What is Boomi?

Alex Kracov: So you joined Boomi last year as a senior revenue enablement business partner focusing on the global customer success team. For those people who don't know Boomi, can you tell a little bit about what the company does and then we can kind of get into who you're working with, who you're enabling and what your job is?

Fiona Simpson: Yeah, absolutely. So Boomi is the data activation company. And what that means is we integrate and govern data across customers' entire business. That could be everything from HR systems to financial systems to logistics and fulfillment. You name it, if it has any kind of data in it that helps you run the business, we're touching it, integrating it together, whether that's application integrations, APIs. AI agents, we kind of touch all of it. Our main focus is the enterprise space, but we also work with tons of S&P and commercial companies all over the world.

Fiona's Role: CS Enablement at Boomi

Alex Kracov: Very cool. So what, tell me a little bit more about your role because I think you actually might be the first person we've interviewed on this enablement podcast where your focus is on customer success. So I'd love to kind of hear more about maybe like the state of the CS team when you joined and kind of what it looks like today.

Fiona Simpson: Yeah, well, this is a unique situation for me as well. I'm really lucky that here at Boomi, we have 17 people on our enablement team, which is wild. And so I originally came in to serve as the enablement business partner for our pre-sales team. I was filling in for somebody who was out on maternity leave in a contract role. And the CS organization had been asking for enablement for a long time and they'd never had it. And so the role opened up and I took the opportunity to stick around. And so now my full-time remit is strictly just the 125 CSMs and their managers and so forth that service our customers. So it's pretty unique because I've never been in an enablement role where I just had one focus, one team, and a bunch of colleagues to service the rest of the organization and help build programs and help manage our tools. So it's pretty special.

Alex Kracov: Yeah, it's awesome. And I want to say mostly to say kind of like diving deep on CS Enablement, but I'm curious, like those 17 enablement folks, like how is the team structured? Is there different business lines or product lines? Is it all CS sales? You take the audience kind of behind the scenes a little.

Fiona Simpson: Yeah, absolutely. So we're split into two teams. One is called the activation team. And so all of us on the activation team are business partners to the different areas of the go-to-market organization. So we have someone who serves our enterprise sales reps, our commercial and SMB sales reps, our SDR team. We have a new digital sales team, sort of a high-velocity team. So we have someone covering that as well, along with a counterpart in EMEA and a counterpart in our Asia-Australia market. And then the rest of our team is called the Programs Team. So they focus on things like product enablement and working hand in hand with product and product marketing to roll out those global programs around a new launch or something along those lines, focusing on tooling, our LMS. And the Programs Team is really more of the L&D side of the house in some senses, but also the structure and sort of like, how do we run our systems as an enablement team? So it's kind of nice to have both sides of the coin.

Building the CS Enablement Program: The QBR Focus

Alex Kracov: Yeah, it's super interesting stuff that makes a ton of sense. Okay, so tell me a little bit about like, you get this role, you're leading enablement for the CS team, like, what's the state of the CS team? What are you trying to solve kind of right away? How did you sort of think about, you know, auditing what's going on and starting to kind of build those enablement programs that you knew would have an impact?

Fiona Simpson: Yeah, great question. So Boomi has been growing like wildfire over the last four or five years. And the CS org actually didn't exist about 18 months ago, 24 months ago, which is really surprising to me. Like I've worked in SaaS for a long time and CS is not usually an afterthought, but it's a variety of different things. Part of it was, we originally started out with more of a professional services structure and then traditional support. We are — our sales team is split into new business and an account management or, you know, expansion renewal and so the account manager has been doing some of the CS type of functions. Professional services have been doing some of those functions and support was doing support and about 18 to 24 months ago they really decided that it was time to stand up that official customer success organization, full customer success managers. And so that has been an evolution. It's been a lot of growth. Most of our CSMs right now have been on the job about 12 months here at Boomi. So we started to grow the program and then did a ton of hiring about a year ago. So people have been in the seat anywhere from four or five years, but maybe with a slightly different title, to 12 months or less if they've recently joined the company. So it's an interesting mix of a newer organization.

They've never had formal enablement before until I stepped into the role. And in some ways, it's kind like the world is my oyster from an enablement perspective, which can be a little scary. So I had to think about how am I going to approach this? What am I going to do? So I'll kind of break down a bit around the strategic side and then a little bit of the tactical side, if that makes sense. I'm a big fan of a listening tour.

Alex Kracov: Yeah, that would be awesome.

Fiona Simpson: So started off just getting to know all the stakeholders, understanding what's going on in the organization, what are the pain points. I always love to ask the question, like if you could wake up tomorrow morning and one thing is off of your plate that's been bugging you for a while, what would that one thing be big or small? And I learned a lot through those conversations. A couple of themes rose to the top. And so I brought some of those themes to some CSMs themselves and those themes resonated with the CSM. So I knew I was pointed in the right direction.

And one of the big areas that I kept hearing things about was our quarterly business review process with our customers, right? Lots of organizations do internal QBRs at the end of the quarter, did you hit your number, all that good stuff. We also do quarterly business reviews with our customers. And so that process takes a lot of skills. Like there are multiple skills coming into that particular moment.

And so I did a few things, both listening to the team and getting feedback, but also leveraging the tools that we have. So we use Gong. I went into the AI builder. If you're familiar, it's pretty cool. I said, hey Gong, grab a hundred QBR calls and give me the gap analysis. Like what's going well, what's not working, where are reps struggling? What are the skills that CSMs need to improve on to really nail these calls?

And that was amazing. It gave me a 15-page document with here's examples and snippets and like the percentage of calls where this or that or the other thing happened, good or bad. And here's some suggestions for programs and things that you could do. And so I took that back to CS leadership and I said, we've got a theme here. We have something going on that definitely needs some attention. And what we realized is the QBR is really a lens for the entire skill set of being a CSM, right? 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? Like, what did they do to make money? And how are we helping that process? And so the leadership team and I decided let's use the QBR as our focal point for the enablement programs for the year.

Some of that might include product knowledge. Some of that might include those softer skills like business acumen, but let's build programs around that. And so got the buy-in from leadership and the support from my enablement colleagues. And so that's really where we're headed in this fiscal year. We did our sales kickoff with a big focus on our QBRs and kind of unpacking the pieces of it. And then I'm in the middle of a road show to all of our different global offices to do some on-site training. And then we're using some tools like Gong and Luster to help individually kind of assess and work on skill sets to really support that.

Alex Kracov: It's a great story of how you took like an insight and started building a program into action on the QBR side of things. I guess maybe like what goes into a good QBR? What are the things that you maybe noticed that people weren't doing so well that now you're building enablement programming around?

Fiona Simpson: Yeah, that's a good question. I think one theme that I could touch on is because we have kind of a varied skill set in terms of just what markets people have been in before as far as their CSM career. Maybe they've been a CSM for five or six years, but they haven't worked with enterprise organizations or they haven't worked in certain industries. There is a fair amount of that executive presence and business acumen that some people just haven't had exposure to. And so they're playing a little bit of catch up. We work a lot with like CIOs, CEOs, COOs — those are the stakeholders, those are the people signing the check to pay for Boomi at the end of the day. And so being able to hold your own in front of those folks is a skill set and it takes a lot of practice. And so that's one area. I think the other one, and I would argue maybe anybody in go-to-market needs this skill, is to really be able to defend your value. Not just to say like, you're paying this much and we're saving you this amount of time or money or person hours or widget overturn or whatever it is, actually being able to unpack the math behind that and show them like, these are the functions that you're executing and the processes that you're executing using automation through Boomi. Here's how long that would take manually, because you told us and you gave us that data. Let's whiteboard this real quick together. That is a little bit of a different storytelling process than like, here's the ROI slide, like figure it out and I have nothing else to say, right?

Alex Kracov: I mean, I think it's so true and something honestly we're trying to get better at Dock too. Because I think it's so easy for a customer success person to just be like, okay, here's our new features. Here's the new product stuff we've rolled out. You should use it like, wait, you had a problem with this piece of the product. Let me help you with that. It sort of can easily devolve into product-centric to customer-support-y. But to your point, like it should be really about reaffirming kind of the business value of why they're using Boomi, you know, even in the first place, right?

Alex Kracov: Yeah, so I think that's a really important point. Were there other programs beyond QBR that you focused on or was that kind of the main gem of the program that you've been building?

Fiona Simpson: Yeah, that's a great question. You know, there's always a thousand things going on at the same time. Luckily, one area that we have a really strong customer-facing program already is in our product training and our sort of product knowledge area. And so we actually recycle a lot of the content from our customer-facing training to help support our CSM team in terms of their product knowledge. Because unlike, let's say, a solutions engineer or someone in the implementation and professional services arena or someone in support who's troubleshooting technical aspects, our CSMs need to have a solid amount of product knowledge, but they don't need to be technical experts. And so our customer-facing sort of, you know, it's broken into like beginner, intermediate, advanced, and professional certification type of levels, almost similar to like a Salesforce certification pathway. Our CSMs can do sort of the initial pieces and get enough to be able to speak eloquently to it, to be able to know when their sort of knowledge is getting pushed and they need to bring in a SNEF or something. But we're really lucky to be able to leverage that content and be kind of prescriptive based on what's going on in an account, a book of accounts or what have you. Some other programs that are a little bit more global and universal that we run across all of our teams are things like how to have conversations about AI. We could dive into that specific topic more, but we're in this very fast moving, high-paced point of change in technology globally. How do you stay on the forefront of that? And how do you leverage AI in your own work? How do you talk about Boomi's AI strategies? That is a talk track that we're doing across the entire company from the CEO to like the intern. So there's a lot of global programs that we pull from as well for the CSMs.

AI for Customer-Facing and Internal Enablement

Alex Kracov: Yeah, let's talk about AI. You can't do a podcast in 2026 without it. I feel like you must have a two-sided kind of thing to solve here where it's like Boomi, the product, the data layer, I assume is powering a lot of these AI agents. So CS needs to be able to talk about the product in a way and bring AI transformation back to the business value. But then I assume you're using AI to help your internal process and your internal enablement programs. Can you kind of talk about that dynamic?

Fiona Simpson: Yeah, I feel like 2025 was the year of companies all over the world going, we gotta do AI. Guys, we're gonna do AI. Let's go have some AI friends. Like, let's go eat some pie, right? And what's really funny is companies come to us because they know that we are a leader in that space. And then you kind of get them behind closed doors and they're sort of like, we don't really know what we're talking about. Please tell us what to do. And so it's kind of been this like buzzwordy thing. And some companies are really like visionary and already two, three, four, five, 10 steps down the road, which is fantastic. That's a small segment of our customer base and they're really leading the charge, which is fantastic because it's helping us model the way for the rest of our customers. And so our CSMs need to be able to one, kind of investigate and evaluate where that customer is in their maturity when it comes to using AI. Do the systems that they have in place, for example, if let's say they're using Workday or they have Microsoft Copilot going and they've got some agents stood up maybe natively inside of some of their systems — do those agents talk to each other? Do we need to pull data and maybe put some Boomi native agents on top of it? Like there's all these conversations around sort of what exists today, what's in that customer's ecosystem? What do they want to accomplish? Is it just automation? Is it true like machine learning type of AI? Is it data transformation? Like there's all these different areas where a customer may want to go.

And having our CSMs have enough of a vocabulary to be able to help guide them in that process is really where we're trying to move the entire team. There are some folks on the team today that have a good sense of that, and there are some that it's new to them, it's new to me too, frankly. So we're all kind of learning it together so that we can help guide our customers into what makes the most sense for their business in the state that it is today and where they want to be tomorrow.

Alex Kracov: And like, how do you think about building training and enablement programs around that? It's such a — like every week there's a new thing. I mean, every day there's like a new dynamic and platform and this thing is better than that thing. And like, how do you fit Boomi into the tech stack? And especially working in enterprises, it's really complicated. You have these workflows that existed for years and years and years. So, yeah, like how do you build programs that help CS teams keep up with the pace of that change? Do you have like subject matter experts in the company come in and do talks? What kind of advice do you have for other folks? Because I think we're all dealing with this problem right now.

Fiona Simpson: Yeah, absolutely. We are very lucky that we have a guy named Chris Hallenback, who is like one of the experts in data transformation and AI in the world. He's written a book about it, literally, maybe a couple of books at this point. And so he and a few other folks last year stood up what we call the AI Center of Excellence. And it is all of the brightest minds in our organization, all of the SNEs, all of the people who have been on the forefront of not just what's happening in AI in general, but how is Boomi building towards that and what do we have to offer? And so we really rely heavily on that AI COE within the company to bring forward the talk tracks, the content, the product market fit, if you will, or what we think of as sort of the business use cases. So if you think of any organization that, for example, takes orders for their widgets and has to process those orders, fulfill those orders, ship them, et cetera, et cetera, and then eventually put money in the bank from that process, that's pretty well known as the order to cash process. How does Boomi fit into that process in their organization and how can that process be improved leveraging AI? That's a very basic and straightforward conversation that we can have with a customer because it makes sense to their business, right? And so how do we bring AI into that conversation in a process that already exists in their business to help them see whether it's faster order processing or fewer returns or whatever it might be in that context. We really leverage that AI COE team to help us direct our focal points and direct like what is the customer base looking for AI to solve? Because if you're selling car parts, you're probably not looking for like implementing Claude to help you write better emails, right? Like that is not an AI use case that a car part manufacturer cares about, but having more accurate shipping data so that you get fewer returns and mis-delivered packages is probably really important to your bottom line.

Alex Kracov: Yeah, totally. I think there's such good advice in there. I love the idea of the AI center of excellence and bringing those experts forward and a place where the CSMs can go. And I think what you were just saying about — you've got to meet customers where they are and understand technology is cool, but it's got to solve a specific problem that's relevant to the customer. So I think obviously reminding CSMs and building programs around that is really, really important.

Fiona Simpson: Exactly. And I think the other aspect of it as well is that it helps us guide our customers away from the noise of AI, right? And have a point of view and offer them some perspective of — 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 that we know is effective leveraging all the tools inside of Boomi. Do that. And ignore the rest of the noise. And I think that's been really helpful for our customers to have some confidence in our ability to support them and kind of cut through the noise.

Alex Kracov: Yeah. And I think like you got to give your CSM team confidence to talk about these things too. I think like that is so important because if they go in there like, I'm not sure — like, no opening. That doesn't instill confidence, right? And the CIO you're dealing with on the other side. That's a tricky part of it. Okay. So what about the internal side? Like I assume you're using AI a lot, like to build your enablement programs to help CS teams. Can you talk about some of the stuff you're doing there?

Fiona Simpson: Yeah, absolutely. You know, we as an enablement team have a directive — not just as an enablement team, but really from the CEO down — to leverage AI for productivity as much as we possibly can. I think that is a baseline. I think most people today are leveraging AI in that capacity to some degree. And watching that happen has been really fascinating because things like — it's almost like this mental Renaissance of like what can't I do? Leveraging, you know, some of your basic things like Claude, Granola. I love Gamma by the way, right, for like quickly making visuals. And then using specific AI tools that are focused on go-to-market things like the AI builder in Gong. We use Luster for call scoring and AI role play based off of the individual skills that people have gaps in on their live calls. So that's kind of the baseline stuff that we're doing. Really interestingly, here's just a silly example. I am running this road show of going to our different offices and I gave a list of all of our CSM teams and where they're located to Claude. And I said, figure out which locations are the most economic for us to host these workshops and divvy people up into groups and also tell me like what time do we need to finish so that people can fly home the same day. And it went bing bing boom boom boom, broke my team into two groups, we're doing one in our Vancouver office, one in our Pennsylvania office, and it divvied everybody up and was like, okay, this person's gonna have to leave at 3:30, everybody else can leave at 4. And it sounds silly but I can't even imagine how long that would have taken me to do all the research and like run the numbers on that.

Alex Kracov: You wouldn't have even done it and the person would have missed their flight, right? Like yeah.

Fiona Simpson: We would have guessed and we probably would have picked the wrong office location and then spent an extra $5,000 on flights and hotels or whatever. But I just said, hey, figure it out for me. And that's been really helpful for me as an enablement person, especially because I'm just one person with 120 people that I'm responsible for. And then from our CSMs themselves, I think they're doing a lot of similar things to help their productivity. So things like doing account research, having different tools digest their clients' 10K or keeping track of movement within the company in terms of personnel, right? Like if this person's left, this person's come in, tell me about the new CIO and do some research on what matters to that person. And then consolidating — there's so much information that we have at our disposal about the way that our clients are using our products, like usage dashboards and all kinds of Power BI stuff. It's a lot to digest. And so a lot of our CSMs are starting to say, okay, like here's my customer's business use cases. Here's what the data looks like in terms of what they're doing in the system. How can they optimize? How can they take advantage of what they're already buying? What are some opportunities for me to maybe suggest some expansion or new products? And so that's really given them some confidence — like a boost — and I can speak eloquently to this customer about their business in a way that they understand, because they don't have to figure that stuff out on their own for, you know, some of them have 50, 60, 80 clients and that's a lot to keep track of. So it's helping them speak more directly to that specific customer in the moment.

Alex Kracov: Yeah, I mean, it's got to help so much pulling together the materials for your QBRs. And like, I mean, does it fully automate like the QBR deck or you still believe in human in the loop, like needs to check everything? How do you think about that kind of distinction?

Fiona Simpson: Yeah, that's a great question. I would say just due to the complexity and the contextuality — if that's a word — of our customer base, we actually have an entire team out of our Bangalore office in India that helps prepare the data. It's kind of digested down for CSMs for those QBRs. And as far as I can tell, they're not going anywhere anytime soon. I think there's just so much context that needs to be in the loop. Now, can we automate some parts of it and is that team working to be more efficient? Absolutely. We've set some really lofty goals for how many QBRs we're going to execute this year. And so they need to optimize themselves in that sense. But we really keep our people in the loop as much as possible because we also can't afford to be wrong and make those stumbles in front of our customers.

One of our CSM managers put it really well. He said he wants our CSMs not to be over-leveraging AI to make a five-minute task take two seconds, but leverage AI to make a two-hour or a ten-hour task take five or ten minutes. And I think that's really kind of the sweet spot right now is — yeah, I can write an email myself. I'm a human being that can write an email and it's not hard. I don't need to be like, hey Claude, please summarize this meeting and write me an email. I could just be like, hey Alex, thanks so much for chatting today. Here's the two things you asked me for. Have a nice day. I don't need Claude to do that and I probably need to retain my brain self to be able to do that. But if I needed to do seven hours of research on how expensive flights are from 17 different places in the US, that is something that I can hand off to AI.

Alex Kracov: I think it's such an important point too. And it's like unintuitive to how we are used to using computers. Like previously, I want my computer to do everything really, really fast. I click a button and I expect an immediate result. But then to your point, like the most powerful stuff you can do with AI actually takes a little bit of time. And like, as someone who's trying to build AI products, it's like, what's the amount of time that's okay for an action to take? And the most valuable ones usually do take like five, 10 minutes, but it's going to automate something that would have taken two hours. And that's like an interesting psychological shift that I think we all need to do as people.

Fiona Simpson: Can I drop in a little shameless plug? Pretty funny. So outside of Boomi, I have my own website that I do some other stuff on the side and I needed to update the copy on my website. And I was chatting with my guy Claude and I was like, hey, I know you have access to Webflow, which is what my site's hosted on. What can you do in there? And he's like, oh, if you want to update the copy, I can get in there through the Chrome extension and do the copy updates for you. I was like, sweet.

Alex Kracov: Wait, this is your Claude and Dog series. I saw this, this is awesome. Yeah, I wanted to ask about this.

Fiona Simpson: So I listed out all the copy updates of like where they were, we worked on it together. And I went and took my dog for a walk while Claude — this is my Claude and Dog series on LinkedIn. Yeah, everyone please feel free to follow me on LinkedIn for more content about things that I do with my dog while Claude is doing work, like updating the content on my website. And honestly, it was an epiphany. And like that's where the joke of a LinkedIn series came out of. I was like, I can go do something else. And it's just gonna go dee dee dee dee dee. And so that's the way I look at it is like, what can I do — either other work that really needs me involved in it — or like take a break, walk my dog and let the machine do the work for me.

Alex Kracov: I was watching some of those videos this morning. It's awesome. Yeah. No, and it's so true. I think AI has come to the engineering function faster than other functions. And you see a lot of engineers like before they go to bed, get Claude to do something overnight, like things like that. And it's such a weird way to work, but like it's way more efficient. Or I have Claude running in one tab and then I go do a podcast or do something else. Right. And it's just like changes how we do work.

Fiona Simpson: Yeah, one of my buddies, he decided just kind of on a whim — and he just like figured this out, this is not his area of expertise by any means — he bought like five Mac minis and basically trained them so like one is the brain and it farms out work to the other ones. And it's just like running stuff all the time. And I'm like, did you know anything about this six months ago? He's like, no, I didn't know anything about this like six weeks ago. And it's just amazing how all of us are sort of finding these areas of efficiency and teaching. I think one of the most magical things, honestly, is that we're teaching ourselves skills that used to be so far out of reach for a regular person. You know, I'm a relatively technical person. I've been a solutions consultant. I've worked in pretty complex industries, but I'm not a programmer. I'm not an engineer. I'm not a designer on that end of the spectrum. But now that I have this ability to explore those spaces and kind of explore without a lot of consequences — like I can try and fail and break stuff and do all that — it's a very different world when it comes to learning and advancing your own just domain of knowledge about stuff. And I think that part of it is pretty cool.

Alex Kracov: Totally, yeah, it's an exciting time to do stuff, especially if you have the beginner's mindset. I think if you're sitting on your couch and you don't want to learn and you just don't want to do things, but if you're excited about learning and playing around with new things, it's really fun. And I spend all my time trying to build Dock AI stuff and it's a fun time to figure out, okay, where do we play in this overall puzzle? And no one knows where it's all going to head, but that's part of the exciting part about it.

The Road Show: In-Person Enablement

Alex Kracov: All right, moving away from AI a little bit. I want to talk a little bit more about this road show because I think it's super interesting. Why did you choose to go on a road show? We obviously have Zoom. You could have just done it virtually. And then what goes into a road show? How do you prep? What are you presenting? What does the agenda look like? Because I think this is something really important for enablement folks to learn about.

Fiona Simpson: Yeah, absolutely. You know, I think my eyes were really opened when we all got together at our RKO in Austin in February. Being in the room, there's something about — I think, you know, our friends in like adult learning theory and like that end of the enablement world could tell us exactly why it is. But 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, and again, this is outside of my realm of genius, but it really does do stuff to like your neuro pathways. Like 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. Like that is something that will be true no matter how many robots we get to do other stuff. Like you have a better conversation. Like even if you and I were sitting across a table, there would be an additional element to this conversation versus us doing it over cameras. Right.

So I believe that personally as an enablement practitioner, and I'm really lucky that my CS leadership team also believes in that. We have, you know, a third of our team works out of our Vancouver office three days a week still, because there's something about being in the room together that that's really valuable. And so we had our kickoff in February, we had a CS leadership meeting the following week, and we talked about, how do we want these enablement programs to run? Do we want them all to be virtual? Do we want them to be virtual and asynchronous? Do we want to do some stuff in person? And all of my leaders said, yeah, let's do some things in person. And so this road show is two-day training workshops in our Barcelona office, our Conshohocken, Pennsylvania office — thank you, Dell, for that delightful space, a little hangover from our former relationship with Dell, great folks, we just outgrew them — our Vancouver office, and then I will head down under at the end of the summer to go to our Sydney office. And the goal of those is to do some hands-on activity and some hands-on learning around specific accounts that maybe are challenging. Like let's say we've been trying to get a QBR with this account, but our champion has moved on or they're really resistant or they've kind of put us to the side — how do we unpack that? And doing that together in small groups with our peers, really like taking an actual account and an actual struggle that I have as a CSM and sharing that with my colleagues in a way that you don't get to do over Zoom — that is the goal, that is the point. It's kind of like literally laying it all out on a real table with the real interaction between the folks on the team to help problem solve and to help get better at the things that maybe someone in the room is great at and has a good example. Their hand flies up and they go, I had that happen and XYZ and this is how I solved it. And you just don't get that when you're all sitting around on a Zoom meeting — people kind of sit back, maybe they're checking their phone, maybe they're firing off an email to a customer. And so the point of bringing everybody together in the room is to take away some of the distraction and open up some of the interpersonal and sort of the empathy and the like, I'm watching this person and they're confused and so I can tell that I need to explain more — and all those things that just don't happen over Zoom.

Measuring the ROI of Enablement

Alex Kracov: So we've talked about a lot of different programs on this conversation so far. How do you think about proving the ROI of enablement as you work with the CS leadership team, the enablement leadership? Do you have a dashboard you look at? Are there specific metrics? Is it inputs, outputs? How do you think about just measuring, was this roadshow successful? Are we doing QBR successful? How do you think about that challenge? Because it's hard to prove sometimes, I think.

Fiona Simpson: Yeah. And, you know, having been in the enablement space for about a decade, I have a lot of thoughts about this. So like, how much time do you have? But I will say a couple of things. I think that there are always going to be layers to what's measurable, right? And moving from one layer to the next, you can push some correlation. I'll use correlation as a broad word because I have some thoughts, but I'll kind of break it down as best I can. So I think when you are looking at something like a training workshop, this is a great example. I have an email going out on Monday morning to the folks coming to this workshop. So it's like, what are two or three things that you want to focus on during this workshop? How confident do you feel today about your ability to deliver a QBR to an executive audience? And then basically I'm going to measure how that changes after the two-day workshop, right? So they have a survey at the end and it'll ask a couple of things. Like, do you feel like you got the things that you came into the workshop looking for after the workshop? Do you feel better, more confident about your abilities and so forth? So I think there's some pretty direct — like this person came in feeling low on the scale and they came out better. That is very straightforward for enablement to do. And I think enablement has always been pretty good at that. The next level is skill improvement. So like objectively measuring — this person was at a C grade level on their QBR delivery before Q2 of this year. They went through the workshop, they did some asynchronous training, they did practice sessions with their team, they had more at-bats with their customers that we were able to grade, and they moved from a C plus to a B minus, or a D to an A, because they're magical and Fiona makes amazing programs. So there's the sort of objective improvements that you can see. And then I think...

It's always interesting and nuanced with CS and it always depends on how things are set up. Like here at Boomi, technically speaking, CS is not considered a revenue-generating organization. It's considered a cost center. And so the pressure is a little bit off. Like I don't have to prove like we improved the dollars coming in the door. How do our retention metrics look? How does our expansion opportunity creation look? Some of those lagging indicators that we can definitely point to. Like we did a lot of training on AI talk tracks and we saw an increase in AI expansion opportunities that were generated by CSMs. There's some areas where I think you can show correlation. I will leave my hot take here for the end, and it's this. I would also ask the people who are asking enablement to prove their ROI — I would also ask them how the light bulbs in the office have ROI. The reason I say that is because everyone knows that not having light bulbs is problematic and having them improves something. And I would argue the same thing is true about enablement. Everyone knows not having enablement is not good and having enablement is better. To me, that's enough. But I also don't run a $4 billion company, so I'm allowed to have that opinion.

Alex Kracov: Yeah, I mean it kind of reminds me of like brand marketing too a little bit. It's like we all know this is important. It's going to grow your brand. It's going to bring in leads. Like you can't always draw that direct line to a business outcome — it can be hard to prove, but it's really important to do.

Fiona Simpson: Right. Like, somebody tell me, okay, so like God bless our friends at PandaDoc, I just got this water bottle, which is probably like a Wella water bottle. It's like 20 bucks, right? Like somebody tell the CEO or the CFO at PandaDoc how spending $20 on this water bottle that I got at a conference is going to bring money into their door. Like somebody explain that one to me and I will explain to you how enablement proves its ROI.

Alex Kracov: Yeah, I've never thought about it like that, but it's a good comparison. Yeah. All right. We spent most of today's conversation talking about Boomi, but you've also spent a lot of your career working at smaller companies where you were like the first or only enablement person. Can you talk a little bit about like what you did differently at those companies where you have to do the whole function as opposed to just focusing on the CS team? How'd you approach that challenge?

Being the First Enablement Hire

Fiona Simpson: Yeah, that's a great question. And admittedly, they are very different. Like, it's an adjustment for me to be on a team of 17 enablement geniuses, frankly. When you're a team of one, or you're starting the enablement function, or you're the second or third enablement hire, you really have to — it's like you have to draw your own map. Like you really have a blank page and you have to just start kind of like plotting a course to somewhere. And I think you have to be a little bit prescriptive when you're in an enablement team of one or the first hire or whatever the case may be. You have to give the organization some guidelines about what you do and don't do. Like a lot of people will call it an enablement charter, which I strongly believe in. These are the things that are part of my role and these are the things that are not. You have to start there because otherwise you become the jack of all trades, master of none. Like you're a smart person, you understand things, people will just start coming to you with stuff. Like I can't tell you how many times I've been reporting directly to the CRO and all of a sudden I'm like planning offsites and like becoming like the chief of staff to that CRO because you're just in this position where you're proximate to everyone in the organization and you just learn things really quickly and you just sort of become like the go-to person for everything. So you have to be careful. I think the other thing that happens at that size and scope — but I think it's really important in smaller organizations — is learning how to, I would maybe say, no gracefully or kind of turn a request back on the person asking for it. And there's a couple of ways that you can do that.

By asking a few questions that are pretty straightforward, but if they don't have answers, then it's really easy for you to go, well, sorry, I can't help you. The first one being like, what's driving this request? What's the data? What's the root cause? Like, okay, the sales manager heard someone say something wrong on one sales call. That is not enough data for me to do a whole program about this talk track, right? So if you don't have like the data to back it up or like a root cause — like, our competitor is acquiring this other competitor and now we need to redo our whole competitive analysis. Like that's legit. There's a root cause for that. But if they can't answer that question, I'm like, I'm sorry, until I know that there's a real theme here, I can't do anything about it. The next question is sort of like, what is the point? What do you want the outcome to be? Is it knowledge acquiring? Is it a skill that needs to be improved? Is it just a total gap of something that doesn't exist like we don't have a process for this or whatever it may be? So what's the outcome or the change? And then — because if you can't tell me the answer to that question, I have nothing to build towards; I could just keep doing this thing into forever with no end result that I can measure towards — and then the last one is always a good one and it's really important for enablement people to keep track of what they have going on for this reason. It's like, okay, here's the list of seven other things I'm working on — kill one of those projects for me to put yours in, right? Or like move one down. And if there's not enough urgency behind whatever this thing is, when they look at the other things that are going on, that's a great way to help kind of weed out the things that are not super urgent or super important. So I think those three questions, right? Like what's the root cause of the data that's driving this request? What's the outcome that you want at the end of this? And what's the priority? Those things will help guide and make it easier to say no when you're getting it from all sides.

Reflect Path: A Framework for Better Decision-Making

Alex Kracov: One of the other great frameworks I've heard you talk about — outside of Boomi you run Reflect Path, which is like a speaking advisory practice. And I've heard you say that most revenue teams spend all their time studying what went wrong and nobody studies what went right. Can you talk about where that idea came from and what's the framework?

Fiona Simpson: Yeah, thank you for bringing that up. So yeah, outside of Boomi, I do have my own business called Reflect Path. And that kind of grew out of an evolution of sort of my own career transitions, working with some people in their career transitions or even like standing up go-to-market functions and things that you just need someone to work through with them. That's sort of the advisory side of things. And what I started to realize is most of the time people kind of knew the answer that they were looking for or they had made a decision and they realized where they went wrong, or they made a decision and they felt like they should go this way and they went the wrong way and they go, I should have trusted my gut on that. And a lot of those conversations kind of led me to this idea of whether we're looking back and evaluating how we ran an opportunity or a hiring decision or should I take this job or not, like kind of personal decision. There's a little bit of a path to that, hence Reflect Path.

And so I came up with this framework and it's five pretty straightforward steps. The first one being situate. What is actually going on? Your boss comes to you with a problem. Is that the actual problem or is there something else underneath it? So just figure out what's going on. So that's first step — situate. The second step is surface. What information do you have? What information do you need? Who do you need to have involved? Does anybody need to be involved? Surface sort of the pieces of the puzzle, the blockers. Are you missing some information? Sort of the, you know, if I knew this, I would be able to move forward stuff. The third step is go internal. And I really deeply believe in this. And this is not like woo woo stuff. This is actual science. The idea of your central nervous system being the fastest supercomputer that's existed until maybe the last like three to five years. We got leapfrogged a little bit by the supercomputers, but for most of human existence, your central nervous system is the fastest data delivery system that ever existed. And so when you feel something like, yes, like that's exciting to me, or like that feels right, or ooh, I don't like that, or like your shoulders tense up, or you cringe a little bit, that's actually information, that's data. And that's a ton of stimuli from everything that you know cognitively, from your outside environment, from your past knowledge, your natural instincts — like all those things are actually getting processed by your brain to give you information really, really fast. And I think it's really valuable to listen to that. And if you go back to like 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. And so that go internal piece, if you can do that before and use that as part of your data, it actually helps you make better decisions going forward.

So step three is go internal. And then step four is decide and commit. So make the decision, like get clear on what the decision is and then actually commit to doing it. So don't just like make the decision and then leave it to the side and get distracted by something. Decide what you're going to do, commit to it, take the action steps, go forward, right? And then the last step is the reflect part. And this is the point that I make a lot about sales teams — we love to pick apart the bad deal. Like this blew up in our face and that was going to be like the thing that got me to club and da da da da, and it blew up and here's all the things I did wrong and my manager can tell me and the CEO can tell me and like, it's all a mess, right? We love doing that because we're all a little self-deprecating. But a lot of people skip this step when things go right. And the problem with that is you're missing out on data to help you make better decisions faster in the future. And so when you go back and you look at the way you got to that decision, did you trust your gut? Was your gut right? It's all data for you internally, but it's also data for your team — like, if you're in a sales org and Bob can't explain how Bob keeps landing these whale enterprise deals, you're missing information that could be useful for your team. So that Reflect piece is really important because it's really easy to skip, but it's where all the data is.

Alex Kracov: Yeah, it's an awesome framework and that makes so much sense. Like we do just as humans, I feel like focus on all the negative. I definitely do that. And it's like, there's actually a lot of good stuff that we could learn and share across the organization. I think one fun place to maybe end today's conversation — this has been awesome — is I think you're a practitioner who's sharing so much awesome information on LinkedIn and kind of building a public presence. And I feel like sometimes people are scared to do that or feel like they don't have anything original to say. Can you talk about your approach to that and maybe what advice do you have for other practitioners who want to do the same?

Building a LinkedIn Presence

Fiona Simpson: Yeah, I think LinkedIn is such a fascinating space to me. I've been on LinkedIn for years, like as a resume thing. And then maybe like 2022, 2023, I just sort of noticed like people were talking about actual things and not just posting like, my company is doing this or like we're hiring. Like people were starting to have conversations and post content on LinkedIn. And I thought that was interesting. And so I just started following along and I was a lurker for a really long time. And then I'd like write a little quippy, like something something.

And then I got laid off in 2023, like everybody on the planet, and I was bored. And I was like, you know what, this LinkedIn thing is kind of interesting because I'm meeting interesting people that I wouldn't have been connected to otherwise. And so for me, it's been a really fascinating way to do two things. One, connect with people in my industry, like in go-to-market, in enablement specifically. Like I got my job at Boomi because of connections through LinkedIn. Sent a video, literally sent a DM video to my now boss and was like, hey, I'm the person you're looking for because you posted about this job opportunity and here I am. And then on the content side, like it's just fun. You know, there's Upton the Pupton, by the way, star of Claude and Dog. He's snoozing on top of my laundry.

Alex Kracov: Yeah, I saw him, yeah.

Fiona Simpson: People take it so seriously and people track their statistics so hard and get all into it. And I'm like, this is just fun. I can share things. I can have amazing conversations in the comments on LinkedIn to learn from other people or they're learning from me. And I just think that's an amazing way to share knowledge. And I think a lot of people get really scared. Like, I don't have anything to say. Nothing I say is that important. Nobody cares what I think about enablement or dogs or go-to-market or whatever it is. Honestly, just start posting stuff. Like, it doesn't matter if it's not good. It doesn't matter if two people and like your mom is giving it a thumbs up. Like, it doesn't matter because there's something about the snowball effect of just getting involved in conversations on LinkedIn and getting confident and kind of growing the muscle of like, hey, I actually — people are interested in having this conversation with me. Even if I'm not saying anything totally groundbreaking, that's okay.

And interestingly enough, I used to be the person that was like, I have to come up with something new and sharp and amazing every single day. And I realized — and some of the people that I follow really closely and that I've worked with about content before pointed out — like, it's actually okay to say the same thing a lot. Like I post about my Reflect Path framework a couple of times a week because that's what I want to be known for. I post about enablement stuff because that's what I want to be known for. Like my friend Lindsay Rios, she talks about poopy pipelines. Like she is the poopy pipeline girl of LinkedIn. And because people recognize that and she's an expert in ICP and pipelines. My friend Ashley, she talks about being an enterprise AE and being a mom. And like that's what she's known for on LinkedIn. Because when you say the same consistent message over and over again, you become an expert in that field and people will come to you for that. So you don't have to be original all the time. And if I could give one single piece of advice about being on LinkedIn — just be there, just show up. That's 90% of it. Just show up, get in the comments. You don't even have to post your own stuff. Just go have conversations with the people and you'd be surprised. I've added 500 people to my network in five weeks, like just by being there. So that's my spiel about LinkedIn.

Alex Kracov: It's amazing advice and it's such a powerful platform and I try to do the same thing. We've grown so much of Dock just based off just being there on LinkedIn, saying the same thing, not being self-conscious about what I'm posting and stuff. So I think it's awesome advice everyone should listen to. Thank you so much for the time today, Fiona. This was a really, really fun conversation and thank you.

Fiona Simpson: Absolutely. My pleasure. Thank you so much, Alex.