Episode 178: Jasmine Jackson-Irwin on Building Inclusive Enablement Teams

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Shawnna Sumaoang: Hi, and welcome to the Sales Enablement PRO podcast, I’m Shawnna Sumaoang. Sales enablement is a constantly evolving space, and we’re here to help professionals stay up to date on the latest trends and best practices so that they can be more effective in their jobs.

Today, I’m excited to have Jasmine Jackson-Irwin from CircleCI join us. Jasmine, I would love for you to introduce yourself, your role, and your organization to our audience.

Jasmine Jackson-Irwin: Awesome. Thanks so much, Shawnna. Again, my name is Jasmine, and I lead Global Enablement at CircleCI. CircleCI is a continuous integration delivery platform that automates the build, test, and deployment process of software applications, so we really want to focus on helping teams shorten the distance between idea and value delivery while ensuring that they have a quality experience for their customers and end-users. I’ve been at the organization since mid-2018 and have built the enablement team from the ground up here.

Prior to that, I started my career in sales at Oracle, and I really credit that time in my career to my first exposure with sales enablement and what really robust enablement programming can look like, especially around new hire experience. I moved to the Bay Area after that and worked in a combination of sales and sales operations and enablement roles for a few small startups. Long before that, I had a background in policy and government, I’ve worked overseas, I’m bilingual, so while that’s not in my work anymore, it definitely has influenced how I approach my current work, especially around cross-functional collaboration, building better communication and information channels, and working with globally distributed teams.

SS: Well, we’re excited to have you here, Jasmine, thank you so much. Recently you’ve gotten involved in a lot of hiring efforts as your enablement team at CircleCI is growing. I’d love to hear from your perspective, what are some of the core skills or attributes that practitioners need to be successful in sales enablement?

JJI: Yeah, I think every organization is different. To me, it’s really crucial to align your criteria to the expectations of your stakeholders, your executive team, and of course yourself as the hiring manager. That can look different at every organization, but for me, the big things that I focus on are stakeholder management, clear communication, and a really clear and strong commitment to process and efficiency.

When we talk about stakeholder management, at CircleCI, we have a pretty large middle and senior-level management layer across our go-to-market teams given that we are also supporting the organization globally. We have teams in North America, EMEA, and JAPAC, so we have a really complex decision-making process, and it requires a lot of consensus-building and alignment.

Anyone joining my team needs to be comfortable managing expectations across that large group of stakeholders and feeling comfortable working in some of the uncertainty and conflicts that can come with having a lot of different voices represented in the room, which gets into the clear communication piece.

Again, having a global team, it’s really important that you are driving consistent communication that is easy for folks to understand, regardless of what their first language is, regardless of which time zone they’re operating in. CircleCI was a remote-first organization before the pandemic made it cool. I think by nature of us working in the dev-ops space, we’ve always had a lot of team members in different locations, so we’re used to trying to accommodate the needs of a lot of different locations and teams, even when those needs sometimes are in conflict with one another. The goal is always to be clear, direct, and accessible in how we talk to our teams. That’s also an expectation that I really hold of my team when working with each other.

On the process piece, our organization moves at a really, really fast pace. I think like a lot of startups, but especially for us, we’ve grown the organization to basically double the size it was at the beginning of this year. Our revenue team when I joined was less than 30 people, and now we’re almost 130 people. There are always multiple initiatives going on at once. It’s really not an organization where you’re ever working on just one project or with one team, so we have to have folks who know how to work effectively and build programs that sustain that scale and velocity of information.

I think that those three things, again, stakeholder management, communication, and process really all feed into each other. I think it’s also important to hire for folks that have a clear understanding of how those three attributes play off of one another and when to employ them in the right situations. It’s not necessarily a skill per se, but I also think it’s really important to build a team that has complementary, but still very different approaches to solving problems and working together. I like to have my team engaged in the hiring process too, so that they feel that they have some amount of say in who they work with on a day-to-day basis and who their peers are going to be. As much as I care about how someone works with me as the hiring manager, I care more that they can work with my team and be a strong collaborator and that we are building in the same direction with an aligned vision and goals.

SS: I think those are some fantastic attributes to be looking for. Now, what are some of your best practices to not only find and bring in the right talent into your team, but also retain top talent?

JJI: Yeah, absolutely. I’ll tackle the first piece on the hiring front. I think that it cannot be understated that hiring is a two-way street. In my interview process, I work really hard to give a very clear vision of not only the company and our goals, but also what is the day-to-day of this role? I tend to overemphasize that because I really want folks to feel confident that they know what they’re getting into when they sign up to work at CircleCI and work on our enablement team. It can be a challenging place to work in really fun and exciting ways, but that’s not always a right fit for everyone.

I proactively talk about the bright spots of the role and also the aspects of it that might be more challenging or demanding. More often than not, folks who are really excited by those challenges and they find that it motivates them to be more interested in the role, in joining the team. Of course, occasionally it’s also going to disqualify some candidates because they realize it’s not a fit for them and I think that that’s completely okay. Like I said, interviewing is a two-way decision and I feel a strong sense of duty to the candidates that I speak to that they feel they have a really strong understanding of what they’re getting into, and they can make a decision that’s right for them in their career.

Once we’re past that hiring stage and folks have actively joined, I really try to focus in the onboarding period of dedicating multiple conversations to understand the new hires on my team, both as a person and as a professional. We have a lot of dedicated conversations that focus around, how do you like to be recognized? What type of praise or recognition is important to you? What’s your communication style? Are you someone who wants everything in writing? Do you do best in one-on-one conversations? How comfortable are you with async communication?

Then we start to get into some of the more personal weeds of, when during the day is the best time for our one-on-one? What factors might stand in the way of you doing your best work on a given day? When is the best time that I, as your manager, can reach you and share feedback and make sure that you feel that I’m supporting you? It all comes down to me asking them, how can I help you be as successful and impactful in your role and also in your career more broadly? I want to use that time to show my team that I’m on their side. As much as I’m going to push them, because that is a given, I’m also here to be their advocate and ensure that they are successful during the time that they’re at our organization.

Another thing that’s important to me is just being really transparent and direct with my team about changes that are in flight or decisions that might impact their day-to-day. I think that that level of transparency as it’s appropriate helps folks feel safe and secure knowing that they’re working on the right things, knowing that their manager has their back, and knowing that the business is making decisions that will make the business and our team successful in the long run. The number one priority that I have is making sure that my team feels that they can do their best work without restriction and that they’re valued for the work that they do and that they know that I’m on their side and I’m going to help them be as successful as they can.

SS: Yeah. As you mentioned earlier in this podcast, I know you’re passionate about building engaged, learning-oriented, and inclusive teams. What are some best practices that you utilize to encourage involvement and inclusion on your teams?

JJI: We use our weekly team meeting as a dedicated time to collaborate as a group. This could be on a specific project or discussing how best we want to handle a request or a concern from the broader organization. I think it’s really easy to just use team meetings for status updates, but I find that carving out the time to workshop as a group really helps us all feel connected as a team and sharing in the learning of what our work is about.

Also, with such a technical product and customer base, we’re selling engineering tooling to software engineers, I try to get my team working with other teams across the business and other departments as much as possible. It’s awesome that we have teams internally that reflect our customers, so we try to work closely with them to help build out the content and the programs that we’re delivering to our customer-facing team audience.

And of course, I want to make sure that we also are taking time to talk about the hard stuff that’s going on, whether that’s at work at home or in the world. It’s been a really tumultuous past two years with the pandemic, and I find that sharing about our own personal experiences and reflecting on some of those big systemic challenges really helps us think about the small changes that we can make in our day-to-day to make our work more inclusive and accessible to our team, and to make sure that we have a good perspective and point of view around where our team might be struggling and what are the realities that they’re facing on a day-to-day basis.

We aren’t perfect, but I think we are getting better and it’s something that we try to keep a really open line of communication about as a group.

SS: That’s fantastic, Jasmine, thank you. Now, you yourself are in a leadership role. How do you help instill the importance of these values and create really a shared mindset around your core goals amongst your team?

JJI: Yeah. My team could probably get rich off of how many times I use the phrase, “make sure that we’re on the same page.” So much of what enablement is about is making sure that you’re connecting the dots across your organization to ensure that best experience for your internal teams. Our team has to mirror that same experience so that we can all move in lock step and make sure that our goals and initiatives are aligned.

I’ll talk a little bit about how we approach our planning process and identifying the work that we focus on on a quarterly basis. Towards the end of each quarter, I work with my team to understand what areas they’ve identified as being the next step so to speak for development from the enablement team. This likely comes from either rep or manager feedback, observations from coaching sessions, or reactions to organizational needs that have been identified, or some combination of all of those things. From there, I’ll work with our sales and customer success department heads to align on those strategic OKRs and make sure that our initiatives fit their upcoming quarterly goals. Where possible, we’re really looking to have a shared metric of success to drive accountability and alignment from the executive leadership layer down to the managers, down to our customer-facing teams.

Then from there, I go back to my team, and I share the feedback and the decisions, and I discuss with them what execution might look like. We take time to account for any changes that we might not have considered in the first place. We do this as a group across all the roles on my team because I think it’s really important to ensure that everyone understands not only what they personally are working on, but what their colleagues are working on and how those efforts may intersect.

At any time when we feel that we’re getting away from what we intended to do, we regroup to identify those gaps and determine a course of action to continually drive that alignment or realignment as the case may be. Making sure that the team has some amount of participation and ownership in that process is really important so that they feel confident I’m working on the right things, I have the support of my manager, and I know that this is aligned to the broader department goals that we have.

SS: Thank you, Jasmine. This is fantastic. I have one final question for you, and it’s actually about a quote that you had in an article recently. It said, “If you see a colleague who routinely delivers high quality timely work and goes above and beyond with little recognition, you have an obligation to speak up on their behalf.” I love that quote. As a leader, how do you not only recognize the work of your own team, but also help to advocate for other teams work across the rest of the organization?

JJI: Yeah, it’s a great question. I think it’s one that’s really important for every leader be they in enablement or not to consider. I think from my point of view, it really goes back to what I mentioned earlier about being an advocate. From, a one-on-one perspective, I try to make sure that I’m providing proactive and direct feedback on what is or isn’t working to everyone on my team. I never want a single one of them to feel that they don’t know where I stand on their performance or output, and I want them to know that their work isn’t in vain and that anything that they do doesn’t just exist in a vacuum but has real impact on the folks that they’re supporting. I do my best to make sure that there’s an open line of communication around that.

Outside of my one-on-one conversations. I also take time to really actively source feedback from our key stakeholders on programs or initiatives that we have in flight and look to understand from their perspective, what have been the highs and lows? In most cases, I’ll share those with my team so that they have the confidence in knowing that their work is valued and that they have a sense of what can be improved on if needed. Again, it all goes back to knowing their personal communication style and preference for recognition to make sure that they can receive that information in a way that will be most impactful for them.

I think the biggest thing that you can do for cross-functional recognition is to be open and honest about how the process works. There have definitely been times when stakeholders on my team have felt concerned about another team’s work in a cross-functional project, and I try to drive clarity around who’s involved? What are their responsibilities? How are decisions being made? What are the motivating factors for that decision that might not be blatantly obvious to everyone? In those moments, I think it’s all about showing that we’re working towards the same goal, even if our approaches may differ. I think from there, there can be a lot of healthy conversation around, oh, I didn’t understand that now I do. Or I think we can make an adjustment on this to make this more impactful. It just drives that collaboration and cross-functional communication.

We have a really incredible internal saying at CircleCI that comes from a former employee called, “that motivates me.” It’s honestly been a hugely empowering phrase for me since joining the organization, and I try to employ it early and often when working with cross-functional groups so that they can understand not only that I, as a leader, I’m on their side and invested in their success, but also affirm that the direction they’re going is impactful and empowering for the teams that I represent. It’s not always sunshine and rainbows. I’m definitely a very fierce advocate for our customer-facing teams and the groups that I support, but I find that keeping that line of communication open for what isn’t working can ensure that alignment continues to get better and better. TLDR, I think that the more praise and recognition you can offer the better and tying it to both small and larger actions at the end of the day is just going to make everyone feel great.

SS: Awesome. Well, thank you so much, Jasmine. I really appreciate you taking the time today to talk to our audience.

JJI: Yeah, absolutely. Thank you so much.

SS: To our audience, thanks for listening. For more insights, tips, and expertise from sales enablement leaders, visit salesenablement.pro. If there’s something you’d like to share or a topic you’d like to learn more about, please let us know. We’d love to hear from you.

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