OneLogin CMO and Co-Founder of Women in Revenue, Dayna Rothman, on building teams and a Will Smith & DJ Jazzy Jeff reunion

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Episode Timeline:

1:07 What’s top of mind for Dayna today?

2:59 Has Dayna had to adapt her leadership style through this?

3:58 Significant changes that Dayna had to make

4:37 How Dayna keep the same connected with Zoom fatigue being a thing right now

8:13 How Dayna’s leadership style has changed as she moved or work through different sizes/ Learnings and strategies that Dayna rolls out

14:33 Dayna’s favorite campaigns

18:43 Stories that don’t go as Dayna envisioned but she learned something to be able to be better next time

24:18 What does Dayna do to keep her mind calm and be able to be clear and be effective

25:34 Mentor or Peer who has influenced Dayna


Connect with Dayna:

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Speaker 1: (00:02)
Welcome to season two of best in SAS, where we talk through the patterns and playbooks and the revenue sprint to 20 million and beyond with the industry's most accomplished executives, entrepreneurs, and investors. Despite the world melting around us, we survived season one with only a few scratches and a couple of bathroom incidents from our resident. Best in sass, puppy, mascot, Stewart, wash your hands and Don your favorite face mask because here comes season two.

Speaker 2: (00:35)
Howdy everyone. Welcome back to another episode. I am thrilled per usual for you to listen in on this conversation, but before we get into it, if you're a regular listener and you enjoy the discussions, do me a favor and let us know by rating and reviewing us on Apple podcasts. It helps other folks find the show and it helps Apple realize they should feature us on new and noteworthy. So that would be awesome with that enough of my blabbing. Let's get on to the episode. So this one I'm really excited for because we're going into planting season. And today we have, uh, Dayna Rothman on the show, um, who has a phenomenal background across a bunch of amazing companies. I mean, you've been you're VP of marketing at bright funnel. You're a CRO at Saster VP of marketing at messes sphere. You're an adviser at San DOSO and you're now CMO one login. So denim.

Speaker 3: (01:30)
Yep. Thank you. Thank you. And also Marquetto too. That was kind of where I got my start.

Speaker 2: (01:35)
Okay. Your teeth and Marquetto, that's a good place to grow up in a marketing org. Um, so let's, let's dive in. I think top planning is so top of mind for everybody at the time of recording it's, we're entering December now. We're about to, and, uh, I think just about every executive that I'm working with right now just has their brain in a spreadsheet trying to figure out next year and do retro on this year. So where's your head at with that? What's what's top of mind for you today.

Speaker 3: (02:03)
Yeah. So we're going through the pretty deep dive planning at one log-in right now, which is like multiple different parts, as you can imagine. We have, um, you know, the planning that goes on on my team itself, uh, the planning that goes on amongst the executive leadership team where we're kind of like duking it out on different initiatives for next year, and then we have the final planning session with our CEO. And so now is the time that we're crunching the numbers and, uh, doing all of that thought process. I think one of the more interesting kind of the different aspects of this year is planning is obviously 2020, um, has been quite, uh, outside of the norm for a lot of organizations. So we saw a lot of changes in just our overall sales process and velocity, lots of, you know, kind of inconsistencies here and there as, uh, you know, COVID and everything that happened this year unfolded. So, you know, looking back at the data from this year, and then also trying to predict like, okay, what is 2021 going to look like? You know, when are our things going to open up, you know, when is there a vaccine coming in? Cause all of that, uh, really impacts, um, you know, our customers and our business as well. So it's been a little bit of, um, I would say more of an agile planning process than we typically have, uh, because everything could change so quickly.

Speaker 2: (03:28)
Yeah. I feel like executives nowadays are having to put on much more of an analyst hat, like normally planning time is when you have your analyst hat on, but maybe even more. So now you're like trying to, trying to read the crystal ball and forecast what's going to happen in a way that we're not used to before. How have you had to adapt your leadership style through this?

Speaker 3: (03:49)
Uh, yeah, no, absolutely. It was, uh, you know, very obviously impactful going from pretty much. I mean, I have some remote folks on my team, um, but most of us were in the office and going from that to being completely remote. Um, and then obviously I think too, in addition to that, just like, there's been so much going on this year. And so people, uh, have all different types of like personal stuff going on, you know, they're feeling emotional about, um, you know, some of the stuff that's going on with the election or civil unrest. And, and so the, my leadership style has really had to adapt to be more, uh, you know, kind of empathetic to people in their personal and their personal lives as well as what's going on at work. Um, obviously, you know, that gets coupled with people freaking out about, you know, the economy and all of that.

Speaker 3: (04:37)
But I think, um, one of the more significant changes that I've had to make is really, uh, how do you keep the team connected during these times? And I think it's, it's waxed and waned like over the year, you know, like fresh out the gate, like had some really great stuff in place that was really consistent, that seemed to work. And then people have gotten kind of zoom fatigue, and that's a bit of what I'm dealing with right now. Like how to keep everyone connected when everyone is like, just kind of like so exhausted, um, honestly, and not ready to go back in. Um, so it's, it's been, it's been quite a ride

Speaker 2: (05:13)
With zoom fatigue being a thing. Well, how do you keep the team connected? Like have you found any, what are your secrets?

Speaker 3: (05:20)
Yeah. You know, I'm still working on it honestly, but so I do, I have, I have done a couple of, for the local people who are comfortable with it. I have done a couple of like local meetups, like outside where, you know, people are socially distant wearing masks, um, where they can come together if they're comfortable. And for the most part, the majority of the team had wanted to do stuff like that. Um, and then, you know, just trying some different stuff on zoom like we're doing and who knows what this is work well, whether this will work, but I'm doing a scavenger hunt in a couple of weeks where I hired like an external, um, you know, I don't know, D virtual gaming place to actually kind of formally put this thing on. Uh, and so while of course that is still zoom, like maybe it's going to be a little bit more unique, uh, in that it's like a whole activity, you know, we've done like cooking classes and like, you know, happy hour mix. It's tough. So I don't, uh, I don't have any like silver bullets, uh, I would say at this moment as things continue on, but I keep trying,

Speaker 2: (06:27)
Yeah, it's a, it's hard to keep it fresh and not feel like forced.

Speaker 3: (06:32)
Exactly. Like, I don't know if you would have you seen work?

Speaker 2: (06:36)
I think it's kind of the same thing. Just trying a lot of little things and having, trying to create some sort of cadence of remembering, you know, cause it's easy to just not do the things. Right. Right. So we've been doubling down on, you know, we have, we have a sanity Slack channel where it's just, everybody's sharing things from their personal lives. And so just trying to really encourage people to like lean into the insanity and share moments from all of that, which I think has really helped codify the team and bring us together in a way that, um, we hadn't prioritized that type of personal sharing prior to all of this, which has been really nice. And similarly looking for unique experiences that are virtual. Like we did a, uh, virtual wine tasting where we had a wine maker come and do you know, I think a lot of people,

Speaker 3: (07:17)
It looks a little bit, a little bit of fun. We also, well, this is, company-wide not necessarily my team, but which is similar to your channel that you mentioned. Um, but we have a, we started kind of this unconference, we called it in the beginning of COVID and uh, really it's like maybe every other week we have somebody present. So it's either like somebody internally doing kind of like personal tech talk style about, you know, whatever they want, like about their career or something on their personal life. And then we have external speakers come as well. Um, and so people will just kind of submit topics that they're interested in learning about whether, you know, it's, uh, staying sane and during these times, and like working on, uh, kind of your mental fitness or we've had some diversity training as well and all different types of things. And we've had it for, uh, I guess almost like however long, eight months now. Um, and we do it about twice a month and people, people love it. They still, they still join. So it still connects

Speaker 2: (08:11)
Nice. So, I mean, you've, you've worked within and led, uh, a variety of different team sizes, right. Obviously starting off in Marketo, much larger. And then some of these other companies you've, you've been a leader within are considerably smaller than Marquetto. Um, how would you say your leadership style has changed as you've moved or to org through different sizes? And maybe if you could share some learnings or kind of strategies that you like to roll out depending on the team size?

Speaker 3: (08:44)
Yeah, I think especially with the smaller teams, um, I look to hire, uh, you know, obviously the people that are specialists in what they do, but also people that can be multifaceted and, you know, roll up their sleeves and pitch in where help is needed. So getting people that are pretty REL well-rounded that can grow in a lot of different areas, um, has been a big kind of strategy to my hiring, especially on small teams where, you know, maybe I just have very limited budget, um, or I need somebody to cover off on multiple things like having people that are like kind of Jack of all trades and that are very like driven and passionate to succeed and happy to, you know, pitch in where needed has been, um, very, you know, impactful. I also like hiring people from unconventional backgrounds and, uh, you know, applying that to, to my team.

Speaker 3: (09:39)
And so I don't always look for people that have like your typical like B2B, you know, five plus years and enterprise staff experience. Like I will very frequently consider people that are, are career changers, um, or that are coming from different industries. So not just like, I have a lot of people that come from B to C, but I've also hired folks that are, you know, like ex attorneys that are looking to move into like a sales role, um, or, you know, people that come from just other spaces that give it a little, have like a different perspective. And I think, um, that has worked very well for me in the past to find somebody that has, you know, people that have a lot of talent that come from these other, um, spaces and I've taken kind of both of those things and, uh, expanding them for, you know, obviously my, my larger teams. I mean, when I hire now, I do, you know, we'll hire really specialized people cause that's generally what I need, but the idea of like collaboration and no job is like too big or too small, um, is definitely something that I've maintained, no matter what size the team is,

Speaker 2: (10:48)
Giving people an opportunity to kind of shout out to some of those people who are maybe earlier in their career, but you mentioned this almost unicorn type of person or so it's always hard to find someone whose enjoy strategy and execution and is willing to jump in and help out team members, even if it might not be in their quote unquote swim lane, who are some of those folks who just have stood out over the years?

Speaker 3: (11:10)
Yeah, gosh, you're going to make me like call out people who may have one of my current one logging team is absolutely fantastic. Um, I'll talk about some of the folks though, uh, that actually I brought with me through multiple different companies, multiple different jobs. Um, uh, you know, there there's been several people that I've have come with me on like two, three, even more companies. Um, so I'll call some of those folks out. Um, so Emilia Avara, she's actually the VP of, or maybe she's the GVP now at Saster. So she, uh, kind of when I left, after she stayed, um, but I hired her originally when I was at EverString, she came from a B to C like beauty industry and I hired her as social media and she just grew immensely in her career. She went with me from EverString to bright funnel to Saster.

Speaker 3: (12:08)
Um, and then, you know, she's, she's there now. So she's been super successful and, you know, somebody that I'm very proud to have mentored, uh, over the years, another similar one, uh, she's still actually at Mesosphere, which is now called [inaudible]. Um, but her name is Elena Makaveli and she is, I originally worked with her at bright funnel where she was the office manager and I was looking for somebody to do events and, you know, there's a lot of similarities between like being an office manager and doing events and, and being organized and, you know, kind of getting stuff off the ground. So she came on to do my events role, and then from BrightFunnel, she went with me to Saster also, and then to Mesosphere as well. Uh, and then when I left her one, log-in, she, she stayed at Mesosphere and she runs, you know, events and demand gen and kind of PR and a bunch of different aspects. Um, so those are a couple of folks that, you know, stand out that I've brought with me over the years. There's definitely a handful more, uh, that I brought with me or that have, you know, landed in incredibly successful roles. But I think that my success as a leader is really defined by the success of the people who work for me, you know, over the years and getting them to that next level.

Speaker 2: (13:31)
So it's so fun when you can bring along like, you know, the old, the old bench, so to speak and kind of go out the next challenge together.

Speaker 3: (13:39)
Yeah, absolutely. And it's fine because now at one log in, um, so there's several people that used to work at Marquetto. Um, that just kind of happened to be on the one login team and they were there before I joined, but it's great working with those folks again, um, like my VP of, uh, demand gen, her name is Anastasia pavlova. I worked with her at Marquetto back in the day. Um, and then now she's on my team, which is great. And then another marketing person, Rick Siegfried, who I worked with at Marquetto and now at one login. So I love bringing the team back together at some at some point and, you know, there's so many great marketers, uh, that, you know, kind of came out of that time period. And, uh, they're all doing really cool stuff. So, so getting us all together is, is, is really great. Nice.

Speaker 2: (14:27)
So, uh, let's talk campaigns, marketing campaigns. You could go with campaigns that your, you know, current campaigns or even just ones that stand out over time and I'd love to do like a call it like the good, bad and ugly. We don't have to cover all three categories, but maybe some of like your favorite campaigns. And then I know in the past, you and I have talked about, uh, figuring out virtual events in the COVID realm and maybe that fall into some of the, the other end of the spectrum. Yeah.

Speaker 3: (14:55)
Uh, so some of my favorite of, uh, campaigns that I've done, I'll kind of talk about, uh, two of them that were a little similar. So before the COVID days, I love virtual. I mean, I love in-person events. Um, I don't necessarily love, like planning all the little details, but I think that, um, in-person events are like really impactful place to get to know your prospects, your customers get your brand out there. Um, and so to me, like that gives you probably one of the biggest things for your buck honestly, is if you could put on a really amazing in-person event. Um, so a couple of standouts, uh, one was when I was at company EverString, they actually just got purchased by ZoomInfo, which is exciting. Um, but at the time we were at Marchetto summit and we were MarTech tool and we wanted to kind of own Marchetto summit, you know, like we were going to be the other vendor that had like the best stuff going on.

Speaker 3: (15:52)
This was in Vegas. So we rented out wet Republic and the MGM to do just like this giant blowout party. And we got DJ jazzy, Jeff to perform, which was like very cool, but even cooler when we learned, uh, that that year Marquetto just serendipitously had will Smith as their keynote. So like we had DJ jazzy, Jeff, they had will Smith and I'm like, how can we make this happen? Like, let's get a reunion going. So we, for like, we hadn't even announced that we had DJ jazzy Jeff yet. So for like weeks, we were trying to contact will Smith, like press people, his agent, like, come on, let's get something going. And finally we got a hold of them and they were like, well, we'll see, we're not going to give you an answer until the actual day. So the day of the event kind of happened.

Speaker 3: (16:43)
We were like just kind of waiting to see if it would happen. And they contacted us midway through the day that will Smith was going to come and perform with DJ jazzy, Jeff. And he had his entourage. Like, it was just, I mean, and I was like pure event fire when everything comes together. Right. And we didn't even have to pay for willsmith cause he was already there. So he just kind of came by, um, and it was their first reunion show that they'd had since back in the day. Uh, and yeah, will and DJ does Jeff. They performed for like a good hour and it was just, it was just amazing. It was just amazing the whole event. We had all kinds of stuff and VIP cabanas that we rented out to partners and prospect, like it was very cool. And so that went down in history of like one of the greatest, I think, uh, events of, of the time.

Speaker 2: (17:40)
Yeah. You're setting like new standards in B2B for this. That was like a Coachella moment almost.

Speaker 3: (17:46)
That's my other Coachella moment real quick as did I Mesosphere, you know, not marketers, we're marketing to it, people developers. And, um, we were at a show, um, in, uh, Washington, Seattle for Coobernetti's, which is a big technology. And I did a, we did an ice cube concert. So we rented out the local concert venue in Seattle and we were like, okay, who are we going to get that kind of, you know, they have to be cool and relevant and kind of retro, like it needs to fit that demographic. Uh, and so we got, uh, ice cube and he was just incredible and the developers were getting down and he had like 2000 people at the show. It was crazy. It was great.

Speaker 2: (18:33)
Yeah. All right. So all the success let's talk about. Is there, are there any stories or any learnings perhaps recently, um, that didn't go quite as you had envisioned, but you learned something from, and now we're going to be able to be better next time, however we want to call it.

Speaker 3: (18:57)
Yeah. So I'll talk about our, um, the recent virtual event at one log-in. So I would put this in the category of like, ultimately it was very successful, but it being, you know, everyone's doing virtual events right now, like you said, and there's a lot of trial and error and it's, you know, and so with this one, it was our first time doing like a multi-track virtual event that was like all day. Um, we, and so there was a lot of learnings, I would say, um, for this particular one, like despite the fact that, like I said, it ended up really well for us from a brand perspective and lead and revenue, but it was, it was tough. Um, so one, I think, you know, there's not a lot of virtual platforms out there right now and, uh, that have like the video and the slides, like there's kind of the old school platforms that maybe don't have the video capabilities.

Speaker 3: (19:47)
And just so we have like a lot of requirements, um, and it's hard to vet them out because some of them are, you know, they're very small organizations too, that haven't done these like big, um, kind of, you know, enterprise type events. So we signed up with, uh, with one and, you know, went through our whole vetting process, which is pretty, uh, you know, pretty lengthy and significant. And, you know, the team had to kind of set everything up and there was a lot of stuff that we missed, uh, you know, embedding the vendor. We had some, you know, kind of issues that some of our developers found, uh, during, you know, during the event itself and before the event, which were, you know, kind of impact would impact the way that the event actually occurred. And so we were on the phone with like the other platforms dev team until like 2:00 AM in the morning, the night before trying to like figure it out so that everything was working properly.

Speaker 3: (20:45)
Um, and I think just we're, you know, making sure that you're covering all of your bases when you're looking at these vendors, making sure that you're checking like the security of it, you know, maybe have somebody on your dev team, like kind of poke around and testing stuff out. The other thing that I thought was kind of, it was an interesting learning, like, you know, and you go to physical events and there's always like the swag people, like the people that come just for the swag, like you go to Dreamforce, you've got the people with the suitcases that are just getting the swag, the exist in the virtual world. They do. And we, it was a whole new experience for us. So like we had, uh, we had stuff that we were giving away and we had like all of these different things that people could do, like round tables and you get certain amount of points for joining around people.

Speaker 3: (21:35)
You would get a certain amount of points for like doing this or doing that. And so we had a few people that, um, were able to, you know, they sign up for the event and they like tried to gain the round table. And like they had, I don't, you know, they either like wrote a script or they had different accounts where they would sign up and like fill all the spots on the round table and like do pretty much just do everything to like, get points over and over again. So that we looked at, you know, looking at the leaderboard, it was like these, the people that were at the top of the leaderboard were these kind of wag type people that came into the virtual space. And I think like, yeah, like what they were doing is I think they would find like a particular vendor that, uh, like a particular, uh, virtual event vendor. And they would understand how their platform works. And then the virtual vendor, they would kind of follow that vendor to all the different conferences that the vendor had put on. Um, and so it was, it was a very, um, interesting learning, I would say

Speaker 2: (22:39)
That's like, it's like wedding Crashers meets like corporate events, like black hat hacking of corporate.

Speaker 3: (22:48)
It was just, you know, they were just in it for the swag, for the t-shirts for the t-shirt. So, you know, we learned a lot about that. Um, and just generally to like what, you know, the heavy lift it took on the team and making sure that we had, um, all of our bases covered that people were trained, you know, and that we were prepared for any like crazy stuff that happens. Like it's, it's almost different than, I mean, you know, in an in-person event, everyone is kind of together in your war room or whatever. I think next time I said, like, we should all like socially distance and get together and at least be in the same room while all this craziness is happening.

Speaker 2: (23:32)
It's nice that you get to at least not be on your feet for the events I feel like is like the one thing everybody's like, Oh, Dreamforce, I'm on my feet for a week.

Speaker 3: (23:43)
But I think one of the other challenge is when you're hosting your own impersonal event, you kind of like get the feeling of the crowd. You know, like if people are really enjoying it, you can feel that if people are really not having a good time, like, you know, that's happening too with virtual world, like you just have no idea. Yeah. That makes sense. If you've no, there's no, it's like a brick wall that you're talking to.

Speaker 2: (24:04)
So, um, I'm curious, what do you do? So outside of work, what do you do to keep your mind calm and able to be clear so that you can be so effective?

Speaker 3: (24:14)
Yeah, that's a good question. And I am, I think you're the second person that asked me this on a podcast and I have not had the best answers, obviously. I mean, I've worked a lot. Um, but I do, I do love, I love writing. Um, I authored a book, a B2B book, which is, uh, several years ago, a dummies book, uh, so similar to what I do for work, but I've been trying to do more creative writing. Um, and when I get an opportunity and, uh, that's been helpful to, you know, kind of chill out my brain a little bit. Um, obviously there's a lot of really great stuff on TV, to be honest with you and, uh, television movies. And so I've been keeping up with my Netflix, um, trying to make sure I, you know, I like get outside and like see people every once in a while, but, you know, I don't ha I haven't created, I'm not like wiggling like a wood or anything right now. Like some people have picked up some serious hobbies and shelter in place.

Speaker 2: (25:12)
Never. I I've never had a wood Whittler on the show, but now I have, uh, a show goal to, uh, to someday cross paths with a wood Whittler. All right. My last question for you is just, you know, obviously at your level, there been a lot of people who have been there for you in your career and, and whether as a mentor or just peers who have influenced you, who are some of those folks in your life.

Speaker 3: (25:37)
Uh, so definitely call out, uh, John Miller, who's the co-founder of Marquetto. Um, and he was early days when I was at Marquetto. He, I report directly into him. Um, and he taught me a lot just about marketing, about writing, about how to, uh, you know, fill in some of my skills gaps, you know, the areas of that I needed improvement. Um, he was always super straightforward, really encouraging, um, to, you know, kind of get me moving to the next level and always allowed me to have a lot of autonomy, um, in, in what I was doing. And so, and I'd say I stayed in touch with him all of these years. So every once in a while we'll still meet up for coffee or whatever, it's been a little bit more challenging during the COVID times. Um, but he has been, you know, incredibly influential to me in many ways.

Speaker 2: (26:32)
Well, thank you so much for joining me on the show and I'm looking forward to seeing what, what you do at one log-in it's it seems like you're already off to the races.