Fair, Equitable Hiring Needs a Retention Strategy (S2E14)

Anita Chauhan (00:16)

Hi everyone and welcome to our latest episode of Looks Good On Paper, powered by Willo. ⁓ I'm reporting in from Toronto and it's really cold. We woke up to tons of snow here today and I'm a little frigid beside the window but I'm so excited and expect to be quite warm, I'm sure, from this conversation with our latest guest. I'd to welcome Gillian Emerson to the podcast. Gillian is the head of talent and partnerships at Toast where she's helping reshape how tech companies hire by making equity competitive advantage. ⁓ Gillian was one of Toast's first employees and she helped build the recruiting function from the ground up. So excited. I love what Toast is doing across Canada, across North America. I think, you know, one thing I did mention before we jumped on here, Gillian, and we can dig into this more, is, you know, how tough it is to be a woman first and foremost in tech. And I love the mandate that you have. I'd love to hear from you. What did I miss in the intro?

Gillian (01:10)

Mm-hmm.

Anita Chauhan (01:16)

What did you get here today?

Gillian (01:18)

Yeah, totally. Thanks for having me. It's very sunny and very warm in Calgary. I don't know why we've traded. Normally it's cold and freezing, but Calgary is very sunny and nice today. Yeah, thanks for having me. Basically, ⁓ I came to Toast right as we were beginning, kind of like by chance, which is what a lot of people in talent acquisition say.

Anita Chauhan (01:22)

What?

Gillian (01:39)

⁓ I did my undergrad actually in Ontario and I did that in psychology and then moved back home to Calgary, did my masters in management and then kind of was going through the motions was thinking, okay, consulting that seems like the natural path for someone to go who's doing a masters in management was not successful in that at all. ⁓ Took a step back and was like, okay, let's think about school, let's refocus on that. And then a project came up. Toast was just launching and they were participating in a project called the Propel Project through U of C. So they get a 50-hour project with a student. I saw their website. It was just like the baseline of a website. They hadn't launched membership yet. It was very vague on like the whole project in general. And I was like, sign me up. And so...

Signed up for that, put in my resume and cover letter and all of that and then luckily was selected. And just was helping out with everything from the

Whatever projects that they needed help with, setting up kind of like surveys and questionnaires, feedback, it very quickly spiraled into going into recruiting, obviously having a background in psychology. I always had talent acquisition or recruiting in the back of my mind. So really started to get involved there. And then... it spiraled and blew up ⁓ into something else. And so we've been really successful over the last three years helping companies hire more women onto their technical teams. And I've been growing alongside April Hickey, our CEO, to help build up that recruiting function on the one side of the business. And then on the other side of the business, we have a membership that supports women in tech.

Anita Chauhan (03:30)

I love that so much. just again makes me so 10, 12 years ago when I was first starting off, first of all, I come from a background that was non-tech and they jumped in from government and I didn't know what I was in for.

Gillian (03:44)

yeah.

Anita Chauhan (03:45)

And now you probably know too, right? Where it's just, you're not prepared. And I think, know, 10 years ago was vastly different, but I think we're seeing more women hopefully in STEM moving into these roles. But you did actually say something before we jumped on that you're seeing a little bit of a drop off or Toast has noticed that with tech, women in tech.

Gillian (03:54)

Mm-hmm. Yeah, I think in general, it's great to get women in, but at the end of the day, you need to be retaining them as well. And so part of what we're seeing is women coming into tech, but then dropping off a few years into that might be around like certain ages, which is really unfortunate. So we are very passionate about building systems from obviously the top down into like seeing representation from leadership, but also embedding diversity into processes. across the board from the application all the way up to interview to offer and then to long-term support to help support more of that  for women.

Anita Chauhan (04:42)

I love it so much. mean, we will dig into it in a bit about that process. But why don't we hop into the first question? So what is the biggest hiring mistake companies keep making even though it's clearly not working?

Gillian (04:50)

It's cool.

Yeah, so tagging onto that, think obviously my short answer is not hiring enough women, not having diverse pipelines, but that is a much bigger problem than just not making that hire when you're looking at all of your candidate pools.

So part of why we exist is to help companies diversify their pipelines. We always start it with an intake call, help me to understand like what goes beyond the job description, what are you really looking for? But then also what does your team makeup look like? Who is leading this role? How many women are on the team? What does  promotion cycles look like and all of that.

then embed that into our process so that we can make sure that our candidates are informed from the beginning. However, the biggest problem that we're seeing with our clients right now is coming to us and companies in general coming to us saying, really want to hire more women. I have a team of all men, people are quitting, whatever that is. And that's great to have the initial kind of like need and want to hire more women because that's what we need to help like work with a company.

have had companies come to us saying, I'm struggling to attract women. I don't know why I can't retain them or hire them. But then they say that their working hours are 60 hours a week and that's the absolute expectation and there's no flexibility. And women are sitting there being like, okay, flexible work matters to me. What if I want to pick my kids up?

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And that's where they can end up seeing the better results. so ⁓ companies, although it's great to have the initial want to hire more women, them not setting up those processes through to the retention model as well ⁓ is enforcing some of that drop-off rate that we're seeing.

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Anita Chauhan (06:37)

you ⁓ absolutely. I think obviously one big thing, this is a global podcast and we talk to people from all over, but you know, just given what's happening in Canada, like we're seeing a return to office mandate and I'm already seeing that this is shifting so many of the way that, ⁓ women work in the workplace, friends of mine, colleagues, it just, it changes how you interact with your job. And, you know, we see that with some big tech companies in America as well. And I think sometimes it is almost a ploy in some cases to me to get rid of some of those because people will voluntarily leave.

But as a woman in tech, I know that this actually increases the barriers to hiring those more diverse teams by requiring things like this.

Gillian (07:22)

Hmm. Yeah, totally. I always say, I think what matters is the choice. I think when people are mandated to do one thing versus another, that's when you cross kind of like the uncomfortableness of it. I always wonder if Toast had an office, would I go in? I think I would occasionally, but given how social a recruiting job is for me as somebody who's
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Anita Chauhan (07:43)

Yeah.

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Gillian (07:50)

an extroverted introvert, get exhausted by the social interaction all day every day. So being at home is my saving grace. I think as long as you give people the choice in how they want to set up their working model, that implies more trust as well. As long as you're hitting your KPIs and what you need out of your job, it shouldn't matter where you're doing that from. So I think the choice is what's really important. It's also very interesting when we've hired internally for our own Toast team,

Anita Chauhan (08:18)
Yeah.

Gillian (08:19)
I've often gotten applications from people that are like, oh, I'd love to work from Toast to work from home so I can be there for when my kids get home from school and I can start dinner. And they say that in cover letters and they think that that's a negative connotation. And to me that speaks volumes of that person being like, yes, I can work my butt off throughout the day and fulfill my day and then...

also be there for my kids and do what's important. That balance is something that we inherently value. And I think companies that don't see that as a valuable thing of allowing their employees to have choice in how they engage in their work every day, it can be really harmful and it can show that they don't trust their employees to be able to

Anita Chauhan (08:49)
Yeah.

Gillian (09:04)
do their best and do what they need to.

Anita Chauhan (09:07)
It's really interesting what you said just there, right? About like flexibility. I find a lot of people almost hide the reason they want it. One, it's not their employer's business, I do want to say. Like you have a life outside of the workplace. How you choose to spend your time, outside of work hours is not really their business. But this is so important and it's really also part of, I find it's very gendered in some aspects where like you're almost ashamed or

Gillian (09:21)
Mmm, yeah.

Anita Chauhan (09:30)
you're like, well, I need to pick my kid up. I almost don't even want to mention that when I'm looking for a new job. So I find it really cool that like, Toast has fostered that environment where they felt empowered enough to actually share that. So kudos to you guys on that. You know, at Willo we have a lot of candidates who are in different life circumstances and it's actually the whole point. Like how we're able to actually now remove like the barriers to interviewing has removed some of the time. Like not just women, folks, you know, that have like a disability, neurodivergent, like,

Gillian (09:35)
Mmm.

Anita Chauhan (09:58)
all these different barriers. And I think it's really cool to see you guys actually have an entire company that fosters that.

Gillian (10:02)
Yes, 100%. I think it's interesting being in recruiting and seeing kind of like the norms that we all think we're supposed to do or what everyone's told me that I'm supposed to do when I apply for a job. And so then I've had a lot of those conversations. If they mention that upfront, I'm like, oh, that's totally fine. You don't need to worry about that.

Anita Chauhan (10:15)
Yeah.

Gillian (10:20)
It's okay. Take my feedback and kind of take it for how it is. I think too on this topic, one of the questions you ask later is what does removing the CV look like? And we do this for a lot of our recruitment processes with our clients where it's like, we scrub the name, we scrub where they went to school, we scrub what company. If they worked at Google, we won't tell our client that they worked at Google or any of the kind of like well-known companies.

All of that is not of pertinence to the actual capabilities and abilities and skill set of the candidate. And there's so much socioeconomic bias and the school you went to and there's foreign work experience bias. So often I talk to talented people who have been in the industry for 10 years and they're like, I have hundreds of applications and I've yet to get an interview. And they're like, I worked in X country.

Anita Chauhan (10:50)
Hmm, wow.

Anita Chauhan (11:02)
Yeah.

Gillian (11:08)
And if that wasn't Canada, that company doesn't think that that is relevant or valuable. And so as part of kind of our process, all of that is totally anonymous. And it's really interesting when you ask our clients, hey, like how did this person stack up? And they give us feedback. Then we tell them, hey, they were the ones that you thought had their work experience at Google.

That person was the person working out of Brazil. That person was the person that has a stay at home parent and that's all they've done for the past three years and now they're coming back into work. That kind of stuff they didn't know or weren't aware of and now they're like, oh my god. And so they have to reset what a great candidate is.

Anita Chauhan (11:41)
Absolutely. So my next question is like, you know, what signal do people use or overlook all the time? And, you know, I like the second part of that question because it's about, you know, what do, what are they missing? Because you said you scrub it. Like, what do you think that people actually need to be looking for? Because I think like, again, like we all default to the CV, default to the name, default to the school, the gender, all the sort of things that shouldn't matter at all. Really, we should be looking for what they're capable of.

So like, what do you think are like some of those signals that you've started to see people overlook or look towards when they do the hire? Because they didn't have that scrubbed CV.

Gillian (12:16)
A lot of it is self-taught and so one of the kind of like examples, most frequent things that I hear from people is I'm self-taught, I'm a bootcamp grad and I am not getting interviews. If I'm a computer science degree graduate, I have a job. If I'm self-taught, I'm just ignored. And like

Anita Chauhan (12:27)
Yeah.

Gillian (12:37)
When all comes down to it, I've worked with amazing self-taught and bootcamp grads that I have placed in jobs where they thrive, they do amazing, they have the skill set. And so to your question around what are the important skills that people should be looking at instead and being a little bit more of an out-of-the-box thinker, it's people that are passionate, that show proof of their learning, proof of their application.

Anita Chauhan (12:52)
Hmm.

Gillian (13:05)
and looking beyond the resume and saying like, a they said that they did this thing for two years and they gained this skill, that's what they developed, but now how did they do that? How can they prove that they know what they're talking about and what they can do? And that doesn't just apply to people that are self-taught or bootcamp grads, that also applies to people who have bachelor's or master's degrees.

Trust that they're the right person to get the job done and figure out the different ways in which you can evaluate that through kind of like the unheard of stuff that like what you wouldn't think about or the non-technical skills or maybe it is the technical skills that come through not through schooling by being self-taught and kind of just like expanding the out-of-the-box thinking.

Anita Chauhan (13:19)
All right. And on to our third question, which we kind of touched upon already. But if you were suddenly to remove CVs or resumes from your current hiring process, what would that look like?

Gillian (13:31)
Yeah, so that's an interesting question. Obviously for us, for like our own Toast process, we were moving that already for working with our clients. When we're hiring internally, I then have to take that hiring manager standpoint and be like, okay, what am I really looking for here? What is the most important? What I always like to do for when we're doing an internal hire is think about the top three things that we're looking for, not to get attracted by the shiny stuff. And that a hundred percent has happened to me.

Anita Chauhan (13:36)
Yeah.

Me too!

Gillian (14:00)
⁓ in the past, especially

when we did our first hire on the talent team of being like the FAANG companies and my God, they worked here. They want to work for Toast What? ⁓ but taking a step back and really understanding like what's important. For example, for one of our recruiters having contingent recruitment experience we have found has been very important for us just in recognizing like the speed, ⁓ and understanding the general

process involved with recruiting contingently. ⁓ And then other parts of examples, like some form of like seniority with it, examples of past success with time to hires, how many hires, cadence that we've seen, and then otherwise trying to just like limit the noise. We try and do something different each time we hire someone.

The last one, for example, we put out a LinkedIn post and wanted to just like extend it to the network. If you know a kick-ass recruiter, sorry, I don't know if I'm allowed to swear. ⁓ If you know a kick-ass recruiter, tag them below, something like that. Just to bring in kind of like those different perspectives, we want the tried and true of working with them in the past and recognizing those really awesome people that might not be out there.

Anita Chauhan (14:58)
when you're a little bit.

I always love that network effect as well, by doing that where it's like friends of friends might even include, bring someone in. Hopefully you're not like hiring with that bias of like, oh, I know this person through this, but it does open up that wider net to people that you might not have already been able to get in front of, right?

Gillian (15:32)
And we were shocked, like, we were shocked at the amount of people and the interest that came through with that. And I was like, oh my God, there's so many amazing people out there that we have never worked with, come across, and they might be even be in the same city as us. And so ⁓ just kind of taking a different approach with it has been important. I challenge people to...

rethink how they evaluate resumes and how they typically look at those kinds of things when they're going through these processes to take a step back and question, why do I look for certain companies? What am I looking for out of those? What are the true needs that I need out of those companies? And then go from there.

Anita Chauhan (16:05)
you

Yeah, no, I really appreciate that so much. It's such an interesting place that Toast sits, right? So you're seeing internally, you're seeing all these other companies. So I think it's, I just really already applaud the system that you have been building with the companies you're working with because, for some people, and this is one of the things that we've seen, it's like the idea of decentering the resume or the CV from the practice is kind of scary, right? We are just so used to it, along with all the other things you talked about, like scrubbing the name and understanding, like, you know,

Gillian (16:21)
This is.

Anita Chauhan (16:40)
where they come from, all this stuff. I think what's really interesting to see is that Toast has done this in practice and that's scaled out and it is actually working. And I love that type of story. I love that we were able to tell that here.

Gillian (16:52)
With every single first submission that we have, we have a detailed explanation of why we do it the way that we do. What are the biases that come up? Socio-economic bias, ⁓ foreign work experience bias. Why are we doing these things?

Anytime that you can attach a why to it, it helps people expand their minds and their thoughts around it. So that's what's been really helpful with us, I would say.

Anita Chauhan (17:18)
Really quick, what type of trends do you see in hiring and recruiting and sourcing for 2026?

Gillian (17:26)
So we chatted briefly about this at the start. The obvious answer that everybody is saying right now is AI. How are you using AI? How is it like better serving you and your process? And for sure, there are so many amazing ways that we have used that. However, what we have been having a lot of conversations about internally within our Toast community on LinkedIn, all of that, is this AI

Can we bring back personalized approaches to hiring while using it in the best way possible? We are also looking into, for this year it's gonna be of top of mind for us, is how our AI hiring process is affecting women as well. So I read a really interesting article recently about how using AI to hire,

Anita Chauhan (18:07)
you

Gillian (18:15)
is hiring people based off of previous successful hires. And when your previous successful hires are white men from these certain backgrounds, then your AI is going to specialize towards that in picking those resumes that demonstrate the kind of matched background of skills experience ⁓ to making those hires. And who does that limit?

Anita Chauhan (18:27)
⁓

Gillian (18:38)
people that aren't there already. And so ⁓ we want to bring it back to making it a people first approach always. Use AI tools to like help speed up your process for sure. Understanding at the core of it, why aren't you hiring women? Why aren't you retaining women? And how can we help introduce you to great people through people? ⁓ But really the AI fatigue is becoming very real.

across the board, I think.

Anita Chauhan (19:05)
I know ⁓

working in marketing, a lot of pushback. There's a big shift. I think it's just, you know, it's in everything. And we see the positive. It's interesting though, as well, at Willo as well, we see a lot of companies asking for, you know, AI, but they don't think they really understand what it means. So I think there's both ends of it. I think that the human things are going to get more human this year. The intentionality of AI usage is going to change significantly. I think you've touched upon that brilliantly as

Gillian (19:13)
Mm-hmm.

Anita Chauhan (19:32)
like I love that Toast is thinking about those types of things and how it actually impacts already, you know, marginalized candidates, right, and giving them access in such a different way. ⁓ Jillian, this has been so lovely. I don't know how the time flew so fast. Thank you so much for your thoughts and insights. I'm so excited to share this with the world. Thank you.

Gillian (19:52)
Thank you. Thank you for having me. I appreciate it.