Katy Carrigan

You could do a whole round of negotiations without even coming to us yet because you have the tools. You're just always looking for 

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Ross Pomerantz  

Say it!

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Katy  

No, I just 

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Pouyan Salehi  

She just went for the jugular, Ross.

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Katy  

I feel like there's so many instances I remember where I was just like, you are slowing down your own deal.

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Ross  

It's Corp here. Pouyan, Katy Carrigan, all the greats are here. We've got a rags to riches story when you think about it... sales savage to CEO. You just don't see it that much! But if you don't mind, just give us the quick background. Your professional career up into this point of CEO and we'll get into the nuances of it. But let's just kind of get that background.

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Katy  

I was finishing college and it was Spring of senior year. All my friends were getting into finance and consulting. I didn't. 

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Ross  

Losers. 

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Katy  

I didn't have a job yet and then I got this job at a tech company in Long Beach, California in sales. And I was like, oh my gosh, someone wants to hire me?! I'm taking it. I went out to Long Beach from Massachusetts started this job in sales. It was your classic come in, go down a list of leads and just make phone calls.

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Ross  

Smile and dial. 

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Katy  

Yes, smile and dial. Immediately started looking for ways that I how can I like get out of this like pit of smile and dial. Then moved into a new role there but I didn't really like Long Beach, I want to go where there's a bit more of a community-feel,  more of a East Coast vibe. And that's when I moved up to San Francisco and joined Dropbox on their BDR team. And from there, I say I created my own rotational program at Dropbox where I stayed for about six years until joining Goody.

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Ross  

Middle of nowhere, Western Mass and you go to Williams. Like you said, everybody's like consulting, finance, and so forth. What do you think the difference was between your peers who ended up there versus like, you? I'm curious, because none of my friends, no one around me went into sales.

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Katy  

Well, I grew up right around Williams in the town next door called North Adams.  They're very different socio-economic-wise. North Adams is historically a mill town, very blue collar. So I didn't even know about like finance and consulting, to be honest, until I got to Williams. So like I remember coming in, and there was like people already on these tracks to get into these jobs and these roles. And they were part of these clubs or teams that would give them binders on how to ace these interviews or do these super days. And I just was like, I was very far behind that. I was just playing catch up. But what I did have going in, I had been working since I was 14, a lot of different types of jobs, a lot of them like customer facing and relationship based. And so looking at the skills and what I learned in a liberal arts, education, tech seemed intriguing to me. And then sales seemed like the a good entry into it. Given that I didn't have the hard skills.

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Pouyan  

You had a really interesting run at Dropbox. How do you take that and now apply it to CEO? "I can put in 14, 16, 18 hours a day," but I'm curious to hear your thoughts on that both on the sales side and now on the leadership side?

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Katy  

Yeah, I think there's a couple things there. Check your ego at the door is like the first one, like there's literally no room for ego. And I think that's really important and making sure that you're leaving space for more open, collaborative ideas. And I think from a sales side, whether that's like partnering with your BDR - like I remember at Dropbox, I had some AEs, when I was in the BDR role, who wouldn't let me touch their AA accounts. And I'm like, that's your loss. Like you're, you know, you're creating more work for yourself, you should have a partnership with me. And we could go and attack your book of business to help you build more pipeline and set meetings. And I think right there, it's like people's ego gets in the way. 'Oh, those are my best accounts. I don't want to let anybody touch them. I own them.' I just don't think you can get that far when you only depend on yourself. And then I think the second one I think a lot about is customer centricity. Kind of no matter what role you're in and who you are, is making sure you like deeply understand the customer and what they need. And I think a lot of times people go in with assumptions or they think they know what the customer needs, but don't really take the time to learn and listen. I think that's important, especially in the leadership role as you get farther and farther away from the customer at times. So like, as a practice, I make sure I listen to one Gong call a day. Just to always, like hear what our customers are asking our sales reps about where they're getting hung up and allows it from a leadership point of view to give our sales reps better training.  Where do they get stuck? Then we can help them and give them better enablement,

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Ross  

Just briefly because I don't think most people will know this, you joined a one year old startup as the Head of Sales. Seven months later, your CRO six months later, your CEO, what kind of change in your perspective, going from like, purely sales focused to now you know, being responsible for everyone, all parts of this org?

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Katy  

I'm responsible for everyone?

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Ross  

Yeah, well, you know?

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Katy  

No, no, no, it's a lot. You know, and I sometimes I feel for my sales leader, because she definitely gets a bit more of my attention. Because that's a comfortable space for me. That's a space I can dive deep into compared to my engineering team. So that's definitely a big difference is when you step up into a role like CEO, you're overseeing every department at a company. And kind of going back to that ego comment, you can't be an expert in everything. So you just have to put a lot of trust in your people and who's around you. But, you know, when I look back on, no matter what role I was in, I was always eager to build cross-functional partnerships. It's how at Dropbox, I did a stint on deal desk. I felt like the deal desk/sales ops of what we were doing there. And it ultimately came out of me working really closely with that team, because I was getting frustrated with processes.

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Ross  

Right because they're so slow and annoying and dumb. Deal prevention team, you know, slow it down more process, just what we need... you know, we should just run 'n' gun. We're a startup!

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Katy  

And once you know those things, you know, you can unblock yourself.

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Ross Pomerantz  

Right? So how big of nerds, generally, speaking is the Deal Desk team? Like if we were just a dive in for a second and talk a bunch of shit, you know, deal desk is ripe for it. Because they get sales in front of ops as if that gives them some cred. But we know, the salespeople know the truth.

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Katy  

I don't know. I think I'm here to stand up for Deal Desk because I think the most frustrating thing for me was like, salespeople won't help themselves.

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Ross Pomerantz  

Also true. Also true. 

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Katy  

There were so many times,  when I'd be like, you don't even need me right now. Like you could do a whole round of negotiations without even like coming to us yet. Because you have the tools. You're just like always looking for guidance.

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Ross  

Right.

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Katy  

So I feel like there's - 

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Pouyan  

Wow, she just went for the jugular, Ross.

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Ross  

She's not wrong.

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Katy  

I remember so many instances where I was just like, you are slowing down your own deal by bringing this to me. Even though you have everything you need to at least go through the first rounds. So I remember, like, at least at Dropbox we had like 15 to 20 terms in our MSA that were kind of pre-negotiated, that we didn't necessarily need to send it to legal. And then there's the areas that if a customer wants to redline this area, then it has to go to legal. And this wasn't secret information. But seemingly, even if it was like an enterprise rep who's done multiple deals, the moment they got red lines, oh, let me forward it away. Like read it first, the amount of people who didn't read a contract!

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Ross  

Right, but you're you're making a gross assumption that salespeople can read. Which therein lies a huge issue. You see, because we operate under the the idea that whining about it is productive. 

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Katy  

Yes.

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Ross  

You know, at least it's cathartic, if nothing else. So I think we'd rather just whine about it and then complain about legal and they complain about deal desk. And so

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Katy  

Then I say go put a ticket in. 

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Ross  

Oh even worse, now we're in JIRA!

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Katy  

Yeah, go put a ticket in right?

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Ross  

No, I'm going to march over to Deal Desk.

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Pouyan  

So how has this changed your perspective now as CEO? So you're out of that, but you're managing it. And so if you're trying to build that organization and build that team, do you just put up with it? Are you trying to solve it in some way?

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Katy  

There's probably a little both. To be frank, we're small. And so I'm kind of Deal Desk at times still to this day, right? Like I will do our DPAs and MSAs and complete that information. So I do start to now at this point, push back a little bit more being like, 'Okay, I've done enough of these you have a template to go off of.'

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Ross  

They're like Katie, what do you think? You're like, well what do you think? 

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Katy  

Yeah.

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Ben Gould  

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Ross  

I'm curious with the recent year that we've had in tech, and you know, now Silicon Valley Bank, like five days ago, nobody prepares you for that. And Pouyan I'm curious about you too. You're both CEOs. Like, again, we've mentioned responsible for a group of humans. Like, how do you navigate through an ultimately, incredibly, uncertain, tumultuous time. What do you do? Other than go off your gut and try to be as decent a person as you possibly can?

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Pouyan  

Love that framing, Ross. As decent a person as you can.

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Ross  

Well, you got to make hard choices, right? You still gotta make hard choices that people are not going to agree with, like, you just can't make everyone happy when you're in a leadership role, like, that's the reality,

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Pouyan  

There's much more of a spotlight on Founders, CEOs, on just leaders in general. And there's a lot more turbulence. It feels like, and Katie I'm curious to hear your thoughts, but it feels like just even in the last few years, so much stuff has happened that is unprecedented in a way. There's no playbook for it. There's no blog post around it. And so you just have to be really good at being like, I don't know. Like, this hasn't happened before, I don't really know exactly what to do, but just figure it out as fast as you can

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Katy  

I try to share the amount of information I have with almost the entirety of my team, especially my executive team, because there are times I don't know, and you're making a call with the data that you do have and the information you do have available to you. And I think people are reasonable. And if they just have an understanding and kind of know the why behind things. And I think knowing the why means you have to be transparent with them.

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Ross  

Yeah, I mean, I can't imagine being in like that type of position. And like you said, there is no playbook. I do think transparency is probably the best way to go about it. I don't know, like what alternative there is.

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Pouyan  

It's really hard. And I think, Katie, if we follow a similar approach. After every board meeting, we pretty much share the whole board deck with the company. Because I view it as hey, we're all one team. Yeah, we're filling in different roles, but we're all trying to accomplish one mission together. I think, and listen we're a remote-first company, but I think it makes it even harder when you're remote. Because when you get some tough news or when you get that level of transparency, and a lot of it is uncertainty and we don't know what's going to happen. You don't have that space to really connect with folks in the way that I feel like it used to be when you were in office or even connected in some way or figure out some off-site. And so the best you do is in a zoom call and it's so hard to have real conversations there. So it just creates this level of disconnectedness and frankly we're still - I'm still trying to figure out how to make that better

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Katy  

The next company that I start or that I'm a part of or when Goody reaches that pivotal stage, like I just don't see a world where it continues to be fully remote. Because to your point, I just think it's too hard for the good and the bad. 

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Pouyan  

Yeah. 

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Katy  

There's just a lot of organic conversation and growth that comes being in person with one another that you lose over zoom and being fully virtual. Now there's a lot of pros to it, of course. The talent that we have from across the world that is on our team wouldn't be available. 

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Pouyan  

That silence [on a zoom call] is one of the hardest things when you are sharing news with the whole company. We do a rotation with our team where we have different leaders lead our like our Friday weekly recap. When they're like oh wow, this is really awkward and hard. I don't know how others are doing this, when you're just talking, you get zero signal back. It is just you're like, Wait, is your screen frozen? Are you just not moving? And listening? Well, Ross, what are you seeing? On the sales side? I know you talked to a ton of folks. I'll just say this. One thing I'm hearing is we're still hiring. We're interviewing a bunch of folks. And what I'm hearing in the interviews is across companies I'm talking to, it feels like more and more are going back to office. Maybe not five days a week, but that's now becoming a trend.

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Ross  

I think it's true. I don't think it'll ever be as Katie said, like five days back in the office, but I do think that return to office is real. And I totally understand the merits of both sides. I understand the rage that creates in people who just plain and simple don't want to go back. I don't know how I would run a sales org, especially in the early stage company without my sales team being together at least three days a week. I don't think I would need them five days, but three days I think would be important. Just for everything you guys are saying, the tribal knowledge, the sentiment that like communication, the learning, like, you know, some discipline?

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Pouyan  

Yeah, the espresso martinis.

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Ross Pomerantz  

Martinis on Thursdays. You know, we go Tuesday to Thursday, we got Taco Tuesday and then we got Thirsty Thursday, and then Wednesday, we just drink for no reason. But you know, so we've got the three best days to do that. But yeah, I do think generally speaking- I think like Salesforce's reason for return to work is to weed people out. I think that is like a strategy of like weeding people out. But I also think it's really hard for some companies that have set a precedent of being remote or hybrid, like, 'oh, wait, the rules are for me, but just because you hired someone who's making the same amount of money and like Oklahoma, we don't have an office, they're like, they don't have to go to work five days a week?' It's just really hard to make a universal rule that everyone has to follow when we've done nothing but make exceptions for three years.

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Pouyan  

What I would look at is, of the companies that are fully remote or the ones that have some sort of an office setup, what percentage of their reps are attaining quota? So that could be maybe closer to that performance or even before that is there a leading indicator to quota?

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Katy  

My BDR days at Dropbox were so critical of building the team. Like that was like just being day-to-day as you said like playing loud music on Fridays in the pod, having like power hours together, hearing other people on the phone! That was so beneficial. Being on a conversation next to another person or hearing someone in conversation getting stuck and being able to pass a note to them. That's what I crave and I miss. Particularly because we have a we have a more junior sales team at Goody and they're awesome and eager and looking to build their sales career and I just often think like if only they could like be in the room together feeding off one another.

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Pouyan  

Or if you're just getting roasted, put it on speaker and have others listen to get a laugh out of it. At least for me when when I was doing cold calls and outbound and you know at that point, it was just me my Co-Founder and then like one other person, but it was such an emotional ride. And that's the piece that you know coaching Yes, absolutely like hearing others, but getting those rejections, getting roasted getting hung up on constantly and having somebody to turn to and just laughing about it together or at least being like man that sucked and recovering. It's just damn hard when something like that happens and you're still in your own room in front of your computer screen and the last thing you want is to get on another Zoom call. Well Katie, thanks so much for joining us and also for the Goody. I'm excited.

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Ross  

Can we get a shameless plug though at least from from Katie? If people want to reach out to you, maybe there's like a sales rep out there who thinks they have some great software for Goody? Who on your team should they reach out to and then plug yourself. Plug Goody. Plug everything.

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Katy  

Well, alright if you have a software that you think we need. Just send it to my inbox. I'm going to open it up.

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Ross  

She's gonna open it, she went might not respond.

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Katy  

That actually is very true. Just K-A-T-Y at OnGoody.com.

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Ross  

And if anybody's like trying to send gifts or anything... 

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Katy  

So I think that's the other part. I think if you want to stand out in that inbox like I just talked about and get a response. Then don't send a usual message, send a Goody.

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Ross  

Science. Data.

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Pouyan  

Let's do it. 

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Katy  

Book it.

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Ross  

Katy Carrigan thank you so much for joining us. 'Til next time.

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Ben Gould  

Are you looking for ways to execute, manage and measure your entire sales process? Scratchpad is your answer. The world's largest sales teams including Autodesk, Algolia, Cisco, GoTo, Twilio/Segment are already seeing better results. Learn more at scratchpad.com

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