularity required according to your unique sales process:

The final word? Stay vigilant about data integrity

The main takeaway here is that if you don’t control where data is coming from, you risk downstream confusion and errors that are difficult to untangle.

Ultimately, when partnering with stakeholders across the org, don't be afraid to hold everyone accountable and have the tough conversations to getting the right data in place—Tana advocates being an 'extreme owner'.    

When fielding new data (or tech stack) requests, understand:  

• What data or capability does an individual want?  

• What are they trying to do? What's the ideal outcome (vs. a prescribed solution)?

Because the more data sources your system pulls from, the more noise and inconsistencies you'll introduce.  

‍Align the swim lanes: build change-management into daily operations

‍Aside from data integrity, RevOps can’t operate in isolation. Success depends on breaking down silos across GTM teams.

And the biggest challenge here according to Tana? Misaligned goals.  

Finance is focused on revenue and invoicing, Marketing on MQLs, and Sales on closing deals. So it’s your responsibility to connect the dots.

Over-communicate shared objectives, and establish a common language for metrics and success criteria. You can make sure teams each understand tech stack rationale, and the overarching data strategy.

For large-scale projects (like CPQ implementation), success hinges on securing strong organizational champions. While working on vendor selection and budgeting, you also need a parallel focus on stakeholder engagement. Tana's recommendations?

• Gather needs early: Even if you have a solid grasp of requirements, actively soliciting feedback shows stakeholders they’re heard from the start. This (and painting a clear picture of the “promised land” ensures excitement and alignment throughout the process). You'll not only strengthen buy-in but also build anticipation for the benefits ahead.
  

• Communicate throughout the journey: After aligning on needs, keep stakeholders informed and engaged by sharing timelines, milestones, and progress updates (really lean into 'informing' based on the RACI framework. To up transparency, take a page out of Tana's playbook and default to including more people than necessary on emails and updates. The more you can build change-management into your comms, the better—even if it'll feel repetitive to you.

On your tech stack: less is more (and don’t force systems to support bad process)

‍For Tana, the best RevOps tech stack and tools are those that integrate seamlessly into existing systems. Her philosophy is clear: less is more.  

We particularly liked Tana's take on how to think about selecting new tools amid a massive landscape of options. As she shared: a system can’t fix a broken process.  

‍Best-in-class RevOps leaders always start by designing an efficient, customer-centric process—then map technology to support it, not the other way around. Constantly tweaking or customizing tools to fit a flawed process only creates more inefficiencies.

Tana also stressed the importance of asking the right questions when evaluating tools:

• Does it align with our CRM and finance systems?

• Can it scale with our business needs?

• Will it add value without overcomplicating workflows?

When evaluating new tech, be especially cautious with anything affecting your core data pipeline (like your CRM or finance system). Changes here create downstream ripples across your entire stack. Experimentation is fine for tools that consume or output data, but your main arteries should remain stable to maintain operational integrity.

‍Balance automation and human judgment

‍When we put Tana in the hot seat on the topic of AI, it was clear she sees automation as a powerful tool—but only when paired with thoughtful oversight.

While technology plays a key role in enabling agility, it’s not a substitute for human insight.

While AI can analyze data, identify patterns, and even predict outcomes better than ever before, it's not having conversations with customers. It doesn’t understand the nuances of a deal yet, necessarily, or the emotions behind a decision.

For Tana, the balance is clear: automation should handle repetitive, data-heavy tasks, freeing humans to focus on strategic, relationship-driven decisions. The combination of AI and human judgment is where the magic happens.

Tune in for more

Check out the full episode where Tana gets into building agility into your forecasting model, plus advancements in AI and automation.