Kirsten Newbold-Knipp, an original member of the Hubspot mafia (listen in for details), shares her in-depth knowledge of how to better unite sales and marketing teams.

She’ll share her insights from years in leadership at some wildly successful B2B brands: BigCommerce, Gartner, Hubspot, and Convey. 

Our conversation covers how to host great user events that drive intimacy with your customers (she started Inbound) as well as some indicators of when exactly your business is at the point to host a customer event. We’ll also help you think about how to measure marketing success and create an inter-channel connectivity as you grow your brand.

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In This Episode You’ll Learn:

0:00 Introduction
2:16 How to host great customer user events 
12:10 When should a business host user events?
26:20 How to have marketing work well with sales 
33:53 Where have you seen sales and marketing break down? 
40:59 Salty Six

Full Transcript:

DR: Today we’ve got a new friend of mine, right across from Proof office, we’ve got Kirsten Newbold-Knipp, who is the CMO at Convey, and since being the 99th employee at HubSpot, Kirsten has been a VP at BigCommerce, Gartner, and is now the CMO at Convey, which is a fast-growing software platform that perfects last-mile delivery for retailers like Eddie Bauer,, and Neiman Marcus.

And so we’re gonna get into Kirsten’s story here in a second, but before we do, as I’ve studied startups, I’ve found that there is a group of people who have changed the internet in massive ways that are affectionately or maybe infamously known as the PayPal mafia, and this is basically a group of the early founders and early employees at PayPal that have gone on to start huge companies like YouTube, Yelp, Kiva, Tesla, SpaceX, and several more. They have basically become this powerful unit out of this one single company, and as I’ve started to do “Scale or Die” and studied B2B SaaS, I’ve realized there is this same thing happening with HubSpot, and I’ve kinda started calling it internally the HubSpot mafia.

I think this is actually our sixth or seventh guest that had early beginnings at HubSpot. We had David Cancel from Drift, who was episode number one, Jonathan Kim from Appcues, Brian Balfour, Kieran Flanagan, a bunch of these folks are coming out of HubSpot, and it’s just amazing how much impact that that one company has and I’m kind of seeing the benefits here.

So I wanna dig into that, Kirsten, and find out a little bit more about it. I guess, in your opinion:

What was it like starting at HubSpot in the early days and then do you see that and do you feel that yourself? Is there kind of this mafia and this kind of zone of influencing happening all over the internet because of your time there?

KN: Yeah, I’ll answer the second part first, and say absolutely. Certainly what’s been really fun is a lot of the relationships that I built during those early days at HubSpot are ones I still have, and we have a HubSpot alumni group that participates on some Facebook groups, on LinkedIn.

We do little reunions sometimes, which are really cool, and even, it was funny, I was listening to a podcast the other day where Brian Halligan was talking about some of his experiences and when they think about the brand that they wanted to build, they even think about HubSpot alumni and what that does for Boston as a market or where I happen to be in Austin, any of the markets that we follow. But if you look at David and Elias at Drift, they’ve done amazing things.

Jonah Lopin at Crayon. Mike Volpe is now CEO of Lola. There are any number of HubSpotters whose careers I’ve followed that some are still doing amazing things at HubSpot, and as a shareholder, I value that, but many have gone on to build their own companies, do a number of things.

One of the weirder ones that you might not think of is even the HubSpot ecosystem outside it. There’s a guy who I built a good relationship with while I was there named Marcus Sheridan. He calls himself The Sales Lion, but he basically has built a whole series of content and education and training around how to sell the Inbound way and this gentleman who used to own a pool company has now gone off to form an entirely whole new training and content company and is killing it. So I think there’s some really cool concepts and great brains and energy around the HubSpot mafia.

So to go back to your other question, which is what was I doing at HubSpot, so I was employee 99 or 100, depending on the person, we sort of go, who signed the offer letter first?

But I was the head of product marketing, so I was the first product marketer that HubSpot hired and then built out the product marketing function, built out sort of the case studies and customer advocacy function, built out the events function, and actually sort of one of the probably most remarkable things that still remains that has some of my thumbprint on it is what is now called INBOUND.

A scene from the Inbound marketing conference

So the INBOUND event is over 20,000 people every year. I started it when I was about nine months into HubSpot as the first ever HUG, which is HubSpot user group. We eventually turned it into INBOUND, but was a huge effort, really fun, and very much scrappy startup get it done. Lots of fun stories about that event.

DR: So you launched the very first event–

KN: Very first. When we started it, it was actually really funny. I had been there about four months, maybe five months, and Halligan, our CEO, was like, you know, we should do a customer user group event, and product marketing was a good fit, but I also happen to have a hospitality and events background, so he was like, you know events, you’re product marketing, it’s you.

DR: Does anybody here–

KN: You own it. Anybody here done anything like this?

DR: Do you go to events?

KN: Right, have you seen one before? Do you know how marketing conferences work? Have you been at a hotel? So it was sort of like, Kirsten, you’re gonna do the HubSpot event. I’m like, all right. And we had started these smaller HubSpot user groups in local regional geographies, and we thought, gosh, this first one, it’s not gonna be a marketing event, right? We’re not going to generate new pipeline. We are going to really drive intimacy with our customers and our partners, so it was–

DR: Was it only for customers?

DN: It was primarily for customers. And that was the intent.

DR: But you weren’t like checking user IDs at the door?

KN: No, definitely not, definitely not. It was sort of like, if you want, if you’re a fan of HubSpot, you can come. And this is probably where the story gets funny. So I was month four or five into my job, and we picked a date. I had four months to plan this event. I do not recommend planning any event in four months, but–

DR: How long do you recommend?

KN: Between eight and nine months. I mean, ideally, you get a year, but you don’t need it. Eight and nine months gives you really ample time to plan. Four months, constraint theory, you will get it done, but it is gonna be painful, because I had almost no help.

Eventually, as we got closer, I sort of co-opted half of the marketing team to work with me on it, but for that early part, it was just me and then an intern, and what we built ended up being so successful. We had said 250 attendees, that will be success. And I found a venue, this and that, where everything’s coming together, content is coming together, and five weeks before the event, we hit 250 attendees. Well, my max capacity was like 275, and so I had some choices to make, and I brought two options to Halligan. I knew pretty well what he was gonna select, but said, “So, Brian, we can do one of two things. “Either we can call it done and just make it “really exclusive and this is such an amazing, “tightly-knit event”–

DR: Kinda call it concierge.

KN: Call it concierge-type, right, make people feel that this is just, like, gosh, you’ve got to get to it next year, get registered early. I said, “Or, we’ve got four weeks left, “and it will be really hard, but if you wanna “make it bigger, I may be able to find another venue.”

DR: Rent out Patriot Stadium and go for it.

KN: Huge! And Brian Halligan likes to go big, so he’s like, “Hell, I want more people!” So I said, “All right. “FYI, I’m gonna not do these two other things “so that we can do this,” which was great, ’cause we had a culture of kind of stand-ups and scrums, and we would say, you know what, this is getting de-prioritized so these other things can happen, and we ended up being slightly over 500 attendees for our first-ever event, which was, you know, blew out all of our expectations.

DR: How many customers did you have at the time?

KN: At the time, we already had several thousands of customers, and a lot of them were Boston-local, which was great, but what we hadn’t anticipated, and this was where it sort of came all together and I think why HUGS was able to become INBOUND over time, because by the second year, we said, this is, now, a prospecting event. The fandom that already existed around the inbound movement was huge. Right, we thought 250 based on X number of customers, this local geography, who’s gonna drive, who can fly. The number of people that flew in shocked us, right? It was amazing. The number of people that were close, but maybe four hours, and drove in and stayed overnight was really surprising for a day and a half event, so we were blown away by how much people loved both the inbound concept and HubSpot itself.

DR: What was that? Like, for other companies that are thinking about doing this, or trying to reproduce that, like, how do you reproduce that? What was really there?

KN: It is very hard to reproduce that.

I think those are, there are, and it’s timing, it is an ethos in the market, it is a sentiment, and it’s a culture. In this particular case, I think part of it was that we were trying to introduce a new way of thinking, right? So we were evangelizing, we were educating a lot as opposed to just pushing and selling, and that, I think, brings people into your orbit. We actually had, at the time, we were going for SMBs, including very, very small businesses. We eventually realized that really small businesses just didn’t have the resources to do Inbound right, so we could either punt them as customers or find another way to serve them.

We built a whole ecosystem of partners to actually serve them and serve them in a way that would work for them, and I think that by being really honest with some of these small businesses and saying, I know that you wanna buy the software, but I think if you can’t put this much resource against it, you will not be happy, you will not be successful. I would rather not sell you the software. I will introduce you to someone who can work with you on it, or, when you’ve hit a point of growth that this will make sense for you, let’s talk again, right?

We would turn away business and that created this trust that folks had, but then on the other hand, you also had employees that really gave a damn. I think there is something about, and you guys have this to some extent, serving small-and mid-market businesses, you truly care.

KN: What was interesting about that ethos and what you guys could potentially replicate as well, is that because HubSpot started with the SMB market and then moved upmarket, there’s this real idea that you’re helping a business.

It’s not like, oh, I’m helping GE or Amazon, which feels like this kind of entity that already is very successful, it’s like, I’m helping Jim grow his 10-person lawn care firm or I’m helping Mary improve her baking business, and if I let her down, I’m really sad. And that actual caring about your customer really came through in everything that we did, and I think that created that fan base.

DR: It seems like people started with I like the way these people think, HubSpot, I like the way they’re thinking, this describing the world the way I’m seeing it and feeling it, and then like past those, okay, I also like their software, where I think a lot of software companies just go straight to here’s our software and you skip over the indoctrination into how we see the world. It seems like that’s always flowed really naturally out of HubSpot. Is that kinda how you guys thought about it? Did you intentionally cultivate that? Or did that just kind of come naturally in your marketing?

KN: I think it was a little bit of a pivot in the sense that when Dharmesh and Brian first started the business, they actually were going for something more like, can’t remember how they exactly described it, but they thought they were building like the operating system for a small business, and it was like every application under the sun, and as they started getting into it, they realized, they were like, holy crap, that is super ambitious and crazy. And as they talked to all of the small business owners they were talking to, they realized that the biggest problem was getting found. Right?

Get found, and that’s actually a lot of the ethos around inbound is around get found, and that’s one of the modules of the product back in the day, so once they realized that get found was the problem, but that the way people were consuming things was changing, right, the internet changed how we search, and that the consumer is in charge of more of the journey down funnel, versus, right, we as the brands get to be in control. They said, okay, we’re gonna change and kinda flip the script on this, but they had to be evangelical because nobody knew how to do it that way. Marketers said, well, this always how I’ve done it, and in order to get people to buy into the idea, we actually had to say, gosh, we’ve got to teach them, we’ve gotta show them why, and it became an evangelical approach by nature, which is sometimes harder, but I think once you actually do get an indoctrination, people believe it and people actually have conviction and you’re no longer selling a commodity.

DR: Yeah, interesting. When do you think companies should host an event, like a user event? Like what stage, how should they think about that? It’s something that, we’ve kind of always wanted to do something big, you know, it’s like when should people be doing that and what should be the main purpose behind one of the first ones?

KN: I think it totally depends on your strategy. It’s actually something at Convey, right now, we’ve talked about to–

DR: Do you guys do an event?

KN: We don’t yet do an event, and part of it, sort of one of our founders wanted to do an event this spring, and once we peeled back the onion, I was like, “So let’s talk about what you think “the goals of the event are,” and we realized every stakeholder had a completely different vision of what an event was for. Our head of sales, 100% prospecting, right? He wants a prospecting event. Our head of customer–

DR: If they’re a user, he doesn’t even want them there.

KN: Eh, it’s like, he’s like he wants them there only so prospects can rub up against him.

DR: Yeah, yeah.

KN: Right? You know, our head of customer success, who’s one of our co-founders, he wanted it for customer intimacy, really sort of bringing those customers together, so his vision was something more like 20 people, customer advisory board dinner. Sales is like, I want a huge blowout, right? Marketing, I want something in between, because I think it serves multiple purposes, and I would say that we as a company don’t yet know what we need that focus to be, so what I’m actually looking at doing is in the, towards the fall, basically identifying what are the key elements that are really important for what the business needs to do in 2020? And what then should an event be in service of if an event even is relevant for us? And for customer intimacy, it’s fantastic. For partner development, events can be great. If you want to do a lot of prospecting, it’s actually really hard to pull that off without first building a community around your content, your thought leadership, your ideas, so thinking about it from that perspective, I think, is important–

DR: And do you feel like you don’t yet have that for Convey? So maybe–

KN: Not as much as we’d like.

DR: Start building that up and then push that prospecting event a year out, or–

KN: Yes.

DR: Just further down the road?

KN: Further down the road, absolutely. And I think that for an event like that to be great, you need to bring speakers and educators and insightful folks who are a mix of customers, prospects, industry thought leaders. That does not come without much budget, and I’ve mentioned in passing, some of our clients are very cagey about sharing competitive intel, so until we can cultivate a few of those who might be willing to speak, it is much more difficult to draw the attention of those folks that you really want.

DR: Okay, so you guys are just looking at it, we want to do this far out. Let’s work backwards, how do we kind of ramp up into that kind of event?

KN: Absolutely. And are there other things that we could do in the interim? So for example, because we’re enterprise in nature, when we attend other events, sometimes we’ll sponsor, sometimes we’ll just do what we call a salon dinner. And a salon dinner, literally, that’s this customer intimacy and prospect intimacy. We’re not pitching. We’re building relationships. We got 10 people having a really nice dinner at a nice restaurant talking about last-mile delivery, talking about the problems they want to solve. And those have been fantastic for us.

DR: Okay, so after HubSpot, you transitioned and got a really unique perspective at Gartner. So you were an analyst there, and so not only were you a marketer, but then of a sudden, you’re analyzing CMOs, right, and I’m curious what insights did you gain about the market, about the issues the CMOs were having about maybe the blind spots that they had, what did you learn from that that you’ve been applying now in your others roles?

KN: So, so much, actually. I would say, what was really interesting about the Gartner role was that you get to be a consultant without the terrible travel of being a consultant, and so you get to peel back layers at a bunch of different companies, and because we served primarily big-enterprise brands, some of whom are B2B, some of whom are B2C, I saw everything under the sun.

And I think the first thing that I saw that I’ve shared with a lot of the people I mentor is that everyone has imposter syndrome. When you look at some of these brands that you admire from the outside and you get under the covers with them, you’re like, wow, this is not what I would’ve expected. You’re not as mature as I would’ve expected, you’re not as buttoned up as I would’ve expected, your teams are kind of running in chaos, there’s a lot of waste, so I think thing one was–

DR: Even the big companies that you think have it all together?

KN: Absolutely, they do not–

DR: So good to hear.

KN: Have it all together.

DR; Yeah.

KN: So we, you know, everyone, I think, has imposter syndrome sometime in their career, and this was, it helped me get over almost all my imposter syndrome because I realized, wow, ton of people at the top of their game are still learning everyday, are still trying to figure it out, still don’t have it all buttoned up.

The second thing that I learned, and this was a bit surprising to me, partly because I got shaped so much of it, both at HubSpot, SolarWinds, and even BigCommerce, we had more, I would say slightly lower price points, a little more transactional model, and because of how we marketed, marketing was involved really far down the buyer’s journey. It wasn’t sort of, we deal with the brand and then we get you a few leads and we get you a few leads and then we’re out. It’s really marketing’s engaging throughout, marketing is nurturing, marketing is getting something to a certain status, and we’re having this super-tight handoff. When I looked at the brands that I was talking to and I would ask them, you know, CMOs, so how do you measure success?

What are you bonused on? How is your CEO measuring you? The number of them that literally were about brand and engagement shocked me to no end. Very few of them measured themselves on pipeline. Very few of them actually went down to revenue. And it was really only the most sophisticated brands that were actually thinking that far through and maybe that even had NPS or other customer satisfaction metrics that were part of the CMO’s scorecard. And what was so interesting is they were sort of like, well, I get them here, it’s everybody else’s problem what we do with them then, and I think–

DR: And how did they measure getting them here? Was it like just super top of funnel, they filled out a lead form, or was it even that far–

KN: Usually it was a, so let’s say it was a B2C brand, it might be brand awareness surveys, share of market, share of voice surveys, those types of things that are interesting but not necessarily indicative of total success. Some of them would have all the way down to share of market in terms of revenue that they were measured on, but it wasn’t necessarily something that then helped the rest of the operation think about well, you’ve got ’em to this level, what do I do now, which was pretty surprising. In B2B scenarios, often it would be very top-of-funnel lead count, and that was about it.

I had one CMO at a company that was something you and I never would’ve heard of, but it was a construction company, they made construction materials at a sort of enterprise global level. I think they were maybe $200 million company, so not huge, but sizeable, and her only metric was PR mentions, and she was the CMO. And it just sort of showed where the mentality about marketing for this particular entity was, so I think, lot of lessons learned around both what does good look like? How should you think about really measuring success? How do you build marketing metrics that reflect the strategy of the company and that can help the company grow? As opposed to sort of taking an order, and I’ve talked to sales leaders who say things like, I wish my marketing team weren’t just order takers, and hopefully, they’re collaborating with their marketing team to try and help them not be, but it’s also the marketing leaders’ incumbency sort of to say–

DR: Who do marketing leaders generally take orders from?

KN: Probably sales.

DR: Okay.

KN: More often than not.

DR: A lot of times, it’s sales saying, here’s what we need, we’ve got to have these requirements, then marketing has to kinda go figure out how to do that? That’s kind of typical, from what you’ve seen?

KN: That’s pretty common. That’s pretty common. And it is not the ideal way of doing it. It really should be a partnership.

Ideally, marketing is both involved in sort of corporate strategy, but also, or go to market strategy, right? How are we planning to develop this? And then working with sales on what are the right tools, assets, leads, you name it, needed to get there? You know the days of hey, I need a data sheet, I need a data sheet, I need a data sheet, those are really reactive and typically, one new data sheet isn’t gonna help you close 20 deals. That’s not the problem.

DR: What’s a data sheet?

KN: What’s a data sheet, that’s a great, it is a very old school B2B one-page document about your awesome product.

DR: Okay.

KN: Nobody wants a data sheet. It is usually–

DR: I don’t want a data sheet.

KN: You don’t want a data sheet. Almost always–

DR: I never heard of one and I don’t want one.

KN: When someone in sales comes and says, we absolutely need a data sheet on this, I cringe and I then step back and sort of try and figure out, well, what’s the problem you’re trying to solve?

DR: Yeah. So what is the role of some of these marketing tactics that are hard to measure, you know, the billboard, the brand awareness, the PR mentions, like these things that, they’re hard to track all the way down a funnel but still move the needle somewhat, how do you think about those and how should a company allocate resources, if any, to that?

KN: Goes back again to what’s the strategy we’re going after and how are we gonna measure success? I think that PR absolutely still has a huge place in broader awareness, and it tends to be something that, right, when I think about how am I measuring PR success, there’s not only the actual sort of quantity of things that occur, but how does that impact basically branded organic traffic, right?

What is my ratio of branded organic to organic traffic? Branded organic traffic is often very influenced by the PR halo that is created through all of the activities you’re doing. You can’t measure all of it, but there’s also the, go to a trade show, have you heard of us before, right? There’s some sentiment that certainly happens with it, but it does mean it’s very hard to say how many dollars should I invest against this, when it’s really easy to see every PPC dollar and what it results in–

DR: Yeah, I think we’re making a shift as a company. We’ve always been super data driven, like I won’t spend a dollar–

KN: Unless you can see.

DR: If I can’t see it come out as $3, you know, down the funnel within the next six months, and with “Scale or Die,” particularly, we’re in this uncharted territory, where it’s really hard to measure how well is this working and, you know, just ’cause the analytics, you can’t track a lot of stuff through iTunes and I can’t see all the way through, plus it’s like, you listened to a few episodes earlier this week, what’s the value of that? If Convey signs up for Proof someday, how much of it do we attribute–

KN: Attribute to that.

DR: It’s just like we’re in this new thing where it qualitatively, I’m hearing a lot of good things. I’m having having investors text me and say, hey, I listened to an episode and really liked it. What’s that worth? But it’s really hard to track down to the dollars, but we’re like, it seems like it’s a good thing.

KN: Yeah.

DR: And we’re in over our heads a little bit with thinking about how do we kind of track this.

KN: Track it. So I think, that’s why I think there’s sort of a bullwhip effect going on in marketing, and in fact, a lot of the marketers I worked with at Gartner had this problem, as soon as their CEOs, or their CFOs, often, would see, oh, I see you’re measuring ROI on all of these four channels, thing X, thing Y, add this, add that, right?

They’re like, why are we doing anything in events? Why are we doing anything here? Why are we doing, re-funnel all of that money into some of into some of these paid media that are super attributable.

Unfortunately, they are sort of missing the forest for the trees, and whatever you wanna call it, different people call it different things, but lift is maybe what, right, because everywhere you go, right, seven impressions, however many impressions it really takes for a human to actually engage with a brand and remember, what you’re doing in these other channels has absolute inter-channel sort of connectivity to the paid media that you have.

So we actually, probably one of the more interesting experiments that we have done when I was at BigCommerce, we actually turned off a couple channels, and it wasn’t immediate, but like three months later, the existing channels performed worse. And so there’s, once you’re at a certain scale, you can actually test a lot of that, and I would say, when I was advising clients at Gartner, really big companies have it a lot easier to some extent because they have the law of large numbers.

They could take a DMA, right, take a specific marketing region and say, I’m turning off all of my thing X over here, or I’m doing zero local PR in this market, and I’m gonna compare it to other markets. And they could actually see that maybe, gosh, our media spend is 20% less efficient in market X over market Y. I understand that my soft elements are creating leverage. I think in the size of business that you’re at, it would depend on hey, what are the other channels that we have going? How can we think about these channels interacting? And probably the most important thing is to ensure that there is a cross-channel strategy, that “Scale or Die” isn’t sort of like, it’s its own thing that sits by itself. How do you ensure that people understand that it is part of Proof’s ecosystem and that that sort of attributes back to you and accrues back to you in some way with the message that’s really valuable.

KN: Yeah, I think with some of these things, they’ve started to act on certain principles that we believe to be true–

DR: And started going with our gut, and we say, okay, with “Scale or Die,” are we having fun doing this? That’s gonna come across. Are we meeting potential future customers? That’s gonna come across, or are we, is this gonna be part of the top of funnel strategy? Just in principle, “Scale or Die” makes a ton of sense to us, and so we’re kind of saying, okay, let’s do this for six months, 12 months, and see kind of, I think at that point, we’ll be able to see some of the actual metrics on it. I don’t know, I guess I think, as I look around, everyone’s so metrics-driven, and we love it, we geek out over that stuff, you know, we’re on Amplitude all day trying to hook up every little thing, but I think there’s become more space available for just taking some risks and going with your gut and saying what is good marketing? What are we trying to do here? And, I don’t know, it seems like it’s opened up a little bit more because everyone’s shifted so hard over to data, data, data, data, data.

KN: Yeah, I think that it’s like anything, it becomes cyclical, sort of goes back and forth a little bit, and I think it depends on the brand that you have, the board that you have, the leadership team that you have and what their comfort zones are with that.

Some people that I talk to have very little flexibility to experiment, and others, and I would certainly say the leaders, typically are either literally carving out budget, carving out time, carving out mind space to actually do some experimenting, because you don’t know what’s really gonna work or not, and sort of coming up with an innovation that is great for your audience, exciting. But a lot of your tasks aren’t gonna work. That’s the other thing, right, there’s the creating a culture where failing is okay.

Fail fast, don’t make the same mistake twice, but be able to take a risk.

DR: Yeah, totally. So I wanna talk about the relationship between sales and marketing.

KN: Yeah.

DR: We don’t have sales here. Feel like this is your jam, how to have marketing work with sales well, how to create agreements there, how to create handoffs well, talk to me about what do I need to know as we think about building out a sales team and having that work well with marketing?

What have you seen? What are you guys doing at Convey? And what works well there?

KN: Yeah, so at Convey, actually, we have, what’s been nice, so I started about 10 months ago, and sales used to run marketing, because it was a really small marketing team, and so there were already really, really good ties between the two people on my team that I inherited, both of whom are fantastic. I was so thrilled to be able to grow them and the team. We’re now physically separate teams, but we sit side by side, and we have sort of created, and I’ve now actually even got my head of sales, Chris, saying the words, “We’ve got smarketing culture.”

And I was mentioning that smarketing is something that, I don’t know if we invented or not, but at HubSpot, we use the term smarketing, and one of our first sort of sales advisors and gurus, who’s still engaged with the company, he’s amazing, a guy named , who would be really fun to interview, actually.

DR: Okay, is he here in Austin, or–

KN: He is not, he’s in Arizona.

DR: ‘Kay.

KN: But he travels a lot, and he’s amazing, and I bet there’s a way to hook that up, so–

DR: All right.

KN: Love to help you with that.

DR: That would be great.

KN: But Dan Tyre sort of created this culture of smarketing, and we cultivated a place where not only were we meeting frequently, but where we sort of understood what do we think the buyer’s journey is, right, and that’s maybe the first and foremost thing to map out. Your buyer’s journey at Proof is gonna be different than our buyer’s journey at Convey.

So what does the buyer’s journey look like? What are the most logical touchpoints for marketing, and how do you think about, well, where is the handoff into sales? What does our buyer want, right? Do they want to get a call up here? Do they not wanna engage until later?

Depending on the persona that they are, that may vary, but maybe, to me, one of the first and foremost things, particularly in a B2B sales cycle, is that marketing actually take responsible beyond the lead, and I have a pipeline responsibility goal. I also have a revenue goal, but that’s a smaller part of how I’m measured, but my pipeline goal is a pretty big piece of how I’m measured from a success standpoint.

DR: And so how do you guys define pipeline? Does that start at the lead and end at the sale, and everything in between is the pipeline?

KN: So the way, we actually, we have different stages, so we have a six-stage pipeline. Stage one is really, it’s still a suspect prospect. They’re actually a lead that we have sent to sales, so it’s an MQL. Sales will accept that MQL if it’s an SAL. That’s stage one. If they see our MQL and they’re like, no, that’s a terrible company, I can see already this is bad, they’ll kick it back.

We have a pretty high threshold for what we send, so that doesn’t happen very often, but from stage one to stage two is actually being able to connect and set a meeting. Until they have a meeting where someone is willing to have a meaningful conversation, sort of post-discovery, it doesn’t go to stage two. Only when it hits stage two for us does it qualify as actual pipeline, meaning that that sales rep has had a conversation with Dave, he’s identified that Dave is not our buyer, but gosh, he could be a great champion, he’s at a company that does have a business problem, and I have a rough sizing, right, is this a $20,000 deal, is it a $2 million deal, and I can put a number that is still a guestimate, but a number, into our forecast that is, you know, it’s discounted down to, you know, it’s like 10% forecast against that number, but until we have a number that goes in the system, it’s not considered pipeline yet. So that’s the stage of–

DR: And that’s them saying, if we land this client, it will probably be worth about this much.

KN: About this much, yeah. And from there on out, it is much more sales-driven, but marketing’s still engaged, right? We’re providing them maybe with content, with engagement, with, we actually even recently added the concept of an executive sponsor, not for all deals, but particularly for really big deals, because I have a marketing background. If our champion is in the digital space, I’m the logical executive sponsor, and I’ll sort of co-travel a deal with a sales rep to really help nurture it and build an executive relationship with the client.

If it is a very technical sale, our CTO might be the executive sponsor, so we’re doing a lot on our very biggest deals to sort of keep nurturing down funnel, whether it’s marketing or the rest of the company, but from pipeline on, it’s much more sales responsibility. Us to pipeline, there’s a lot of engagement. In particular, right at that spot, in fact, I was telling Austin earlier this week that I had a little bit of a come to Jesus with my partner in sales because we were seeing things that, yeah, we have an SLA, and it’s less about gosh, did you do it in two days or not. It’s more about are you having urgency, are you working on great-quality leads that are coming in and we saw a bunch of really phenomenal conversations that myself, my CEO, and our head of sales had had an event that were not being followed up on. And, right, just like any startup, we’re fighting for every ounce of revenue, right? If you let those go cold, those opportunities are totally gone.

DR: So you said SLA, so you guys sat down, you kinda said okay, here’s what we think we can provide you and he kinda comes back and says okay, well, we need this and that, and you say, okay, I can do that, but I need you to follow up. That seems like a really critical agreement–

KN: Yeah, super critical agreement.

DR: To have.

KN: Right, we say, if pipeline needs to be, call it, I’m gonna make up a number, pipeline needs to be $4 million going into Q2, and we said, in our case, we said, you know what–

DR: And that’s $4 million if you added up the dollar amounts of those–

KN: You added up all the dollar amount of those potential deals.

DR: There’s $4 million in here right now.

KN: $4 million in here right now. And of that $4 million, you know, X number will melt out and we’ll nail one or two million, let’s say. Let’s pretend that that’s–

DR: Check.

KN: So then we say, great, marketing’s gonna contribute 50%, sales is gonna contribute 50%, that’s our goal. And not every company is a 50/50. Many companies have like 20% marketing generated, 80%. It varies–

DR: What does that mean, marketing would generate 50%, like don’t you generate all of it?

KN: Meaning that they’re coming from our leads, our sales, our–

DR: Because sales is also doing outbound?

KN: Sales is also doing outbound, correct.

DR: Okay, but if it was all inbound, it would be 100% marketing.

KN: If it it’d be 100%.

Precisely, which is where, like at HubSpot, one of the reasons this probably became my ethos is we were all inbound to begin with. We later added some outbounding and partner channel, but to begin with, it was all inbound, so if marketing wasn’t producing it, sales wasn’t getting it.

So in this case, right, enterprise, it is much more common for there to be more sales outbounding, but so we agree on what our split is. From there, we back into if we have these conversion ratios, then this is how much we should be putting in at each stage, but what we observed is that our conversion ratio compared to historicals was going down at a certain stage in the funnel.

Peeled back the layer and said hey, we’d already agreed that you guys are gonna work on it two days, we’re gonna do this, it’s not happening, right? Stuff is falling on the floor. Do we need to add more PDRs? Do we need to add more, and it’s not a you’re bad, it’s more of a it’s not working, how can we make sure it works? ‘Cause the conversion ratio is decreasing even though we actually increased quality.

DR: Interesting, and if they let those fall through the cracks, again, no one’s fault, just fix the problem. If those fall through the cracks, that’ll reflect on you and your team and your metrics.

KN: Absolutely–

DR: Because you’re not getting the sales.

KN: And the whole company. We’re not getting the pipeline built, which is an early indicator that we’re not gonna sell, right? And all of those opportunities that are actually there for the taking aren’t being worked.

And what was interesting is we identified two process problems that were unbeknownst to us and then one culture problem, and both things have been addressed, and actually in the last three weeks, the company, between both sales and marketing generated, has built more pipeline than we’ve ever built in any stage in the past, right, so–

DR: Very cool.

KN: Needing a tough conversation, but not a I blame you conversation, very much a something’s not working, let’s drill down, let’s look at the numbers together. Let’s understand is it behavior, is it process, is it tooling? And it could be any number, and we found literally two process items that just had created some issues.

DR: Where have you seen sales and marketing break down at other places?

KN: Lot of areas. Probably the first one is when it becomes a he said, she said or a blame challenge sort of issue, right? I could’ve probably gone into this tough conversation with my head of sales and said, your team sucks, they’re not doing their jobs, you need to shape up or I’m gonna go tell the CEO, right?

That could’ve been the conversation, but that would feel very juvenile. Instead, it was, this isn’t working, we have a problem. Here are some things I’ve identified. I’m not gonna say it’s one person, one thing. It could be lead quality. I need you to tell me if that’s what it is, but let’s drill down and figure it out. P.S. safe space conversation.

It was some of the things that I shared with him, I’m like, nobody else is ever gonna see these numbers or these things, like, we’re gonna solve it. If we can’t solve it, then we could ask Glaid, but we don’t need to ask Glaid. I know you and I can solve it together. So I’ve definitely seen people play the blame game. As well, there are also areas where maybe you have a sales team that isn’t process oriented and that won’t adopt a process, and that’s really hard. In today’s day and age we have so many tools to help us do a better job, and if we’re not able to see in the tools themselves what people are doing or not doing, and it’s sort of like, I’m a sales person, I go into my corner, I pick up my phone, and I do my thing without reporting out on any of it, we can never know what is or is not working, and that becomes really hard because it’s sort of a black box when there’s no communication between the teams.

But similarly, I’ve also seen sales organizations that look to marketing primarily as a collateral engine, and they’re just saying I need data sheets–

DR: Give me this, give me that.

KN: I need brochures, I need you to make a pretty booth. If that is all they believe marketing has to contribute, which is generally not the case, then it’s already gonna create a relationship that’s suboptimal.

DR: Have you found, this is something I’ve seen and heard, that when buyers in B2B SaaS come into the market, they’ve already checked out companies. Sales is not this thing that it used to be, where it’s like I’m gonna come in, I’m gonna tell you about us, and I’m gonna sell ya, I’m gonna move you across the line. It’s more so, hey, I’ve already looked at you, I know everything about your product, I know everything about your competitors, got a few questions, is this right for me? Have you guys found that to be true?

KN: To some extent. So I would absolutely say that’s the sort of, as sales and marketing become more inbound, people have so much access to information early on in the buyer’s journey–

DR: Because of things like Gartner, because of G2 Crowd.

KN: Absolutely.

DR: Because of these things, it’s like–

KN: TrustRadius, you name it.

DR: I’m not gonna get on–

KN: Total–

DR: Without knowing a lot.

KN: Exactly. I know a good bit. Now I will say, our category is quite complex, so there is a lot you can’t know until you get into a conversation, and/or, right, they’re sorta saying, I’m trying to compare you to party X, party Y, party Z, and we have competition, but none of our competitors are, who have square, head to head, we all do the same thing, so there’s like, we do these five things. This company does two of ’em, this company does one of them. And they do three others–

DR: And I bet in your space, there is a lot less transparency. You had a website, and it’s gonna be like, we’re not gonna show you the product. You’re gonna have to fill out this form, we’ll hop on a call–

KN: Exactly. Not to mention, if you were to demo our product, for example, without context, you would not know what you’re doing. You would be like these are, so great UI, easy to use once you understand what you’re trying to achieve with it, but it’s not something that is self-service, you could just log in and immediately know what to do. Because as well, you have to connect APIs from a bunch of carriers, from your own order management system.

Until you do some pretty technical heavy lifting, the product has no value to you. So there’s, from that standpoint, we absolutely are, sales is engaging later in the buying cycle than it was, but maybe not as late as something like Proof, where sales never engages, so far, because you can self serve all the way through. But certainly, there’s actually a lot of research talking about how that’s changing, and how far along the buyer’s journey B2B buyers are before they choose to engage with a sales rep.

And I think that means that that’s why also sales reps have to change their behavior and sort of look at gosh, what are the 22 pieces of content that they’ve looked at before they decided to pick up the phone and let me call ’em.

DR: What are the biggest metrics that you and your team are measured on and track, when you’re just like–

KN: Number one is pipeline. And it’s sort of–

DR: And how much, and that’s just your pipeline, pipeline that’s attributed to marketing.

KN: Well, I would say, I look at all pipeline because I care about the whole company, right, and are we succeeding? And even if, it’s interesting, where we actually had this conversation the other day, even if marketing hits our pipeline number, but if sales hasn’t hit theirs–

DR: Still a loss.

KN: I’m not gonna celebrate. Yeah. I’m gonna be like, okay, we hit ours, stuff is working, what can we do to help over here? If it was like this, then I’d be like, okay, sales, how come you guys are doing so much better on pipeline on your side? What can we learn from you?

Right, because ultimately, we together wanna hit this one pipeline number that means we’re all gonna hit the goal. So pipeline’s number one. Then we have some leading indicators into pipeline. I would say, pipeline, and then ironically, brand awareness, while a vague phrase, there are a couple of things that we specifically are trying to do. We’re in the–

DR: You’re back to brand awareness.

KN: I’m basically category awareness. We’re trying to create a category called delivery experience management, and to the extent that we can actually start building traffic around a specific key word term that we are attributing meaning to and get, literally, there’s things as fuzzy as if an analyst says it back to me, right?

I didn’t tell you I’m a delivery experience management company, but you tell me, hey, I heard of somebody looking for a delivery experience management solution. When we hear that, we know we’ve succeeded in creating a category, just like a HubSpot created inbound marketing.

Maybe one of the hardest things to do, but there is an aspect of sort of brand and category awareness that we’re looking at right now, and there are hard metrics and soft metrics you can put against that around traffic and the like, or some of the sort of , and pipeline. Those are the two–

DR: That is fun to hear back the word you’ve been trying to pump in. We came to this with, we called it social proof marketing. I mean, a few years ago, that wasn’t a thing. It was like, you add social proof to some things And then we’re like, social proof marketing–

KN: Marketing.

DR: And it was probably like six months ago, I was talking to someone, they were like, they were looking at us like, hey, I’m trying to shore up my social proof marketing and I’m looking at different tools, and I was like, what? Like two years ago–

KN: No one would’ve said that.

DR: No one would’ve ever–

KN: Right, no.

DR: That wasn’t a thing, there wasn’t anyone to look at, it was just like, this is amazing–

KN: It is.

DR: That this is now this thing you’re saying back to me, so–

KN: Isn’t that exciting?

DR: I know the feeling, so exciting.

KN: One of our customers, actually, it was, we were at the Home Depot, and a very senior leader, we presented them something, and he literally said, “Delivery experience management. “I like that. “I think I’m gonna steal it.” And I just said Hallelujah. Say it all day long, right, please go preach to the choir on our behalf.

DR: That’s hilarious.

KN: Yeah, it’s pretty cool, so–

DR: Very cool.

KN: So yeah, those are my top two, and then we have lots of subsidiary metrics, right? MQL velocity, quality, quantity, conversion rates for different channels, you name it.

DR: Those are all leading–

KN: Leading indicators–

DR: Up to those.

KN: Into what’s actually happening pipeline.

The Salty Six

DR: Very cool. All right, well, we need to wrap up here, and we always wrap up with the Salty Six. You’ve heard some of these on past episodes–

KN: I have.

DR: I switched ’em up for season two, which we’re in season two right now. This is always my favorite part. Not that I don’t like the other parts here, but the Salty Six, are you ready?

KN: I’m ready.

DR: All right, number one, what do you do for fun?

KN: Mostly, I cook and I drink wine.

DR: Nice.

KN: And I play with kittens, so that’s a, but those all go hand in hand.

DR: I feel like that’s all one night.

KN: It is all one night. It’s all one night. The kittens come over and they wanna snuggle while I’m cooking, and I love food, so my first career was in hospitality, and I am a total foodie. Love to cook any number of things. We had a tamale party a couple of weeks ago. Intimidating food category to make.

DR: Wow.

KN: But delicious, and not as hard as you think. If you ever need tips, I’ll tell you.

DR: And what favorite wine do you drink?

KN: My number-one winery is Ridge, and they make an amazing zin. The best bottle that I love from them is called Monte Bello. Awesome.

DR: Okay, Monte Bello. We’ll put that in the show notes here.

Okay, number two, do you have a morning routine, and if so, what is it?

KN: So it’s a sad time. I used to have a great morning routine that involved like six days a week some sort of workout, ran with friends three days a week, went to the gym. I have a back injury, and currently my routine is to do physical therapy exercises, and that’s all I’m allowed to do. So I’m starting to go a little crazy because it’s been three months since I’ve gone for a run.

DR: When will you be back out–

KN: Unclear, there is an MRI in my future.

DR: Okay, all right, but exercise in the morning or doing something physical–

KN: Exercise in the morning, yeah.

DR: Okay, number three,

How do you focus during the day with a lotta stuff coming at ya?

KN: Not well, not well. Probably the thing that I will tend to do most if I really need focus time is, you know this, we have a balcony on the other side. I go to the balcony and I ignore things, and I just crank on something on the one screen–

DR: The one screen is helpful.

KN: The one screen helpful, right? You can’t multitask as well. You’re sort of focused. There are certain pieces of work that aren’t great on one screen, but for certain things, it’s really focusing.

DR: I agree, yeah. Two screens is nice for copying stuff over, but when I gotta do, I do the same thing. Pull off the extra monitor, you go to one screen, and you just work.

KN: Yeah.

DR: Okay, what is a book that has impacted you deeply over the last few years?

KN: So it’s an oldie but goodie, and when I think about marketing, one of my favorite books for marketing is Al Ries, “Positioning.” It’s a classic, and it has so many things in it that are really, really valuable, so I go back to the classics to some extent.

DR: I read that a couple years ago. That’s where he talks about Avis versus–

KN: I think so.

DR: Whatever the number one is, yeah, their positioning–

KN: We do it better versus–

DR: Yeah, yeah, yeah, we try harder.

KN: We try harder, yeah.

DR: Yeah, it’s like, we may not be better, but we try harder–

KN: Harder.

DR: And that worked.

KN: It worked.

DR: Which is cool, we were talking about that the other day.

KN: Absolutely.

DR: Okay, cool.

What’s the best purchase you’ve made recently under 150 bucks?

KN: I have two. One, I love my AirPods. I thought I would lose them. They’re fantastic.

DR: Love ’em.

KN: The quality of sound is shockingly good to me. And the other are really inexpensive, kitten toys. Our kittens love, we have these little, tiny little fuzzy mice that have a little rattle inside. The endless hours of pleasure from about a dollar, it’s really good.

DR: That’s good. Yeah, I fell asleep with my AirPods in last night. Woke up, they were still both in and my ears didn’t hurt.

KN: That’s surprising, ’cause it seems like it would like–

DR: Seems like it would, but they’re just so well-designed–

KN: Do you sleep on your back or your side?

DR: I’m all over the place. I’m like upside down–

KN: That’s impressive.

DR: Yeah, it was awesome. I was like, these are really cool.

Okay, the number six of the Salty Six, what’s one trait or characteristic you have that has led to the success that you have today.

KN: It’s, I think it’s one that is for so many people, it’s around drive. We talk a lot at Convey about skill versus will, and though we have lots of smart people and lots of great skills, you can have all the skills in the world. If you don’t have the will, you won’t succeed. And I’ve definitely had folks have worked for me, sort of be like, wow, you’re constantly going, you’re always, you know, you’ve got so much drive, is pretty much what I would. I have some other unique attributes, but that one’s huge.

DR: Where does that come from for you? Like why are you so driven?

KN: I think it’s cultural in my family. My dad was super hard worker. He was an immigrant from Germany when he was 17, no college degree, no anything. He started from basically peeling potatoes at the Royal York Hotel in Canada and made his way up to general manager of an entire hospitality company, right, so self-made man, and I saw what it took for him to succeed, and I think that sort of instilled, we’re like, that’s how you do it.

DR: So it’s more normal for you to be this way than–

KN: Than not.

DR: Yeah, to not be.

KN: I literally don’t understand if my husband’s out of town and I’m home, I don’t sit down and watch TV, because that’s just not something I do. Maybe I’m calling a friend or I’m working on the garden, or I’m doing work, or working on one of our many, we have several side hustle businesses, so there’s always something that you could be doing to progress yourself, your career, your life, your family, your friends.

DR: Yeah, I was talking to my dad last night on the phone, you know, we talk once a week on the drive home. We started this whole tradition, and he had just sold off, he sells insurance, and he’d just sold off part of his business, and then he was telling me he’s just hired a consultant to train him on new prospecting methods, and I was like, and he’s gonna retire in like five years. I was like, prospecting, and I was like, Dad, what are you doing, he’s like, this is what I do.

KN: Yup.

DR: He’s like, you sell off part of the business, he goes, and I’m diving back in. He’s like, I don’t know what I would do otherwise.

KN: Exactly.

DR: It was like, it’s just such a good perspective for me to see, like, this is just what you do.

KN: It is what you do, and maybe you change slightly how you do it, but I think a lot of people, when they stop working, stop having fun, or stop seeing certain things, depending on what their hobbies are, and drive.

DR: Yeah, yeah, totally.

KN: What you do.

DR: Very cool. Well, Kirsten, this has been awesome. I learned a ton about, especially about the sales and marketing relationship as we start to kind of implement that at Proof, so thanks so much. If people wanna look you up, find out what you’re working on, where can they find ya?

KN: They can find me at, they can find me on LinkedIn, and they can find me on Twitter @kirstenpetra, so.

DR: Do you tweet hot takes on Twitter?

KN: Not often, I’ll admit.

DR: Is it, now do you think of Twitter as personal, or is it more business?

KN: Twitter’s more business.

DR: And do you have a place where you do personal?

KN: I’m nerdy. I’m still on Facebook.

DR: All right. I’m still on Facebook, too.

KN: And people that are like, I have friends in London who have babies, how else am I gonna see the babies, right?

DR: That’s true.

KN: I need to see the babies, the kittens, the families, and Facebook’s great for that.

DR: Okay, very cool. Well, thanks so much for watching. This has been “Scale or Die.” We’ll see you guys in the next episode.

This interview has been edited and condensed.