How to Build a Super High-Retention Sales Team | Twilio SVP & GM Alice Katwan

for all of us today. So what I want to discuss is how to build a super high retention sales team. It's often said that success is the sum of all the efforts repeated day in and day out. So talent is so critical to the health and success of our businesses. It's so important that we execute on a series of activities, not just one activity, but it's the collect— the collective activities that will help us produce the amazing results that we want. So I want to start by sharing a few stats with you. The number of job openings in the US in December, 12 million. The number of people that quit their jobs in December, 4.3 million. The ratio of engaged versus disengaged, 2 to 1. It's clear that we're in an era that now folks are calling the Great Resignation, or the great realignment, it's so critical that we're intentional in the efforts that we're making to retain our talent. I know for me, starting my role at Twilio during the pandemic about 14 months ago was one of the toughest experiences that I've had in my career. I manage 75% of the company's revenue. I have an org over 600 folks in the, in my org. And not only did I interview virtually, I onboarded virtually, I had to figure out how to make connections with my teams virtually. I was really limited to the ways that I can hire, retain, build a culture. What we were used to in the past just has shifted. I couldn't travel as much. So it was really hard to figure out how I was gonna build this team, continue to scale as Twilio continued to grow during the pandemic, all over Zoom. And also, you know, I'm a very personable type of person, and it was very difficult for my authentic self to really be seen seen and understood over Zoom. So that was the biggest challenge that I had to face. So I quickly adapted to 4 key strategies that I want to share with you today. Attracting great talent is one. Investing in your personal development. Creating incentive plans that enable positive outcomes. And being intentional about the culture that you want to build. One of the challenges that I faced was how to continue to scale the organization at Twilio and build a world-class team to support our growth ambitions. All of this in this new virtual setting that we're in. And one of the first tasks was, I really needed to expand my leadership team. I was looking for 4 sales VPs. And in under 6 months, I was able to hire them. And I'm really proud about the team that I've built today. But I wanna share with you how I went about doing that, 'cause I think it's really, really important to share that, to share the how. So the first thing that I did was I leveraged my network. So not only did I reach out to my network, but I also asked my team to reach out to theirs. The 2-degree, um, separation is so important to have that reference and the referral and just that warm introduction. But at the end of the day, what really, really matters is not only your brand as a leader, your brand as your company's brand, and the brand of the candidates. And to give you an example, one of the leaders that I hired, VP in Canada, I had a second-degree separation with, with his two degrees, sorry, two-degree separation with him. And he worked with my husband. And we both fact-checked each other and did backdoor checks with my husband being the common connection, in order to better understand, did he fit the culture that I was looking for? Did he have a proven success record? Is he going to strengthen our team? And for him to understand, is, you know, am I a leader that he wanted to work for? So having that brand really mattered, and it really helped that Twilio has a solid brand in the industry. I think it's important to also share the structure of what I was looking for and the qualities of the folks that I was looking for. And diversity was a big piece of this. And when I say diversity, I not only mean gender or ethnic, diversity, but also geographic diversity, skills diversity. That is really important. My leadership team consists of various folks with different strengths, backgrounds, and perspectives. Some are tech— more technical than others. Some come from the industry that we're in, some don't. Some have strong negotiation skills, others are more operational savvy. But I believe that by creating the diverse thinking and skills, gender, all of that, it creates a strong working team. Once I've scaled my team, I shifted my focus to retaining and developing them. It's not lost on me that even if, even though 50% of my organization is new, hired during the pandemic, that they're not going to get the phone calls, that they not going to be interested in looking at other opportunities. So it's really, really important for me to understand the career— their career's ambitions and goals. And I really, really take the time to spend with them to understand what they want to do so I can help mentor and guide them and provide them ongoing feedback. And when I say feedback, like, not just in one-on-ones, but ongoing to ensure that we're continuing the review cycle and helping them get to the place that they want to be. And one thing that I always emphasize is the importance of taking ownership of their career paths and development. As leaders, we can help enable and guide them, but at the end of the day, they own it. And I often hear folks say, this happens all the time, I didn't get the job or I didn't get the promotion. And my response to that is, did you express interest? Does your leader know? Did, what steps did you take to show that that's what you wanted to do? And so again, I'm gonna go back to it. It's super important that they own it, but we invest and help them get to where they need to be. It is also important that we enable an environment of psychological safety in our organizations. This is critical because people want to feel like they're being heard, that they're part of a team, that they have a sense of belonging. This is important because I know how it feels to be in an unsafe environment, and I know that when it happened to me, I shut down and I wasn't able to make the impact than I typically make in an organization. And that was a disadvantage for me and the organization. So it's really, really important that we give everyone a space to be able to share and open and say what they want to say. So at Twilio, we do this and we're very intentional about creating safe— a safe place. And we do this by, you know, to start, I share a weekly email with my leaders to talk about what's top of mind for me, my priorities. So they understand what is going on at my level. I also have regular one-on-ones, and I'm very, very focused on ensuring that they don't move around too much. And then we have skip-level roundtables. I just came back from New York last night, and I held a roundtable discussion in New York with cross-funk— you know, different segments within my organization and different leadership teams. And it was really good to get to know folks. To understand what some of their challenges are, to show empathy, to build relationships. We're going to continue these roundtables. I've also opened up office hours every other Friday, and I was very surprised. They fill up super fast. I have really enjoyed those conversations that I've been having with the team, and at first I didn't really quite know what to expect and where the conversations were going to go. I was pleasantly surprised to learn that they just wanted to get to know me and they wanted me to get to know them. And that's what was missing in this, you know, virtual world where we can't be in person. And so I will continue those office hours. And then the other thing that we are actually kicking off, we'll be kicking off here shortly, is an employee engagement council. This is a group made up of different level team members, tenure at Twilio, diverse leadership styles, so that they can represent the voice of the organization across the business so that we can get ahead of any challenges that we may be having, or if there's something that's working in the organization, so we can cross-pollinate it across the organization and build a culture that we want. Building— we want to be a destination organization. So I talked about attracting talent, investing in your talent. The next pillar that I want to talk about is rewarding your people. This is very important in a sales environment. Sales are motivated by rewards. But it's important to keep your teams motivated and engaged and reward them for the right behavior. And at Twilio, we are kind of transitioning into selling multiple products, to selling software. And as a result, we have multiple selling teams. That we need to collaborate with. So for me, it's very important that when I look at creating incentive programs, that I'm driving the right behaviors, which is collaboration. And that if I put out a SPIFF, the SPIFF is inclusive of all the different business participants that are contributing to the outcome that we want to get. So this brings me to my last strategy. One of my favorite quotes Related to this strategy is being intentional about the culture that you wanna build. And Maya, this is the Maya Angelou quote. I've learned what people will forget what you said, people will forget what you did, but people will never forget how you made them feel. People will never forget how you made them feel. How you make people feel is the key to building a successful culture. And at Twilio, we have a guiding principle and value, wear the customer shoes. And when I say wear the customer shoes, it's not just an external customer. It's also an internal customer. If you think about, you know, in sales or not even just in sales, cross-functional organizations, we have internal customers that help us every single day. And we rely on each other to ensure success. And how you interact with people and the experience that you have really truly does matter, and it helps improve the overall culture. And one way to do this is to really take time to build personal connections. Investing time to understand a little bit about pers— people's personal lives, what happens at home, showing people that you truly care. I share stories about my family all the time. I have 3 boys, 2 in college. One graduating from high school. I'm so proud of the accomplishments that they've had. I constantly share stories with my team. And what I am really surprised about is, and what makes me feel good, is when my team members connect with me later and they ask about my stories and they follow up on my stories, 'cause they really intentionally listened and care. So other ways that we also connect with our teams at Twilio is through team building. Every month through Zoom, we try to do a happy hour, some sort of building, you know, team building event. But this last week, we were in Napa, and we had an offsite where we brought the leadership team together to team build. And at the end of the QBR, I went around the room to all the leaders and asked them, you know, one thing they learned while they were there that they didn't know. And you know what they— what some key takeaways And just about everyone there talked about the fact that they learned something new about their peers or someone in the room, and that they were reinvigorated. They had a sense of belonging, and it just made them feel stronger as a leadership team. And that makes me really happy because that, that increases the collaboration amongst the team. So now that we connected the leadership team, We are rolling out a second phase of what we call hub tours at Twilio. And we are going to visit our corporate offices— or not corporate offices, but our offices. We have an office in New York, Atlanta, San Francisco. We will also visit teams that are in Chicago and Austin. And we bring these teams together at these various hubs. We have roundtable discussions. We'll have happy hours. We'll get our teams together. And just so you know, at Twilio, 50%, over 50% of the company was hired during the pandemic. So just imagine all the folks on the team that don't know anybody. These hub tours, now that we can do them, are going to be really, really critical in making those personal connections. And lastly, it's so important we celebrate success, big and small. Whether we recognize, you know, our typical behaviors around sales and closing deals, or employees that embody our values, it's really important that we, you know, acknowledge accomplishments along the way. I know for me at home, we have a tradition. When something happens that's positive, whether it be kids' grades in school, et cetera, we— our tradition since they were younger is we'd go for sushi and we'd have ice cream. And most recently, my youngest son got accepted to a few colleges and my husband and I weren't home. And my older sons came back to continue that tradition and they took their brother out for sushi and ice cream. As leaders, we can take that too into the office, right? If we set the— if we set the tone, it will trickle down within the organization. If we recognize certain behaviors, if we thank legal for helping us on a contract, if we thank the sales ops team for helping us go through annual planning, these little gestures of thanking them will go a long way, and it will trickle down with the— within the organization and create this tremendous culture of success that we want within the organization. As we wrap this up, a few things to remember. Your brand matters. As a sales leader, you know, for the company, it is really, really critical, whether it's you, your company, the candidate, your brand matters, and that will help you attract the right candidate. Leveraging your extended network to cast a wide net is going to really help you in this virtual world as well. And then diversity does matter. Again, not just race or gender, but hiring diverse skills. It's important to encourage your teams to proactively take ownership of their career paths. And developments, as well as you to enable them and support them throughout that journey. Being intentional about the culture that you want to build is really important. Keeping open lines of communication, being accessible, celebrating success, and then leading with empathy. And then lastly, just be mindful of the incentive programs that you build so that you drive the right behaviors and outcomes, and that they align with your business priorities. So to close, I hope you're walking away from this with, you know, some key takeaways that provide you value to help you elevate your organization as you lead through success. And I am going to open this up to questions. Thank you for, for having me today.

So we've had quite a few questions come in. Let's start, Alice, as one saying, what are some of the things Twilio is doing to address attrition issues?

So we're doing a couple things to address attrition issues. So one thing that we're doing is we're having candid conversations, and actually this came from an all-hands that we had most recently. Our CEO Jeff had asked us all to take the time to really ask 3 questions to our team members. What career interests do they have? Where do they want to go or be? And then what are the things that they're get— they're getting in the way of them doing their jobs? And by having these conversations, this will help us understand where they want to go and we can help enable them. We're also closely monitoring our compensation to ensure that we're competitive with the industry. And then we conduct an employee survey twice a year. And we take those results very seriously. And what we do as a standard practice is we take away 2 or 3 things from that survey that we want to focus on and execute actions against, and then we address them throughout the business. And then I think, as I mentioned, we have the employee council that we're launching here shortly, and that should help as well.

Alrighty. Um, another question is, how do the type of sales reps and sales managers change as the company gets multi-product?

Yeah, so it's not changing, um, it's more of changing the mindset. So it's more of changing the mindset of we're not just selling one product, we're selling multiple products. But for Twilio, it's a little bit slightly different because we're going from selling, let's just say, messaging to go and selling more software products that have lengthier sales cycles that are more complex. So enabling the teams, having them shadow enterprise, more enterprise-type sales motions is going to be really, really critical. And for us at Twilio, the frontline managers are the most critical in helping us get there and make that transition.

Okay. The next question is that you talked a little bit about this in your presentation, but it's how do you structure one-on-ones for retention? How much is action and KPI-oriented, and how much is growth and feedback-oriented?

Yeah, so, um, so one, the way that we have, the way that I structure one-on-ones is I have them, some are weekly and some are biweekly. It all just depends. But they're not necessarily KPI-driven. We have other calls that talk about the business and the KPIs of the business. One-on-ones are typically structured for what's top of mind for you, how can I help you, And how do we follow up on any career conversations that we're having? And those are typically the 3 pillars, or if there's any business challenges that we're having. From a KPI perspective, managing the business, etc., we do those on other— we have other calls for those, but this is more of a one-on-one connect. We also keep a living doc of topics and agenda items that we want for these one-on-ones, so they're very, very focused when we get there. And then we have a tracking mechanism to track the conversations that we've had.

Um, our next question is, what are some of the biggest lessons learned and things that didn't go as well as you'd intended them to?

So I would say for me, because I wasn't accustomed to the virtual world that we live in, is just I realized how important it was to get creative to get to know your team. It was, it was really, really hard, you know, with 600 folks in the team to— how was I going to get to them fast enough? And I think I would have made a bigger, a bigger effort up front to actually just focus on just doing that, rather than onboarding, is just to get to know the folks on the team and try to understand the dynamics of the team.

All right. We got a question from Rob saying, when do you make the decision to grow sales using outside resources versus trying to hire your own, maybe with a lens towards targeting small, mid-sized businesses?

Yeah, that's a very good question. And at, at Twilio, we do, we do focus on trying to nurture our talent internally and to, I would say, train our talent so that they can be ready for that next step so that we can promote within. I also do think that there is value to also infusing the sales team with hiring talent outside of the organization. Because by seeding the talent, by seeding the organization with talent from the outside, You're bringing in, again, diverse thinking and different perspectives that will help the team. Also, the folks that you bring in from the outside can also help expand the network of the organization. So again, it's bringing different perspective to the organization and expanding. Now, I do think it's critically as important to, uh, promote within because you wanna show career trajectory and you wanna ensure that people understand that there is a path to continuing to grow within the organization.

Another question is, can you share some screening questions to ask an incoming sales candidate?

Yeah, um, I like, I like asking questions to understand how they built relationships with customers, um, how they've solved business challenges and business outcomes. Um, I think that's really important Also, like, if I want to understand if they have a builder mindset. So in small, you know, in companies like us, I look for builders, for folks that are okay with challenges. Every organization has challenges. We all have growing pains. We all have different aspects of the business that can be challenging. And what I look for is I want to ensure I ask the right questions to ensure that they're up for that challenge. And I set proper expectations and transparency of what, you know, what the opportunity looks like. I think that's really important and will help with retention. And one question that I would ask too is, if there's one thing that you can fix today at your company to help enable your sales team's success, and money wasn't an object, like, what would that be? Because I would love to see how they problem solve and how they view challenges.

Okay, again, you trust— you touched upon this a little bit in your presentation, but in what ways do you believe that diversity is directly related to the success of a team in sales, an area that is fundamentally based in more objective insights and measures of growth?

So I, I have focused on diverse thinking, and I think I did touch on this in the presentation, diverse thinking and diverse skills. And I truly believe that having diverse skills on the team just builds a stronger team. So we can, we can then lean on each other and rely on each other. And this, that like aha moment came to me when I was building a team at a company prior to being at Twilio. Because there are skills that I have that, and that I lack. And when I was looking to hire a leader, I really wanted someone with technical expertise, because I knew that that was a strength that we could leverage on the sales, on the leadership team. And so I went and looked for a leader that had that skill. And sure enough, she was our anchor and for us to be able to ask specific questions. But if I also look at the team that I built here at Twilio, we do have that same type of diversity and it really has improved. I see the collaboration. They, they collaborate on Slack and they ask each other different questions. And I can see the collaboration and the strengths of each of the leaders coming out. Based on the challenges that they're up against. So I truly believe they're able to tackle these challenges and bumps along the way by being able to leverage each other's strengths.

And we're on our last question, which is, what are tips and actions for when a new hire doesn't seem like they'll work out in the long run?

Yeah, so that's a difficult one if it's a new hire, but I am— so I am of the mindset that you provide them and enable them with what they need to be successful. And if that— if you notice early on that that is not working, you try to— we believe in the buddy system at Twilio, so we try to buddy up all of our new hires with a 10-year Twilion so that they have a mentor. And so I feel strongly that if you tie them with a mentor, you provide them with clear actions as to what they need to do. That would— that, and if they are not achieving those goals, I think you act fast. And that could be a challenge based on where you are and some of your corporate values. But going through the steps that you need to take to potentially remediate is very, very important. But I always try first to make sure that I understand the challenges and see if we can— help enable them to be successful. And if at the end of the day that doesn't work, I think having a conversation with the candidate is very important. Maybe there was a misalignment with the hiring or with the expectations that were set. And so I think it's critical that you have that candid conversation.

I think we have time for one last question, and something just popped up from Mian. We see a lot of companies hiring at the VP or director level, asking for a lot of experience, but the way that selling and managing teams has changed to the sense-making sales approach, how do you balance experience with new thinking and giving opportunities to less experienced folks to bring that mindset change?

I love that question because, um, that is something that is near and dear to my heart because I believe that we have to give people a chance. Someone gave me a chance. So we are all in the biggest jobs that we've been in, right? I didn't, I didn't get here because the job that I had before this was at equal footing, right? And so I think it's really important that when we look at candidates, we don't, we don't necessarily have to check every single box. I always look for the candidate's potential. The candidate's potential to grow in that role. What other aspects can they bring to the table that can add value to the team today while we help them grow into that role? And even at Twilio, when I look at promoting within, when you promote within, you're taking someone that's never done that job before and you're moving them into a bigger job. And you're taking that chance to move them into that bigger job. But there's something special that you see in them You're taking a chance in them. And they are not going to want to let you down. And so if you work together, you can bridge that gap to get them there. I love that question. Because all of us, everyone here, you're always going to interview or try to go for that next job that is not— doesn't fit the current bill of the job that you're in today. Otherwise, you wouldn't want it, it wouldn't be considered a promotion, it wouldn't be the next level. And we need all of us to be thinking about, how do I give the next person that opportunity?