Building a Sales Org From Scratch During COVID | Kaylin McNamara (Sr. Director, GTM at Owl Labs)

Carter (00:06.92)
Well, hey, Kalen, introduce yourself. Tell the people who you are, how you got to out what you what you're doing now, how you got to owl labs.

Kaylin McNamara (00:17.996)
Yeah, my name is Kaylin McNamara. I am at OWL Labs. I live just north of Boston, about 10 miles north of Boston. And the company that I work for is a hardware technology company. We are headquartered in Boston, but because we build technology and hardware for hybrid work, we don't have any mandated in office days.

despite some feelings by my CEO, you can't really claim that hybrid work is the way of the world and then make mandates. I spend a couple days a week, maybe on average one to two days a week in the office downtown and commuting in from Marblehead Mass. And I've been at OWL for six years, just barely six years at this point.

Carter (01:10.966)
Nice, yeah, that's pretty nice with the hybrid work, that makes sense. And take me back to the beginning, you show up at our labs, were, it sounds like at least from your LinkedIn, you were thrown into the deep end, you had to build the direct sales motion from the ground up. How did you do that? What did you do first?

Kaylin McNamara (01:26.22)
Yeah, it's a great question. I actually came on board because my CEO, Frank, the current CEO, I knew him when I was at CarGurus. I never worked directly for him, but we sort of worked on some events and projects together, specifically in Canada when I was on Team Canada. And we're sort of two sides of the same coin. He's always been much more senior than I have been, but he was overseeing sort of our...

like advertising business, whereas I was selling our, you know, SaaS product directly to the car dealers who would list their cars on the site. And so we'd have a lot of overlap in events, you know, like trade shows and also customer events. And I think he realized pretty quickly that...

I'm a little bit of a bulldog. I may not know everything, but I'll figure it out. And so a couple of years later after he had left in 2020, I think, honestly, I almost ran him over with my car when I was driving through Somerville. So we stopped, we had a little chit chat and he was like, hey, you should consider, this is a really, really great product, which is weird to say. And there's this sort of maniacal fan base around it. Again, weird because this is a

a B2B purchase, but our businesses and our customers in the early days of Owl were purchasing it like they were consumers and sort of talking about it quite a bit. So he said, come, you know, have a conversation with me and the rest of the go-to-market team, which I did. Little did I know because I'm a little bit dense sometimes that the conversation was an interview. I only realized it like once the third person came in. So

Carter (03:11.318)
Right.

Kaylin McNamara (03:11.948)
Thank God they gave me a little bit of leeway there on my informal first, first half hour of the interview. and essentially what, what Frank said to me was, Hey, we have this product. We have an e-comm motion, right? Most of our sales occur on our website or through, Amazon. Cause we were selling there, but we're really picking up steam and I'm wondering if we need to actually build out a sales org to support this and to continue growth.

And I said, wow, okay, I'll try to figure that out. But like 10 days after I started, the pandemic hit. And so pretty quickly, I was exactly thrown into the fire, but it was for quite some time, like very much to our advantage. One, because there's nothing to get you ramped up quickly, like an influx of activity and noise and motion and sort of all that stuff.

And that first month where everyone was like at home and no one knew what was happening, it was pretty quiet. We were sort of just surviving and figuring out what was going to happen. And then that second month, somewhere around like, you know, April, May-ish, it just went kind of cuckoo, went crazy. I think all of a sudden we all realized that hybrid work and or remote work was here to stay. And OWL Labs has been sort of at the forefront of

developing technology for hybrid work prior to COVID, right? We were founded in 2017 and our co-founders essentially came with the point of view that you needed to have a camera speaker microphone system at the center of the table instead of at the front of the room in order for the natural conversation between two people in the room to be captured for the folks who are not in the room, right? So the whole premise was equitability between remote and in-room folks.

And again, prior to COVID, we probably don't remember any of this, but like that was unusual. I think less than 5 % of meetings had a remote person and, you know, everyone was in an office together. And then literally overnight, that statistic flipped. Less than 5 % of meetings now do not have a remote person in them. And so it really sort of solidified our positioning and our belief that you have to come from a different...

Kaylin McNamara (05:34.287)
physical and metaphysical perspective to best serve anyone who's working on anything, right? This could be a Bible study group, a house of worship, something like that, all the way up to a Fortune 100 who's hosting meetings across literally hundreds of thousands of conference rooms. So it's great. The first thing, honestly, I did when I got here was I sold. I was the only person.

here and I hadn't yet had the chance to sort of say, hey, who can I bring with me? And how many people do I need? So on and so forth. And again, I was shaken up pretty quickly, but I think now that'll be a necessity wherever I go next, right? I will myself, no matter what the position or seniority level, sit in seat and essentially try to take a prospect from, you know, top of the funnel, cold outreach or brand new inbound lead all the way to sold, right?

Not single-handedly, of course. It always takes a village to get the prospects to the right state, whether that's closed one or closed lost, unfortunately. yeah, I sat in the seat and I did 12, eight, 10, 15 hours of work, which again, what's better as a salesperson than being that busy? Not much. So it was great. It was like a total fast track of ramping myself in the industry with a customer base.

within our total addressable market, all that good stuff. So that was pretty awesome. But then I realized like, okay, we need to ramp up a team that is more than just me. So essentially I took what I knew after the first couple of months there about again, our ICP, our key personas, which did not exist, right? This was just stuff in my head and kind of instincts.

Carter (07:22.913)
Yeah.

Kaylin McNamara (07:25.49)
And I reverse engineered what I thought would be the best profile for who we needed to hire and how we needed to build out the rest of the sales folks or the sales org. And a couple of things stuck out, right? I knew right away this was a highly transactional and very, very quick sales cycle. Yes, partially because of the unprecedented, I hate using that word, but it's true, nature of what was going on with COVID. So I need people who could...

Carter (07:50.613)
Right.

Kaylin McNamara (07:52.4)
frame switch who could multitask, who could keep themselves organized without having, you know, a script in front of them and a step-by-step 15 page playbook. And then, you know, an SE and a BDR and all this stuff. I really needed like essentially Swiss army knives that could move really quickly. Obviously sort of carte blanche, I think in all sales, but good discovery and qualification skills. The whole 70 30, right? The prospect should be talking 70 % of the time.

to the 30 % of the sales rep. That is grounded, I think, in good discovery and qualification. And then really I looked for folks who could take initiative and who had evidence in their careers so far or in school or their personal lives or whatever, who could sort of take something on, like find a problem and go take the initiative to solve it or figure out a way to be more efficient, right? Like, if we actually...

use this type of tool that's already built into our HubSpot or our Salesforce or whatever, it can shave even a couple clicks or a couple seconds off of each activity. So that was kind of what I looked for the recipe for success on who I needed to hire. And I began hiring, right? Which is always fun, but very, very time consuming. So by the end of 2020, I had two folks who worked directly underneath me. And then in January of 2021, I think we hired

six folks all at the same time. And a couple of those, three of those were BDRs and three of those were like direct more senior sellers. So we could scale up and handle the activity that we were seeing, which was awesome. Yeah.

Carter (09:34.583)
When you were bringing salespeople on, was it difficult because you guys are a tiny company or was Alabs pretty hyped with the whole pandemic and everything and it wasn't actually that hard to get quality people?

Kaylin McNamara (09:43.5)
You know, it wasn't that hard. think it's, it's been harder since in other sort of seasons that we've had to hire. it definitely wasn't then and you know, it was definitely a COVID boon and I hate coming on things like this or talking to folks and being like, yeah, I couldn't recreate that if I tried, but it's, it's sort of true, right? Cause no one can take that as advice and put it into their own life. But, really it was.

Carter (09:53.495)
Hmm.

Kaylin McNamara (10:13.515)
It was really about showing the prospects, the candidates, that we couldn't, for the life of us, recreate this opportunity in this market under any other circumstances. We were exactly in the right place at the right time. We had a great foundation as a company, again, going way back pre-COVID, and we weren't one of those companies that just popped up because of COVID. So we had a lot of legitimacy.

and a huge install base already of, again, avid fans. Who knew you could be a fan of video conferencing technology, but apparently there are. And so I really anchored in sort of our legacy already as a company, and then took that history and said, but now look to the future. We are in a hybrid meeting space, and we are mission is to make sure that people outside of the room feel as if they are there insofar as you can when you're not physically there.

and create an equitable environment for everyone and productive, right? And once I sort of married those two things together, I think most of the candidates were like, I get it, I see it. This is gonna be a really exciting, but also really taxing time to join, yeah.

Carter (11:25.751)
I was curious, did a lot of these early playbooks that you were doing, did they come from stuff you were doing at CarGurus, or sort of the playbooks CarGurus was running? Or was it really you were just learning on the fly and figuring things out as time went along?

Kaylin McNamara (11:34.231)
Yeah.

Kaylin McNamara (11:39.404)
A lot of it was learning on the fly for sure because again, I was sort of drinking from a fire hose. So it was great because I learned faster than I probably would have otherwise. The playbook honestly didn't really come to fruition for about a year because first I had to stand up processes and systems to build a foundation to build a playbook, if that makes sense. So for example, when I started, like there was no automatic motion that would even create an opportunity when someone was working it.

Most of our opportunities were and sales were flowing through our website. That wasn't even funneling into our CRM. We were in HubSpot at that point. And so I stood up just like sort of basic processes around lead management, opportunity management, like minimum inputs. It sounds really boring and sort of technical, but required inputs and validation rules so that we could start to gather Intel and data, right? We didn't have an ICP. We didn't have a key persona group. And really it was...

much hard, like pretty hard to do that anyways, because everyone was having hybrid meetings. And so like, it's wonderful to have a huge total addressable market. But that doesn't help you strategize on your go to market motion, especially with a very small team. And so I had to build those sort of like new muscles or new motions and processes within the org and sort of slowly evangelize them to sort of adjacent teams as well just be like, hey,

we're actually gonna start to measure our opportunities and we're gonna make them have these 10 required fields or whatever it was. And when something goes close lost, we need to know why. When it goes one, we need to know why. All of that was again, the building blocks so that we could do analyses of our install base and therefore look to the future and say, if our install base looks like this and we want more of that, or maybe we actually want less, depends on, you know, the sort of overall product strategy and go to market strategy.

You can't do that if you don't have the data set. So that's what I really focused on first alongside like a rev ops slash business ops ally, I would say. She had to do a lot with me and for me. Bless her. She's still here now doing the same thing. So that's where we started. We built the playbook out though.

Kaylin McNamara (14:01.008)
about a year and when we've realized myself and the other kind of sellers and sales leadership there that we needed to sort of divide the sellers up into a couple different buckets, right? So we decided to have direct sellers like I'd already hired that sold directly to our end users. But at the same time, we're also standing up our channel sales and channel sales. You know, some people are familiar with it, some aren't, but essentially there's a whole host of

channel partners out there that are called value added resellers or, you know, systems integrators. And really they resell your products and services by also adding value. So for example, maybe they'll install the devices for the customer, et cetera, or even like larger enterprise organizations. They would never really come directly to a manufacturer's website and do all the research themselves. They would go to their trusted, know, reseller partner and say like, hey, and some of them have had the same

reseller partner for 20, 30 years. Say, hey, I need new video conferencing equipment. Like these are the spaces I'm looking at. Who should I be in touch with? So we were standing that up because we had so much interest from our channel partners that were coming into us directly and saying, like, my customers keep asking about this. Like, where can I get it for them? Can I get it from you guys? Can I get it from a distributor? And once we were standing that up, we realized there was a lot of conflict, right? So someone would go to their partner and shop.

for OWL and then they would come to us directly and shop for OWL and we're competing essentially against ourselves. So that made it pretty clear that we didn't want to compete against ourselves and race to the bottom on the price and also undercut this sort of nascent burgeoning partner environment or partner cohort that we were just sort of standing up and building. So we took like two roles there, right?

Carter (15:32.513)
Got it.

Kaylin McNamara (15:54.993)
enabled the channel account managers to go work with our channel partners and enable them and incentivize them and educate them on why OWL versus our competitors and why OWL period. And then our direct sellers focused on all the leads that we had coming to us directly and then, know, proactive outreach to the end users themselves to evangelize your message. And then lastly, we said, hey, the volume is so high right now, again, blessings for us, that we need to take the smallest

segment of companies that are coming to us and we need to actually put them in sort of a BDR motion and our BDRs still do that to this day. They actually do the full sales cycle for any companies that come to us directly under 200 employees, right? Because essentially those companies, they're wonderful. We love them. They are like our bread and butter. We are very, very great in the SMB space, but they have a low ceiling, right? They're not going to have

15, 20, 30 conference rooms. so because there is that sort of low ceiling, we always stick by them and give them the demos they need and the post sale support and all that good stuff. But we realized that was better in more of a fast, quick to move through BDR motion while we wanted the more senior resources focusing on the larger accounts and building relationships with those larger accounts.

Carter (17:14.39)
Yeah.

Through this whole journey of scaling the sales organization, what would you say were the biggest challenges? Was there anything super crazy, like the most crazy, difficult thing to deal with? Or is it of just a mix of a lot of things?

Kaylin McNamara (17:26.766)
Hmm. Honestly, this is probably a cliche, but I think things changing so quickly was the hardest thing. So I was thinking about our playbook and how, you know, it took me a year to even start putting pen to paper on stuff like that. Right. it basically existed up here or in 5,000 Slack messages. but even when we would build a playbook and write it down, by the time you're finished writing the playbook, it's changed.

Right? Our structure within the sales org has changed to match sort of the ebb and flow of who, which type of customers we're seeing. Our focus on our ICP was changing because especially during COVID, like a big cohort of our prospect and customer base were EDUs, especially K-12, right? They were looking for anything to keep their classrooms online and keep kids learning, which was so, so, so important.

But then after COVID, that cohort sort of shrunk down a little bit, right? Because kids could rightfully so get back in the classroom and you cannot, no matter what you do, no matter how good the technology is, you cannot recreate in-person learning, especially in K-12 environments, with even the best technology out there, right? So because things were changing so much and so quickly, I think that was the biggest challenge. But again, as long as you sort of set the right expectations with the people you're hiring and the candidates in the pipeline,

and also you interview for that trait, the ability to handle ambiguity and lots of change, I think you'll be okay. So all in all, I would say in six years, we've probably had maybe six of a total of 35 people who've come and gone through the sales org, like leave voluntarily. And I don't think, yeah, I don't think we've had to.

really ask anyone to leave on purpose. we have a really great team and they're here for the long haul and they've done a great job of sort of rolling with the punches, good, bad and otherwise.

Carter (19:32.939)
Yeah, that's very nice. And that's one thing I was curious about too, because you made a bunch of jumps at this company in the last six years. And of course the company's grown a lot. Why do you think that was? It was just getting the results, taking on big problems. Is there like a lot of politics that you had to navigate or not really? You just crushed it. You you're scaling things. You did a good job. They promoted you. Or is there more to it than that?

Kaylin McNamara (19:54.032)
Yeah, yeah, it's a really good question. mean, I think anywhere and especially even at OWL, the results have to be there, right? And they have been, even though we've had such major fluctuations in revenue, revenue targets, right? We're trying to sort of right size what is the new normal going to be? Again, something over quoted during COVID, but we saw this huge influx. We knew that it was going to be sort of

rocky for a while, mostly in a good way. But post-COVID, I was thinking about it in the middle of COVID, I was thinking, what is our revenue going to look like and how do we get to consistent, predictable revenue in a post-COVID world? And so the results were there and that was the basis for sort of taking on more because I don't think any of my bosses, the few that I've had here, were going to, rightfully so, say, yeah.

you can take on more and therefore sort of inch your way up on the seniority scale, if you will, if you're not doing what your, you know, main priority is, which is driving revenue. It's that simple in sales, right? And it's that black and white. It's that easy to see. So we did great there. And then essentially I got more involved in, I mean, it sounds like a no duh, but the more senior parts of planning and strategy. So,

building, I think, 2021 or something, somewhere around there. I was working with my former boss who was here for a while, Josh Allen, on building a bottom-up sales goal, right? So looking at our historical data across the whopping three of us who were selling and saying, hey, we did great. Here's where we had success. Here's where we did not. What should the revenue targets for the sales org be for next year?

And I had never done that before at Cargurus or anything like that. And then eventually taking on International because we had, again, had a sort of nascent contracted sales team in Europe. We were nowhere else at that point. But I sort of worked with my boss, my manager to say, we've built a little bit of a process and a little bit of a playbook and sort of some guardrails or swim lanes.

Kaylin McNamara (22:16.291)
in North America, like let's go replicate that elsewhere to the extent that we can so then we can find predictability and consistency in these other markets. And eventually got to the point where we stood up Australia, we stood up India and a couple other international markets here. So it definitely was not politics and I'm lucky for that. We are too small of an org for politics to come into play, I believe.

But I will say on the political side of things, like you still have to have a good reputation and a good brand, if you will, outside of just your org, right? Your direct reports and sales leadership are not the ones who are single-handedly going to get you promoted, right? Hopefully they give great reviews of you and, and, know, they can see the value of the tough love conversations and the pats on the back, of course.

but you really have to have this full sort of 360 reputation and brand that you are dependable and consistent and again, proactive and take initiative. And I think a lot of my colleagues, especially like on marketing or on business ops or even in supply chain could see that, I wasn't gonna drop the ball on something that they needed help with. And eventually sort of,

took on this role as the knowledge base for the sales org, especially because I essentially built it from the ground up, so it made sense. And then ensuring that I was still evangelizing that. getting to a point eventually where I'd be like, someone would come to me and ask a question. Hey, who do you think would be a good customer for?

Carter (23:52.266)
Right, right.

Kaylin McNamara (24:05.69)
a new case study or testimonial and I would point them instead to my colleague Bob, my rep Bob or Bill or someone else like that, right? Like I wasn't having as many conversations with customers as they were. They're the experts. So you sort of, it's a two way street, right? Like you should be able to build this reputation again in this brand where everyone else at the org wants to come to you to get questions answered. But once they do, you also sort of, I guess, delegate them out or sort of

redirect those folks to the other experts, especially if they're your direct reports. Because A, like I said, those guys were more experts in exactly which customer would be great for a testimonial than I was at that point. And B, it helps up level them, right? It helps teach those folks, those maybe more junior sales reps, how to work cross-functionally or maybe manage up, right? Maybe it's a more senior person who's asking this request or something like that. So,

So yeah, that's sort of how I kinda kept notching it up. And truthfully, again, this is one of the ones that when I was much younger in my career, I really, really hated. But I was doing the job already before the title or the compensation really came with it. And honestly, that was not some benevolent, like, look at me. It was more so just out of necessity. Something had to be done. And there are definitely times where I would get pretty upset or pretty mad that like,

Carter (25:20.289)
Okay.

Kaylin McNamara (25:32.078)
felt something I was doing was really under the purview of a different person or a different part of the organization and I'd eventually get over it and be like yeah and no one has the time or bandwidth or tools or whatever to do it and I still need it done so I just have to go do it myself.

Carter (25:47.916)
Yeah, that makes sense. And then just a final question. Is there like the biggest, what's the biggest lesson you've learned as a sales leader that you wish you knew earlier and any tips for future sales leaders that are seeing this?

Kaylin McNamara (25:58.812)
Yeah.

Kaylin McNamara (26:02.258)
I, okay, I'll give you two answers here. One of the most important parts I learned about being a sales leader was when I was actually an individual contributor. And it was really about how to raise up concerns or highlight issues or problems in a professional way. So I am an emotional and emotive person and I really care about the work that I do.

sometimes more than I would like to. And so, you know, I found myself at some points very early on in my career sort of being the bad apple on the bunch or sort of pointing over there and saying like, this is not right or this is definitely not a smart way to do this and yet not coming with recommendations or solutions, right? And so one of my bosses at that point, think it was Jason Abrahams, took me aside. We went on a nice little walk and he was like, listen, you're...

great at analyzing these things, you're great at finding these opportunities for improvement. But there's a couple of things at stake here. You can't be the bad apple that brings the morale down. And you also need to come up with solutions. And I pretty quickly implemented that. And now I make sure that probably the most important thing that anyone who works with me or directly for me learns is exactly that. Like I love the people who sort of put their finger in the air and say,

but what about this and what about that or anticipate problems that we think our customers might have with, for example, a new product launch. But I also work with them to make sure, you know, we're not rehearsing a tragedy as I like to say, or that we're coming with solutions. So I think that is the underpinning of any next position. It doesn't matter if you're an IC or a leader, especially not in sales or really elsewhere, but really specific.

to leadership is I really believe you have to lead with the why and set really clear expectations. So when I'm implementing a new process or even if it's something as simple as like, need you to click one more button in Salesforce, I'm very cognizant that I'm asking my team to do more that they may not see as productive or a good use of time, right? And so I have to lead with the why behind the ask.

Kaylin McNamara (28:25.467)
and especially show that this is why it is productive or a good use of time. Maybe it helps us do a better job predicting earlier in the sales cycle when someone's gonna say no or when they're not a good fit, right? Or maybe it helps us, I don't know, get to a closed one a little bit faster or ensure that a lead gets to the right person more easily. Whatever the case may be, I'm very cognizant of asking for more from my team and always leading with the why behind.

anything, good, bad, or neutral, right? Once I do that, then I set clear expectations hand in hand of, and I expect you to do this on this timeline, with this timeframe, here's where you can see it, here's where the measurement lives, right? It's not just like in the ether somewhere. And I think that has won me a lot of trust with the folks that I've worked with. yeah, a lot of...

a lot of, I can't think of the right word, like good rapport when we head into really tumultuous times too. When we're saying like, hey, actually you guys just ramped up into this new campaign or this new process or effort, but we're going to pivot and we're actually going to go 180 degrees in the opposite direction or something like that. So yeah, leading with the why and setting clear expectations.

Carter (29:49.42)
Yeah, that makes a lot of sense. Well, I think this is pretty good. I'm going to end it here.

Kaylin McNamara (29:53.8)
Okay, great.