How to evolve as a CFO: Lessons from Allen Shim of Slack

How to evolve as a CFO: Lessons from Allen Shim of Slack

Author: Jesse Klein
Read time:  21 minutes
Published date:  June 6, 2017
At the Carta CFO summit, Slack's SVP of Finance & Operations Allen Shim and our CFO talked about the challenges he faced at Slack.

At the Carta CFO Summit in San Francisco, our CFO Charly Kevers sat down with the Allen Shim, the president of Finance and Operations at Slack. They talked about his experiences at Slack and answered questions about the challenges he faced. Below is the video and transcript of their conversation.

More from the Summit:

To see Eileen Treanor’s talk about Lever at our CFO Summit click here.

For our post on the address given by Stephanie Gantos click here.

Charly: I’m the incoming head of finance at Carta. Day five on the job and they already put me to work. So, to help with the later stage discussion, I’ll invite up Allen Shim, who is supervising president of finance and operations at Slack. Hopefully, all of you know about Slack. It’s a small software company that’s pretty successful in the city. We’re huge users of it, and love it. Thank you so much. I think what it’d be useful to start with is just getting a little bit of background. What did you do before Slack, and when did you get onto Slack? How long ago?

Allen: Well first, thanks for having me. We are happy customers, and we’re both mutually happy customers. I really enjoy, by the way, Stephanie and Eileen’s talks. I thought that was great, and I wish someone had told me some of those things a few years ago.

So, I joined Slack a little over three years ago. We had just released the public pay product. We were a 20 person company, so stepped into a role of, basically head of everything that Stewart didn’t wanna do. Stewart, of course, our CEO. So, all G&A, all marketing, all sales, all everything that wasn’t our idea, we’re customer support.

Before Slack, I was at a company called YuMe, which is a video asset company. Essentially, they were fairly early, about 30 some odd person company. I eventually helped take that IPO, around about 600 people, and then left to join Slack. I specialize in small cap. And, before that I was at Yahoo. So, that was my start. I think of myself more as a finance and operations person.

I think that is an important shift that we are all seeing about the role of the CFO, is you cannot be the bookkeeper, you must be a strategic partner to the CEO. So, I think that’s where Stewart and I have been developing a really good relationship since then. So, that’s my background.

Charly: All right, thank you. And now, can you give us some sense of what types of issues were you dealing with when you came in? You were one of the first hires to look at the operations in finance. What were the problems you really started to tackle when you came here?

Allen: Well, some of the issues I was dealing was, do we have enough toilet paper? Do we have enough soda in the fridge? So, what’s the Instacart login? After I dealt with that, on to the real problems. I think everything that you heard already is, and I’m going to just tack over the things that I heard. Those were really, really, great, great talks, and very insightful. I’m just gonna give you my perspective.

So again, I have more of a finance background, so it’s easier for me to think that. I think maybe the advice I would give is, it was very easy for me to index on the things I did well. So, I’m good at potential modeling, I know enough P&A, I know enough driver’s analysis, I can think about growth.

But, I’m not a CPA. I do not have an accounting background. I’m not a facilities person or an IT person. I’m not a lawyer. So, it was really just looking at a span across where was the greatest need, and then it’s like whack-a-mole. You whack one down, you go to the next one, you whack one down, you whack one down. And, I think it’s just being okay with that.

It’s living in that constant sense of nothing is ever gonna feel right, and you have to be okay with that. For people who are perfectionists or you’re high achievers, it’s in survival mode and it was anything and everything that required attention. And, it was being okay with making mistakes and just moving very, very quickly, and just having a very short term memory of what you screwed up on that day or that week, and just plowing ahead to the next problem.

Charly: Bravo, thank you. And, how do you think as the business was going, how do you think about building your team to support the business and comment on what you asked for and brought in house and where we go from here.

Allen: Yeah, so again on that theme kind of survival, I wanted to make sure that nothing would break in the beginning. So we had payroll outsourced, some of the bookkeeping was outsourced, and the first hires I made were to basically offset some of the things I was not good at. So, I brought in an accountant, a senior level accountant person in the beginning, and then brought in a confidential analyst just to give me more bandwidth. That hiring didn’t happen until almost a year into the job. So, I did a lot of things on my own in the beginning. You just kind of have to.

I think over time, though, as we move from, survival to I said oh my God Slack’s actually a business and I’m getting paid here. You shift to instead of planning out the next month, you plan out the next year, right? What does your team need to look like? What type of things do we need to solve for? And then I started thinking about control organizations so then I hired a controller, a director of finance, kind of key leaders to start to build out those teams. And when I say teams, I mean we’re about to hire one or team people , but eventually provide that core foundation and a little bit of that forward thinking on how it would work.

And the reason I think that’s important is because I think there is that tension between you want to save money, you want to hire just what you need, maybe a little ahead of what you need, and then you run into a problem where say you hire a finance manager. They took a bet on you. Now you’re a 100 or 125 people and you want to tell them hey listen Johnny, we’re gonna hire a boss over you. What the heck, Allen Shim? Where is the loyalty? Like I bled and sweat for you and so I just don’t want to feel bad and then try to resolve that.

So it’s much more peaceful and productive to have that thoughtful conversation up front and to be thinking about your organization up front and how you can build and scale that.

Charly: Thank you, and how many countries do you operate in today?

Allen: We’re in seven countries. Is that right? Nine offices. Yeah, that’s right. So we have a funny dynamic, because we started out as a game and we have this legacy history about the company. It started in Vancouver, but we lived and worked in San Francisco. So we had a dual identity from the beginning, both U.S. and Canada.

The funny anecdote that I’ll share with you is that the hardest thing I had to deal with in the first three months was moving over from the Canadian version of QuickBooks, because there is no migration between U.S. QuickBooks and Canadian QuickBooks. I wish I was making that up. But if you look on the QuickBooks help page, you’ll probably search the question I posted to the community to say, “how do I switch from Canadian QuickBooks in to U.S. QuickBooks.” I still get pings every once in a while, that say someone replied to your thread, someone replied to your thread. Thanks guys. Thanks community.

So, yeah we’re in some countries. The really this or that was that our customer support is one of the things that Slack prides itself on is providing a great customer experience. A lot of that is driven by the fact that there are people answering your questions around tickets that you might submit to the system.

So we started out in San Francisco and Vancouver. Clearly those are not economically grow and scale a large mass of people. So we went to Dublin the next one and then Melbourne to provide certain coverage. So we’re fortunate to have a pretty big national customer base. So providing that real time coverage was really, really important for us over time. We’re more recently developing a direct sales motion and having presence in those areas was also helpful in being thoughtful about where we wanted to be to build out other functions besides customer support.

Charly: Great. What did that mean for you on the finance diet? I assume it started out with complexity. Why don’t we start with that.

Allen: Yeah the complexity I would say is more administrative in the beginning than financial modeling. So most folks are operating costs plus structure. You’re going to see some of the entity and you’re not necessarily gonna have too much bookkeeping intact. You’re gonna have to think about all the transporting supplies, but you can pay someone a little bit of money to do that, right?

It’s more telling the organization that it’s expensive to go international. Not necessarily expensive in dollars, but it’s expensive in retention. It’s expensive from the tax it puts on how you do things. And culturally, and you know it’s expensive.

So that was the hardest part, right, the hardest part was that you now had a group that was on site with you all the time, but never actually on when you’re on. And when you had events or announcements you know they came out while they were sleeping or when we had all hands, you know, do we have all hands very early so that Dublin can be involved? And that’s really the cost of being international. I think it just really depends on the person. So as long as everyone thinks about the business case for being international and who all can take off the costs, because guaranteed most of it will fall on you. Because you had to do all the set up and all the burden of international payroll and international employment contracts. And if you’re in France which union are you a part of? And you just don’t want to deal with all that if you don’t have to.

Charly: Thank you, Looking at the financing that Slack’s is raising due to funding. What was the first round of funding you were involved in? I’m curious to hear how you got involved or your team got involved in rounds and how to structure all that.

Allen: So we have raised somewhere over 500 million dollars. So the first rounds that we did was about a month after I had joined, it was one of the main initiatives was to bring someone to refinance. Because it was less of modeling as you can imagine, because the company had a ton of organic growth and we were very very successful early on. So it was more of a matter of who was going to do due diligence, because that wasn’t going to be stored. And setting up the data room and dealing with that. So in the beginning it was more administrative.

As you have data to share and financials to share, they want to hear from the finance person. As far as how do you think about the business in terms of economics? How do you think of this in terms of the occurring margins over time and the cash flow that you think you can generate? Not just this year but two, three, five years from now and that financial division is something that you’re responsible for.

I think someone asked earlier, what is the Head of Finance? How has that role changed over time? In the beginning I would say you’re a bookkeeper and then you become an analyst in what are financial analysis so you kind of go from IC to manager to leader. And I say that really mimics what in financing … what this role has to be. They need to see you as the leader of an organization, not the manager of the books or even the manager of the growth, because there are plenty of people that can do that.

Charly: Great, and when you look at all the stakeholders that you have today and all the employees. How do you manage equity? What are the tools and the structure operationally to manage that?

Allen: Yeah, so we use Carta. There you go. Well, no, no I mean seriously. I think most of us are probably using them here. It’s a crappy system. Carta isn’t a crappy system. Equity is a crappy system. (read more about equity here) So obviously the big users of slacks and we try to have our vendors use Slack as much as possible also with their lawyers and our contractors and such and that makes it really easy to work with.

And the reason I bring this up is because when you deal with cap table and law firm over email, you just want to shoot yourself on a given day, right? Okay so Carta has been super helpful and I think employees really value the transparency.

And obviously there’s utility for me and for my team to manage it and it does help our team to scale. So there is one person can actually handle quite a bit on the equity administration part of things. And then I have a lot more clarity and certainty of what the numbers are in terms of fully diluted, how the grants have been done. So that’s been really really helpful. I think I was mentioning to Charlie earlier that we have a small fund where we invest in private companies as well. So Carta has been a tool for us to manage that because some of those companies have been adopting Carta so then I can just track that portfolio on Carta in a very streamlined way which was kind of unexpected but a nice benefit along the way.

Charly: That’s great. Do you have a dedicated person to look at stock admin?

Allen: Yeah we have someone who looks at payroll and equity mapping and she’s wonderful. And she has one other person on her team which was a pretty recent addition. But the fact that one person could manage at that time probably 600 people global is pretty incredible.

Charly: That’s great to hear. And with the success of the company, I assume a lot of the employees have significant equity and options and shares and so have you done any secondaries? Curious to hear more about that and how you structured it.

Allen: I think secondary just depends on your culture. So I’ll give you one opinion, so we value it mostly because Stewart in general when we hire people, part of what we’re saying is please take lower cash and higher equity. And in most cases you say “Well can I tell you five years later that that’s gonna be worth anything?” And that kind of sucks so Stewart is very thoughtful and empathetic in these areas. And we’ve definitely taken in probably a proactive approach in thinking about equity and monetizing equity for folks.

To answer your question directly. We’ve actually done a few secondaries and we’ve done a couple of them on Carta. It is a process which I would say is administratively difficult even with a tool like Carta. Even though, they make it a lot easier than if you do it outside. If you don’t have your cap table and you do your secondaries on different platforms. But secondaries are more of a cultural question, right? so you know a lot of our rules that you set on how much people get with cash out. Who should be eligible? Employees versus non-employees. What type of comps you do for the company? Because not everyone will be eligible.

So there’s a lot to consider and unfortunately it will fall disproportionally on you and the People team. So if you bash the People team it will fall completely on you. Mostly around things like coms and you know like hey should you be having someone come talk about taxes and how AMT works. We did. And it was brutal. And it was painful. And I wouldn’t not do it. I would probably scope it back a little bit and have it be a bit more targeted. But you know this is the stuff that people will come to you and expect from you, because you didn’t do it, you’re completely not thoughtful and insensitive around the fact that not everyone understands taxes the way that you do.

So I would just be very very thoughtful around how you consider that. Its a great idea and people have at the same time been able to put down payments on houses and you know pay off student debt you know real value, right? Not just that people are all of a sudden buying Ferrari’s or something. So I think you just gotta find the right balance that makes sense for your culture.

Charly: Thank you. That was helpful. As you look forward in the scale of the business and potential IPO. What are things on your mind today as the head of finance and where. What you’re really trying to continue to do to have the business scale and get through this stage of the republic.

Allen: So, if any of you guys have read the “Five Dysfunctions of Teamwork”, five or six. There is the concept of first team, you know who is your first team, right? And I think the main thing that has changed for me over time is really changing that definition of first team to the executive team. And that might sound obvious to folks, but in the beginning, because I was so in the weeds and I had to be part of the day to day, I didn’t understand the week to week my first team was my team, right? The people who were important to me, right? We’re those in the finance team or the sales team or the IT team or the analytics team. And now my first team has been for some time now I’d say the last kind of year plus at least in the way that I orient myself is the executive team so CEO, VP, CTO, you know Head of Sales.

And I do something, at least I try to, and I encourage all of you to do it. Because you know in Slack, I feel like I was a part of four or five different companies in the last three years, just at each stage. And one thing that I found super valuable is calendar bankruptcy whether you do that every quarter or every six months or every year is look at where you’re spending your time. Start over from zero and then put in the most important things after that then put in the most important things and see if you end in the same place that you have today and I can almost guarantee and I would almost put money on this but we don’t have to do that. That you’ll end up with something different.

Because it requires a thoughtfulness around what matters, not what’s interesting. Not what could be valuable, but what can you uniquely affect? What can I uniquely affect? And that’s been super helpful for me because it then actually helps me to delegate a lot more to my team. And it also helps me to focus on things that I think will have a disproportionate impact where one unit of energy in this next thing will yield more result than another unit of energy in a different thing, right? And that is a hard choice and that is a bet that you have to make based on your judgment. But if you don’t do that then the organization will feel that.

One thing I say on my team is that, you’re gonna end up with a lot of things that are 80% done. Which means that nothing is done or things that are okay or good which its kind of crappy, right? You want to be building things that are excellent. You want to be building things that are to completion because that’s where the organization realizes value.

So for me where I’m spending my time is I’m spending a lot of time in sales. Sales is a new thing for us. If we get sales right in terms of a scale, its gonna be hugely valuable for the company so its gonna be worth my time to spend 50, 60 percent of my time in sales than what I would probably do on an average blended across the things I look at 20% and that two and a half, three X makes all the difference because now I’m talking to Bob, who is the Head of Sales, every week if not two or three times a week. His team one or two times a week. Talking to recruiting about hiring the people thinking about com plan all the time, driving the CRM changes.

And the fact is that’s a bet that I’m making. That means I’m not spending time in IT. I’m not spending time in facilities I have to trust my team in those areas. And honestly if you find that that doesn’t work then it’s probably because you have to upgrade your team. And those are the harder questions that you’re getting paid to figure out, right? That you’re not gonna take it to your CEO and say, “Hey should I hire a new head of facilities?” “Well what the heck am I hiring you for?” You make that call and come back with a recommendation of what needs to happen and then we make that happen. So that covers it.

Charly: Yeah that was super helpful. Thank you so much for your insight.

Audience Questions

Audience Member: Well, first question. Did you guys coordinate the outfits? It’s great. No, it’s really great. My second question. Alan, so with your Canadian president, I’m just curious, did you guys make a conscious decision to do stock options denominated in Canadian dollars and US dollars or did you have cross-border, full-time, currency denominations. Why so or why not?

Allen: One, I hope it’s because you like our shirts. Yeah, so it’s twice the goodness. You know we didn’t give that a ton of thought, honestly. I think the bias was to keep it simple and to keep things standardized. As I mentioned, we had Canadian from the beginning, so the last thing I wanted was to add some kind of complexity to a 30% company. That’s my simple answer for you. I’m not going to say it long, I’m sorry.

Audience Member: I thought what you were saying about international was really interesting because we had to go international super early on, because our clients have employees all over the world. One of the challenges that I’m experiencing right now is the laws in the Netherlands, where we have a lot of employees, is completely different than Switzerland, and is different than this and this and this, right? We accidentally promised stock to employees in Australia, for instance, and we’re going to have to fix that.

How would you stay on top of it all? It’s so much information, right? How did you handle that and stay on top of that early on?

Allen: The main thing was discourage them to go.

Audience Member: That hasn’t worked.

Allen: No, no. No. What we have decided is that even though we have seven countries that are not all equal, not just from a revenue perspective, but how we interface with them, right? We decided early on that Dublin would be the international hub. We built operations so that that became hub and spoke versus equal centers everywhere.

Even that adds a lot of clarity because then people know that they’re more satellite than they are main hub of that region. But there was a lot of you know, “This is gonna be a club for Slack,” even though using Slack to try to communicate, it’s hard. I mean, we had to create a concept called XFN, short for cross-functional, and there was one specific for international cross-functional where I basically told the team one time I was fairly upset because I was surprised, which surprise, as we all know, is a four letter word in our profession. I was surprised by something that the team brought to me on international. I had no visibility on it – zero. Even in a world where we’re all using Slack all the time nobody pinged me. I said that’s just not acceptable. We created both app. You just have to build in that cadence of communication.

I mean, that’s probably the only thing I can really offer to you because it’s not … there’s no silver bullet that we found either. Honestly, if I’m gonna kinda mind read a little, there are probably problem areas that you have versus what you’re reacting to, so we gotta fix the problems. Either you have to get those people out, or someones gotta talk to them, or you gotta bring in a new leader there and once that noise goes down, your standing level goes way way way up.

Audience Member: So as finance leaders we have to make some pretty tough and difficult decisions. Interested to hear your thoughts around how you go about, sort of navigating some of those more trivial trade-offs and challenges as a finance leader.

Allen: Number one, my first reaction to that is communication. I would say that, and ask you guys, if you were to ask your CEO, on a scale of 1-10 how much do they trust you, what do you think they would say? And anything less than like a nine is unacceptable because your ability to be effective has to come from a place of fully supported in what you do. And if you’re not there, it doesn’t matter because in a place of high trust there’s no difficult decision, it’s just one that’s probably more complex and more time consuming and more administrative. If it’s a decision that they believe you need to make and they will support you in making it. That’s the main thing that I would say, and you can apply that then to a, “Who’s your first team?” How do they think about you? If they hate you, then all decisions will be difficult. Even, “Hey I want to take one head count away from you,” or, “I’m gonna cut the consulting budget for like ten kids.” You know, “I hate you, you’re so unfair and you’re screwed, and you don’t think about growth in this company.”

And I wish that was a caricature because it is very emotional for folks. Just kind of cut through the BS and find where there’s no trust, fix it. And where it really really matters, build it. Again, everyone’s wired differently. If you have to go have drinks with someone, you have lunch with them, you talk to them, you have a weekly check-in, you send them data to show them you’re thinking about what their needs are, do it. Do that first. And that’s an answer.

Audience Member: How do you think about competition? How much time you spend as an executive. Talk to me about competition.

Allen: Well we think about it a lot more these days because we have more products out there. I heard a great, someone showed a great article to me which was, when you look at, kind of, the David versus Goliath, it’s an HPR study or something where you have, “Hey, when you have David, competes against Goliath,” they win, surprisingly, a significant minority of times and I remember that percentage, let’s say 25%, but when that David uses the tactics that made him successful and employs that skill, they succeed the majority of the time. And I think, I share that because we talk about competition because we have to know about it and we have to think about how to pull resources from a partnership perspective, an ecosystem perspective, a customer perspective, so sales, ED, corp-deck, all that kind of stuff, but, we think about it last because we are succeeding and they’re taking notice of us because we’ve done things a different way that they don’t know as well, so our ability to succeed is doing what we do well, more and more and more of that, versus changing the ways that we operate to mimic that. That’s kind of the way we talk about competition. It definitely is more time, you know like 10% of the time for that conversation.

Audience Member: What does your team look like today, and what do you see as the next step?

Allen: So what level I want to tell you? I’s have to say “Don’t tell my team this,” because I haven’t had all those conversations. Just quick history, it used to be everything, kind of one minus R and D and customer support. The things that clearly didn’t make sense, marketing sales, so those started to move out pretty quickly. The things that started this is, for me, a story of focus. So, kick up marketing sales. Then take out people which will be kind of a more recently organized project we’re going to do. Then take out … security at one point too. Security. And the future, probably take out product analytics and some parts of IT development on the developers side. Basically, everything else is me. Finance, accounting, facilities, IT, I have a group called program management. And then in the future, hopefully, all things work out well, investor relations. So that’s probably where I’m going to focus my time. Again, not equally across those areas, but things that would be the areas. I’m sorry legal left awhile ago too. But, can you believe that I was head of legal, well, for a long time actually, so that was kind of scary.

Audience Member: What kind of accounting challenges have you faced working at five different continents?

Allen: Okay, so I built the control organization fairly early on, so that was probably my fourth hire in the team, at least in terms of the finance team. I just delegated all that to him. And he built the team around that. I’m also pretty liberal with using consultants on stuff that we just don’t know, so technical accounting, very specialized things, because the cost of missing it is just too high relative to the crazy rates that they charge you. It’s the same stuff as anybody, rev rec (revenue recommendation) we spent a lot of time on, equity, especially when we did a secondary that’s a very new thing of accounting that you have to spend a lot of time with your auditor on get tax advice on as well. I would say those

So we actually got a tax person last year. So I did migration of the non-US I&P into Ireland and Singapore, but basing out of the US. So that was a big tax question we had to deal with. And then arguing credits, we sort of looked at buying region, but Canada is one where that’s actually something that we’re taking advantage of right now.

Audience Member: What’s the percentage of head count in finance and accounting?

Allen: I think it’s somewhere between three and four percent or so. But can worry about getting rid of people now, We get the benefit of 3% of people team, so it’s actually kind of large.

Audience Member: What about earlier on?

Allen: Earlier on I indexed the doers. So bring on the doers that you think can scale, and the things that they can … the output they can provide for you. And in things I do think you need that additional capacity, but the

Audience Member: You mentioned that you’ve owned a lot of priorities. What I’m also curious about is where we’re encountering these situations in business situations that you may not have experience before or maybe your pioneering areas. How do you get smart on that?

Allen: I’m going to interpret that a certain way and you tell me if I’m off base. The main area where that typically might happen is accounting, accounting treatment. We have a technical accounting group that helps us get ready for an audit and helps us get ready for the thing about rev rec (revenue recommendation), so that we can have the memos ready to go when the auditors come in. That’s the main thing we do, is we reach out, and we ask a lot of questions. If you have an auditor already, then they’ll tell you they want to engage with you on it, at least on a partner level to talk through it, international and all the BS. That’s generally what I do, is more active communication and reach out, and we ask a lot of questions. Here’s what we’re thinking, and does that rattle you in any way.

Author: Jesse Klein
Jesse was born and raised in the Bay Area. She crossed the country to go to the University of Michigan before heading back to her roots in San Francisco at Carta.