Leading Growth to a Massive Exit and Beyond, with Freshly and Wikibuy Growth leaders

On January 26th, we sat down with two executives who have led the growth engines of innovative startups through incredible exits. Adam Gassman shared about his experience overseeing growth at Freshly through their $1.5B acquisition by Nestle and Luke Fernandez spoke about his time growing Wikibuy from less than 100 users to over 5 million and an acquisition by Capital One.

In our first clip, Luke shares his learnings around hiring during his time working at Wikibuy. He discusses how investing in the right people earlier could have lead to bigger outcomes, faster.

Next, Adam talks about how his experience working with an executive coach help him up level his work in unexpected and surprising ways.

Watch the full video here

About Our Speakers:

Adam Gassman is a Growth & Marketing executive with a decade of experience driving user growth for both content & D2C brands. Adam previously led growth at Freshly from its earliest days through its 1.5B sale to Nestle. Currently, Adam is leading Lane 529, the boutique marketing shop he founded after leaving Freshly.

Luke Fernandez is a Consumer SAAS and e-commerce user growth leader and advisor who is always looking to share knowledge and meet great teams. An early hire at Wikibuy, Luke worked as Head of Growth to lead the company to its 2019 acquisition by Capital One where he went on to become Head of Growth Marketing for Capital One Shopping. Today, Luke is a growth advisor and angel investor.

About our Moderator:

Anish Shah is the CEO & Founder of executive search agency Ruckus. Anish has worked in-house in Growth roles at Snapfish and Getable. He started Bring Ruckus as a Growth consultancy 11 years ago working with 40+ clients, then re-focused his firm on executive recruiting for Growth leaders.

Read the Full Transcript

Kayci Baldwin (00:03):
All right. Thank you everybody for joining us today. We are going to be talking about leading growth through a massive exit and beyond featuring Freshly and Wiki by growth leaders Adam Gassman and Luke Fernandez. I am so excited about this conversation. Both because we have two growth leaders with track records that really do speak for themselves. But also because they are both incredible human beings who are really proud to have as a part of the Ruckus community here. If I can go over some quick housekeeping for the conversation today, I’d love to do that with you. Next slide please, Ally.

Kayci Baldwin (00:45):
So this webinar is being recorded. All of the questions that we’re going to be diving into today were submitted by registrants for this conversation. So we are excited to be able to be diving into the topics that are interesting to you. We will send an email to everybody who registered for the event with the full playback of the conversation. And so keep an eye out for that over the next few days, and then feel free to submit any additional questions that come up in response to the conversation in the Q and a, and if we have time, we will definitely dive into those as well. And with that, I will pass the Baton to Anish, who is our founder and CEO here at Bring Ruckus to introduce himself and introduce you to our panelists.

Anish Shah (01:29):
Hey, my name’s Anish. The first portion of my career was helping to run growth both full time and as a consultant for different companies for about a decade. And then went on to build an executive search firm focused on hiring kind of leaders across a wide variety of areas with a, with a bit of a specialty in, in growth and marketing. And yeah, that’s me and us. Now we’re a team of 20 across the globe.

Adam Gassman (01:55):
Hey, Adam, Gassman here and have spent the past decade working with content and DSC brands to help them grow initially launching my own content website after graduating law school and deciding wasn’t what I wanted to do and, and grew that to a peak of about 6.8 million monthly active users, and then led digital at, at PBO, which was also a content startup before joining Freshly as an early growth hire playing key role, leading growth from it from its early days to its successful 1.5 billion exit to Nestle. And then recently after leaving Freshly decided to go out on my own, similar to Anish and launch a boutique marketing shop that I’ve been doing since July. And looking forward to talking to you all about the overall process and growing pains, we saw it Freshly through the exit in 2021.

Luke Fernandez (02:58):
All right, what’s up guys? I’m Luke Fernandez spent the last 10 years working in tech first as a product manager, managing engineering and design teams for a company called mass relevance. We built the technology that put social content on TV, and then I pivoted into a joint marketing and product role as a second business hired a company called Wikibuy where over the course of six years built a large growth function that span product marketing, design and engineering. And today I’ve been working with early stage consumer brands on building their growth roadmaps, hiring and, and executing a lot of the great work that they have cut out for them.

Anish Shah (03:42):
All right. So folks who registered for this event upon RSVPing you were all asked to put in a question that you’d like to, to kind of ask to our experts. And so we, cherry picked the most interesting of the questions here, so we can figure out yeah, basically what the audience is interested in learning and knowing. So obviously when you’re, when you’re at an early stage startup, you’re kind of doing a little bit of everything and you kind of have to do everything because you don’t have the money, resources, people, et cetera, to do other to, to, to sort of just invest in scale. But you know, being part of a scaling business on the later end, that’s a very different job and a very different role. And you have to kind of adjust to that. So when that transition was happening, you know, was there a really impactful decision that you made and it doesn’t have to be, you don’t have to have the pressure of choosing just one impactful decision, but would love to learn any, any decision or collective of decisions that was really impactful when you were going from being, you know, kind of small and scrappy to the later stages.

Adam Gassman (04:46):
I, I think there’s a couple of things. The first is I, I don’t think the transition is so clear until after the fact in a lot of ways. I think after the fact, when you realize the budgets have dramatically increased, the risks have increased. I think you make the decision and transition from taking a lot of risks that are not necessarily calculated in the early stage of a startup to making very calculated risks in bets on what’s going to pay off now, but also for the long term. And I think like one of the most critical decisions is really knowing, even if you could do it a little faster if you don’t start to delegate and elevate to people, you’re going to reach a sailing rather quickly, and it may work for right now, but a month or two months down the road, either you’ll burn out or your team will burn out. And I think that was definitely one of the more impactful decisions that was made during that process to really set us up for success.

Anish Shah (05:48):
How did you go about delegating into proper way that that made sense? And wasn’t sort of foreign,

Adam Gassman (05:54):
I’m going to be very honest and upfront. It was by learning. There were definitely mistakes made at different parts of it. And I think you really only get better as a manager and as a leader by learning and reading and taking advice from others who have done it before you, I think what’s fair to say at most early stage companies versus the large scale corporate entities, it’s not like you’re given a training menu all on how to be the best manager. So it’s essentially learning by doing and listening very closely to what people who are working for you and supporting you are doing and what they’re saying to make sure that you can kind of hear them and work with them to build the most cohesive unit as well, by doing it with them, not just guiding and dictating to them how it should be done.

Anish Shah (06:48):
Thanks. That’s super helpful. And yeah, it is very difficult to go from scrappy ICS to, to delegating, especially with a lot of first time managers kind of jumping in the organization. How about yourself, Luke, with this, with this same question?

Luke Fernandez (07:00):
Yeah. I, I very much a, a similar train of thought in when you’re working as like the first hire to startup, you’re focused on solving the, the problem in your lane. Like you, you are the go-to person to provide the answer and, and the best answer for the, the problem in front of you. When you start scaling up, it, you, you move from having to be the person to solve the problem, to having to be the person who has to build a system to solve the problem. And that system is kind of a combination of both process and people for on the process side for a lot of different roles, especially in marketing, there’s a set of always on things that your team should be doing from both an offensive and defensive standpoint. That probably covers 60% of, of like where there is value on the people side.

Luke Fernandez (07:46):
You know, your job becomes finding intelligent action oriented people, coaching them to their full potential and throwing them into that process so that they can nail the 60 to 70% with clear expectations and then use their own intellectual thinking and action oriented capability, et cetera, to, to figure out the other 30 to 40%. And I, I think it’s, it’s always, it’s usually a weird inflection point where people kind of take a step back and say, like, I’m not the person that actually needs to solve every problem anymore. I’m the person that needs to build the system to maximize the number of problems that we’re solving

Anish Shah (08:23):
With that system. Like what, what is it like, like how do you create a system so that people who are a little newer to your organization, haven’t been through solving as many problems before, how do you make it so that they’re not only, you know, I think on one side it’s empowered, but on the other side, it’s actually, you know, confident and know the right decisions to make

Luke Fernandez (08:44):
It, it

Adam Gassman (08:45):
Go ahead.

Luke Fernandez (08:46):
No, go, go, Adam.

Adam Gassman (08:47):
I was going to say, I, I think it’s critical for process. I, I would say early on, I was not a fan of process. I was not a fan of creative briefs to say the least as it’s, as you scaled, it became critical that you had someone you could rely on if you couldn’t do it. And I would never say that is one of my strong skills. You had someone who could help guide the processes and make sure you were running efficiently. I think that’s probably one of the most key areas is to notice where your weak link is and to help cover for that and support that. And also understanding where your strong links are to help support the team in that direction as well.

Luke Fernandez (09:30):
Yeah, I’d say like most, you know, like let’s say we’re all solving for a formula where in a lot of marketing and growth roles, it’s the output metric is some function of volume and return on spend or return on the, the resources that you throw at that before you hire and staff people, you have to understand have a, a pretty strong take on what are the inputs necessary to drive those outputs. And you have to like obfuscate yourself from that system and say, okay, what are the sets of processes that we can build such that those inputs are always being fed to the machine in at least a clearly directed way. So is it some threshold of creative testing? Is it some cadence around campaign management? Is it some cadence around competitor analysis and, and seeing the things that you can take and, and, and test yourself once, once you have that, that basic system in place, if you have a junior employee, you can bring them in, show them your roadmap, help them understand how you arrived at the set of inputs and outputs that you related to task them with kind of driving those inputs.

Luke Fernandez (10:32):
And then also task them with understanding where those inputs were wrong or where the output itself was wrong and how, you know, and figuring out how those things should change over time. What are the, what are the sets of always on things that we should be doing? What are the sets of always on things that we should stop doing? Because they, they, they provided literally no, no value to the output metric that we were looking at.

Anish Shah (10:56):
Yeah. I actually particularly like the point of removing certain things that, that you eventually learned, don’t add value because when you start editing process, sometimes you can get really overboard with certain processes and no one’s actually stepping back to evaluate, wait, was this actually necessary? Or does it just make the process much more lengthy to get anything done? Don’t add a lot of value. So..

Luke Fernandez (11:18):
Hundred it’s it’s actually like a very good part of leadership change. Like as, as, as great. As I think I was in, in my role at Wikibuy, I bet there was a lot gained by the company from another marketing leader coming into my position. Once I left looking at the system I had built and saying, and like having their own take objectively on, on the sets of things we were doing and weren’t doing that, you know, we, we, we should stop or start.

Anish Shah (11:42):
Yeah. That’s fascinating that it looks to the value of someone from the outside either it’s someone new or coming in as like a, a short term consultant or anything like that to take an extra set of eyes and everything that’s going on. I guess that’s a, it’s a great, it’s a great pitch for management consulting or other consulting.

Luke Fernandez (12:03):
Or advising like hire Adam to be, to be your advisor. So party objective look at, at these things,

Adam Gassman (12:08):
Appreciate the shout out, Luke, I’ll give you a referral fee after the.

Anish Shah (12:12):
Yeah. And for, for those of you looking to for a, for a rent, a CMO you know, Adam is phenomenal and, and maybe Luke, if you, if you ask nicely to, to help look at what’s going on. Cool. Let’s jump in the next one. Yeah. I mean, both of you had some very lengthy 10, 10 years, and Adam actually has a little bit more of an interesting story in that he did leave and then came back to, to the company that eventually ended up exiting. So he’s been on both sides of that. So I’ll start with you because I’m sure your story is, is, is pretty interesting there, but like, you know, long road, most people don’t stick around startups for a super long time. Both of you, you kind of did Adam’s a little bit more of a nuanced story, but would love to learn more about that. Like what gave you the confidence and stick around and when you were wavering, what made you wave? What made you kind of no longer wave? So we’d love to dig into that, Adam.

Adam Gassman (13:07):
Yeah, of course. I, I had a feeling, my, my story would be a bit interesting. So, so what I would say, I think there’s some parts that are very typical of the startup story to a successful exit. Some parts that are not parts that are, is in my first or second month. I think it’s fair to say. A lot of people didn’t think that we were going to make it to a series B and did think about, okay, I should start looking, but really enjoyed working with my boss at the time and another marketing person as well, that it felt like a lot of camaraderie. And like we were all back up against the wall. It was not individuals. So even though I was looking and thinking about it each time, I always swung back to staying. And I think for any marketing or growth leader that is high up at a successful, fast growing startup that is getting a lot of press, they’d be lying if at certain points, those LinkedIn reach outs for elevated roles were not appealing.

Adam Gassman (14:16):
And so at points you’d have those conversations, but I think what always brought me back was the people I was working with and that it did feel like a family I’m still very close with the early team at Freshly on a regular basis. And I do look at all of them like families. So that played a big part. Eventually what led me to leave for a bit was we were waiting to add another facility at a certain moment. And so the bulk of the early part of 2020 growth was going to be capped. And so was really going to be status quo for a little bit, obviously, no one’s saw line of sight of what was coming mid 2020. That felt like that wasn’t going to be a very big challenge to grow by a few percentage points week over week. And that wouldn’t be as fun.

Adam Gassman (15:06):
I wanted to do something outside of direct to consumer perishable e-com and so decided to leave and enjoyed my time at vault health as well, which is now doing great things for COVID testing across the country. What eventually brought me back is a couple of things. One family the camaraderie, the third thing is having the opportunity to drive home in exit, which one is rare for a lot of growth leaders or marketing leaders, but even rarer is being able from an early stage to see it grow and reach that exit. There were a couple of different lanes to go down that wasn’t necessarily to sell. Some thoughts were to go public or IPO. And to me that seemed like a chance that I couldn’t give up. And, and that was what made it really exciting to come back in a lead role and really drive growth and eventually exit exit to Nestle in October of 2020.

Anish Shah (16:10):
Thanks for that story, by the way, that’s super helpful. And that transparency of what made you leave in the first place for for that first stent. And yeah, telling a growth person, Hey, by the way, we’re just not going to really grow this year while we take care of other things. It, it can be a tough build to swallow. So definitely understandable. Was it a tough conversation when you moved on to say, Hey, by the way, what we’re doing strategically will leave me in a place where I can’t really do the things I’m very good at.

Adam Gassman (16:36):
No, no, look, I think going back to FA I think like everyone was supportive, they were appreciative. That’s great for everything that I had done to date and were appreciative as mentors for, for when I moved on. And like we still stayed in touch. It, it wasn’t that, I think one of the things that’s most important and advice that I got and advice that I would give it’s very easy for relationships to fall apart on the way out the door. Yeah.

Adam Gassman (17:01):
You, you give up on the work. I think there’s nothing more critical than making sure you leave on just as good of terms when you got higher. And sometimes that could be difficult, but I think it’s really important because we also work in a very small world. Yeah. And I, I think relationships are critical. And so I valued that and still to this day have great relationships with everyone on both sides. When, when I departed both Freshly and vault.

Anish Shah (17:32):
Yeah, absolutely. And it makes that conversa and like to, to, to point to the value of that, to walk out the door in a professional and positive way, even if sometimes there was some level of hurt within you or, or stress or trauma from whatever that situation was. And look, everyone, everyone is welcome to do whatever they think is best for them at their moment. If, if it just feels really great to give the middle finger on your way out, you know, go do it. But you know, it also makes the, the conversation so much easier when they’re inviting you back. Because on the other side, you know, the employee can feel a certain way and, and walk out feeling pretty gross about the situation. But the, the CEO or the founder, whoever is, is in charge of managing and hiring can also feel gross a about the situation and be super rude to someone out the door.

Anish Shah (18:20):
And, you know, I’ve seen both situations happen a lot. And you know, when I’ve seen that happen, either from a founder or CEO being that way or an employee, it’s definitely stunted them, you know, both where they never picked up the EQ that’s necessary to grow in their career, that they were, that they were hoping for, even from a founder’s perspective, they weren’t able to pick up the EQ to keep their employees. And from an employee perspective, they were always wondering why they were never being tapped. And I’ve talked to multiple people that we interview who are wondering why they’re not being tapped for higher level roles. It’s, you know, back channeling is very real. And you know, if you’re talking to your former founder or CEO and they’re like, Hey, this person like just, you know, I get it, we didn’t get along, we can exit, but you know, it was just the way they left was pretty unsavory. It cancan definitely get around. So.

Adam Gassman (19:14):
Yeah, and if I could add one thing, the other part for me, my growth as a leader was Freshly getting me an executive coach that was incredibly, both rewarding professionally and person to really increase EQ, but even more my own self-awareness of impact on employees that were working with me, even if we were being successful at certain points, that was an eye opening experience. And I think for anyone on the call that is looking to move up, if they can talk to their company about getting an executive coach, because the power of that is both rewarding for you on a personal level or rewarding for the company on a long term level, that they have someone who is fully capable of stepping into a big leadership position with a little bit of an investment with an executive coach.

Anish Shah (20:06):
I love that actually. So I, I mean, I, we talked about that earlier. The transition from IC to manager is actually pretty rough for a lot of people, and I’ve seen it be really rough, even like a midlevel manager, not necessarily having a big team, but even one or two people kind of reporting in it’s, it’s, it’s pretty rough for a lot of people to, to, to make that switch. So I like that idea of bringing in external coaches think

Luke Fernandez (20:30):
Your coach, or how’d the company find them? I, this is, this is something like a therapist where I think like so many people know they need it, but they, they stop the moment that it comes to actually finding the, the person, because it feels incredibly daunting to amongst a sea of options, like pick the person who’s right for you and right. For the company.

Adam Gassman (20:49):
I think one of the, one of the leaders that Freshly had hire is really who pushed the value of executive coaching. Prior to that, I, I knew what a therapist was. I, I didn’t necessarily know what an executive coach was or wasn’t, self-aware enough to know. I need an executive coach within a couple of weeks of having an executive coach. It was very clear that I was someone who needed an executive coach

Anish Shah (21:16):
Yeah. Is there a difference between an executive coach and a therapist or what, like what, what what’s I, and I don’t want to get too personal. I don’t know if you’ve had both, but like, I, you know, like what is the, where, where do they, where does one start in one stop

Adam Gassman (21:31):
For me, I’d say like executive coach wise. I, I think you’re just more focused on professional work or how to prevent personal life from intruding upon how you are in a professional environment, I think is the only place where there’s probably some overlap. But I also think like you’re talking to ’em about your stressors, the things yeah. That really drive you to get angry or respond. I, I think in some ways slack contributes to unnecessary like intense conversations, that personal conversations don’t, it’s just how work has changed because some of the feedback that I’ve given to people that had worked on my team is when they are complaining about someone’s slack. And I also got this feedback. If you read that with the best possible interpretation from your friend, would you get just as upset mm-hmm and if the answer is no, then maybe that’s not what they meant. And look, sometimes people will be rude, but you reacting doesn’t really solve it either.

Anish Shah (22:38):
Yeah. I love that point about slack content context is very difficult over text oriented communications. Great. How about yourself, Luke? What kind of kept you going on the ride all the way through when obviously, you know, there were opportunities to do other things.

Luke Fernandez (22:53):
Yeah, so I almost left twice, like had the conversation, had the offer in hand. It basically came down to one realizing how going through a, you know, going from like beta to a full exit with a single company how impactful that would be for my specific personal goals, which were becoming a founder or CEO. And then to, I had a great, I had a great boss who coached me through those decisions and did it honestly like looked at the opportunities and said, like, this is where I think it’s better. And this is where it’s not. And if you were to get a better opportunity or want to get a better opportunity, we, we, we, I will actually work with you in the interim to go find something that’s better than you’re looking at. But one, one was basically like almost joined a, a VP of growth for an international startup in, in Germany, like series a the, the thing I’ll say for both of these is like, if you’re part of a rocket ship, if you’re the first first hire, you know, first lane lead, et cetera, as a part of a rocket ship, it can fundamentally change your career.

Luke Fernandez (23:56):
But both from the standpoint of like your career trajectory, because you like, your success is dependent on basically the company’s success. And then also from the same point of equity, like if, if, if you’re early, early on at the right company, you just have a completely different outcome financially than some of the other places. And so I think this is a question that people should actively consider, right? Because joining the right company does is one of the only things that can actually create a step function leap in, in, in the different roles. But basically like had a VP of growth offer at a, a series, a company in, in Germany. I think I, we were two years into the Wiki V journey, still figuring out what our product was and what the product market fit was. And it, that, that one, one and a half, two year journey is so exhausting.

Luke Fernandez (24:44):
Like if you’ve ever been a part of a company that is just feeling like they’re treading water, trying to find their place in the market and trying to find how that place is actually scalable. It’s, it’s, it’s pretty tough for somebody who is coming into an opportunity on the basis of trying to find that rocket ship or, or a, a function step. And so what happened was, you know, I think I looked at the opportunity, realized that we were at the end of the, the product market fit journey at, at Wikibuy that there was real momentum and that the tide was turning. And the opportunity for me at Wikibuy would be so much greater as somebody who had been there in the beginning had the product market fit context than it would’ve been. If I went and joined a company, AB absorbed a team, and like hadn’t been there for the early years or had this super, super deep product and industry knowledge.

Luke Fernandez (25:32):
The second, the second opportunity was basically joining a VC fund. I, I had like a great, great opportunity to join what, what I consider to be one of the best consumer VC funds in, in San Francisco. And when I zoomed out, you know, I said, what do I want to do? I want to be a, a founder and CEO, you know, what’s going to get me there. Well, to get there, I have to be both somebody who can build a vision, but be an incredible operator. And while VC is shiny and oftentimes like a great pedigree stamp on your profile, the hands on experience of scaling a company, you know, owning the evolution of strategy at different phases, hiring and coaching a team it’s just not there. Like it may help you develop a vision and, and the means to under, you know, identify big market opportunities, but it doesn’t help you become a great operator. And I realize that, you know, being a part of a, a high growth startup for another few years was, was going to be the thing that gave me the operating experience that I felt was, was even more impactful going to, to going to start something myself in the future.

Anish Shah (26:33):
That’s great. And, and one thing that’s, that’s, that’s common in both of your stories, was there was sort of someone above you that you enjoyed working with, and it seems like who nurtured you and was fairly honest and, you know, Adam, in your case, let you go, but then still maintain a great relationship. Didn’t, didn’t do something jerky or anything like that. And Luke that you similar situation, except you just decided to stay instead of leaving. Which is, you know, when, when, when I talk to people and having, in terms of having a career chat, obviously you know, my, my, my role fundamentally, you know, is as a vulture and, you know, getting people to, to kind of move around different organizations. But no, fundamentally I tell them like, look, think about how much enjoyment you have working with your team currently. And do you enjoy working for the person above you? And you know, if that’s in a good place, you should really think twice about new opportunities. Because you know, the grass is not always greener and funding and press, and you know, all those things that, that add some level of of excitement to certain companies generally do not outweigh a group of people that you may not enjoy working with. So

Adam Gassman (27:40):
I think the grass is different.

Anish Shah (27:43):
That’s a good point.

Adam Gassman (27:44):
Yeah. And someone gave me that feedback as well as I was making that decision. And I think it’s spot on, there’s going to be some upsides of the new place and some downsides. It’s just, what’s the different environment that you want to be in. And what, what outweighs it the most, I think is probably the most farest way to look at it. It is never going to be completely greener on the other side.

Anish Shah (28:06):
No, no. And also like intuition and just sort of, I think emotion goes a lot into it, right? If you’re burnt out, if you’re sick of the people you’re working with, your emotions are going to push you out. But if you feel like, Hey, maybe this company won’t work out, but I actually enjoy some of these people, Hey, why not just go along for the ride a little bit longer, at least I know I’m going to enjoy coming to work. So yeah, a lot of what gets our candidates kind of moving forward into other new roles or keeps them at their current jobs is, is probably more emotional than logical. Cool. Let’s jump in the next one, ally. And thanks for sharing both of your stories as transparently impossible and, and the other opportunities we put in front of you. Yeah, this is a, this kind of leads to some of our earlier questions, but with more specifics. So for one quick question, were both of you kind of like ICS when you joined your, your organizations?

Luke Fernandez (28:57):
Yep. I was,

Anish Shah (28:58):
Yeah. Great. Great. And then, like, by the time it was exit time, like, you know, how large were those teams and though also, what did you learn when attempting to structure? And did you make any mistakes with structuring the teams? Along the way?

Luke Fernandez (29:15):
Yeah, definitely. I’ll jump in on this one. Definitely made mistakes. I think like the biggest mistake we, we made as a company and, and this comes down to me is like, we did not hire quickly enough where, where we needed to like marketing. I is a, is an operationally intensive organization. And there’s ways to get leverage from agencies or through hiring. I don’t think we did either one of them quickly enough. Like we wanted to be the smartest people in the room who were also the best executors in the room. And you know, I think when we look at kind of the, the bigger player in our space and, and what they did differently, this, this was one of the biggest differences. You know, in, in, in the beginning, like when, when you’re in, in a beta or, or, or like pre-market a lot of the question is, is product market fit, right?

Luke Fernandez (30:05):
So like my role started out assisting the product team running a beta, like talking to communities, getting the feedback from the specific people who should be using our product so that we could make changes, whether it was on activation or retention that got us to a place that we felt like had good enough unit economics to go raise around and then to start spending money against it. So once we had that round, the, the, you know, the problem really became product channel fit, right? Like how, how do we scale with the economics that we have? And the, the, the team ended up being built kind of as a function of that. Like I, as an IC, ran an portfolio style test tested a bunch of different channels, found the ones that worked well for us and doubled down on them and started building an organization to kind of unlock the growth on that channel so that I could then go heads down strategy on another channel and build a similar org.

Luke Fernandez (30:59):
And so by the time we exited at capital one, like a say, we were a fairly light team. There were probably six ish direct people on our team, me a mid-level marketer, that’s doing a lot of management across performance marketing and product management two engineers, and then two creatives mix of like producer and design to help fuel testing across the, the entire funnel that, that we were a part of. And so, you know, I’d say like strategy was kind of owned by me and, and my boss, the chief business officer, and, and co-founder which channels to prioritize on what were the biggest levers on those channels to, to pool and how we were going to get leverage against those channels. And then we slowly built like a really great execution org across like creative and engineering. And we had great sup support resources from other organizations like design and QA and in places where we could plug in, in and out.

Anish Shah (31:58):
Awesome. Any mistakes that you made along the way that you can kind of point to in terms of structuring those teams? I think what, I guess, what you, you talked about just not hiring fast enough anything structure wise that kind of like ended up that you had to switch it along the way based off of iterations and learning.

Luke Fernandez (32:14):
Yeah. To a, a couple different things. I think we were always very proud that like the first hires we made were engineers. We, you know, we had the mantra that like you can automate or augment your way out of almost every single piece of execution. And the way to do that was, was via engineering. When I look back on that, I like in, in hindsight, I think we did not appreciate the amount of technical debt that was created in like building your own systems for bid and budget management or creative production, et cetera. And so we ended up spending so much more time building systems that were probably only 5% better better than out of the box solutions that we could’ve worked with specific vendors on. And so I probably would’ve spent less time building, like in internal tech more time working with vendors on that. And then would’ve used those hires on people who could drive strategy in, in thinking and analysis on the channels, not necessarily execution.

Anish Shah (33:13):
Okay. That makes a lot of sense. Thanks for, thanks for that. How about yourself, Adam?

Adam Gassman (33:18):
Yeah, so I would say first off a lot of trial and error that, that we went through to find the right hires and the right structure. I, I think starting first with the mistake that, that allow us to probably reflect a bit more is earlier parts hiring to fill the hole of today, not hiring to fill the hole that we’re going to see 12 months from now and where the world will likely be. I think a perfect example is just looking at where we are today. Verse 12 months ago, 12 months ago, we were still dealing with artificially low rates from COVID 12 months from now. We’re not seeing that at all. And the things companies are dealing with right now are very different from 12 months ago. And then you go 12 months back. It’s even more different when you look at January of 2020 verse, January of 2021.

Adam Gassman (34:06):
So I think that was one of the biggest mistakes we had made. What then became a strength was really focused on hiring for where we see we need to be 12, 18 months down the road and led to a structure that had a new customer growth side of the team had an onboarding and loyalty and creative operations that was servicing both of them to produce best in class content on both sides, both new customer growth and also onboarding and loyalty. And one of the key things was making sure the KPIs were aligned and they were not totally separate and in silos because that would create unnecessary conflict and did at different points throughout the journey. And I think that was very key. Were there mistakes? Definitely. But at each point we learned got a little better and made the tweaks necessary to build the team. The team was probably still a little bit lean right, as we exited, but it was in a good place for us to continue to grow.

Anish Shah (35:07):
Makes a lot of sense. Thanks for that, Adam, jump on the next one, ally. Yeah. does this change, so when you’re defining KPIs and strategies you know, early on, it’s probably some target of row as target of new customers, you’d like to drive some, some level of target of repeat purchase rates or, or for a subscription product, you know, lowering churn. Does that change over time? Are there some new kind of nuanced things that, that pop into there as a business and a company matures or its kind of the same goals, but maybe different ways to back into them?

Adam Gassman (35:52):
I, I, I think there, there are more things that contribute. I, I think beyond the KPIs at different phases, it’s also what investors are asking for that changes as does then the KPIs within internal companies. I think the KPIs should be highly dependent upon where you are from attraction standpoint, your business model, what your AOV is to really understand whether you were getting market adoption or not, and not necessarily CAC. The problem tends to be. And I’m sure Luke, you’ve seen it at companies you’ve advised in earlier stages is early on. It just only CAC LTV will figure out later on. Retention will figure out later on, later on it’s CAC matters a little less. We should only focus on retention. Both should be optimized early on in a balanced way and focused in a very balanced way that nobody in the industry is just going to give you complete credit because you have the lowest C in the world, but nobody stays around.

Adam Gassman (36:50):
You have a leaky bucket. On the other side, I’ve also seen companies that talk a lot about how great their retention is, but their new customer sate $500 and they can’t grow. And neither of those are great companies finding a balanced approach and building your outcome KPIs and Northstar metrics. That way is what you will do to set yourself up for a long term exit, or be best positioned for that. Then say, it’s stage one to raise the next round. We gotta grow. And Cox gotta B X stage two. We gotta do this. And stage three, the more balanced you are from the beginning, the easier it will be to stay focused on both and not ignore one for the other, which ultimately inevitably causes problems internally.

Anish Shah (37:35):
That’s awesome. I have a lot of thoughts on north star metrics actually, and, and ones that I feel like I’ve seen that I don’t feel like I cared about, but was forced to think about because someone else cared about it. Mainly someone like read a blog post and it said that you should care about this particular metric without any logic behind thinking all the way through it, but yeah, would love would love your thoughts on, on that as well, Luke, in terms of the different phases and the strategies and KPIs and how that change. And that was a great answer, Adam, where everyone’s just going to be focused on acquisition at the beginning, but once they learn that churn is real you know, what do you do then?

Luke Fernandez (38:10):
Yeah, the, there’s a, a couple points here most of which are echoing Adam, obviously there, there are like performance metrics that you’re always trying to solve for. And it’s some, it’s some version of, of volume and return on spend. And I think the expectations of those changes as you grow over time, but the, the subtle nuance that would that I think like Adam is calling out is if you’re a VC backed company, there are expectations for, for those for those metrics. And it, in many scenarios, they kind of create a minimum KPI that you need to solve for the raise expectations are almost always around growth rates and the payback periods. And then you know, you have the cash constraints of, of the business as well, which also play a role in setting the, the return or the, the payback metric.

Luke Fernandez (38:57):
How quickly are you using the cash and how quickly is it coming back to the business? And I think that that’s just like a huge learning for, for somebody new to VC company is like, Hey, listen, there is actually a rate that we have to be able to put on a slide in order to attract a certain, a certain type of investor. I think over time, depending on your business what you see happen is teams get more confident on their ability to bet on the future improvements of those rates. Like you may target a lower payback in the very beginning, but as you learn the industry, as you’re in a consumer sales product, as your Mo monetization team has a clear, a clearer and clearer roadmap and a, a better and better track record of kind of like hitting that roadmap and, and making improvements then you can start to lean a bit more aggressively on, you know, like expected payback or expected Roaz in three or six months from now.

Luke Fernandez (39:52):
And, and I think that teams kind of should be, you know, as soon as they have clarity on, on, on those potential improvements, they should be leaning in aggressively. I, the truth is, is that most teams lean into aggressively early on without understanding some super basic fundamentals, what are their unit economics and what are the roadmaps that are going to actually change those? But there are also those teams out there who have a reason to bet on themselves because of the work and progress that they’ve made against those metrics. And sometimes don’t lean lean into a a as aggressively as they should to, to the earlier comments earlier about how the role changes from I IC to team lead. Some of the KPIs that you start to think about as a people leader are more about your employees, KPIs, partially how they’re being scored in the organization, partially how they’re lanes are laddering up to the, the, the core KPIs. But I think I’d spend more and more time thinking about kind of the performance in some quantitative format of my individual team members than I do necessarily the only the KPI that I’m in charge of

Anish Shah (41:00):
That makes a lot of sense. And I like that, that you’re, you’re not, when you, when you grow a team, you’re not just, they’re not just people there to do the things that you want them to do. You’re there to be responsible for making them successful, and what’s going to make each of them successful is very different. And you have to put that under your shoulder to make sure they’re in a good place and going back to KPIs. I think I think there’s multiple KPIs that I hear companies talking about improving and being proud of themselves, where I, I feel like they were sort of useless stuff. And I think not useless, but not the north star. I hear a lot of companies talk about conversion rates bumping up, and I think that’s a poor north star. And I’ve had to untuck and lose this battle very frequently with a lot of founders that like conversion rate is a terrible metric in terms of the growth and success of your business.

Anish Shah (41:45):
It’s a great metric in terms of AB testing. You know, if you have eight different pages, of course you go with highest conversion rate, but if you, as a company are growing your conversion rates year over year, that just might mean you’re over segmenting and your foreseeable population is low. And then the one I really don’t love is AOV either. It doesn’t matter if the basket size is not high, as long as the top line is great and, you know, lowering your basket size and lowering your prices is a great strategy. I’m a, everyone talks terribly about discounters. I’m a big fan of discounters, and I know Luke, you, you built a business that is pretty much around helping people get discounts. And so yeah, I think both of those are, are terrible kind of, kind of north stars that I’ve seen companies over index on. When I think it could, it could really just index on top line and margin and really keep it as kind of simplistic as that in terms of north stars.

Adam Gassman (42:46):
One thing I don’t think either me or Luke talked about, but I, I think we would both agree certain stages of your business. There are going to be KPIs. You just have to hit to keep the lights on. Sure. especially when you’re a venture back company and that could change. And that leads to do things that are very short-term focused and that should only truly be short term focused.

Anish Shah (43:07):
Yeah. Definitely some sales are out of desperation and that’s okay. You know, if, if someone, I used to work in an organization that basically said, if you don’t hit your quarterly numbers, we’re just going to start firing people. And they were very, very open mind open, like open about that. Like people are just going to lose their jobs. And these were, you know, I was a little bit younger in my career, but there’s a lot of people who were kind of pretty scared about losing their jobs. And so what happened at the end of every quarter, 70% sale, everything everything’s on sale, everything is discounted. All right, we saved, we saved your jobs for another quarter. So it was, it was a fascinating experience on poor management and then what happens with poor management as well. Cool. thanks for that ally, we can jump in the next one. This is a good one. It’s probably very difficult to also pick one thing. But and oftentimes mistakes are the only ways to grow. So, you know, it’s good to make ’em as long as the ending is in a positive place, otherwise, you know, how would you ever learn anything, but looking back, are there certain things that you’re like, oh yeah, maybe if I did this thing differently or this thing differently, this could have, this could have gone a little bit, bit better. Yeah,

Adam Gassman (44:28):
I, I would definitely say there, there are a number I, I think the most that call out Freshly different from Wikibuy was very day to day given it was a perishable business, weekly capacity had to hit a number. So oftentimes your head was in the day to day and you didn’t spend enough time above level thinking long term and doing more deep thinking about things to implement over the course of the next 12, 18 months. And I think that’s one thing that I wish I did did more of, I think the secondary thing is spending more time planning for the worst case scenario and how to operate within the worst case scenario, then planning, what is the most realistic scenario and how to operate within that and what levers you’re going to pull. If things are going a little south here and a little better there, what are you going to do? Because they think, look, we all learned year and a half, or I guess two years ago now the unexpected can happen and it continued to happen. And the better prepared you are for the worst case scenario, I think just overall the better you are prepared to handle as much as possible. I don’t know that no matter what you did in 2020 planning, would’ve prepared you properly for, for the year we had. But I think the more you plan for worst case scenarios, I think the better position you would’ve been

Anish Shah (45:52):
And with that so that’s just really risk planning and yeah. Okay. So risk planning, really, of things that could come down the pipe and contingently plans of what to do in case they do. Okay. How about yourself, Luke?

Luke Fernandez (46:06):
Super different business. And, and, and I, I, I think like some of the answers is going to color that you know, I, I I’m, I’m hesitant to, to give my answer because I, I think it might be fueling like a very dangerous fire for early Sage companies. Like, I, I, I think like most early stage companies burn because they’re not thoughtful enough because they lean in too aggressively on building teams because they lean in too aggressively on spending dollars without a clear return. And they basically end up in a place where they look at their bank account and realize that not only are they out of money, but their metrics suggest that they’ll never be able to raise another round. I would characterize the the, maybe the thing that we could have done better as being the exact opposite of that. Like we were not aggressive enough in building our organization and in flexing dollars where they were and that kind of comes down to just like people leverage.

Luke Fernandez (47:00):
Like we didn’t probably have enough people where we needed them and we didn’t bring in agencies where they could have dramatically accelerated execution. The, the truth is, is like returns on great employees are in the hundreds to thousands of percents. Like the, if there’s any variable in your formula, if you get the right dedicated owner for them, they can tour four X that variable. And sometimes organizations are so hesitant to make that a hundred thousand dollars hundred $50,000 investment on that person. But at the same time have absolutely no problem raising the budgets on their ad campaigns to just dip in a little bit more aggressively to return on, on ad spend. And I think it’s, you know, we, we, we had a little bit of shortsighted thinking there and I totally take credit for that as a leader where people could have provided us a better return than just leaning into, to budgets in, in some scenarios.

Luke Fernandez (47:57):
A again, I, I say this outta caution because I think actually most early Sage companies don’t need to hear be more aggressive, but somebody once gave me analogy around scaling that said, scaling is like building muscle. You have to bulk and then cut. You can’t build muscle quickly by dieting. And, and sometimes I, I think like the hiring approach I, I took was a little bit more, more diet oriented. Like, I, I, you know, like the answer is almost different, the completely opposite of Adams or where I, I feel like we should have planned for what could have gone. Right. There’s a ton of great opportunities that were scoped and we didn’t staff them quickly enough. And yeah, you know, it’s, we, we had a major competitor in our space, honey, who, who had a completely different outcome than us at a different valuation. And that was because they scaled much more quickly and that demanded a completely different premium in, in, in the market.

Anish Shah (48:54):
Yeah, absolutely. That, that, that makes a lot of sense. And the whole point of these conversations with two leaders is to see where some of your thoughts, you know, come together in similarity and then also kind of, kind of diverge. And I think one thing Adam mentioned, actually, I forget which one of did. You mentioned to tell the truth, but talked about like hiring for 12 months down the road, instead of right now. One thing I actually pitched to our clients regularly is hire for right now hire for immediate needs. And don’t hire some, all of our clients want to hire people who have the hottest backgrounds coming out of the hottest companies that have scaled the best and have the best track records. Those aren’t always the best people for early stage anymore. Right? Tho those aren’t the right ones, because they’re used to having resources.

Anish Shah (49:39):
And the next thing they want to do maybe is a little bit bigger. And so it ends up becoming a mismatch very consistently with someone who’s just seeing things at massive scale, going back to something now that’s not always the case. Some people have seen things at massive scale really did not enjoy the level of bureaucracy they have to deal with at that point. But yeah, I I’ve generally been someone who says, okay, you have these problems right now. Don’t overhire and think about what’s coming down the pipe in the next 12 months and do it in a step ladder fashion. You know, don’t hire five people right now because you see that foresee this 12 months down the road hire one person right now than the next person and the next person and the next person. Now is that true for, for every single organization?

Anish Shah (50:23):
No, if you’re swinging for the fences aggressively and you want to be a deck of corn in two years and you got the VC backing to do it, you know, swing go, go aggressive. And you know, in today’s market, especially the VC’s looking backing you. So you know, that advice is not always correct. And again, it goes back to being situational with company by company and, and, and what your individual goals are and even appetite for, for iterative hiring and iterative learning versus just screw it and, you know, just, just, just go heavy in every direction. So yeah, it’s, I, I guess there isn’t a right answer for every single situation.

Luke Fernandez (50:59):
I think a lot of the over hiring or early hiring issues happen because like the opportunity isn’t scoped well enough, right? It’s more like this person has a shiny background. Let’s bring them in, they’ll create value. Or we think that something that we want to do is interesting. Let’s go hire somebody to figure it out. I think when you’ve set a quality bar around knowing, you know, having enough confidence that that’s a direction that you guys need to go in, then you, you kind of can’t let yourself be limited by going in that direction, yourself long enough, such that you’ve built the initial system and need to go, hi, hire somebody. It’s, it’s a weird balancing act of like having enough context and not

Adam Gassman (51:38):
The one thing I’d also add is on the hiring front. I think some of the best hires were people that were incredibly intelligent, super hardworking that were not necessarily experts in the particular channel or area they took on to control that were so dedicated to it. I’d say myself included early on that they were the best at it. And I think sometimes, and we sort it also at Freshly hiring people with the greatest resume and the greatest companies, they come and expect to be treated a certain way and care a little bit less about delivering and more about providing theories which can be problematic as you’re trying to scale and grow and really need people’s brains and minds focused on doing and planning because the theories are great, but they just don’t work to grow a company 10 X or 15 X. That is the ask that you’ve been tasked with in those leadership roles.

Anish Shah (52:43):
That was exactly the same. Next thing I was going to say, which is a something I really try to push on our founders and more often than not lose because they want that shiny background. And look, I get it our situation is very unique. because a company is paying us a pretty penny to go find these people. And you know, when we find those people, they just want the shiniest backgrounds. But there’s something really exciting about, I mean, not to wax too poetic about back in my day, but like, you know, 10 to 15 years ago when people were building startups, it was a group of people. You know, startups were not for people who were very experienced to be employees. And it was meant to be a group of people who were inexperienced, shove them all in a room for a, something magical might come out of it of a bunch of people kind of not knowing what they’re doing, but they all had a ton of optimism in trying to figure out how to make it work.

Anish Shah (53:33):
And I think you really alluded to that, Adam, that like it’s, there’s a lot of great hires and not knowing what you’re doing is a great motivator to, to push harder because you want to challenge yourself. You want to, you want to face those lessons and grow in your career. And so I think fast forward now it’s completely changed because you, you know, back 10, 10 to 15 years ago, you didn’t have, you know, 40 different startups that have come out in the food kit space. You know, you didn’t have, you know, whatever, 15 to 20 different like, you know, coupon tech providers, you know, now everyone’s just like, get me someone else who’s super senior from another coupon tech provider, you know, get me someone else who’s sort of scaled another food kit company. And realistically like there’s a lot of value in someone who’s never done either joining that organization and taking it on upon themselves to work harder because of that.

Anish Shah (54:24):
And, and not necessarily the hours, but just the intent to, to, to, to get over a learning curve. So, and I think both of you had little to no experience when you joined both of your companies in the spaces that you joined and that propelled you, I’ve never recruited before starting become running a recruiting firm. Like I, I didn’t know what I was doing. I was figuring it out still am. And so yeah, I think for all the companies hiring out there, there’s a lot of value in smart, hungry people who don’t know what they’re doing but are dedicated to, and, and interested for their own personal careers to grow

Luke Fernandez (54:56):
A thousand percent. You you’re always balancing potential and experience with any candidate that you’re hiring and time and time again, I’d bet over potential in the form of like raw, raw intellect and, and action oriented right than I would around experience time and time. Absolutely.

Anish Shah (55:14):
Absolutely. well this was awesome. I learned a ton from this conversation. Thanks a lot to you, Adam. Thanks a lot to you, Luke. This was awesome. And we’re going to have this recorded. We’re going to send it out to all the attendees and thanks a lot.

Luke Fernandez (55:30):
Thanks so much was a pleasure Anish. Thanks so much, man,

Anish Shah (55:33):
As always. Yeah, both you. Bye.

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