How Fiona Simpson Built CS Enablement from Scratch at a $500M Company

When your CS team is 18 months old and has never had an enablement program, where do you start?

Boomi is a $500M data integration and activation platform serving 30,000+ customers—including more than a quarter of the Fortune 500. It has 17 people on its enablement team. And until about eight months ago, none of them served the Customer Success org.

Fiona Simpson walked into that situation in September 2025. Her title is Senior Revenue Enablement Business Partner, Global Customer Success—which in practice means she's the sole enablement partner for 125 CSMs and their managers across a global organization that, by her own description, didn't formally exist 18 to 24 months ago. 

Boomi had grown so fast that CS, as a function, was almost an afterthought: professional services handled implementation, account managers handled renewals, and support handled tickets. Then leadership decided it was time to build a real CS org—and did a lot of hiring in a short window. Most of Boomi's CSMs have been in-seat for 12 months or less.

What she built in the eight months since—how she identified a focus area, built buy-in with CS leadership, and designed programs that actually move skill metrics—is a useful blueprint for anyone staring at the same blank page.

Growth Bytes

Top takeaways:

• Start with a listening tour. Before building anything, ask stakeholders: "If you could wake up tomorrow and one thing is off your plate, what would it be?" The themes that surface consistently are your program.
• Use QBRs as a diagnostic lens. Instead of building separate programs for every CSM skill gap, Fiona anchored all of Boomi's CS enablement around the quarterly business review—because it surfaces weaknesses in executive presence, business acumen, and ROI storytelling all at once.
• Three questions protect you from scope creep. When a stakeholder brings a request, ask: What data is driving this? What outcome do you want at the end? What do you want me to drop from my current list to make room for this?
• Measure enablement in layers. Start with confidence surveys before and after training, move to objective skill scores, then look for lagging business indicators like expansion opportunities. Don't expect to skip straight to revenue attribution.
• Use AI for the two-hour tasks, not the five-minute ones. A Boomi CS manager put it well: AI should compress a ten-hour task into ten minutes—not automate something you could knock out yourself in five.
• Study your wins, not just your losses. Revenue teams obsessively debrief failed deals but skip the same exercise when something goes right—which means they can't replicate it.

The three questions that keep a solo enablement act intact

Walking into a brand-new CS org with no enablement history and a blank page is, as Fiona puts it, "a little scary—the world is your oyster." The requests start coming in fast, from all directions. And if you're a smart person who learns quickly and sits close to leadership, the scope of what people expect from you expands just as fast.

Fiona has been the first or only enablement hire enough times—CINC, GoNoodle, Otelier, D2L, and now effectively the first dedicated CS enablement partner at Boomi—to know what happens if you don't protect yourself early. 

"I've been reporting directly to the CRO and all of a sudden I'm planning off-sites and becoming the chief of staff because you're just proximate to everyone in the organization and you learn things quickly."

The way she protects against it: three questions she asks any stakeholder who comes with a request.

1. What's the data? What's the root cause driving this? A sales manager hearing someone say something wrong on one call is not sufficient to justify a training program. A competitor acquisition that reshapes the entire competitive landscape is. If someone can't answer this question, Fiona can't help them yet.

2. What's the outcome? What do you want to be different at the end of this? If there's no answer to that question, there's nothing to build toward and nothing to measure. The program would run forever with no endpoint.

3. What do you want me to drop? "Here's the list of seven things I'm working on—kill one of those projects for me, or move one down." If the new request isn't urgent enough to displace something already in flight, it probably isn't urgent enough to do at all.

"If they can't tell me the answer to that question, I have nothing to build towards. I could just keep doing this thing forever with no end result that I can measure toward."

These questions work whether you have 17 enablement colleagues or none. The difference at a company like Boomi is that you have people to hand things off to. At most of the companies Fiona has worked at, saying no was necessary to stop from drowning.

Why the QBR is the lens for everything

Before building anything, Fiona did a listening tour with CS leadership, frontline managers, and CSMs themselves. 

Her go-to prompt for those early conversations was blunt: "If you could wake up tomorrow and one thing is off your plate, what's been bugging you?" 

She heard a few themes come back consistently, but one rose above the rest: quarterly business reviews.

QBRs are the recurring moment where CSMs present business value back to customers—often to executives like CIOs and COOs who are signing the check to keep Boomi in their tech stack. 

They are a proxy for almost everything a CSM needs to be good at. They require executive presence, business acumen, ROI storytelling, and deep enough product knowledge to connect Boomi's capabilities to the customer's actual business model.

"The QBR is really a lens for the entire skill set of being a CSM. They have to be able to speak to executives. They have to be able to defend the ROI and the value of what we're bringing to the customer. They have to have some business acumen around what does this customer do with Boomi? What is their business running on? And how are we helping that process?"

To get a clearer picture of where Boomi's team was falling short, Fiona went into Gong's AI builder and asked it to analyze 100 QBR calls. The output was a 15-page document: skill breakdowns, call snippets, percentage breakdowns of what was and wasn't working, and program suggestions. She took it to CS leadership.

Two gaps came up repeatedly:

1. Executive presence. Boomi's CSMs work with CIOs and COOs, and not every CSM—regardless of years of experience—has had that level of exposure before. Holding your own in front of a C-suite audience is a skill that takes real practice.

2. ROI storytelling. There's a big difference between presenting an ROI slide and walking a customer through the math: here are the processes you're running through Boomi, here's how long they'd take manually, here's what that costs, let's whiteboard it together. Most CSMs were doing the former.

From that analysis, Fiona and CS leadership aligned on a single organizing principle for the year: build all enablement programs around the QBR. Product knowledge, business acumen, executive presence—all of it would ladder up to making CSMs better in that one high-stakes customer moment. 

The approach rolled out at Boomi's sales kickoff in February, and Fiona is currently midway through a global road show to reinforce it with in-person training.

Why the road show isn't on Zoom

Fiona’s road show—in-person, two-day training workshops across Boomi's Barcelona, Pennsylvania, Vancouver, and Sydney offices—was a deliberate choice over the obvious alternative.

Fiona made the case for in-person after watching what happened at Boomi's revenue kickoff in Austin in February. Something shifted in the room that doesn't happen on a video call. 

She's careful not to over-explain the mechanism ("this is outside my realm of genius"), but the effect is real: people listen, respond, and engage differently when they're physically in the same space

"There's something about being in the room together that changes the way that you learn. It changes the way that you listen. It changes the way that you respond. You just respond differently when you're physically in the room with other human beings. And I firmly believe that we will never lose that."

The format of each workshop is built around that premise: CSMs bring real accounts—ones where they're stuck, where the champion has churned, where the customer has been resistant to scheduling a QBR. 

They work through those accounts together in small groups, with peers who have solved similar problems. When someone says, "I had that happen and here's what worked," the whole group learns from it. 

That exchange simply doesn't happen at the same rate over Zoom, where people are toggling between tabs and the social pressure to contribute is lower.

Proving the ROI of enablement (and when to stop trying)

The ROI question follows every enablement leader everywhere. Fiona has been answering it for a decade and has developed a clear framework for thinking about it in layers.

Layer 1: Confidence and self-assessment

Before a workshop, she sends participants a survey: what are two or three things you want to focus on, and how confident do you feel about your ability to deliver a QBR to an executive audience today? 

The same questions go out at the end. Someone who came in feeling low on the scale and came out better is a direct, measurable result. Enablement has always been good at this layer.

Layer 2: Objective skill improvement

Call scoring in Luster gives her a grade-level assessment of each CSM's QBR delivery. After the workshop, the asynchronous training, and more at-bats with customers, that rep moved from a ‘C’ to a ‘B’. You can show that data point to a CRO.

Layer 3: Lagging business indicators

The third layer is the hardest and the most contested. After building out AI talk tracks for CSMs, Fiona saw an increase in AI expansion opportunities generated by the CS team. 

It’s correlation, not causation—but correlation that moves in the right direction is still information.

"I would also ask the people who are asking enablement to prove their ROI, how the light bulbs in the office have ROI. Everyone knows not having light bulbs is problematic and having them improves something. I would argue the same thing is true about enablement."

What CSMs actually need to know about AI

Boomi sells data integration and AI activation—which means customers show up with urgent, demanding questions about AI. But then, as Fiona puts it, they "come behind closed doors and they're like, ‘We don't really know what we're talking about. Please tell us what to do.’"

For Boomi’s CSMs, navigating that dynamic doesn’t necessarily require deep technical skills, but rather the ability to assess a customer's AI maturity and guide the conversation from there. 

• Does the customer have agents running in their existing systems? 
• Do those agents talk to each other? 
• Do they need Boomi-native agents on top? 

Instead of jumping to teaching customers about AI, CSMs start with structured discovery that moves the customer from "we should probably do AI" to "here's the specific process where this will impact your bottom line."

To build that capability across the team, Boomi leaned on its internal AI Center of Excellence—a group of the company's sharpest technical minds, led by Chris Hallenback, whom Fiona describes as a genuine world expert in data transformation and AI. 

The COE’s job is to translate the frontier of what's possible with AI into business use cases that CSMs can actually bring into customer conversations. For example, the order-to-cash process—taking an order, fulfilling it, shipping it, and collecting payment. 

How does AI improve that process for this customer's specific business? What does faster order processing or fewer returns actually mean in dollars?

"It helps us guide our customers away from the noise of AI and have a point of view. We know that you're getting as much AI nonsense coming out of your eyeballs as everybody else. Here's something that will actually impact your bottom line—and here's a process we know is effective. Do that. And ignore the rest of the noise."

The internal side of AI is a different story. Boomi has a directive from the CEO on down to use AI for productivity as aggressively as possible. 

Fiona uses Claude, Granola, Gamma, Gong's AI builder, and Luster (for call scoring and AI role-play against individual skill gaps identified from live calls). 

CSMs are using AI to digest their customers' 10-Ks, track personnel changes, and synthesize usage data across 50 to 80 accounts into coherent account narratives.

The principle that guides it all came from one of Boomi's CS managers: "He said he wants our CSMs not to be over-leveraging AI to make a five-minute task take two seconds, but to use AI to make a two-hour or ten-hour task take five or ten minutes."

Fiona gave an example:

She needed to plan a road show across 17 different cities, figure out the most cost-efficient office groupings, and calculate when each person would need to leave to catch a same-day flight home. She handed the list to Claude, went to walk her dog, and came back to a fully organized plan: two locations, two groups, per-person departure times. 

"I can't even imagine how long that would have taken me to do all the research and run the numbers. We would have guessed, picked the wrong office location, and then spent an extra $5,000 on flights and hotels."

Study what goes right

Outside of Boomi, Fiona runs ReflectPath—a speaking and advisory practice built around one observation: most revenue teams study what went wrong. Nobody studies what went right.

After a deal blows up, there's a full debrief. The manager weighs in, the CRO weighs in, and the rep catalogs everything that went wrong. But when a deal closes—especially a whale—the team celebrates and moves on. The muscle for extracting lessons from wins never gets built.

"If Bob can't explain how Bob keeps landing these whale enterprise deals, you're missing information that could be useful for your team,” says Fiona.

The reflection that matters most, in Fiona's framework, is whether you trusted your instincts and whether they were right. That shoulder tension when a deal starts sideways, or the gut feeling you have about a hire before you can articulate why? That's real information.

"If you go back to any decision that you've ever made that blew up in your face, most people, if they stop and reflect on that, go—ooh, yeah, I kind of thought that was a bad idea. But I did it anyway. And I should have trusted my gut."

The value of studying wins is that you get to verify the reverse: your instinct said yes, you committed, and it worked. That's data too. And it's data you can share, teach, and repeat.

Most enablement programs are built around diagnosing what's broken. Fiona's work—at Boomi and through ReflectPath—starts from the other direction: figure out what's working, understand why, and build programs that let the whole team do more of it.

Watch the full episode

Watch Alex and Fiona's full conversation on Grow & Tell, Dock's podcast for revenue leaders.