Chandler Perry:
Welcome to this session of WinLossWeek. The world's largest online event dedicated to win-loss analysis. This event is hosted by Clozd. We'd like to thank all of our partners for their contribution to making this event a success. The title of this session is Gaining Strategic Insights From win-loss analysis. Today, we're lucky to be joined by Brandon Penn. Brandon leads Twilio's customer collaboration and pre-sales consulting team as the global head of Twilio Foundry. Prior to that role, he built and led market strategy, sales intelligence, competitive and benchmarking programs at Twilio. He is passionate about the customer experience in creating authentic, connected experiences between businesses and consumers. Brandon, it's great to have you today.
Brandon Penn:
Great to be here.
Chandler Perry:
Awesome. Well, to start at a high level, we'd love to understand why win-loss at your company and what prompted you to go down this avenue?
Brandon Penn:
Sure. I joined Twilio, actually three years in October, to build out our competitive intelligence, market intelligence, and win-loss program. At the time, our company was about 900 employees and we had this really aggressive growth plan to triple in employee size over the next few years. As of today, we have about 3,400 employees worldwide at a run rate of 1.6 billion. win-loss is just such a fundamental part of, in my opinion, supporting strategic initiatives and having those insights to make actions, and pivot and adapt to the ever changing environment, whether that be insights related to product, to sales experience, to marketing and positioning, to all the different ways we engage with customers and their overall experience with us as a company. We've been at this for 11 years now. For those of you who haven't heard of Twilio, we were created to migrate the world's communications from its legacy and hardware and physical networks to its future in cloud.
If you think about cloud communications, anything that has to do with being able to text someone, to call someone, send an email, or go through an IVR, developers and companies can use our API's to create those experiences. When I joined, at this point in time, prior to that, we've always been very, very developer-focused and we wanted to really build out our go to market our sales motion. win-loss served us such a crucial part in that and understanding our personas and who we're actually selling to and giving us feedback on how we should position our various products, what features enterprise are actually looking for and getting feedback on the overall sales experience that we can continue to provide the experience possible to our clients.
Chandler Perry:
That's great. In building out your go to market strategy, what questions did you specifically want to ask through this win-loss channel?
Brandon Penn:
Yeah. It's a great question. If we think about building out our good market notion, that's such a huge initiative. When it came to that, we wanted to get insights not just on, if we think about why we're winning or why we're losing, it actually touches a handful of things. Everything from how they actually heard of us and what they're trying to achieve. Are they a business buyer or more technical? Which we actually worked [inaudible] team on tailoring our interview guide and getting a lot of best practices around that, but also things around our product offering.
How easy are tools to use? Are there certain features or bells and whistles that they expected that we didn't have in our platform that we should invest in on our roadmap? Or were there certain competitors that we were just inferior to, in addition to everything related to pricing and packaging to, as I mentioned earlier, the overall sales experience, how was it buying from Twilio? What was it like working with our sales team and what was the impression on your experience with Twilio overall, if you one, decide to go with us and be a customer or two decided not to go with us. Those were some of the questions that we tried to answer through our win-loss program.
Chandler Perry:
Yeah. Awesome. Well, you mentioned how broad of an initiative this could be, I'm sure your customer base is large as you sought answers to these questions. How did you determine which accounts or which individuals to contact?
Brandon Penn:
Yeah. That's a great question. I guess to provide a little bit more context, our sales team is really broken up by a segment. We have about four different segments. Everything's spanning from, I'll probably just give employee sizes and not the name of the segments, but we have different segments that sell to different size of companies. We have a segment that sells from one employee to a hundred employees. We have a second that sells from two companies with a 101 employees to 2000 and then 2000 above. Then of course named in strategic accounts. Because there were just so many differences in the size of these companies, the way they buy what they actually care about. For us, we wanted to figure out how can we get a good mix between not just industries, but across the segment size and a good mix of both developers and business buyers to get a full picture of like the 360 view of what their experience actually is with Twilio.
If I were to talk about maybe some of the insights that, one of the biggest things that we've found across interviewing all the segments was one, competition was drastically different across different segments. In the lower tier, we came against usual suspects who sold APIs that were similar to messaging or voice in one of our channels. But then as we moved up the stack, we saw more and more software vendors. That really interested us because we want to figure out well, we're selling APIs, but then as we move up the stack, we're also selling our software solutions and more SaaS solution. It helped us define a lot of how should we think about our market positioning and tailoring our message to meet the needs of every company, regardless of segment, regardless of region and regardless of industry. Does that kind of answer your question?
Chandler Perry:
Yeah, absolutely. It's interesting. I feel like building out an ROI equation and on an initiative quite like win-loss analysis. It's often difficult to know what our efforts will yield. Any other thoughts on what strategic initiatives or what effects this program has brought to your organization?
Brandon Penn:
Yeah. When we started with win-loss three years ago, again, we did start with more of that broader approach. Looking across every segment, geo-industry, but over the last year or so, as we've matured as a company, as a go to market organization with product, et cetera. We wanted to focus in on certain initiatives that we thought would fuel our future growth and where we should continue to make investments. An example of that is we acquired last year SendGrid, which is the world's largest email provider. We also wanted to understand, well, one is, why do we do this? We actually found that a lot of our customers through these win loss interviews were also purchasing from companies like SendGrid. We thought it was just a perfect match.
When you think about customer engagement as a whole, everything from SMS to email, to voice, I mean, they should be integrated and they should be together. It just felt like such a perfect match for us to be able to add those email capabilities to our offering. That's one example, but more and more, [inaudible] to focus on certain products as well. We wanted to hone in on maybe just looking at deals that had to do with our voice product or our video product so that we can enable our product leaders to understand some of the feature functionality that was missing or that we can do better on.
That really helped us solidify the roadmap and add some improvements on that and be able to also just from marketing aspects, socialize that if we were seeing some commonalities or themes that customers weren't going forward with us for voice or video, because they were missing stuff sort of product or didn't know that we can do something, which we could, well, we needed to make sure that we're getting that message across. We decided, long story short, we started out broad, but then as our program matured and is continuing to mature, we're now really starting to focus on what are the annual company initiatives, whether that be product or R and D or sales that we can align our win-loss program to is that we can provide our senior leadership team with actionable insights to achieve us in accomplishing these goals.
Chandler Perry:
That's awesome. Yeah, we hear that insight quite a bit. You can go broad, but you can also drill down on some of these narrower aspects of win-loss . That's great. Brandon, you have a lot of experience in this arena that our listeners could profit off of. As you look back on the time and energy you've invested into this initiative, what would you have done differently? What would you have, improved or done day one of this initiative that you know now with your experience?
Brandon Penn:
Yeah. That's a fantastic question. I think overall it would just be alignment and getting that buy-in from the top down. An example of this is, in my organization, we can't just be, we have this thought, and we're just going to go reach out to customers without telling our account executives that we are going to be reaching out. We don't want to cause any friction they're already in the sales cycle. An example there is, if we are conducting a research study, we need to look at the end-to-end experience of what we're trying to prove, who we need to communicate to, when we need to communicate to them and make sure that our stakeholders, our sales reps at those accounts, our sales leaders, our product, our marketing leaders are aware of the initiatives that's going on so that there's no confusion.
I think there are always a handful of times where a rep will reach out and say like, "Hey, I had no idea that you were communicating my customer. They asked me a question. I had no idea how to respond and XYZ." We want to obviously minimize that friction because on the customer side, if they are asking a question to [inaudible], that's the overall bad experience. We want to make sure that everyone is aligned on our research initiatives and that if we are reaching out to clients, that we also let the account team know, and then overall being able to tie again, as I mentioned, this past year, year and a half, we focused more on certain company initiatives that we set out every year.
we want to just be able to be able to provide as much context as possible to support those initiatives. One thing that we really tried to focus on too, it's just overall, this deals with sampling strategy and good market research design is ensuring that we have a good mix of customers across segments, diversity in the personas, and that we're really covering all basis to get the full picture of what's actually going on so that we can provide a more compelling hypothesis and thesis as to what we should do.
Chandler Perry:
Yeah, that's great. I mean, there really needs to be alignment both on the front end and the back end. I'd be curious if you don't mind me asking just on the backend, when you get these insights, how can you create alignment when you have all these unique findings? How can you, spread that and provide meaningful change in a rather large organization like yours?
Brandon Penn:
Yeah. With a lot of our insights, we do like to... Well, if we think about insights, insights are just so crucial to every single functions in an organization, in my opinion. If you are a business leader, if you're a sales rep and you aren't looking for research or looking for the insights, I find that it's hard to do your job effectively. For us, one of the biggest things for us was when we're getting research, we know that, we want to make sure that we pull the common themes and we test that with what else we're hearing in the market, or what we did that moved the needle in a certain stance.
An example is if we find in the first half of the year, that a lot of our insights are telling us for losing, because our pricing packaging is complex. If we make changes to it in the second half of the year, we want to ensure that, well, did that resonate? Are we seeing that we're losing less because customers now have a more, we are more transparent with our pricing packaging and they it's easier to understand. Just being able to continuously measure over time what our insights are telling us, but then overall I'd say just being able to set a cadence of that. It's hard to look back and say, okay, each one out of all these themes, this what we noticed. [inaudible] we noticed, but to get that you have to report up your insights on a cadence.
What we've done is [inaudible] cadence, we have send out our interview transcripts that we've got, just the raw interview transcripts to like our entire distribution alias, but then our monthly report, we would pull all these together and look at what common themes there are and continually report that up as well, in addition to looking at other sources of data. Within win-loss , interviews was a portion of them and speaking to customers, but then actually looking at our Salesforce data to see what's reported and figuring out some of the top reasons there that are all, of course, [inaudible] reported. Just cross-referencing that data to see, are there commonalities or themes that we should be looking at? Just being able to communicate effectively on a cadence. In doing that, we'll be able to find more themes and measure how we're doing against our initiatives and actions that we do take based off of the insights that we received.
Chandler Perry:
Yeah. Looking across all the channels and then aggregating the results of all these customer opinions to really embark on transformational change. That's really cool. We've covered a lot today, Brandon, we've talked about the questions you ask, the problems you're seeking to solve through win-loss and what strategic insights you've gained, any other thoughts that you would like to offer for our listeners today?
Brandon Penn:
Yeah. Yeah. I'd say overall get gathering insights and data is one thing, but the most important thing is what are you going to do with that data? I think that is so crucial because one of the biggest things actually that we found with our win-loss program, as I mentioned I previously built out the competitive organization and market research. As we were approaching on, going back to what I mentioned earlier in the call, this whole go-to-market motion and really building our sales team to sell to the enterprises. One of the biggest things that we found in our win-loss program was that we weren't necessarily losing to any one competitor specifically, rather the biggest reason why customers weren't moving forward with us, it was because of the status quo. It's because they actually, Twilio us being an API first platform, it does get complex sometimes to understand all the things that we can do and all the use cases and solutions that are possible with our platform.
As we decided to explore that more, as our program matured, we found more and more themes that our customers and who we were selling to needed that extra hand and that support to move forward with making a decision. Funny enough, that's actually what led me to my role today. Foundry is a customer collaboration program where we support our clients with understanding not just the art of possible, but best practices to move forward, use cases specific to their industry, and really giving them that extra support, whether that be design [inaudible] workshops or custom ROI, financial analysis, anything from journey mapping, to looking at their architecture, to make a decision. Honestly, I'd have to say if it wasn't for win-loss and the program and insights that we've [inaudible], I wouldn't be doing what I'm doing today.
Yeah. I thought that was a really big thing. Overall, that just really solidified our initiatives within marketing, within product, within sales to be successful in the enterprise market. I guess, if I were to close with advice, I think often when companies, just speaking with a handful of my peers as well, who have tried, or are currently building out their win-loss program, I think the most important thing is, sure, it's important to have a vision, but the most important thing is just to start. Whether it's 25 interviews a year, 50. Start small and [inaudible] just be open to adjusting. We have worked so closely with our vendor closed to really tailor our interview guide every single quarter actually. We would sit down, we would look at the data, we would revisit it and figure out, could we ask questions in a better way?
Is this too biased or are we leading them to answer something versus getting just open and honest answers? I think the most important thing is just start, but know that you can continuously iterate over time and I wouldn't worry about getting it right, right away. The most important thing is just starting. The insights overall are just incredibly value. We have to close out, we have this one value at Twilio which is where the customer shoes. I love this value because every single person that's onboard in Twilio, we go over our company values and its value just sticks to me. That really stands out to me the most because every single organization in our company is so customer focused on listen to the customer, what do they want from us? That really just in everything that we do in our decisions that we make, how we act, everything that we do is based off of this philosophy of wearing the customer's shoes and really trying to understand them. Our win-loss program, and a lot of the tools that I mentioned really has helped us get to where we are today.
Chandler Perry:
That's awesome. I love those final two insights. Get the ball rolling and get in the customer's shoes. That's awesome. Well, thanks, Brandon. Appreciate your time, as well as your thought leadership regarding win-loss analysis. To everyone in attendance, thanks for attending WinLossWeek. Have a great day
Brandon Penn:
Been a pleasure. Thank you so much. Bye.
