E30: Breaking Barriers: From HR to Sales Leadership with Emma Cahalane | Sales Leader ex Google/ DoorDash

Emma Cahalan is a high-performance sales leader. Her single-minded focus on developing herself and making a positive difference saw her move from an HR role into new business sales and from new business sales into leadership. And along the way, taking on responsibility for the diversity program at Google and making a difference in diversity and revenue across companies like Sonder, Pin, and DoorDash, as she basically drove revenue across these organizations and saw them through a scale-up phase. Her advice, tips, and her story is inspirational. So let's jump right in. Emma, how did you get into sales?

Well, I was at Google about 3 years at that point. Before Google, I started in HR, and when I joined Google, I was with I joined within the People Ops team. So at that point, all my friends and all my like really good close colleagues were all within the sales team and they were all working in SMBs or with enterprise businesses. And I was definitely very curious and I really liked the idea of working with small businesses and helping them grow and it was really appealing to me. So I kind of made the mental decision that I want to make the jump from People Ops side into sales. However, it wasn't as easy as I first thought. So even though I was within Google at the time in the Dublin office, I applied for many, many roles within both SMB and the enterprise teams. But, you know, I didn't have sales experience. And, you know, earlier in my stage as well, earlier in my career as well, that I probably wasn't interviewing or giving the right example. So there was lots of learnings there. So I think I applied for about 4 or 5 roles over about a 12-month period and just kept getting rejected. And there was one team, it was the new business sales team that were solely focused on acquiring new customers. And it was basically the team that nobody wanted to join. So I remember a role came up and I was going to apply for it. And literally all my friends and colleagues told me, don't apply for it. It's really challenging, you know, XYZ. But, you know, I went for it. I got on with the manager really well and he took a bet on me. So I was successful in getting the role and I was actually, I found out later on that I was the first internal transfer globally into this team. Normally people wanted out of the team, but I was the first internal.

Wow.

But, you know, it was a really great experience. I got the, probably the best sales experience in my career, literally cold calling, focusing on the UK Ireland market, selling the Google suite of products. And it gave me a great foundation of what a good sales experience is. Not without its challenges, which I can go into for sure, but that's basically how I made that first transition. Okay.

And tell me, you know, how was that, you know, initial 3 to 6 months? Because I would imagine that would've been a very challenging phase. And the fact that you are, you know, a repeat sales leader with some very interesting companies now, you stayed, whereas others could have left.

Yes, the first 3 to 6 months was really challenging. So when, you know, when you join a new team in Google, they have a great program where you get a buddy and you're paired with somebody that can really, really help you ramp up. It was quite a unique experience, but the team was obviously super competitive. You're literally, you know, going after deals in the market and you kind of all have individual targets. So it's very competitive. I was one of 2 females within that team of a team of 20. So, in terms of diversity, that was, you know, very unusual circumstance of a team to join because I came from the opposite when I came from HR, like it was all women. So, to go from stark contrast, but that experience taught me a lot because the buddy that I was assigned actually would give me incorrect information that would literally like set me up for failure because in her mind, if I fail, then she would succeed. this is not a typical thing at Google. I think it was this unique person and this unique team, but that gave me— obviously it was a very challenging experience to start off in the team, but it gave me a sense of I need to take ownership and learn this myself, and I kind of can't trust a lot of people in this team. And over time, you know, I built really great relationships and I figured it out, and I figured out who can I trust, who can I go to, to get really, you know, learn the business. But it was, it was a very interesting start to moving into the sales team. I'll never forget that my first day moving from HR into sales, like somebody asked me, you know, oh, what team are you moving from? And I said HR, and they're literally, their response was good luck. Well, I guess I kind of had something in me that I had something to prove. And the person, Rich Pollan, who took a chance on me, I wanted to, you know, work really hard for him because He did take a chance on me.

Oh, that's fantastic. Tell me, what was the gender dynamics in that team, in the new business team when you first started?

Yeah, so it was split across the UK-Ireland team, a team of agency, working directly with agencies and working directly with clients. I was on the client side and yeah, out of 20 people, 2 females, including myself. If you looked at the overall in sales and especially in new business, that's kind of typical. But yeah, as I said, a very stark contrast to moving from the HR team and you began as the outlier, right? So I believe that kind of gave me a competitive edge though, when I was talking with customers and, you know, I could connect with them in a different way that was kind of unique. And so I kind of saw it the other way.

Yeah, absolutely. And I think that had you not seen it a different way, you may not have continued down the path. So what made you push through the early challenges of going from HR to sales and that to new business and clearly being a very different dynamic in that team at the beginning?

Yeah, and I knew that, you know, this isn't like a forever role as well. Like, this is the platform that is gonna give me more opportunity to move into other teams within sales later on. So, I said, You know, I'll do this for a year, I'll get the experience, and then that opens a lot of doors. And that's essentially what did happen. So sometimes just having faith in yourself, you just need to get through this kind of rocky or bumpy kind of start to get an opportunity later on.

And why were you so determined to succeed in that role?

Well, I guess I have it in me that, you know, if anyone tells me no, it'll make me want it more. And then I think, I think a lot of salespeople are like that. And then I think that number one, number two, that this person took a chance on me as well. I wanted to prove to him that I could be successful and, you know, you know, give back to him as well, that, you know, it was the right decision. And then, you know, I wanted to progress in my career as well. And I knew having sales experience, no matter what route in your career you take later on, that will always stand to you. So if you're opening your own business, if you're you know, stay in sales, but if you move into any other route, like the majority of CEOs, they either have like accounting backgrounds or they have sales backgrounds. So, I think it's just great experience to have.

So, tell me then about your move into leadership. You know, why did you want a leadership role and what did you do to go about and get a leadership role?

I think a lot of people become managers for the wrong reasons, first of all. So, I think if you look at opportunities to progress in your career, generally becoming a manager is the only way to do that. And I think there's a lot of poor managers out there for that reason. I think different stages of my career, uh, I've had a lot of poor managers. And I think for me, I learned a lot about what I would— I don't want to do as a leader, more so than actually what I did want to be as a leader. How you treat people, how you make people feel, how you develop them. So, I kind of— I learned a lot there, and I also just naturally gravitated towards like coaching and wanting to mentor and develop people. I just always had a natural interest in it. So I knew when I became a leader that I wanted to do it for the right reasons rather than, you know, progression or money. So yeah, I guess my first leadership position was at Google when I was in the Australia office and I was given great opportunities and there was management development programs at that organization too, to be able to kind of set you up for success, but I generally think, yeah, a lot of the poor managers I've had in my career is probably one of the reasons that I did want to become a manager because I wanted to have a positive impact on people's careers and help develop them for the right reasons.

Emma, tell me more about your experience at Google with the diversity program.

I joined the Women at Google program, which is part of the Employee Resource Group, in, I think, 2016. So I co-led the resource group with another leader at Google. Basically, when we joined, we really wanted to bring it back to life. I think at this point it had been, I think a lot of the challenges that the committee were feeling that they were responsible for driving the metrics, that there was very little movement in changing the data in terms of the amount of females in leadership positions and overall at Google. I think there was a lot of frustration. So, we joined, we kind of, we basically worked with the committee to bring in new people, bring more life, get more leadership involved. Jason Pellegrino at the time was the MD at Google Australia. So, we got him really involved and he was a big champion. So, we wanted to bring it back to life, come up with the mission and what we actually wanted to achieve and what those pillars looked like. And essentially, it was really around creating community, fostering relationships, not just internally but externally to Google organization. I think at the end of the day, the challenge with these resource groups is that they are not able to move the numbers. Like, they should not be responsible for changing the numbers of women in leadership. And I think if you set them up with that, they're always going to fail. You can influence, you can lobby, and you can get people involved, but that's at the end of the day all they should be responsible for. So, I think a lot of people forget that. And then secondly, they also forget that these roles are projects that are on the side of their already 100% full-time jobs. So, they're doing this to create change and to drive a positive impact. And, you know, it is quite a big lift to be able to do that as well. So, that's kind of just a background of the women at Google organization. And yeah, it's come leaps and bounds over time, I think. Over that 2-year period, myself and Renee Gamble created Connected Women. And essentially that is an organization that we created between the major tech companies in Australia. So Facebook, or Meta now, Google, LinkedIn, and a few other tech companies where women come together once every quarter for different speakers and events where they can network. And that created a huge community, not just internally, but obviously externally, because I think the industry in recruitment and opportunities very much is who you know, not what you know. And that created a lot of opportunities for women to actually move externally to those businesses later on.

Understood, right? And moving on from Google, as you worked through Sonder and DoorDash, what were some of the things that you saw as potential challenges? at an early stage, and how did that experience and your own journey shape in what you were able to do in those organizations?

That's a really good question. I think it really varies in experience from different size of organizations, which you touched on. So, when I joined Sonder, I joined as the general manager for the Vancouver market initially, launching at that market. When I joined, my experience was that throughout the entire interview process of 6 or 7 interviews, I didn't have one female interviewer. So, For me, as a candidate, that was a massive red flag, and I actually did a lot of research, like, how many other female GMs are there? And there was only actually 2 in the organization of 15 GMs. So, I think companies really need to think about, you know, what is the process and how can you create an inclusive process? Because the candidate is also interviewing you, the organization, not the organization just interviewing the candidate. And I definitely had reached out for some conversations to get an understanding of the culture before I accepted the role. And when I joined, I did give that feedback and I did try to change that when I joined. So that was kind of one side. And then when I joined and I gained credibility and built really strong relationships, I used that credibility to try to create change. When I joined the business, we were 180 employees. Before I left, we were 1,000. That was over a 2.5-year period. So the rate of scale of people and business was incredible. But what I kept seeing was that we kept hiring more and more male GMs, that we're never hiring female GMs. And this is like the most senior positions within these, you know, within the organization. And that it wasn't just happening in that role, it's happening throughout the organization. So, I knew the recruitment team really well, and I knew they would be open to listening. And I had really trusted relationships within the business. So, When I kind of addressed it and shared a bit of background of my experience, they were just oblivious because they were just so focused on hiring and hiring and hiring and scaling. And when I kind of shared a bit more of the numbers and the things that I kept seeing, you know, they really wanted to solve the issue. But I think number one is actually the awareness and bringing them along on the journey. And then when we kind of began to address the challenge, we addressed it as a team. So, One thing, there's a few tips here we can definitely go into, but number one, like the job description, you know, it was a million requirements. And we all know that if a female generally can't tick 100% of the requirements, they're not going to apply for the job. Whereas a male, they on average 70% of the requirements, they will apply for the role. So we started breaking down like, what are the true requirements and what are like the nice to haves? And that really helped, I think, more female candidates apply. So, that was step one. And then, number two, we kind of dug into, okay, so, of these roles, how many male and how many female candidates are actually applying? And, you know, 9 times out of 10, to be fair to the recruitment team, it was generally male applying because it was generally an unknown business at the time, maybe a bit more risky. So, we needed actually to create a stronger pipeline of women, but we actually had to do the work ourselves. We had to start reaching out. So, not only did the recruitment team take ownership, they started reaching out to more female candidates and more diverse candidates, not just female, but also the leaders. We need to take ownership. So, we started reaching out and building our own pipeline as well. And those were the things we began to change over time. And I think within a 6 or 7 month period, we hired 5 female GMs across the company, which was actually an incredible change. You know, the head of recruitment at the time was just so open to making that change, and they truly wanted to make the change as well.

Fantastic. That's really impressive. And I think that it's when the push has come from, you know, within the business and you've taken that feedback to the hiring team, I think that's really great that they go from being oblivious to at least being aware. And then there are some clear strategies that you need to put in place. And I see the same thing over and over again. People ask me all the time, how do we bring more female AEs because it's a bit of a boys' club? We have people, 100% male team. How do we ensure that we bring more diversity, more female sellers, more female leaders into the team?

I think the big thing there as well is that the leadership themselves need to be bought into the benefits of diversity. So, I think I had many conversations with different leaders in the organization, and a few didn't truly believe that there were benefits to it. They didn't actually believe the research that economically there is better profits if you have a diverse team within the business and a diverse leadership team. So I always joke with their CEO of Sonder, Francis, we're good friends, that, you know, I bought him the Sheryl Sandberg book, Lean In. Yeah, I asked him to read it just to build his own knowledge and his own awareness, because you have to push people to want to learn sometimes and open their minds, you know.

Absolutely. So, off the cuff, what are some of the significant benefits you have seen over the years in having more diverse organizations?

Well, at the most basic level, I think you need to look at who your customers are. So, unless your customers are all one gender, all one color, and all think the same, then, like, which most likely they're probably not, like, your workforce and your team should reflect the customers that you have, because at the end of the day, you're going to create a more diverse product that is going to appeal to your audience. And obviously, you're going to have more profitability and create a much more, like, a much more informed product because of it. So that's like at the most basic, basic level. There is lots and lots of research out there that have shown that having females in leadership positions actually do yield and more profits than having, you know, not a diverse organization. And I think there's actually a lot of research in terms of having female CEOs as well, that actually the profits generally are stronger and they take much more calculated risks. Beyond that, like doing the right thing, you know, like we should be giving equal opportunities to everyone, not just females. Like, I think that's just the most basic thing, but there's a lot of business benefits as well, of course. Also, you know, when I'm in a room, like, I want to be challenged, right? Because I'm not always going to have, like, the best or the most informed opinion. So, if we're creating organizations and teams with meetings that we're having different opinions from different perspectives, like, we're always going to just have better outcomes, right?

Absolutely. So, you've given me some really good insight around hiring practices. Tell me a little more around how to develop and retain, you know, more female talent for the longer run once you've brought them in?

Yeah, yeah. I think everyone always thinks that bringing them in is the hard part. I disagree. It's really actually developing it and retaining them for the long term. So, I think one thing that's really worked for me, and I think being in sales helped me do this, is being able to create sponsors. So, Who are those people that are going to be in the room when your name comes up and speaks highly of you and creates opportunities for you? So, we all kind of hear of mentorship, but we don't always hear of sponsorship. And I think building those relationships and building authentic relationships that are two-way, not just one-way, I think they're really the best way to create sponsorship. At Google, when I was part of Women@, we actually created a program that paired the females in the organization actually along with males, with senior people within the organization to actually create these relationships, not as organically, but as a stepping stone. So when I was part of that organization, we didn't think of just females in every approach. We actually wanted to include males as well, because if we didn't actually create programs that had both, we actually couldn't change. how things were structured and how people thought. So we wanted ourselves to be inclusive. Absolutely. I think sponsorship is one. And then number 2 is, I think, really creating other opportunities outside, you know, the 9-to-5 cookie-cutter full-time jobs, things around part-time opportunities, job sharing, and creating those opportunities. Because I think with the economic condition right now, like, those are the first jobs to go. And what are you saying to your workforce? And what are you saying to the market that if these are the first jobs to go, then you're saying you don't value diversity, you don't value people that have amazing experience, but potentially for X, Y, Z reason aren't able to work full-time.

That's really good. That's very, very good. And how do you ensure that you create an environment that creates progression? Because it's very easy for a manager to really like someone who's in their role and they're doing really well in their role. And you want to keep them stuck in that role. So what's your advice to someone who's trying to figure out, you know, how do they create some progression if their manager is not supporting them?

Yeah, it's a really good question. I got good advice from Maile Carnegie, who was the ex-managing director at Google. And basically before she left, decided to make the move, she's at ANZ Bank now. She said 2 years out when she decided that she was going to leave Google, she started building her relationship and started building her exit path. Now, different in timeline in terms of seniority, but like at least 6 to 12 months, you should be building those relationships. So even if you want to stay with the company and you're happy and progress internally, you should not be closing out external opportunities because you never know what opportunities can come. One thing, definitely when I was making that transition from HR over to sales, every single week I had a minimum 3 to 4 coffees of people I did not know in different teams. Because I was trying to inform myself what was out in the market, what roles had I potentially not even heard of that exist. So, big lesson for me has been building my internal and external network, because that kind of just covers your bases in terms of progression internally and externally. Beyond that, yeah, obviously, you know, there's a lot of favoritism internally when you're looking at promotion, and there's a lot of factors that are in Like, out of your control. So, obviously, agreeing what those goals are that you need to hit and being very explicit on those, you know, writing them down. If I hit these targets, is that basically providing the opportunity for promotion? And being very explicit. So, earlier in my career, I think I drove my managers crazy because I'd be like, in every single one-on-one, okay, I'm hitting this, this, this. Am I up for promotion? And basically kind of hounding them. Because sometimes it is, you know, it's kind of being a politician, right? It's, are you going to be on them, like, to create that opportunity for you? Because potentially if you sit back, you mightn't get it as quickly. And then showing up, and I think people need to really think about their brand. So again, when your name is mentioned in that room, when you're being a performer, like, what are people going to say about you? Are they going to say, you know, and that is like hitting, smashing numbers, so hitting target as a base. Is she supporting her colleagues? Is she creating great culture? Like, what are all the things that the organization care about? And are you nailing those and being really explicit with your manager, XYZ, these are things you need to do to be successful.

Fantastic. Thank you so much, Emma. I can see, I'm guessing you were potentially a misfit in HR, which had to relocate into sales rather than the other way around. You know, when I'm listening to you, Talking about, you know, obviously, what do I need to do to get here? I love that. So that is so refreshing, you know, just having that intentionality. Because I can tell you, a lot of people who have an intentionality to become a leader or to build their career, they are far more likely to rather than those who haven't. I get a call every other week saying, well, I finished an MBA program, so now I'm ready for leadership. Well, you didn't need the MBA program to be qualified to be a leader because leadership is that, do you see that ability and the desire in yourself? And do you create opportunities as you go along the way? I see those people succeeding far more because the power of intention, your attention is powerful. And if you're looking for those opportunities, you want those opportunities, you're taking those chances, others are sponsoring you, you are going to be more successful.

It's interesting though. I was given really good advice from Karim. He was the head of APAC for Google for many years. And he was speaking at a conference once, and we were just talking about how do you know whether to accept XYZ role? And he just gave really good advice, which was basically, you need to think about your career of like, not the job that is being offered today, but the next, next job. Where is that? Whether it's 5 years, 10 years, whatever. And is this role going to be able to help you get that role? And they all need to contribute because if you don't know what that role is in the future, how do you know whether to say yes or no to this job? Because the reality is you're going to get offered probably a lot of jobs in your career, but unless you have that vision, you're going to be lost. So, I think that has really helped me. And, you know, you have stumbling blocks along the way and, you know, people make mistakes and things don't work out, but I think Just having an idea of where you want to go has definitely supported my career up to now. And you know what? You never know where those relationships bring you as well. When I was interviewing for a company post-Google, reached out to like a blind reference to this leader to ask for a reference, even though I actually didn't provide the reference. But, you know, that's how small this tech community is that if you have those relationships, you know, they're going to vouch for you and they sponsor you well beyond. actually working with them directly. So just keep that in mind too.

Fantastic. This has been an absolute masterclass. Thank you so much. It is going to be so useful, you will not believe, both to people who are at early and mid-stage of journey, as well as those who want to create more diverse, empowered teams. So thank you, Emma. Really appreciate it.

Thanks so much, Priyank. Thanks for having me.