Ragini Holloway is currently Senior Vice President of People at Affirm and is an advisor for PeopleTech Partners and tech startups, including Shift.org and Pinkaloo Technologies.
Ragini helps high-growth startups scale recruitment and People processes, often from scratch. She took Credit Karma from 40 to just over 500, and has similar ambitious hiring goals now, already taking Affirm from 100 to nearly 1,000.
Ragini advocates for collaborative hiring practices and facilitates organic and authentic work cultures where people come together and discover common goals. Ragini is heavily focused in building diverse teams and designing employee engagement programs that drive ongoing workplace satisfaction and high retention rates.
Gabe is VP of Engineering at Checkr, building a fairer future through a better understanding of the past. The team is bringing automation, consistency, and fairness to the manual processes behind background checks. Gabe has led several teams through high growth periods, most recently at Airbnb, and prior to that in the crowdfunding space at Tilt, and the Cloud Servers team at Rackspace.
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Ragini welcome. Hello, Gabe. Great to see you. Great to meet you both
Gabe Westmaas: Hello, great to meet you Patrick
Ragini Holloway: It's great It's to be here.
Patrick Gallagher: Take it away. The live stream is yours.
Gabe Westmaas: Awesome. Thanks so much.
Welcome everybody and Ragini you and I have spoken a few times this week, and I'm really excited to have this conversation with you. So, Before we get started. You know, I know when you first started at Affirm you, one of your roles was as head of DEI and yes, we do want to talk about the diverse pipeline, but I think it's also really important to think about think about this holistically.
Can you talk a little bit about how we think about diversity, equity and inclusion holistically?
Ragini Holloway: Yeah, I think I'm glad that we're starting the conversation that way Gabe because a lot of times, you know, you want to kind of solve for the now instead of really looking at what the. what It looks like what the picture should look like and what you're really trying to achieve. And so you kind of just start with recruiting, but you're not actually looking at what's happening currently with your workforce? How are you retaining folks that are coming from underrepresented groups? How are you, how is engagement so forth and so on? Do you have the right programs in place?
Because you can build that diverse pipeline and bring folks in. But it needs to be authentic. They need to come in and then they should have programs that really support their growth and development with the companies.
So it's important to look at it holistically and I'll just share personally, you know, I wasn't looking for a career to lead DEI. I literally talked to Max, our CEO during the interview process, because at the time this was like four and a half years ago, he was interviewing me to be a Head of Talent and the company was about a hundred folks.
And we got into a conversation around DEI and really, it was important to me as, as a woman of color, to really understand coming into the company... what are, what does diversity look like? How am I going to be set up for success? I was asking through the lens of a potential, like a candidate as a potential employee.
And then also understanding as coming in as a Head of Talent, like, what am I signing up for? What's going on here. Right. And do I really feel like I'm going to have the executive support to move the needle forward?
And what I told him was like, look, I'm going to come in. And I'd love to be able to create a diversity inclusion program. I actually don't want to be Head of DEI. But I need to create, create that space for myself so I can thrive. And that was really important to me. And I had that opportunity
And I want to clarify what I said. I don't want to be a Head of DEI. It's more because it's everyone's responsibility holistically. It's the hiring manager's responsibility. It's the recruiter's responsibility. The executive team, the board, a people manager. Whoever you are, it is your responsibility. Even if you're an employee who shows up day to day. Somehow it also touches you. It's your responsibility.
So holistically you have to think about that. It's not just hiring, but it is everything from the candidate experience through the employee experience, through alumni. And if you can holistically build that picture, then that pipeline just comes through naturally, rather than this forcing function where it just consistently drops through your hiring process.
I hope that kind of sets the tone of philosophically, how I think you should be thinking about it.
Gabe Westmaas: Absolutely it does. And you said a couple of things that I really want to follow up on. I'm trying to decide which way to go first.
I think first you said a word that I really love, which is authentic how important it is to be authentic in this. And I would love to hear first of all, have you found that you've been able to show that authenticity throughout the hiring process at Affirm? And have you found that that helps with your recruiting funnel as well? With your diversity of your funnel?
Ragini Holloway: Yeah, I think that that's super important because there are a lot of times that companies spend a lot of times figuring out how to talk about DEI in the interview process or how to position it on the careers page and so forth...
And the intent typically is to position you as best as possible because you're trying to attract talent. That's really not the way to do it. you should not be I don't want to use the word afraid, but it's, what's coming to mind... where you kind of think, well, if I, if I really tell folks, honestly, that "we are not diverse, but we really want to move the needle."
People are just going to look at us and they're going to be like, no way. I'd rather go to the company that is. That's not actually true.
People are looking to understand what they're really signing up for for when, when they actually execute that offer letter. Right. And that it's authentic. So that's important. And when I came into Affirm, the company was not diverse.
And I wouldn't say that I, I, I asked those questions in my process because I didn't get that indication where I was like, poking holes to see like, oh, you're seeing your you're diverse and so forth and so on.
So, we, what we did was we took our brand and we thought about it from the perspective of how do we tell our story in an authentic way. And that was through our diversity inclusion report. Which we started to say, we're going to go public with our data, even though we're small and private and it's not that great. We're going to be public with it. And we're going to have this conversation consistently year over year with the tech community. And we're going to consistent where we're holding ourselves accountable to show progress against our goals.
And so what we did then was everything that we did, we incorporated that into our talent brand. So everything, and then every part of our program had a lens of DEI.
So we didn't just do sourcing sessions. We did URG sourcing sessions and URG means underrepresented groups. So we did URG sourcing sessions.
We didn't just do a university program. We shifted it. So when I came in, it was really focused on the Stanfords and MITs and everybody who's listening right now knows exactly what I'm talking about. So it was all of that.
Instead we thought, okay, how do we shift that to women's colleges, HBCU, State schools. And see what happens over time, which Gabe you, and I talked about offline, which I want to bring here is you start to move towards a more non-traditional routes of what you think is the expectation of building a great engineering team.
How do you define great? Traditionally in the market and what I'm excited about seeing the shift that's slowly happening and all of you really have to help make that shift... is what marked a great engineering team was the school and the credentials that they had and where they were coming from.
And I'm not discounting that. I'm just saying that what makes a great engineering team is a diverse team. You're all coding behind the scenes and doing all the great work that actually builds the product. And your consumer base needs to reflect the team that's building it hundred percent, there's a valid business case there.
And so I would, I would encourage you like to think through that lens when you're building your brand period and take the incremental steps to get there.
And it's, you know, give your engineers a voice in the blog. We give a lot of our women of color engineers just generally people of color and straight just women engineers in general, we give them a voice in our blogs to really share not only the work that they're doing, which is pretty freaking awesome. But it's also, you know, what it means to be on the team and talk about the good stuff and the bad stuff. And that's what I mean about sharing with the tech community.
We're not afraid of that, right? Like if you actually just go and take a look at our blogs, you'll see a lot of examples on this.
Gabe Westmaas: That's great. I love the way that you described that authenticity. And you, you mentioned some of the data that you shared. I want to come back to that in a minute.
But you also talked a little bit about in, in your first introduction, the importance of making sure that this is everybody's responsibility.
And I think that that's just super important to think about. Something that might happen and, and you and I both heard these objections from both executives and from some of our hiring managers, is when you're thinking about building that, that diverse pipeline w we'll hear this objection of, well, I need to balance hiring the headcount that I need with building building these diverse teams.
Can you share your point of view on that?
Ragini Holloway: Yeah.
That's like, that's... I have that conversation a lot. I'm sure a lot of you are thinking about this, right? Cause that's, that's why we're having this conversation to begin with.
So there's hiring for velocity and then hiring for diversity. Why are we talking about them in two different conversations? Or two different initiatives? They're not. They're not. And if you have your mindset like that, you'll never be able to move the needle in a meaningful way.
Right? Whether it's in getting executive, buy-in getting the board there. Whether you're talking as a recruiter to your hiring managers, or as a hiring manager, you're talking to your VP of engineering. Whoever it is, the more that you keep these two buckets separate you're not going to make the progress that you're looking for.
So instead reframe it! If you're focused on, if you're, if you are having that conversation, the good news is, is that you're really got a lot of great intent, you want to actually hire for diversity, right? So that's there and that's the challenging piece that you're trying to solve for.
So then just think about is how do we create more velocity to hire for diversity? Now you just made it one initiative. And that's it.
So when you're talking to somebody, think of it that way. And you know what, like you might say philosophically, like, "that sounds great Ragini but like, I really have to get engineers in and I've got..."
You have to have those conversations. And then as a business, you have to understand the trade-offs and, and, and do that. Right. Like, I think people typically are just like, well, you, you, you just, you feel kind of that. "Well, I don't have a choice. I have goals. I have KPIs. I have OKR'sI just have to do it."
But how were they set initially? Were any of these things, actually a part of those discussions before those KPIs and OKRs are set. So if you don't feel like you're empowered to do that or that you're trying to have those conversations and folks aren't listening, next time there's planning, bring it up in the room or ask your VP of Engineering and bring it up in the room. So you can actually shift it at some point.
Right? Don't just keep on. It's kind of like them being just kind of a hamster. I hate saying like that, but a hamster on the wheel, just doing the same thing over and over again. And guess what then a year goes by and you've added 200 people or whatever your goals are. Maybe even just 10 people.
Which makes an impact quite honestly, because the first hundred at Affirm to shift it the way we have it. I'm so glad that I've been at Affirm for four and a half years to see that progress. It took a long time. And a lot of conversations and a lot of reminders. So it was not easy.
So what I'm positioning here is something that you have to work on all the time. And like I said, like, I still have those conversations. We're in the middle of head count planning now for the next fiscal year. And I'mhaving those conversations again. So, never ends, you just have to, if you really want to, if you really want to make progress.
Gabe Westmaas: Yeah, makes sense. And I think it's just really important to reiterate making this part of everybody's responsibility and part of the same program so that it's not sort of off in a corner. But it's really just part of how you operate all the time. I think that's great.
Gabe Westmaas: Let's move over to some of the data that, that you look at.
What are, what are some of the ways that you hold your team, yourselves, hiring managers, executives accountable? And how do you measure that?
Ragini Holloway: Yeah. So we do it in a few different ways. So I can talk about kind of who should be responsible for the data and speaking to it and holding themselves accountable versus like what metrics you actually should look at, depending on where you are.
I'm going to start with the latter cause that I I'm sure you're all eager to know those things.
So, you know, depending on who you talk to, it's going to be different. I'll speak to where Affirm is or was and where they are now. Cause most companies are... the challenge that they're having, and a lot of you have joined this conversation because.... you're trying to figure out how to hire for more diversity. Right? So you should stop at the, you should start at the top of the funnel.
Now they're going to be people who not necessarily in this industry believe that. I do. Because I think it, it tells you a lot about what's going on. I think people are really eager to jump to hire stats. But as you know, there's there are a lot of steps along the way. And you have to build an exceptional candidate experience that's extremely inclusive to get to that hire.
If you're only looking at the hires, you have no idea what's going on. What's working. If you're doing a really good job. Awesome. What's working? Can you share that with everybody? Right. And what's not working except that you might be hiring a bunch of engineers, right?
So you got to start at the top and look at how many folks are applying. When you source, how much of your reach outs are actually going to folks from your underrepresented groups? you know, how, you know, how, when you look at referrals how diverse is your existing workforce? And then those referrals, do they, do they actually move it away from the goal that you're looking for if you're hiring for more diversity? Or do they amplify IT because you're already a diverse workforce.
So you have to be really strategic in how you think about the top of the funnel. And then once you get that right... and also your brand, like when people apply, do they convert, you have to look at all those things.
And then as you start to go stage by stage in the process, you can then start to figure out, oh, are a bunch of people falling out at technical? Why is that happening? Do we see any themes there from a demographic perspective or not?"
So you start to look at that. And then you can look at the hires. At least that is the mindset that I've always thought of.
Now who's responsible for that. A lot of times folks say that it is recruiting's responsibility to hold the company accountable. I do not. I'm not from that mindset.
First of all, I think the recruiter's responsibility is to empower, to educate, to promote, to ensure that the process... where we are, we are the champions of the process. It takes, it takes the entire village to actually make that hiring, to build the team.
So the hiring managers really have to make sure that when they are bringing the team together to, you know, this is what works with, this is the focus areas and so forth and so on. They play that role.
When there's a debrief. If we're going to move forward with the engineering or not, they are there the recruiters there, but they actually have the power to really bring the people together on whatever the objective is. And the trust is within that team. The hiring manager is building their team.
So we actually, in our engineering team they have to make, they make the business case. They talk about the metrics. We have regular meetings on we look at the entire funnel. Have conversations around how diverse various teams are. And so the engineering managers end up holding each other accountable rather than the recruiter holding the hiring manager accountable or vice versa.
And that has actually really lent to you know, the conversations haven't been so fun. They haven't been that fun all the time either. They've been really, really difficult, but extremely healthy in, in helping us figure out kind of how to move the needle forward.
So I kept that pretty high level. I don't know Gabe, if you want me to dive in any deeper, but I think holistically that's, that's kind of the way to, to approach it.
Gabe Westmaas: I think that makes a ton of sense. And we can wait to see if anybody else wants to dive in. I think one thing that you, you said that struck me is I spent a lot of time looking at the cases where somebody drops out of the funnel for, for whatever reason. But I have forgotten in the past to go back and look at where we've been successful and making sure that we're doubling down on that.
So I have to remember those wins.
Ragini Holloway: Yeah, you've got to, you've got to talk. Yeah. You've got to figure out why people are accepting and then build that into your brand, whether it's in your, the recruit, the sourcers reach out or the recruiters pitch or in the hiring managers close, like you've got to incorporate all that in there.
And also if you have employee resource groups or community groups in your, in your company, talk to those folks! Survey them. Why did you join? Why are you still here? Do you feel supported?
Like you, you definitely should work with whether it's your people team or your diversity inclusion manager or your people business partner, however you're structured. But there are folks there that have a lot of information that they can offer you, rather than you trying to figure it out on your own.
Back to what I was saying, it becomes everyone's responsibility. I think when we started this conversation, I was saying even down to an employees just coming day to day and doing their work can offer valuable information on how you can, you know, improve the pace of your hiring and also increase diversity.
Gabe Westmaas: And again, they can make sure that you're being authentic.
So obviously we want to pay really close attention to these numbers and the stats, but I think it's also possible for you to hit all the numbers that, that you set goals around, but not necessarily build a successful program. Can you tell me what you think a successful what success looks like really when you're, when you're thinking about DEI.
Ragini Holloway: Yeah. I mean, in sense, essentially move away from the picture of success, looking like it's just hiring because the worst thing you can do is you might feel great in the moment that you're hiring for diversity, but if you don't have the programs in place those communities won't be able to thrive as much as you would like.
And so, there's two ways to do this. You either really focus on the programs... and you don't have to have, is this not to be a perfect picture, but you have to start to think about what that should look like, whether it's your engagement program or, you know, your feedback and development cycle, compensation and equity your just your general diversity inclusion program. Whatever it is, you've got to kind of work with that and then you can work backwards and then decide to hiring.
If you don't have the luxury of waiting for that, then what I would suggest is that you really be thoughtful in how... back to the authenticity of your brand... You kind of really relay that we're still trying to figure out what a picture of success looks like. And we're figuring out as we go.
So, hey, you might not be coming in and we have all the programs, but understand that we're asking everybody to kind of join in and figure that out along the way.
And then even though I said too, there's a third option, which is, I can't believe, I didn't realize this is what Affirm did...
Which is we just, literally, as we were hiring for velocity, we then at the same time applied everything that we did was through a lens of DEI. So every program that was in place, we immediately reevaluate it through the lens of DEI. We brought third-parties in so there was no bias. We all got all hands on deck. Not just recruiters, people, team, the engineering team, the executive team. We then also let our board know. So everybody was understanding that this was initiative and it was really successful for us.
And so like that to me, if you can get that in your DNA and the fabric of what you do, like somehow, like if you're early on right now, you have so much advantage to really put in your cultural values in your mission statement and so forth. That is what success looks like.
And nobody can tell me that you can't do it. I'm not saying that Affirm, Affirm definitely has a lot more work to do. But we are doubling and tripling head count every single year.
Right. And so we still, that's why I'm saying it's, it's going to be a, it's a constant evolution and it takes a lot of dedication. So you might not see your results overnight.
Gabe Westmaas: Well, that makes sense. Let's see. So we talked a little bit about making sure that this is part of the program overall and bringing this up in the planning meetings.
Have you ever had conversations with a hiring manager who has gone through the interview process with somebody. But it turns out that you know, maybe they're, they're not going to improve the numbers and this is the only hire they can make. Um, How do you help them through that conversation and, and the decision on whether to hire that person or not?
Ragini Holloway: Yeah, that's a good question. So we focus a lot on, sorry, I'll take a step back just to understand our process. We ... there's a couple of things that's important to note.
We don't move forward with the hire, unless everybody gets onboard. Now, the hiring manager ultimately has the decision, but it's the hiring manager's responsibility to get everybody on board.
So, if there are folks that have say no hire or strong no hire we'd really drill in. And we have checkpoints and audits all through our offer approval process so that is flagged along the way. All the way up to me, if it has to come up to me so that I understand like, "Hey, why are we moving forward with this person?"
We've had engineers who are just like, I mean, amazing like where you're just like, "wow, like how did they do that well, throughout every single technical screen?"
but from a cultural perspective, or if it was questions around our diversity program, if there were flags, we do not bring them on. And we have that commitment from our engineering team, which I think goes a long way.
Gabe Westmaas: yeah.
Ragini Holloway: ...that's important to understand.
As far as answering the question our hiring managers are responsible for the diversity inclusion component of our interview process. Not the recruiters. So they have to ask the questions. And in the scorecard it is a required field.
So, you know, that's really important to understand. It, what I'm trying to say there, it becomes top of mind for them all the time. Right.
Now, as far as the candidate, which is kind of where you're really driving it, I think which is they need to hire... we try to balance it out.
We have a prioritization of how we think about engineering. We try to think about, well, does his engineering, maybe we should put this engineer on another team because great talent is great talent. Right?
And so if we're going to hire somebody. And, you know, everything checks the box, the person's qualified and we want to move forward. And we, we did everything we could. Can we move forward?
Yeah, we move forward! But we think about, is this the right team? Maybe we move to another engineering team. Like, let's try to figure out how we can balance that out a little bit. So then we start to have those conversations and we bring the candidate along the way to make sure that they're a part of that conversation. And they also feel.
Like yeah. That for them as well.
So, it's not perfect right now. We have some work to do there. But that situation is very valid and it does come up quite a bit.
Gabe Westmaas: Yeah. And making it, making it top of mind early on is very important. like we got some questions, so I would love to turn it over to the audience.
Patrick Gallagher: Thank you. thank you Gabe.
Ragini, this question has sort of been asked at different points throughout the day today. And I think your perspective here is going to be really important for our community.
So the number one problem that a lot of people have shared has been sourcing. And so I think when you think about a lot of the insights have been around referrals and doing different ways to, to build out the sourcing funnel.
But without this element of... and looking at it through a lens of diversity, equity and inclusion, I think a lot of our community are missing a really important lens.
And so I, was wondering if you could share, maybe some of the programs or partnerships or different strategies that you've seen work really well to help build a more robust sort of sourcing part of the, of the funnel. Are there certain programs that have been really effective in helping open up more opportunity to underrepresented engineers?
Ragini Holloway: Yeah. So, I'll take a step back and just kind of under understand philosophically if you want to build a diverse workforce... and I shared this with Gabe offline. This is something that actually Lightspeed, if anybody's interested, Lightspeed, they're a VC, they have a report out on this, so you can check it out and look at that,
But it's called the Third Rule.
And so a third is our folk from your, from your, your candidate pipeline, right? A third are sourced, a third are referred, a third applied. And if you can do that and keep to those numbers as best as possible, you're likely to be able to move the needle down the line.
We operate by that. Our referral rate barely goes over 35%. Which most of the time in engineering teams, you really do focus on the, the referral rate. We don't go higher than that.
With our sourcing strategy. We, so our, our sourcing team, we have a dedicated sourcing team and most of our hires in engineering come from our sourcing team. So I would say roughly 60% come from our sourcing team. Which is huge. When we first started, it was probably 30%.
So we had to over-index and why did we over-index and go away from our third rule was because we started to move towards hiring mostly senior and staff engineers. Which are really hard to bring in, right? Like they're not they're more passive candidates. So you have to be realistic about the third role.
But the referral piece you have to be, you have to, unless you have a diverse team already, which you likely don't. You have to be careful with that one. and then applications that's as you continue to build your brand and so forth.
So with the sourcing piece all of our sourcing programs internally, when we sit down with the engineering team and we have sourcing jams or sourcing parties, or even just with the hiring manager with the LinkedIn seat and we source with them, we only do urg sourcing sessions.
That's it. We don't focus anywhere else.
Now that doesn't mean that they can't source on their own if they would like to. But in partnership with recruiting, that is what we focus on. And we give them the tools. We have like a whole library of job boards and directory and so forth and so on. It's a list of like a hundred to hundred and fifty things that the team, like I said, the recruiter's role is to educate, empower and so forth. They put together that list, they all sit together and they figure out like, "Okay, Let's look at this HBCU. Let's look at the directory there." So forth and so on.
So we have compiled a thorough list that we source from. That's how we partner with the team. Then our sourcing team is responsible for their own reach out. So their goals their goal is to do roughly 40%. It used to be 30%, but 40% of their reach-outs on a weekly basis would go out to under-represented groups. They're actually now at like 55%! So they're naturally over-indexing because there's so much it's so top of mind with the hiring managers probably requesting that. Cause the recruiting sourcers are going to go in that direction.
Right. Which is beautiful that I never saw the numbers that high that's been like the last few months.
And so the sourcing team uses the same directory list and just kind of through various tools that we're using and so forth and so on.
What you're speaking to our programs which we don't necessarily consider from a sourcing perspective.
I know you're using sourcing, but usually they... that's separate. They're like their third party partnerships.
There's a bunch out there, right some of them we're partnering with some of them we've checked out. We haven't actually partnered personally with Dev Color. We've looked at them and I highly suggest them. But there's a lot of different ones.
But really what we decided was we've got all this data, all, we, we actually got everybody on board. We designed our own programs. So we have our own apprenticeship program for non-traditional backgrounds, right? So we actually bring folks in, train them and then convert them into employees.
And so we're at the stage now, again, we're now global, we're a public company. We're 1500 people, very different from when I started, I don't think we would have been able to pull off an apprenticeship program back then.
So it takes a long time before you can build your own programs, but if you can do that that would be beneficial.
But if you're just kind of looking for like how to get started, get partnered with your recruiter and just say, "Hey, let's build a directory. Let's invite our employee resource groups in community to contribute to that. Like where do they look when they go look for a job? What events are they going to?"
And just compile that and build out a directory and then source off of that. That's a great start from there.
Patrick Gallagher: That was great. That was going to be my follow-up question for, for folks that maybe are early stage and don't know where to start. So that anticipated the question.
And, and what you shared about the growth programs or heating match some of the trends that people mentioned that one of the big things that's going to differentiate companies is going to be the ability to build those types of either apprenticeship programs or internal growth like development programs to help your employees grow into, into new roles and new skills.
Gabe, thank you so much for, for helping guide a really thoughtful conversation. Ragini thank you so much for sharing your wisdom, expertise, and experience with us.
Thank you so much. Gabe, you're the best moderator. Thank you so much. Our panel, I don't know what to call, but you were awesome! Thank you so much for making me feel comfortable.