Navigating the Tech Stack Maze in RevOps: A Conversation with Jacki Leahy

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While the tech stack makes life easier for RevOps, it certainly brings its own set of challenges.

How do you manage incoming tech requests? How to evaluate a tool? How to handle budget constraints?

To get answers to all these questions and more, we spoke to someone who considers the tech stack her love language: Jacki Leahy ? . Jacki shared her practical approach to managing the tech stack and the key factors that influence her decisions.

Head over to In Depth to read the insightful conversation!

In Depth ??

Navigating the Tech Stack Maze in RevOps: A Conversation with Jacki Leahy

There are currently 14,106 MarTech products on the market. Yes, that’s a lot!

And that’s before you even consider the sales tech tools.

As a RevOps professional, you’re responsible for selecting the right tools to optimize processes throughout the revenue cycle. It’s easy to feel overwhelmed, especially with suggestions coming in from your sales and marketing teams, who are constantly discovering new tools from influencers on LinkedIn. Your time is valuable, you can’t afford to spend too much of it on exploring new tools every week.

So, what’s the best way to manage your tech stack? Let’s find out!

How do you qualify and prioritize incoming technology requests from within the organization? Do you have a specific system or workflow for managing these requests?

Jacki Leahy: First of all, I have to manage my enthusiasm because tech stack is my love language. I need to go against my nature and really take a look at what's happening in the revenue engine.?

To do that, I use the ‘Winning by Design’ bowtie model and identify the largest constraint. Sometimes, a super thorough data analysis isn’t necessary; by talking to people and reviewing the numbers, you can often get a sense of what the largest constraint is. Once you solve for that, the entire system shifts.

A lot of the process involves just talking to people. I usually capture everything in a LucidSpark document, transfer the high level points in a Google Doc or Sheet, where we list all the things that are happening and then prioritize them. But beyond that, we need to look at the system as a whole, and align on what the biggest constraint is.?

Plus, you should know how to handle the people involved in change management.?

There’s no clear process for managing people, so it’s all about socializing, using informal influence strategies, and employing tactics to drive alignment.

Even if the biggest constraint lies in customer success or new client onboarding, the challenge might be getting the sales team to understand that this is what’s best for the entire revenue system right now.?

And even when they agree, your job isn’t done - you need to keep the priority top of mind, keep everyone satisfied, engaged, and aligned, so they don’t stray from the agreed-upon focus. It’s about securing their buy-in and maintaining it.

What factors do you consider before talking to vendors when purchasing for tech stack? How do you ensure that you ask the right questions and evaluate the tools effectively?

Jacki Leahy: It can be really challenging, but I usually have a good sense of what tools I should be looking at and what questions I need to ask.?

I spend all day in Slack threads reading hot tips and insights. So, I typically have a solid idea of where I’m headed and what I’m asking.?

I particularly appreciate it when salespeople are knowledgeable or at least self-aware. Nothing frustrates me more than when they try to bluff their way through a conversation.?

I’m very specific about the business use case, and I have particular technical questions I’m determined to get answers to - that’s how I approach it.?

It’s crucial to understand the business case thoroughly and to know the specific technical challenges you’re trying to address.?

For instance, sometimes I'm looking for specific ways I can trigger a sequence, and it's going to vary based on the use cases. It can be as detailed as understanding how a tool interacts with a GitHub instance and how to access that data. And when it comes to lead routing and scheduling, I need to know exactly when the system connects to Salesforce and how it integrates into the customer journey. These are the kinds of detailed insights I aim to nail down.

Take HubSpot, for example - it’s an amazing tool, but if you want to automatically trigger sequences, you’ll need the enterprise version. It’s about narrowing down those granular details and getting to the bottom of them.?

I make it clear in conversations that we’re not moving to a demo or involving decision-makers until I have the specific information I need.

How do you ensure that your tech stack is aligned with the customer journey?

Jacki Leahy: I like to map things out visually on LucidSpark. As said before, I use the bow tie model and then I use specific shapes and colors for what things mean and map it across the customer journey.?

The goal here is to reach the first impact as quickly as possible, removing all the friction possible in the customer journey. I start by identifying the biggest constraint and then focus on solving it step by step. In one case, my client had 22 lead statuses, many of which were unnecessary, of course. We simplified it to three few key statuses: open, working, and connected. From there, the rep either converts the lead to an opportunity, or disqualifies it, or the lead goes into nurture. Simplifying the process allowed us to gather more directional data and improve efficiency.

From your experience, how do you balance the need to buy tools with budget constraints, especially in smaller businesses?

Jacki Leahy: Honestly, a lot of the time, you don’t need all the fancy tools right away. You can start by crawling and walking until you’ve really established a repeatable process. You need to get your basics covered - like being able to communicate with prospects, gather the data you need, and manage those prospects effectively.?

You don’t even need a CRM initially. You could probably run an entire company using Notion, Airtable, or Google Sheets. So in earlier stages, the decisions are often more straightforward and clear-cut. There might be just a few people in the team, and everyone is aware of the pain points. It’s less about formal evaluation and more about acknowledging the biggest blocker and deciding to invest in solving it.

Usually, at some point, the process that the team follows will reach its limit and start to break down. And that’s actually a good thing! It’s a sign of growth, which is positive. At this stage, the tools should act more like medicine than vitamins - you only bring them in when they’re truly needed.

Once you’ve achieved go-to-market fit, and you’re ready to start hiring and scaling, that’s when you want to have a robust tech stack.?

A lot of the decision-making comes down to the company’s funding and runway. You don’t always need to know the exact numbers—you can usually sense whether or not there’s money to burn.?

It’s about right-sizing your approach. For example, if you have a data hygiene problem in Salesforce, something like DataGroomr for $2,500 a year that automatically takes care of all your duplicates is a no-brainer.

How do you handle the problem of having multiple tools with overlapping features? What processes do you put in place to remove our redundancy?

Jacki Leahy: Again, I think mapping it out is key. And this might be a bit controversial: I don’t necessarily see having multiple tools with overlapping features as a bad thing. In fact, that’s just the reality of the tech landscape right now.

It’s really about the specific success you’re aiming for. You want to use the tool that’s best suited for the task, especially if it’s a top-priority activity.

Consider this scenario: HubSpot has a calendar feature, but if there’s another tool that does it much better, like Calendly, which costs $12 a month, I’d recommend using that instead. It’s about applying common sense - using the right tool for the right job, rather than forcing one tool to do everything just because it can.

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