Twilio, a cloud communications platform, is rethinking career development, talent mobility, and succession planning through a skills-first lens, all while undergoing a broader talent transformation.
At Cultivate ’25, Casey Smith, Senior Manager of Career Development at Twilio, joined Rosanna Arias, Customer Success Manager at Eightfold AI, for candid and practical discussion about Twilio’s journey.
It isn’t just about technology adoption — it’s about redefining how employees experience growth and opportunity.
Smith explained how the company moved from siloed, outdated frameworks to a unified platform that brings transparency and consistency to skills, roles, and progression paths. Their story is as much about thoughtful change management as it is about innovation.
With a clear focus on employee value, Twilio’s approach offers lessons for any organization exploring skills-based transformation.
Whether you’re starting out or deep into the journey, this Q&A offers practical advice, honest reflections, and inspiration for putting employees, not just systems, at the heart of talent strategy.
[Ed note: Quotes have been edited for clarity and length.]
Casey Smith, Senior Manager of Career Development at Twilio, discusses the importance of becoming a skills-based organization.
Rosanna Arias: I know you have not been with Twilio very long, but you all have been a critical part of [their] success so far. Talk a little bit about the business need for driving skills-based transformation — what can you share for the folks here who might be thinking about it, what that business need was, and what you’re seeing so far?
Casey Smith: We wanted to think about what’s that future of the workforce? How are we going to think about talent? Is there a space where you don’t think about exactly the role? You don’t even use a job description, it’s just kind of a focus of what skills you need, and everybody’s more adaptable and able to move — that has been part of the conversation and why skills became important to us.
We’ve started on a roadmap of first thinking about what “skills” means in our organization. We’re saying the word skills, and sometimes when you say words over and over, I don’t even know if it has a meaning anymore. When I say skill … what is it? What’s present in our organization? That’s what Eightfold is definitely helping us figure out.
Then how do we think about how it can influence different talent practices. Succession planning — do we look for successors with certain sets of skills? Talent reviews — do we think about your potential through a skills mindset? When we think about hiring, are we aligning skills and internal mobility and giving people a little bit more stretch assignment?
We’re thinking about it as a core building block for the ways in which we communicate with one another. That was what the business need was — to be a little bit more adaptable. I think organizations, particularly ours, are [flattening], so you have to think about lateral movement versus vertical. How do you make people feel like they’re still growing without feeling stagnant but knowing that there’s less and less opportunities the more you go up in an organization?
R.A.: That’s such an important point, especially in smaller organizations. It’s not necessarily rethinking how you get promoted, it’s not necessarily about the next role up. It could be a role in another team where you’re learning new skills potentially that might be of interest to you.
I’m curious about how this might be different from what you all have done in the past. I know Twilio, for context, is on a full talent transformation journey, so we’re focused today on skills. But it’s the full talent ecosystem — moving into succession, talent acquisition, all of that. How is this different from how you have done things in the past?
C.S.: I’ve been there a year, but from just my understanding of what I’ve seen in the business, everything can also be so disconnected. You have one business or engineering area, and they’re doing something different from your legal team. Everyone is doing their own language, own conversation, and that’s a little bit of what we had.
Each business area would create their own frameworks, and they would take months and months to update them. By the time you update them there’s a reorg, and half the roles that you updated [the frameworks] for don’t even exist.
That was the state we were in: half in, half out. We rolled out the talent management portion of Eightfold to the business at large in March of this year. We’re still getting [questions about], what about our career development frameworks — do they still matter? We’re trying to navigate the business understanding our transition to using the Career Hub getting people to switch their mindset a bit.
Smith shares how Eightfold’s Talent Intelligence Platform has enabled Twilio to understand the skills required for each role in their organization.
R.A.: I want to go back to something you said earlier. Skills — what does that even mean? Could share how you made skills a core part of the process versus an afterthought? I think a lot of organizations say, “We want to be skills based, right? That’s our focus. We think that’s important.” And I think it’s a buzzword in some ways, but you all have done a good job of defining those and putting it front and center.
C.S.: With the Eightfold Platform, the Talent Design piece has unlocked that for us. We decided we wanted to get all of our roles in the organization into the platform. At that point, we needed to understand what are the skills with these roles? How are we defining [skills] when individuals go into the system and they need to see [the skills] required by role?
Skills became the centerpiece of how we had conversations with the business. We worked with our HR [business partners] and let them know that we were interested in having validation sessions for these roles and the skills they need. Then they would select managers or leaders within the organization to sit down for our session and talk about what skills are needed by level.
For context, we have about 1,800 roles in the organization. We were able to have conversations with leaders about what they saw as a skill set needed based on level and based on management. It really brought them along. We were able to use the platform to show them the market skills available. We talked about proficiency and what that looks like at each level.
The tool facilitated us being able to have that conversation and to get people to understand what we mean when we want to say we want to use skills and identify what the work means through that.
R.A.: I think it’s so important you all did such a good job of being intentional in the process.
We’ll talk about one of my favorite topics, change management, next. I would love for you to share a little bit about how you’re managing that change because sometimes organizations will do like a pilot with a small set of users, but then it doesn’t launch broadly so it stagnates in that pilot. I think you all have done a really good job of launching to the full organization and making changes in that pilot originally.
How are you managing change, and how has it been received so far?
C.S.: We’re doing a drip campaign, but as you mentioned, we did a beta test of the talent management functionality in October of last year. We had select users across the organization — people that were impactful to what we’re trying to push out our future business. We also used business areas that are always open to testing, and we asked them to really give us their experience.
We created user guides. We did office hours to answer questions that people had. We did surveys to get feedback along the way. We got a lot of user insight. They were really helpful with getting us some feedback and recognizing what metrics we wanted to measure.
We looked at profile creation, ease of profile, customer sentiment, what they had and how often did they see themselves going back into the [Eightfold] Platform, the ease of creating career development plans. I think we got a lot of good feedback on what was easy to do and what was a little bit harder to do. We [also gained] some insight on skills.
As the Platform parses your résumé, you might get a whole bunch of skills — how do you decide which ones you want to showcase? It was very helpful, and now we’re continuing to focus on profile creation and getting people into the Platform.
Our leaders are focused on what data is available, and we’ve helped them in a change management space. It’s been a change of [helping] people to understand when the value will show up.
Then, most importantly for me, I want the employee to feel like it’s useful. If it doesn’t feel useful for them, then that’s the part that we need to work on. While we’re driving profile creation and driving people to get in, I truly want people to feel like it’s a value add to them when they are in it.
Smith talks about Twilio’s success with onboarding employees to their Career Hub.
R.A.: One of the metrics that we like to measure is returning users into the platform. You don’t want someone to go one time — great, you created your profile, you updated your skills, but are you coming back? Is there a reason for you to come back? If there is no reason for you to come back, then we are not going to take an extra step.
We’ve talked about some of the positives so far, but I would love for you to share some of the challenges. I think with any tech adoption, there’s some hiccups along the way. What are some challenges that you saw?
C.S.: One that is always prominent is job architecture. For us, it was one of those things that was definitely behind the scenes. It was never employee facing. Now, when you have a platform that’s going to showcase all of the roles in the organization, that junk closet becomes wide open. So we were like, “All right, we probably need to clean this up a little bit but not detract from the work that we were trying to do.”
It was an interesting way that we had to deal with it. Job architecture changes were always out of scope for us, so we wanted to keep moving forward. We just showcased it as this is what we’re seeing.
We had about 600 roles with no one in them, so we had to decide if we wanted to get rid of those or deactivate or [figure out] the future use case for them. Do we want to spend time having leaders go through sessions and validating skills for roles that we may not use? We did keep the changes out of scope, so that was one of the bigger challenges.
From a tech perspective, we’ve loved collaborating [with Eightfold]. There are things that we thought were going to happen and then the system didn’t necessarily do it that way. I think one of those [questions] was with the skills. We were interested in seeing the market-based skills for the role versus what skills the employees had and populating [them]. It was fun to work and collaborate and figure out, to figure that part out.
R.A.: Sometimes the system is designed in one way, but we have that conversation with teams of, “We understand the current behavior, but is there room to change it or to make it more helpful for the employees?” Keeping the employee front and center is important.
I also think the other point that job architecture is not typically visible to the employee is interesting. It resonated a lot with me in previous organizations — sometimes you don’t even know what the next potential move could be, and that usually drives people out.
I know right now it’s very early [in your transformation], and you haven’t reported on a lot of things, but I’m curious — how are you measuring success, or how do you plan to measure success with your leadership team internally?
C.S.: We have gotten a lot of support from our leadership team. A company OKR that we have is 50% of our employees have active profiles in the system. The entire organization is behind it, and that’s been really nice to be able to anchor into something that is going to drive some impact.
With that, I think we also have to manage behavior. I don’t want leaders chasing people down, forcing them to do it. There’s a little bit of balance there.
We definitely have the profile creation as one of them, people being in the platform, we are also looking at the utility of it. Are people creating career goals? Do we see people creating career paths? Do we have the returning users?
We also have a space we’ve launched within the platform where you can do a survey. We’re going to look back at that feedback and see what the customer likes — a quick five-star rating, if you would come back, or would you tell your colleague to come back into the system.
We have career development on our employee engagement survey, so we’re looking to see if the scores there change, as well, to see if we’ve provided a tool that allows for that. We’re still looking to figure out what else is there, and we definitely have people interested. People are asking for data. They want to know what the top skills are.
Once you launch, I think especially that talent management portion, it’s important to be prepared. I’m excited once we start to understand what [our data] can tell us to be able to drive the business.
R.A.: Any words of advice that you want to share? It could be for folks that were early in the process or maybe something you wanted to know early on, something that you’ve learned.
C.S.: I think two things. One thing is be clear on your in-scope, out-of-scope because that out-of-scope can creep in and be a distraction. I think that was really helpful for us in defining it.
And the other piece, for me, that is most important is putting the employee first. I think when we are in this space, we’re implementing a platform. We’re trying to sell it to leaders. You’re selling it to managers. You’re selling it to employees as well, but you want to show the business case and the ROI.
For me, it’s really important that the employee feels heard and respected and that all decisions are transparent and actionable. Without that, it’s mostly useless. I would say anchor in that employee experience because that’s the core of what you’re driving. I found that has been helpful when I give some insight or push back on an expectation because it’s not core to what the employee’s experience is going to be.
Watch the full Q&A from Cultivate ’25, available now on demand.