PandaDoc CRO, Nate Gilmore on building teams to support the revenue triangle


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Episode Outline

[04:39] Nate’s background

[07:16] How does one focus on team building, service delivery, customer experience?

[10:13] The ability to build a revenue engine that works with the product engine.

[11:18] Understanding marketing and sales channels as your platforms

[12:04] What to look for inside of an eCommerce transaction funnel or inside of a marketplace

[14:34] What could also serve as instrumentation panel for success

[16:35] How to ensure strategic direction is implemented

[17:04] The art of balancing competing priorities

[19:22] Use empirical evidence to decide stages of your opportunity funnel.

[20:19] Moving from discovery of that into something predictable, repeatable, and scalable.

[23:19] Begin the experiment for the best customer experience

Nate's inspirations

Brian Balfour

Barret Foster

Damon Schechter

Connect with Nate



Elias Rubel (00:02):

Hey there all you cool cats and kittens. And welcome back to another episode of best in SAS, where each week we take you behind the scenes from conversations with some of Silicon Valley's best and brightest operators and investors, crack a beer, get comfortable and join us on our quest to find the patterns and playbooks that accelerate the sprint to 10 million of that good stuff. That repeatable stuff, that stuff we call a R R. All right. So today I'm really excited to have, um, a seriously acclaimed revenue leader here on the show today. Uh, Nate Gilmore, he's currently the chief revenue officer at Panda doc. He's an investor advisor. He was a growth hacker and EIR leading, um, growth at 500 startups and their shares a team Nate, welcome to the show.

Nate Gilmore (00:54):

Thank you. It's an absolute pleasure to be here.

Elias Rubel (00:58):

So I love the fact that you're, you started off as lawyer. Um, and, and it makes a lot of sense now being involved with Panadol, but, um, how, how on earth do you go from getting your JD, being a lawyer and then, um, becoming a revenue leader?

Nate Gilmore (01:14):

Um, yeah, I actually, I went to Santa Clara law and graduated in the, uh, late nineties. Um, I, I think it starts with like, like recognizing at some point that you're sitting in the wrong seat and then wondering how the heck you get out of the seat into a different seat and then wondering which seat you should go to. Um, all of that happened for me maybe a year and a half after I'd passed the bar and was practicing law. And I was like, I, I'm not sure if I like, uh, this career path I'm on. And so I started the discovery path for where do I go next and found out that the law degree is insanely transferable, um, across a whole lot of different industries and functions. Um, and I, I did a bunch of inf like informational interviewing with a whole lot of different companies and like was, uh, blessed with a lot of generosity from, um, people in everything from corporate real estate to PR to, um, revenue leaders and got into business development and sales and joined an eCommerce startup back when they didn't call it SAS. Uh, they used to call it a, an application servers provider markets. So, um, joined, uh, a small startup. And that was my, that was my start into tech and revenue.

Elias Rubel (02:37):

If we still had to call it application service provider, that the podcast name wouldn't have the same ring to it. Correct. Yeah. And so what was it about that transition? Like what drew you to it and enough for it to stick?

Nate Gilmore (02:52):

I think ultimately, like one of the things that was interesting about law, I didn't spend a whole lot of time in corporate law. Um, I was mostly dealing with stuff after somebody had already tried to build something and it would kind of fallen apart and they were picking up the pieces. There's like a whole aspect of law, which is, you know, um, the, the, the business, the, the, the building of contracts and the kind of inside counsel side of law that I actually didn't get into. Um, I got into that much more when I got into startups and realized that, um, I could also do a lot of that inside, inside counsel work with them while I was also helping doing sales. So ultimately I like to build things and be on the, on the creative side of the business. Um, and I, I like to doing that on the business side more, and I've just found a legal degree to be very helpful to help

Nate Gilmore (03:49):

Move, um, uh,

Nate Gilmore (03:52):

Like coordinate the paths, especially if two different companies and like help them come together.

Elias Rubel (03:59):

Totally. So, and then now you're, you're a chief revenue officer, so you're overseeing both sales and market

Nate Gilmore (04:06):

Sales, marketing, and CS. Yeah.

Elias Rubel (04:09):

Perfect. I'm curious in previous rules, I mean, a lot of the time, and this seems to be less of an issue now that the kind of chief revenue officer role has become more of a thing, but it used to be that sales and marketing frequently would kind of be in their own camps and be at odds with one another. And wouldn't be partnered to the degree that they should be. I'm curious, like as a CRO, um, how you've seen that landscape change. And if you think it's gone to the point where it needs to get to for sales and marketing to truly be aligned.

Nate Gilmore (04:44):

Yeah. I think there's, there's almost two questions in there. Um, and one of them is, is we will try to answer both of them, but, um, uh,

Nate Gilmore (04:56):

I've, I've, I spent a lot of time in marketing. I spent a lot of time in sales and yes, um, when those two organizations get along and they hand off and they have great handshakes and there's actually like a certain amount of tension, I think that's where growth really occurs or having a healthy tension there when it gets unhealthy. That's when there's problems. Um, uh, from my perspective, especially early stage, um, I think in many ways this CRO role has, has come about for companies at the, you know, eight to 10 million, or even a little bit before stage, um, because also of the rise of the technical founder that, um, or two product founders that are just hyper product focused and they want, they want to partner with a business leader to help them scale the business side of it. Um, and for me, I've spent a huge amount of my career in SMB SAS, as opposed to enterprise where product driven growth is a key driver of that.

Nate Gilmore (06:03):

And so, um, having one revenue leader that allows the, the founding team to really stay focused on, on building the product business and building the, the product led organization, and then leaning on a revenue leader, um, to help scale the revenue organizations, at least that's my, that's been my experience here at Panda doc. And I consider myself to be a kind of a partner to Makita and Sergei is they, they do this, I kind of serve, I serve their needs and try and build the organization that is going to, um, be, uh, be something that can live whether or not they need a CRM, but that's, that's what, um, it's, it's like building these functional organizations that work together to build a revenue engine that works with the product engine completely. Okay. So,

Elias Rubel (07:03):

Well, before this call, we were, um, talking about how there are these bands and there maybe it's an overgeneralization, but for the sake of kind of breaking these up into pieces, there's the zero to 1 million revenue band, totally different set of problems than the one to 10 and the 10 to 20, if we were to simplify it in that way, um, for the purpose of this show, you know, we're really focused on post product market fit. You're probably somewhere around or over a million in ARR, and now you have your sights set on that first big milestone of 10 million. So I'd love to hear kind of w w when you jump into a company that is in that position, and I know Panda dock as well beyond that, um, what are the, what are some of the playbooks or thoughts and experience that you've brought from your prior engagements that you bring to a company like that, like, what's top of mind, what are the first steps that you take?

Nate Gilmore (08:02):

So I think in zero to one, it's like making sure you get that product market fit, and you've started to get a channel that looks scalable. One to 10 is really about scaling that burst channel and making it really predictable, repeatable. Um, and then starting to add the second or the third channel underneath that, and as click thinking of like your, your marketing and sales channels as your platforms, or your boards of revenue growth that you need to build to build a stable floor and just keep on growing the size of your house. And so in one to 10, it's all about getting those first channels, stable, scalable, and then predictable, and then starting to work on efficiencies. So, as I kind of like, think about that, like, like, especially in SMB, SAS, it's, it's, it's about funnels and it's about finding, um, finding what's, uh, what works building it, instrumenting it, and starting to scale it and watching it break down and fixing it and scaling it and watching it break down, but looking at your conversion points where it's, you know, lead to opportunity, opportunity to close or inside of an eCommerce transaction funnel, or inside of a marketplace, looking at like watching each one of these funnels.

Nate Gilmore (09:26):

And that's one of the main things that 500 startups coached in their growth accelerators is breaking it down into funnels. And then, and then, um, getting your kind of KPIs and your North stars inside of your funnels and, and watching those.

Elias Rubel (09:45):

Sure. So when you're thinking about new channel development in this phase, and you're testing for viability, how do you like to approach those tests? And at what point, I mean, it can be pretty painful when you're testing new channels and handing off those leads to sales to figure out if, if the conversations that you're starting are worthwhile conversations with the right audience, how long do you usually like to invest in the channel before you deem it to be not viable?

Nate Gilmore (10:16):


Nate Gilmore (10:17):

That's a really interesting question. Um, cause you asked the negative Gloria DEMA to be not viable. Um, so, so there's this, um, you know, I'm a really big fan of like Balfour Brian Balfour and the reforged method. I don't know if you've ever had him on your podcast or you consider that like, um, I actually, I don't know him personally, but, um, the, the, the model that he, that he put out with, um, early on when he was at HubSpot and they've kind of followed it up as like test iterate, continue to like build a hypothesis for a specific channel or for specific specific what you're spying to test on that channel. Um, and then build a hypothesis, test the hypothesis. And if you get return on it, can you scale it? And so inside the first pieces of the, of the channel is really, can you, um, uh, can you get some type of traction and then can you improve that traction?

Nate Gilmore (11:20):

And that's why I think, like designing the funnel, knowing which what you're trying to aim at, what, like, I have a hypothesis that if I, you know, uh, build this landing page, this specific way, my visitor to lead conversion is going to improve 10%. We'll do it, test it. Did it work great if, so, leave it in if not start to back it out. Um, and just a repeated, scalable, like testing scenario, um, an iterative model of, of looking at channels and always kind of trying to improve them. Because I think that the question you asked is like, when do you decide a channel? Isn't good. Like if you've tried everything, you can possibly try to get it to really grow and improve and you can't make it move. And it's probably not a good channel, right? But if, if you're getting market improvement with the things that you're working on in it, then you can continue to grow that channel, whether it's an inbound channel

Elias Rubel (12:16):

Channel. So I get to push a little further on that, because I think a lot of the time, one of the things that these early revenue teams struggle with is

Elias Rubel (12:25):

Figuring out the right way to

Elias Rubel (12:29):

This might not be the right way to phrase it, but like buy enough air cover to get run through those tests, even when you're not seeing what to kind of out on a holistic level is market improvement, but you might be making these little wins and getting closer and kind of proving out some of your hypotheses along the way, but to say like the CEO or the board, it's like, when the hell is LinkedIn going to work as a channel for us, you know, is it, should we take our spend and put it elsewhere just as a pseudo example? So how, how do you handle that? The kind of the relationship side of, you know, you're running through your hypotheses, you're trying to prove out a channel. Well,

Nate Gilmore (13:05):

It hasn't clicked yet. How do you handle that side? Yeah. So especially early stage when you're, when you're making a bet on a channel, they're like, okay, this is about the size of the bet that I want to, I want to make on that. And then, so it's a question of like, what do you think you're going to be able to get with that bet. You're not going to be maybe humble. We think I probably not going to get to predictable. Repeatables where I know how much money I can dump into this channel over time to scale it. But I want to, I want to build the box and the, the assumptions to be, um, uh, reachable for the amount of investment I'm capable of making right now and being able to set those expectations. Well, right. So like, if, uh, if the bet was, let's use your example of LinkedIn, Hey, we're gonna use LinkedIn sales navigator.

Nate Gilmore (13:51):

We're going to try and do some outbound. Um, the idea is we're going to invest this amount of time and this amount of money, and we're going to try and get somewhere close to this. Um, this return on leads, not necessarily revenue, let's say, let's see if we can get this, this amount of traction and leads, and then we'll figure out if we can turn that into revenue, um, at, at, uh, at the next part of the test, right? So I think a piece of this is, is really trying to understand what you're trying to accomplish at what stage of that sales cause just like we talked about, like one to 10 is much different from a sorry, zero to one is much different from one to 10, all channels start at zero to one, they all start there. So even if you're a one to 10 company, you're always at like, we're at paddock, we're adding a new channel now. And it's like, how much investment are we going to make in this? What are, what are some of the things we're really testing that? How do we know when it's going well? And how do we know that we're, that we're on the right track and we want to continue to plow money into this investment. We're at those are the, I think breaking it down is really helpful.

Elias Rubel (14:55):

So yeah, I really liked that. So now, but you brought up the next stage, right? You generate you're generating a bunch of leads and then you're saying, okay, well, how do they convert at that next stage? So in that handoff, I'm curious what you like to set up as far as the relationship, the mechanism of the handoff itself. So that, cause obviously there's a ton of great feedback that can be had when those leads begin to be qualified conversations begin to happen and you're trying to move them through the rest of the funnel. So how do you ensure that the feedback loop is there between sales and marketing?

Nate Gilmore (15:30):

Um, so at both 500 and at Panadol and candidly at Shipwire before that, um, one of the first things that we, that we've done is we've, um, uh, like designed what the, the, um, design, the language and what each stage means of our funnel. So what does a marketing qualified lead mean? Who's handling that what's the next step is the next step of, um, is the next step and opportunity, or is it, uh, a connected lead or something else? So like between sales and marketing, you literally map out the stages of your funnel and you define the Gates and what each gate means. And by doing that, you actually now have the agreement of, of what has to occur for that gate to have passed and who owns what portion of the gate. So, um, that I, I think is that helps, uh, design the, the, the, the conversation between sales and marketing.

Nate Gilmore (16:42):

Um, and it serves also as the instrumentation panel for success. So, you know, Hey, you know, marketing is going to generate this many marketing qualified leads as defined by X. At that point, either the STR team or the sales team is going to take it depending on kind of the type of the company, or I'm going to have a marketing development rep or a BD rep handling it through. And this is what the next stage looks like. And when did hands to a closing rep or a demoing rep or something like that. So every business is slightly different, but if you divide like design that it's absolutely critical. And there's a lot of blog posts out there on designing that funnel and those language of sales, qualified, lead, marketing, qualified, lead opportunity, and then the stages of your opportunity funnel. So you can look at those on the sales side, I think

Elias Rubel (17:33):

It totally does. Yeah. Thank you. So speaking of defining things, going back to this transition from one millionaire out of 10 million, and then there's some sort of defining moment, maybe it's not a moment, but it's a series of things that happen in general, the 10, 20 sprint looks different. So what do you think if it isn't that specific number, but it's kind of the culmination of a number of

Elias Rubel (17:57):


Elias Rubel (17:58):

What are those things that culminate together to change the game from 10 to 20?

Nate Gilmore (18:05):

Um, yeah, I think it's number of channels you're dealing with and whether or not certain channels are kind of like topping out, or you've got kind of a lot of, um, blue ocean you can sail into there. So like the question, I think a lot of companies, you know, Peter out at like seven to 10 million because they haven't found a channel to get them to the next growth phase. And so it's really adding another channel of developing it. Are you, you know, are you all inbound driven? Are you inbound and outbound driven? Are you review site and PPC and SEO, like adding all of those channels up? Are you generating great growth as you're, as you're moving forward? And then are you adding different? Um, typically one to 10 you might be focused on one specific type of customer or one specific size of customer. And then 10 to 20 are starting to add, um, you either can really grow in one particular either mid-market or enterprise or SMB are going to continue to grow into that. Or you're starting to add a little, like another cohort of customers that you're really gonna focus on and moving from discovery of that into something predictable, repeatable, and scalable,

Elias Rubel (19:23):

What are their systems? So let's say, you know, you, you crossed that milestone,

Elias Rubel (19:28):


Elias Rubel (19:28):

You sit down with the board and they're like, alright, Nate, what, what things need to change now in order for us to prepare ourselves for this next stage? Like, what are you rolling out?

Nate Gilmore (19:41):

Yeah. So, I mean, the, the board's job is to constantly be like pushing you for what is the next growth lever. And, um, and how, how do we, how do we approach that? How fast can we approach it? Can we do it faster? Um, and how much growth is there going to be? So like, um, you know, my experience at, at, at Panda doc is a balance of growth and efficiency. And literally they're like telling me, like, it's a, the balance is on the growth side, especially from my position. It's like, you gotta go grow. Um, and so, uh, it's all about looking at specific Understanding what opportunities you have in front of you and being able to figure out which ones are closest and most efficient for your team, that you can reach in this, and then whether or not something's further out that you need to go start building to get to that some of the thought processes that, that I'm actually going through right now as we're reaching for more growth levers. Interesting. Okay.

Elias Rubel (20:46):

So my last, before we transitioned

Elias Rubel (20:48):

To, um, winding down is around, um, going back to the negative. So what, what would maybe let's pick three, three things if you're sitting down with a revenue leader, um, let's just say they're, they're responsible for sales and marketing at a company that's in that sprint from 10 to 20, what are the three top three things you would say, you know, make sure you don't do these things, make sure to avoid falling into these traps. [inaudible]

Nate Gilmore (21:17):

Hmm. There's a lot of negative. Um, so avoid these things. Um,

Speaker 3 (21:31):


Nate Gilmore (21:32):

So avoid, um, uh, like one, one great question I'd love to ask myself is, um, if somebody else came in and did my job, what would I kick myself that they did next that I didn't do? And oftentimes you'll know what that is. Right. And so if you're like, if you haven't added a specific channel, don't wait, start that experiment. So like, like avoid, like don't, don't wait to start these experiments, get them going and start working on them. So you're constantly trying to like, crawl towards that next revenue that next, that next source of revenue, um, don't, um, you know, customer experience and, um, and you know, don't wait to, to start looking at expansion, don't wait to start looking to go, you know, up market or into new markets. Um, so all of these are like ways to get you out of your comfort zone and working on the engine that is most comfortable. And you're looking at, I think this is like what, like, um, a really healthy board is also pointing to the CEO and the revenue leaders going is what's next? How are you going to go do this? How are you going to grow? Is this, is this how scalable is this channel? How do you know how scalable it is? And it's all about getting you out of your comfort zone, make sense. So don't wait to get out of your comfort zone.

Elias Rubel (23:02):

Great takeaway. So winding down now, I like to ask, you know, who, who are the folks out there you've had an amazing career so far, um, who are the folks who have been inspirational to you or mentors folks that you look up to? They can even be peers.

Nate Gilmore (23:18):

Yeah. Um, one of, one of, uh, when I was at concentric networks, I still talk to a gentleman named James Isaacs. Who's now a CEO multiple times over. Um, and I love to when I get time with him, I love it. Um, I, you know, I, I, I said, uh, Brian Balfour is somebody I really look up to on the growth hacking piece of this. Um, I have not gone through, Reforge have not done this, but I've, I'm a follower of what he does and I really appreciate it. Um, I've never even met him. Um, and then, uh, from a coach perspective, I've, uh, there's a, the CRO at Reich is a gentleman named Barrett foster. Who's been very helpful, um, to me and helping point me in a lot of right directions. Um, and then one of, uh, uh, my last CEO at, at Shipwire, uh, or the only CEO I worked with at Shipwire was, uh, a man named Damon Schechter who, um, uh, was an amazing product leader who could, um, who built a very scalable and was willing to take on, you know, Amazon and Amazon's game, uh, in the fulfillment space.

Nate Gilmore (24:35):

And the team I'm working with now is unbelievable, unbelievable from Makita to surrogate, to the revenue leaders, like, um, Richard, uh, in, uh, who runs finance for us, just unbelievable leaders right now that candidly, I'm just learning immense amount from the team that we brought in here. And then the new VPs of product and sales and CS and marketing that we've had here feel very humbled to be, uh, working with this group.

Elias Rubel (25:02):

Well, Nate, I can't wait to continue to follow along with the Pandora Panda doc story as, as you build it up. Um, and thank you so much for sharing all of these insights with us today.

Nate Gilmore (25:13):

Thank you. Thank you for having this. I appreciate it.

Nate Gilmore (25:21):