E02: Mike Macaluso, Finance Manager @ Yesware

E02: Mike Macaluso, Finance Manager @ Yesware

Our Guest

Mike Macaluso is the Finance Manager at Yesware.

Mike worked as a fractional analyst for a variety of seed to Series C startups for the first 4 years of his career. At Yesware, Mike is responsible for day to day finance, accounting, and reporting. 

The Podcast


Today’s guest is Mike Macaluso ,Finance Manager at Yesware.

Sagar: Tell me a little bit about your background.  It looks like you got started as a fractional CFO, is that the term?

Mike: Yeah, we were doing contract consulting work in a CFO capacity.  So if you're a seed round or a small Series A you don’t need a finance professional full time.  We would get you started off, get your accounting set up, operations, HR, get your payroll set up and guide you through that.  Most young companies only need 10-20 hours a week of dedicated finance help so we would do that and hopefully get you set up for a successful start and then hand it off to whoever you eventually hire full time.  We started off doing that and worked with a handful of software companies and some biotech companies then I eventually hopped on board with one of my clients who hired me and I’ve been with them ever since.  That’s kind of what’s gotten me to where I am now.

Sagar: Cool.  I think this fractional CFO thing is super interesting, when does it make sense to bring in a fractional CFO versus full time head of finance?

Mike: It’s tough to have a blanket generalization because every company is so different.  The way I always explain it is that you wouldn’t go build a bulletproof engineering infrastructure as you're launching a product so you wouldn’t build a full finance infrastructure if you’re doing the same thing.  The idea would be to get you something that works, probably doesn’t scale to a huge company but gets you through 10-30 employees and by the time you hit your stride of 30-40 employees you’re probably ready for a COO or VP of Finance.  It’s so different between different companies and different types of companies.  I think you can survive a while longer with a software company but if you’re in biotech there's tons of regulatory stuff that happens sooner than you may be ready for.  I think it depends but as you start to raise more money, especially with venture backed companies, and you’re into the 40-50 employee range, it probably makes sense to hire a full time finance person but it’s different for everyone.

Sagar:  It sounds like there is and isn’t a playbook that you try to follow when you go from company to company.  Are there a lot of commonalities that you go through that cycle?  Where do things start branching [inaudible/crosstalk].

Mike: It’s not completely uniform but there’s things that just aren’t going to change.  Your basic accounting stuff, for the most part, is going to be the same.  When I was hired initially to do this at a father and son company, the father was super knowledgeable and I found that he didn’t really need to know the technology.  We were working with companies like Bluefin Labs they got acquired by Twitter and they were doing this super technical big data pipeline of parsing all this Twitter data as people are watching prime time TV.  It was really technical but he didn’t need to know the technical side to figure out the basic drivers of the business and then he could back in through that.  I think there’s some stuff that's probably never going to change whether you are a small business or a VC  backed business, like the systems and that.  Then there's also the drivers of the business that look out a little bit more and do the forecasting.  I think those are the big things. Obviously technology changes really quickly and every company is going to be different but there’s basic stuff like a common thread that you can use to build the initial infrastructure of all these businesses that we would rely on.  The basics would be the accounting systems, the HR systems, and then the forecasting systems, those are the three main things.  Everything else is in the details from there, that’s mostly how we do it. I think things have changed a little bit, I think tools have gotten much better but that was how we could get in early and take some stuff off the plate of the CEO or whoever was running the operations  at that point.

Sagar: Can you talk through the timeline a little bit more? How long were the engagements with the company and what did you do first?  Was it the accounting system and then did you bolt on the HR system?

Mike: That’s a good question.  It would actually start before that, the speciality that was helpful to CEOs was when they were raising money my managers had seen a lot of term sheets and how deals worked.  That was helpful from a practical standpoint if you were raising money as a founder.  Then it was the most basic stuff like if you're a first time founder of a VC backed company, where do you bank?  Do you go to Bank of America?  I think that would be a good question for anyone.  Do you know that there's a specialized bank just for venture backed companies to go to and they understand the highs and lows of it.  Silicon Valley Bank is what most startups use but it’s hard to get into that without mentorship and direction.  You start there and through the fundraising process.  With a seed round you’re not going to have too much information on the company to begin with but as you get into a Series A or Series B there's a lot of due diligence that institutional investors or VCs are going to want to look at.  Liabilities and all the top line revenue, they want to make sure all your ducks are in a row and that the basic business is running well,organized, and the cap tables clean.  That would be where you would start with most of that stuff all the way to the end.  We’re happy to get out of these companies as they get bigger, that’s the end goal.  You want a successful company, you want to hand over clean financials, HR, and payroll.  As you’re hiring a full time financial person you want to start them off on a good foot where they’re not cleaning up too much stuff.  That’s kind of the life cycle very briefly from the start, raising money, getting you set up, all the way through to a really clean handoff where you could feel good about your work and then have someone who can come in and hit the ground running and is up to date on everything.  Whether it works that clean every time is tough because it doesn't always work out that well.  You have to have a lot of trust to give over your bank account, payroll, and sensitive employee information.  This isn’t stuff that you hop in one day and grab all the passwords to all this stuff and you can pull out easily.  A lot of times it's a very slow transition to make sure all that information has been transferred over properly.  I think that’s the other side of the coin.

Sagar:  Interesting.  There’s a few things here that can [inaudible] try to generalize what you just said; it sounds like there’s three distinct skills that a fractional CFO should possess when working with a new startup that's raising money.  The first one is experience and mentorship with the process, the second thing sounds a little more like accounting when you say due diligence.  Do you really need to have an accounting background to support there?  

Mike: No, due diligence can be everything from making sure the cap table is clean, that's probably one of the biggest things an investor doesn't want to worry about.  I say not to worry about it because they don’t want it to be an issue, I don’t think aninvestor is the most 

interested in how a cap table looks.  It’s everything from accounting to your general liabilities, it can run the gamut.  Accounting is probably a pretty small fraction of that in an early stage company.

Sagar: Gotcha, so when you get through that process it’s a little bit more operational.  It’s identifying the right tools for the business to support growing your headcount and scaling up your accounting and finance practice.

Mike: Exactly.  

Sagar:  Interesting, so what took you from that world to wanting to go full time?

Mike: Well, it's really cool to see the infancy of a lot of these companies.  You’re going from this idea to watching someone raise money to hiring their first engineer, first marketing person, then their first ten employees which is great.  But you can only do that so many times.  I was interested in the mid-sized scale of the business where they’ve gotten passed raising a seed round or a Series A or B.  I wanted to experience a company growing a little bit more but in a more intimate way.  I would have four or five small companies that would be the main point of contact with the consulting role but I was looking for something more full time where I was thinking about the business all the time. That’s where the migration from the early stage contractor role to a full time role which I thought was interesting from watching the companies go from zero to ten to 40 employees was cool but I was looking for more of after that.  How does the company work and grow and those challenges, it has been great and perfect for me.

Sagar: Awesome.  Any fun learnings you’ve had along the way?  What’s been super surprising for you going into that world?

Mike: I think maybe just like the growing pains of watching a company  go from 10 employees or a hacker/coworking space to we’re a real company now.  I love the early days because it’s really scrappy and you’re trying to make it work.  I remember Yesware, they were in text[inaudible].  They had some office space in the CIC in Cambridge, it was a shared office and it was really crazy.  Kendal Star was getting so expensive that they decided to rent a two bedroom apt and work in the living room and use one bedroom as a conference room.  The cofounder from Brazil would sleep in the second bedroom and then we would have a full stove and fridge which is great because no office has that.  That’s what they decided to do, it was great.  I would go in a few times a week and do what I had to do and check in.  I remember being on the elevator and someone asked if I just moved in, I didn’t know what to say.  Moving from that to our first full office space where we would do a build out to the second office space,that feels like a real office.  I think it’s more the genesis of watching a company grow, not knowing if it’s going to work or be at a company in twelve months to being a real company with real problems that have to be figured out.  Like not having enough bathrooms.  The entire lifecycle of an early stage company, going from the uncertainty to a little bit of having the rhythm and figuring out how to grow.  That’s been the most fun part of it.  Probably not a surprise. 

Sagar:  Awesome. You mentioned that as a fractional CFO around Series A/B you would hand off the keys to the full time CFO.  It sounds like in this case you handed it off to yourself.  Did 

you kick yourself about any of the stuff you did in the early days?

Mike: I think the hard overarching thing about this is that you’re in an early stage company and you have the decision of making an iPhone app or building a better billing system.  The least sexy thing you can do is build a better billing system.  No one wants to do that, it's boring and so those are just the trade offs.  Engineers have technical debt and I think a lot of times we as finance professionals have operational debt.  We put off the billing system for three years and we’re still paying for it, you take responsibility for it but it’s the trade offs and what you do with the resources you have at that point.  There’s tons of stuff, if I can go in the early stage and make the perfect tech company with all the bells and whistles it would be great but also a waste of time and money.  If the company isn’t there in three or four years what’s the point of having this bulletproof finance system. Obviously you want to do the best job you can, and you try to, but at some point resources are constrained and you make decisions, whether or not it was the right one.  It’s funny being in a full time company now because you see what you should’ve done, but hindsight is 2020.  I think I’m making decisions today that myself, or someone taking over for me, will be like “what was this guy thinking? This is so stupid”.  You almost wish you could talk to them and say this was the decision and there’s obviously a lot of things impacting it.  This was the most optimal but far from decision we could make.  

Sagar: Let's dive into it, you mentioned the billing system, lets start there and keep peeling back the onion.  What was the trade off you had to make with the billing system?  Why did it take three years to [inaudible].

Mike: With anything like this, when you’re in your own finance bubble you can do a lot, your team can do what they need to do, but you start to cross into other areas of the company when you’re like “ I need a lot of engineering or marketing time”.  When we changed the billing system the marketing folks aren’t going to like the data that’s coming out because we’re going to have to rejig it, when things start to become cross operational you need buy in.  We need a bunch of engineering time as any startup in NY, Boston, or Silicon Valley knows, engineering time is super expensive.  All the buy in, all the stuff you could be working on, for them to move from that to a billing system is probably not the most exciting thing from a product standpoint.  That’s the biggest thing.  Resources are constrained so to jockey for those resources is tough, that’s probably the biggest thing.  You’re going to be affecting other parts of the company that may not be ready for that kind of change.  The value added for them is not the same as it is for your department.  That’s the biggest thing, it’s a bit of a barter so to make a compelling case for a billing system like “look we might not be able to have really clean, auditable financials if we don’t have this billing system but it’s only 5% or 10%” .  As you grow that stuff gets more and more difficult to back out.  The first year it’s like “ok it’s only 5% of our billing” or however you want to quantify that but in a growing company that’s different.  In two-three years that's different so I think in any of those operational decisions you’re thinking about the trade off.  It’s not the perfect decision but it’s only x or y,  as you grow and get more customers (or however you want to measure growth) that kind of thing becomes more difficult and you have to back out your mistakes.  I think that’s the biggest thing, it’s a decision on resources and again you want to have the perfect scenario but there’s never really the perfect scenario. 

Sagar:  Gotcha.  I wonder how much of it is...it sounds like there’s some technology limitations too.  When I think about implementing a CRM that’s heavy.  It requires buy in and people have to build processes on top of it.  But the things you tack onto the CRM are now plug and play.  I can go in and install Gong and have the sales team make recordings there.  And I can switch to another tool like Chorus.ai tomorrow with almost no problem.  It’s only that one team and it takes them maybe a week or two of implementation, but with finance I don’t know if it’s ever that way.  What billing system are you on that required so much custom work from engineers and marketing?

Mike: I think that with Salesforce you’re not switching off because that’s what everyone’s using, or Hubspot.  Some of the systems are so big that they are hard to move.  You can charge people on Stripe tomorrow and have two customers that want their credit cards charged today, we can set that up and that’s fine.  They’re paying month to month for that stripe set up but what happens when you just get into huge recurring charges?  Then you’re thinking about the cost.  Stripe is probably a bit more expensive because it’s so easy to plug and play but what happens when you have different credit card processes and refunds?  Or you have different products that are charging annually or now have a discount.  Any time you make a decision whether it seems very small like “hey we need to build in something for this customer who needs a refund” it ripples across the whole population and it’s much more difficult to apply that for thousands of customers.  I think that’s where the complexity starts to build really quickly.  Any small decision that you make is going to have trade offs later, especially with billing.  A more overarching theme is that generally you want your finance and HR type systems to be very standard and you don’t want to be switching them.  What if you told your finance people who come to you tomorrow and say “ hey, ADP is not working we’re just going to swap it out really quick with like a different payroll system” then you have six W2’s.  You have to not only carefully decide your initial systems but you also have to be consistent with your systems too.  To move over an accounting system, some think it can’t be that bad it’s just numbers, but it really is a beast and you want that continuity among those systems.  I’m jealous that you could plug in Gong and you’re good to go but I think for the most part with sensitive information and stuff that you want a long papertrail of you really want to choose carefully pushing those systems past where they are comfortable and then switch really thoughtfully.  The changeover costs are just way too high for a lot of these systems, it just can’t make sense to be chasing the new technology.  There’s a little bit of stagnation, some of them are tough to use, it is what it is.  But engineering, marketing, and sales, I think there’s some stuff like Salesforce where you are probably not swapping out but the third party stuff on top of it is probably great because the switch cost is not too great.  I notice that as much in finance and HR.

Sagar: So it always blows my mind how small finance teams are. I keep hearing and reading online where everyone is like when should I switch to NetSuite, when should I switch from NetSuite.  

Mike:  That’s a good example.

Sagar: In sales it’s an absolute nightmare.  Not just on the NetSuite implementation but just the idea of doing it especially when you’re in a growth phase, like why would you bother doing it.

Mike:  Yeah, it's a good question.  QuickBooks is probably the place that you start, it has the basic finance functions.  You could get financials out, it’s amazing what you could get for $100/month.  It’s a really incredible software if you think about being in accounting 15 years ago compared to today.  But it has limitations.  If you went into your billing system and wanted to incorporate your CRM, all the stuff you could make huge productivity strides in, or look at your data combined with your financials is going to be tough to integrate with QuickBooks.  I would say that it’s like moving to Salesforce where it's heavyweight where you can do a lot but you have to know a lot to really get the full use out of it.  It’s a really difficult decision on when to switch too.  There’s a massive cost to switch, it’s far more expensive but  as you start to grow as a company those things start to outweigh what you’re doing in QuickBooks, then you have to start to think about it.  There’s that element of it.  It's easier to switch earlier then it is to try to play catch up and think we should’ve switched two years ago like “this is brutal, now we have all this data all over the place and we have to sort of get it cleaned up”.  I’m in a slack group for controllers and people talk about that all the time.  I probably switched too early but who knows. 

Sagar: So you already did it, you don’t have to worry about it anymore.  

Mike: Oh no you worry about it all the time.  You’re still like why does this look weird, why is something going on there?  And that was the date we migrated over from our old accounting system.  You know exactly the cut off date and what’s going on there.  It’s your biggest system, it’s your most important thing and to open up a lot of the efficiencies so many other companies paved the way for what you have to do.  QuickBooks is great and it’ll get you far but at some point you’re just like we're running out of things we can do and we have to upgrade.  It's a tough decision anytime you’re moving all the stuff at once and I think it’s hard for non finance people to understand the hype about why it’s going to be so difficult because its like you upload some CSV’s it can’t be that bad but there's just so much detail it's difficult to get it right.  I did it by myself and it took two to three months.  

Sagar: Instead of reliving that nightmare let's talk about the now.  What is finances’ role at The Esquire.  I feel like people say “that’s my finance team” but it’s so different depending on who you talk to.

Mike: Absolutely, isn’t it crazy?  A finance team could have a ton of buy in on the HR side or they could not exist at all. I would say our core responsibility right now is timely monthly close, a lot of regulatory stuff like sales tax is huge, we also do some HR stuff because you’re so intertwined with those folks.  Another great example of a grey area is where the customer support folks can get you pretty far but they can’t make decisions on when to refund people so we have a huge hand in managing those responsibilities. It’s something that we want to be in charge of so that we know we can thoughtfully administer that stuff so it makes sense on the finance side but also makes sense on the customer care perspective so that’s a big thing we do.  The bulk of the work is that but I also think as is the case with a lot of finance teams there’s just a lot of stuff that falls through the cracks that are not anyone’s specific responsibility and so it will sort of trickle down to us and we’ll make a decision. It could be something stupid it could be something that just doesnt find squarely in marketing, support, or sales.  I think we’re the catchall for things that need a decision made and we back into that.  I think those are the biggest things but any given week it could change depending on what we’re doing.  

Sagar: Do you find that your finance team...I feel like finance professionals especially FP&A tend to be the most analytical people in the entire company.  Do you find that you're called in different parts of the organization to drive strategic decisions and pull data? 

Mike: I think a little bit on the executive side that’s true.  We have a small team.  I think that’s an interesting thing comparing finance teams to other companies as well.  We are basically at three-ish people right now so having a small team at the executive level they’re definitely getting pulled in because those decisions need to include finance.  A lot of times we can push back and give a different perspective.  On the other side, a lot of companies have much larger finance departments where you have a dedicated FP&A person, we’re not quite there yet but I think there are a lot of strategic decisions that are much better off if you’re including finance early and often.  If you don’t, and a decision gets made, it can have adverse effects if someone has a blind spot to that kind of thing.  I think it depends, but for the most part I think we are included in that.

Sagar: Gotcha.  It sounds like in your finance team you’re the glue, you’re the utility man, you get pulled in a bunch of different directions depending on the day and what kind of work is coming in.  Is there something you wish you could spend less time on to spend more time somewhere else?  What are your competing priorities?

Mike: That’s a good question.  Probably anyone in the finance world has recurring stuff that can't be automated but need decisions made around it and they’re not the most exciting decisions.  A lot of times it’s like monthly close, you spend a lot of time doing that.  It would be great to get that time back but it’s valuable to be in the weeds of it because it gives you some insights into the business. There’s elements of the operational side that would be great to not have to do as much but it’s a tough trade off because often those things give you a really good feel for the business working on a more intimate level that you would be.

Sagar:  Is there anything that comes to mind that you’ve observed recently while you’re in the weeds?

Mike: I feel like when you’re reviewing month end billing type revenue stuff and you can dig into the data and look at that, but I don’t think I have anything specific.

Sagar:  We can come back to it.  What do you see happening in the next three to six months from a finance perspective at The Esquire that’s keeping you up at night?  Where does your brainspace go?

Mike:  Well, we are doing our financial audit right now so that’s always something you’re constantly thinking about.  I don’t know if there’s anything keeping us up at night.  A huge opportunity for us is that we did migrate over to NetSuite and I think after this crunch time our focus will be to automate a lot more.  I think we’ll have more breathing room to do that.  That’ll be three to six months. I'll have a bunch of things that we’re not leveraging as far as an upgraded ERP that we’re looking forward to having downtime to work on.  I don’t think there's any big stressors at this point.  I think everyone is generally in a COVID world worried about sales and the unpredictability of your customer base and everything related to that, but from an optimistic standpoint we're getting the most of our systems that we haven't been able to do.  That’s something we’ll be spending more time on.

Sagar:  What kind of stuff are you trying to turn on?

Mike: We want to get Zora pushing to NetSuite which will be pretty big for us.  There are small things within that suite that are huge timesavers.  Using their modules to hook into Zora for collections or ZenDesk integration. There’s tons of low hanging fruit that we’ve put off that would be huge gains for us.  

Sagar: Is it automation that it will kick off a collections ticket or a support ticket?

Mike: Yeah, exactly.  We have stuff like that now through Zora but to merge it all into one system so that you’re looking at NetSuite everyday rather than at the end of the month when you’ve ripped through and closed all the books.  That’s the big thing we’re looking forward to doing. It's just not the most urgent.  You can get by not doing it but it would be great to have it set up so that it’s one system dumping all into the same place.

Sagar: That sounds like the 5% you were talking about before. Trade offs, not the thing to do now but whoever inherits this is going to kill me.

Mike: It’s like why didn’t you do that, and I promise you I wasn’t slacking.  Little stuff like that.  When you can use the system and get those efficiencies it's nice to use because you have it set up like you want to and it’s giving you good information all the time.  So we’re looking forward to doing things like that.  I feel it would be really useful from the overall company perspective rather than just straight finance.  

Sagar:  Is there a revenue or a cost {inaudible} tied to all those organizational improvements or is there focus on speeding up time to close.  What’s driving your focus in that direction?

Mike: That’s a good question.  It’s mostly selfishly, and a lot of other finance professionals would say the same thing, it’s great when you can save six hours a month on doing something stupid like the controller group I’m part of.  A lot of people ask “well when do you cut it off, how many business days are you closed” and that's really important to us.  Every company is different,there’s big public companies that need to be closed eighteen hours after midnight on the last day of the month.  We’re for the most part more casual because this month we’re doing an audit so I can’t spend the first week doing a close.  A lot of it is improvements on speed, you’re better, faster, you can make decisions faster now that you have that.  That’s a big selfish motivation, more broadly for the company it's great if you could push out financials completely baked in a few days because then people can make decisions on what was happening last month, what was wrong, what to double down on.  Sometimes they have their own answers and their own world but if you can shed some light on some engineering costs quickly to them that's really helpful to them.  Or marketing, if you’re spending a lot on ad words or trying to do more incremental ad spend it’s good to have those final numbers.  “This is what we’re reporting to the board, this is what we’re spending” so that we're on the same page on what you spend.  I think it’s really good to give folks that feedback.  I think there’s selfish motivations for us personally in our group and then there’s like good broad buy in from other departments that are good to have and would be useful to have whether they have access to that or not.

Sagar: I don’t know if it's a sensitive topic but what hang ups do you guys have in the financial close process that seem to keep happening that you’re trying to chip away at? Is it a bunch of little things?

Mike: It's really not hang ups as much as with a company and team our size there's probably always a bigger fire to put out.  Sometimes things are just more important that you have to jump to, I think that’s just part of the business.  When we’re doing an audit we’re doing something different outside of the following month that doesn’t make sense to get the books closed when we have other things in our way.  I don’t think there's ever a thing where we get stuck on a close because after a while you can get a good rhythm.  There’s going to be hang ups here and there and they’re unpredictable but for the most part with a smaller team you just try to figure out what’s the most important thing I should be doing right now and you run with it.  

Sagar: Your classic small business problem.  Limited resources to do the things you need to do.  Sometimes the close is the most important and sometimes it isn’t.

Mike.  Exactly and there’s just things that are going to be more important so you just try to prioritize and try to figure out what you should be doing that day, that week, or to start off the month.  You don’t want to use that as an excuse, it's tough to drop everything and always hit your close day no matter what.  As your company gets bigger that stuff you really can't ignore or push it a few days.  I think every company has different sensitivities to their close day.  You try to make it happen.  Some places aren’t going to put you on anything else other than the close, you are in it, no distractions, but with early stage tech companies i think generally hard to speak for everyone in my position but I just think sometimes you’re going to kick it a few days and that’s going to be alright.  That’s kind of where we are at right now.

Sagar:  It's interesting, now that I'm out of an operations role and more on the marketing side and have a bit of a budget, small but it's a budget, I’m trying to figure out how much of it I have spent and how much I have.  I’m already feeling this one month in. I'm trying to keep track of it on my own but I know that I’m not going to get the number from finance until halfway through the month and I’m curious about how they make these decisions.  I don’t know how you communicate this with your team, how do you help your CMO figure out how much they spent, how much they can keep spending.

Mike: Yeah exactly.  I think the one thing I do as a casual check in, especially if you’re managing people who are doing the spend.  A lot of times if you have a lot of people in marketing working under you and you’re okay spending 20k on ad words i’ll just circle back when I see unusual spend or just to check in with head of marketing like “hey it ended up being 24K, I got the final invoice for September”.  I think just doing the bulk of the cost and checking in with whoever has a final say tend to be helpful whether I’m like shoot me a note letting me know you approve or saw this, I think that’s good because whether they have a spreadsheet or are eyeballing it, it gives a feel for what we are doing.  That always the first-second day of the month I’ll send them a couple things “hey ad words goes here, some Bing ads, let me know if you saw this” they generally appreciate that because i'm not asking them to spend a ton of time i’m just asking for a heads ups because there was an unusual increase or increase we hadn't’ planned.  I think that’s helpful but as it gets more formal and you need to manage a budget I think it’s more useful if you could send them something within a week of the previous month and say “hey this is all the stuff we’re putting in marketing”.  There will be things in there that you’re going to look at and say it wasn’t you, or it got mischaracterized, a mistake, stuff like that.  It was thrown in marketing but sales was doing something with the same company but different application.  It’s an AWF cost but checking in with the people managing that on a more time on a formal basis later is also helpful.  Everyone’s different as I’m sure you know, some people want it down to the penny.  I’ll work with engineers who are like “I’m off by a couple bucks” and they want to dig into it.  And then you have other people who are like some sales guys who aren’t looking at the spreadsheet and don’t care.  Everyone learns differently and pulls information differently so I think as with anything you get a feel for how your coworkers like to digest information.  Be transparent about that, put stuff in front of them if that’s helpful or if they want the full workup later.  When I  have everything  and my ducks in a row I’d love to send it to you.  I find that really helpful from a finance standpoint, making sure everythings going to the right place, that someones reviewing it, etc.  I would rather have that open communication where if there’s something we need to fix or got billed wrong that we can fix it quickly.  I’d much rather do that than six months down the line, “we haven't used this service in a year why are we still paying for it?”.  With all these microservices like Gong it's super hard to track.  Sometimes you’re asking “has anyone used this, can someone please respond” sometimes the only way to get an answer is to cancel the corporate credit card and wait for the declines to come in and wait for folks to come to you.  That’s my break in case of emergency because you will just be screaming into the void, I don’t want to pay for this anymore.  As soon as the credit card gets shut off everyone is like “hey where did Gong go? I was using that” .  It's tough you want to be proactive in managing the stuff but sometimes it's not really yours to manage, it’s a little give and take. 

Sagar: Interesting.  I have one last question for you and then we can take this off the air and close up.  Where do you go to learn more about your trade, what do you read, who do you talk to?

Mike: I’ve found this is very difficult.  I was on Twitter the other day and someone whose a VC investor was like “what’s the best finance podcast that you know of”.  Every industry within tech and VC backed companies have people who’ve built these huge audiences.  Marketers are so good at self promoting, their whole business is doing this so they’re natural at it.  You have VC’s who have podcasts, you have all types of people who have podcasts.  I think it’s really difficult with finance because there’s a modicum of trust that you have to have whether you hand off your banking information to the contract CFO or your finance folks.  It’s tough to go and blog about the problems you have at a business at the most intimate part of the business.  I think that's tough.  I love to listen to podcasts so I would obviously love to hear someone day to day like a COO who does this.  I love to follow people on Twitter who do this, but those people are super busy.  They’re definitely the busiest people.  You can justify being on Twitter all day if you’re a CEO of a hot start up because it’s part of the advertising.  You’re always in peoples face, you’re a thought leader and people respect that, investors are seeing you, customers are seeing you.  If you’re a COO or VP of Finance on Twitter all day it’s probably not a great look so podcasts and Twitter.  There are some great follows on Twitter but you can tell those people like David Saks, he was the COO of Zenefits and a bunch of other big companies, now he’s out of the operational role and he’s on Twitter all the time.  From a peer standpoint the best thing have been slack groups.  It’s really good as far as people working on day to day problems and there’s a little privacy, of course it’s not completely private if most people can get in but I find that talking with peers from NetSuite pricing to payroll holiday happening now where you’re deferring all these payroll taxes until next year.  People had this great conversation about not doing it, communicating that to employees, and shared their template.  People feel comfortable sharing in a way they wouldn’t on a more public space like Twitter so that’s probably been the biggest thing.  It’s only gotten popular in the last year but it’s been really great because it’s easy to find a group of accountants but to find someone specifically dealing with a tech company and all the tools we use and the stage of the company that's really been great.  It’s been valuable and a lot of people in the group, although not terribly active, are great when you need a recommendation for a tool when you need to manage your cap table or moving QuickBooks to the next ERP.  I think pound for pound that’s been the best information so far.  

Sagar: Do you have a favorite Slack group?

Mike: Right now I’m in a Slack group called Controllers Collective there are 400 people in there right now and probably 20 different channels for tax and payroll.  It involves a lot.  One of my colleagues is in human resources one and she’s found that valuable as far as building a network and the day to day problems that people figured out, or are figuring out between them.  That would be my main recommendation. I think the nature of the job it’s tough to have this great public blog about sales tax problems.

Sagar: It’s super exciting stuff, everyone’s going to read it.

Mike: It’s great, I'm not going to say it’s exciting, but it’s great when I could find a blog post that’s the exact problem I'm having but it doesn't make for great entertainment.  Marketers have great stories and engineering is nice because I can solve a technical problem publicly but with a lot of this regulatory stuff you’re not going to go blog about a weird ongoing tax issue.  It's tough to have the influence of finance and accounting in this world.  If someone could do it well I think they could do great but for now the semi public Slack room seems to be the best place where you can get a little bit of trust in a small community and learn a lot too.  I think there are other Slack rooms that are like this but this seems the most popular between Boston based.  

Sagar: Awesome, thank you for your time Mike.

About the Author: Sagar Velagala
Sagar is the Director of Growth at Lola.com. Before this, he worked in analytics, finance, and operations roles at companies like The Boston Beer Company and HubSpot.