Lessons from Crossing the Series A to C Chasm with Ruth Zive

‍Ruth: Whatever assumptions you're making without having had that experience are probably wrong. So get in front of as many people as possible, really test that message and that value proposition, learn the sales motion. Then you can start to refine it.

Trinity: Welcome to The First 100 Days, a show for revenue practitioners by revenue practitioners, giving you unscripted access and tips to help you navigate any new transition or initiative both in life and at work. What assumptions are you making about your market today? More importantly, how often are you testing those assumptions. For our guests, the key to success as a revenue practitioner is constant experimentation. Ruth Zive is the Senior Vice President of Marketing for Ada, an automation platform that bridges the divide between brands and the people who love them. In this episode, she shares how she guided the company from series A to series C in just three years and how constant experimentation, and always backing into decisions with data is a secret to increasing your win rates.

You've been with ADA for three years, essentially help Ada cross multiple chasms. And as a marketer, like, everyone reads Crossing the Chasm. So the fact that you brought the company from series A to C and achieving the unicorn status in only three years, that's amazing. Is there any like tips or advice you can give to like marketers or even sales listening to this podcast?

Ruth: Every company is different. What I will say that it is that in Ada's case, the urgency from A to B was really more so around volume of pipeline. So how do I build out those systems on the demand or growth side to just put in front of sales as many at-bats as possible. That was the key driver from A to B.

That was, you know, when I arrived on the scene at Ada, I just knew that I had to throw as much crap up against the wall as possible to figure out what was going to stick. And then, I think, from B to C, I started to turn my attention to quality. So, you know, A to B we kind of turned all the faucets on and the water was flowing.

And then from B to C, it was more about, like, what's the quality of the water. Is it the cleanest, best-tasting water that we could possibly deliver to sales. And so we started to really refine our strategy, turn our attention more to brand, really define that ICP, and zero in on what was the best quality for sales and they were able to close with the highest win rates.

So, that was kind of our progression. And I think that that would be my advice right out of the gate. You really just want to pitch your company, your value proposition, as many times as possible because you can't, whatever assumptions you're making without having had that experience are probably wrong.

So get in front of as many people as possible, really test that message and that value proposition, learn the sales motion. Then you can start to refine it. 

Trinity: So I want to double click into that a little bit more. You say, like, a lot of assumptions that you had, or, like, whoever has it tend to be wrong. Right?

So that's what you want to keep testing and testing. So, the first question, was there any assumption that you came in or the company had before all these tests, testing, that turned out to be wrong? What surprised you essentially? 

Ruth: I'll give you an example, a sort of tangible example. We knew that we wanted to take on consumer-facing verticals.

We had some really great customers already in the travel and hospitality space, telco. We thought that banking, insurance, that those were going to be really ripe verticals for us. We didn't know what we didn't know. We struggled in the beginning to really position ourselves effectively inside of those verticals. We underestimated the compliance consideration.

We underestimated the complexity of the sales cycle, backend integrations. What we found after having lots of at-bats inside of lots of industries, because I didn't constrain my ideal customer profile by industry at that early stage, and what we learned was that we actually were most resonant and most effective inside of digital-first industries, industries like e-commerce for instance. So, we zeroed in on those industries. Now, that said, the pendulum's always swinging in marketing and sales between volume and quality and now we're revisiting those initial industries because we're much more mature, our product is more sophisticated and robust.

We have lots of backend integrations. We've met certain compliance thresholds. Once we understood the challenges in those industries, we could return to them. But I think that the takeaway is that in those early days, we really, the industries where we thought we would have the greatest traction were not the ones where we actually had the greatest traction.

I guess 

Trinity: it's 

a tricky balance because, for User Gems right now, we're at series A, We've spent a lot of time trying to understand, like, define the ICP, also bias, because my background's in product marketing. It's like ICP first. But then, what you said made sense, too, because at the beginning you're still kind of exploring and it's the early stage of, like, the growth, so you want as many people to know about your product as possible, and maybe there's someone outside ICP that's not ICP now, like in your case, like, financial services later on could be ICP. So how do you balance that without risking spraying and praying and just advertise it everywhere? 

Ruth: I think it depends on the stage of the company.

It depends on your resources. I would encourage everyone to make data-informed decisions so internally you have one point of view, especially in product marketing. Product marketing sits on my team. You know, you do a lot of research to try to drive the right conclusion, but the best research is really by going through the motions and putting yourself out there and having those conversations. Listen to the sales discussions. Do the analysis on the full breadth of pipeline and use that data to inform how it is you define your ICP. So, we were able to see that our win rates inside of digital first industries – like, e-comm or SaaS or FinTech, we had way higher win rates, deal velocity was much higher. Competitive win rates were much higher.

That data was, sort of, the "aha" moment for us. It was like, oh, okay, now we know what's working, let's really triple down on that, and then we can go and figure out how we can be more effective in those areas where we're perhaps falling short. And in order to 

Trinity: get that data in the first place, you, kind of, have to be willing to go a little bit broad, a little bit, just to get a data in.

Got it. Got it. That's great. So from like the B2C, when top of the quality, so essentially that's when you, kind of, hone in and define which industries. Are you still experimenting with other areas, or is C kind of like, now let's just scale 

up 

Ruth: what works? 

No, definitely not. I mean, I think what changed for us with the series C round is that we can really take, we now have the benefit of being able to take a longer-term view of the market.

So before the C, we were much scrappier and it was very much quarter-over-quarter and we'd plan maybe one year in advance. You know, we'd set the target and then we'd measure very carefully quarter-over-quarter. I think that the real advantage to having the series C investment is that we now have lots of runway to go and be bolder and longer-term in our thinking and our approach.

And so we can experiment more. We can make bigger investments. Absolutely not. We're going to continue, like, our bread and butter is going to continue to be where we've proven that ADA fits and the value that we provide. But how do we then expand that and take on – expand the total addressable market is really what I'm always thinking.

So we've played in a slice of the market. How do we continue to expand that market with new marketing experiments, new product, new ICP, new use cases. 

Trinity: So talk about the experiments. You say marketers should experiment with at least three to four demand gen channels before optimizing, essentially like recapping your journey from A to C, what has been your most favorite demand gen experiment?

Ruth: That's a great question. I do think you should always be experimenting. One great experiment that I introduced before I was at Ada, in my last role, we worked with a company called Do Good, and they set meetings for you with leaders in your space in exchange for a donation to the charity of their choice and do good organized the whole charitable piece.

I thought that was a really novel and creative way to drive interest, and actually delivered some interesting results for us. Also helped us to get to know the prospect a little bit, what they cared about. It was a great conversation starter. So that was a great experiment. I think that since COVID, we've experimented a lot at Ada with remote events, as have a lot of other companies. We actually launched our inaugural Ada conference remotely, a few months ago, called AC Expo. It was really a great success for more than a thousand registrants. So that was an experiment that paid off. And I don't know that I, we learned any big lessons with remote events. It was really an unexpected and exciting result for us. I think it was just a lot of hard work.

We really decided that we were going to prioritize our customer stories at that event and I think that that was really a big driver of interest. People want to hear from other folks who have experienced success. And so that seemed to really work well. 

Trinity: So a lot of companies are trying to do like remote events and then the remote, like all the gifting, and et cetera, but since everyone's doing it, it becomes, kind of, flat now at a lot of conferences. Was there anything that your team discovered in running the events or conferences that maybe surprised the team in terms of, like, ROI or feedback? 

Ruth: I think we're still learning. And I think as you know, this remote paradigm persists the appetite for remote diminishes.

I don't disagree with you. I think remote will continue to be part of the marketing mix. No doubt. But at Ada, I think, I think what matters is that we approach these activities very cross-functionally. It can't just be an events team in a room by themselves driving interest. It needs to straddle product marketing and the customer success organization and the BDR team that is critical in helping to promote, and sales to pull in existing pipeline opportunity and put it on their radar.

And so I think it's that cross-functional. I think actually this is a trend in marketing generally that everything really needs to be very integrated and coordinated. And the more that you can do that in all of your marketing activities, the greater, the likelihood of success. That makes sense. I'll tell you, I'll tell you one tip though.

One tip from the AC Expo that I think was super effective. We gave everybody a free lunch coupon who participated and we didn't make the coupon available until lunch started.

So that was really interesting. People stuck around until lunch. They were excited to get the lunch. We actually had very little drop off in the event, but there was a lot of appreciation from participants that we considered their lunch hour and that we were giving them something to enjoy during that lunch hour.

That is 

Trinity: cool because I always, I love the virtual conferences, but then how do you mimic the real life in person? And that is one of that. Oh my gosh. That is cool. 

Ruth: I can't take credit for that idea. That was my team. So, you know, shout out to the events team at Ada. 

Trinity: So to piggyback on, you just mentioned about having the business development team roll up within marketing, which I think now is becoming more and more common.

A lot of companies are transitioning BDR, SDR over to marketing. So has it always been the case where for ADA, that BDR rolls up within marketing and if not, how did you manage 

Ruth: the transition? It has always been the case pretty much at ADA. When I joined, there was one BDR and she was on my team. When I started, we have now quite a large BDR team.

I'm pretty opinionated that the function should sit within marketing. I think it really serves as a healthy, forcing function that drives better alignment between sales and marketing. It gives me a deeper line of sight into the funnel and the leads that I'm delivering to sales, and it gives sales a much better qualified meeting or opportunity because we've touched it several times before it lands in their hands and it meets a lot of other qualification measures. And so sales can focus on more down funnel activity, which I think is effective as well. So whether you're transitioning from BDR, from sales to marketing, or whether you're building it out that way right out of the gate, a few things need to be true in order for it to succeed.

The first is that you need a willing sales partner. They have to sort of buy into this paradigm. The second is that there has to be a clear progression path for BDRs into sales. Most BDRs do want that path available to them. So again, you need the sales organization to really be supportive of that. That is absolutely the case at Ada, which is great.

And my sales partner is extremely supportive of the model that we have. So, I think if those things are true, then it makes a lot of sense for the team to live on marketing. I 

Trinity: think the part about the career development path, I feel like for BDR, there could be so many different paths – could be sales, which is the common one, could also be like BDR leadership.

Or go into rev ops, sometimes even to marketing. So I feel like, that, as BDR rolls up within marketing, I'm speaking from a personal perspective as well. That's the part that keeps me up at night. How do we make sure that they get all the development and coaching so that they can choose and thrive in the paths that they select?

So, in your case, you mentioned that the sales team provide a lot of support so that BDR can transition to AE. Can you share a little bit more on how that cross-functional coaching 

Ruth: happens? 

The BDRs worked very closely with the AEs. Every BDR is paired to about three account executives, so it's not a one-to-one pairing at Ada.

I actually don't think a one-to-one pairing is healthy. I think it should be spread a little bit more thin, but not so thin that BDRs are overwhelmed with too many relationships or vice versa. But they're really working in lockstep with their AE to identify the right accounts. This is for the outbound function. To identify the right account, to pursue them the right way, thoughtfully, in coordination with whatever the AE is doing. And then as we progress a BDR through that career path, there's more and more opportunity for them to experience later stage activities, so they might join the AEs on their later stage calls. They'll get some of that coaching and training. We do have a progression at Ada where you start out in our mid-market organization and then you might move into leadership positions or more senior positions on that team. Then you'd move into the enterprise organization, similarly progressed through the tiers on that team, and then you would move into an AE role.

So there is a real progression of responsibility and the AE's are very involved in that. Then when BDRs are ready to move over, there is an interview process. They go through the same steps that a net new candidate would go through and the AE's help them with that process as well. I 

love 

Trinity: that. Thank you for sharing, because I think I might copy that progression path.

Previously, companies I worked for usually it's under sales – so, like, the coaching happens within the team versus this. I just want to make sure that there's this handoff. 

Ruth: I think it's not different when it sits inside of marketing. Like I said, as long as the sales leadership is supportive of that progression, it can still happen very organically.

But to your earlier point, I think there should be opportunities not only into sales. We have BDRs that have graduated into manager positions on the BDR team. I also have BDRs at Ada that have graduated into the partnerships organization, for instance, or onto the demand. Like I have a BDR recently who moved over onto our demand teams.

So there should be multiple career paths depending on the interest of the BDR, just like any other role. That's 

Trinity: great. I took so many notes when I listened to a bunch of podcasts that you did in the past. And in one that you mentioned that, like, marketers always need to be like learning and adapting, which like as marketers, we all know that. But I love what you said about marketer needs to really understand and be honest about what they're good at and then learn to broaden their skills, but don't lose sight of your core competency.

I think it's really great because a lot of the time we tend to focus on like where we can improve and trying to be good at everything. But as marketing leader, you can't be good at every single thing underneath it. So I'd love to hear your story, your journey, of like broadening the skills, but still not losing sight of your core 

Ruth: competency.

I'm definitely not good. I'm not really good at everything in marketing. Early in my career as a marketer, it became, it became clear to me that my core competency was writing. That was sort of my superpower. I always used to get feedback along those lines that I was a great writer. It came very easily to me and I built a whole business off of just that skill for a little while, but I also knew that I really didn't want to be a writer forever. I was curious about too many other things. So I used that skill is, you know, an entry point into new clients, new opportunities, new jobs, but I kept pushing myself into new areas, things that were really outside of my comfort zone that I didn't know that weren't as familiar. So I got on the front lines of the BDR function many years ago. I started to dig into product marketing and social. I even, very early in my career, I learned HTML and I built my own website and all of those net new activities were, kind of, anchored by my writing skill. I used my writing to really showcase how I could take on this new challenge and I don't think, candidly, I became expert in any of those other things, but I learned enough to become dangerous and to understand what expertise to bring onto my team that was really going to deliver what we needed. But writing always anchored all of my activities in those early daysand it's what gave me, frankly, the confidence to go and take on new stuff that wasn't as familiar or comfortable.

So, always come back to your superpower. Figure out what it is. What are you really good at? What comes easily? What do you love doing that you always gravitate back towards, and lean into that while you also grow those things that are less comfortable and familiar. Is there 

Trinity: anything you would have done differently if you had to turn back 

Ruth: the clock?

There's only one thing that I would have done differently and that would have been second guess myself less and take risks more. I played it safe for a while and some of that was just a function of circumstance. I was a new mom. I had a crazy life. I had a daughter with special needs. My attention was very much focused on my family and their needs.

And so my career, like, I needed it to be a little bit steadier, but looking back, it's not so much that I have regrets. It's more that I think I could have gotten further faster if I had been a little bit more eager to take on those risks and get outside of my comfort zone. So I had a bit of imposter syndrome as many women do, but that's a whole other episode, right?

Yeah. 

Trinity: One day I will do like a panel and invite all the female leaders who are super successful and we will talk about the imposter syndrome because I feel like every interview I've done so far, everyone says that a hundred percent. I can't believe it. When you said it, when everyone said it, I'm like, are you serious?

Ruth: We've all been there. And it's only after we've sort of realized, for me, like, so much later in my career that it was so unwarranted, but I don't know that I could have gotten there differently. Like it was only through those net new experiences and good mentorship and, you know, success through failure that I was able to really realize, like, what was I so scared of?

So that's why I don't really regret because I think it's a function of the journey. 

Trinity: So, for those that, like the Ruth of 10, 15 years ago, that's going through this right now and heard what you said and say, okay, I should take more risks. What are some of the things in terms of, like, risks that they should take?

Ruth: I think it's, like, it's very person specific, but I think it's don't be scared to take on something that you're not convinced you know how to do. The only way you're going to learn how to do it is by going through the motions and if you fail by the way, it's okay. Like that's your opportunity to learn.

That's how we get better is through those challenges and missteps and failures, frankly. So just take it on and if you're super scared about it, start small. Like, just think about like, what is something small? You know, building that first website – and this is honestly going back before websites were easy to build, we're talking like almost 20 years ago. I didn't know what the heck I was doing. I just sort of took on the challenge and did it in my bedroom in my spare time, because I wanted to learn, like, what is this all about? How do I do this? So, take the risk, figure out what you think you can manage within the context of your life, but don't be scared to do it.

That's 

Trinity: great. My last easy question is what is your number one do it yourself life hack?

Ruth: I don't know that I have life hacks for do it yourself. I think the best way to learn and understand anything obviously is to do it yourself. But oftentimes, if you want to move quickly or you need to move quickly, the best DIY hack is to find somebody who knows how to do it better and then get them to do it for you. If you can't get them to do it for you, then copy them. That would be my hack. Not everything needs a new playbook, you know, there's some things, yeah, you want to be fresh, you want to be innovative, but some things just work already and it's okay to copy those things.

Christian: Yeah,

I think Ruth, she's very, very organized in the way she presents information. Like you can see that she said she's really good at writing, and I think that just in structuring her thoughts in an instant. So that's why, let me talk about the three things I like about Ruth and the first one is, and this is how she 

Trinity: would answer. Yes, very structured.

I think that's why it's one of my favorite episodes. I think I tend to really like content, or just in general, the people who can structure their thoughts in kind of like almost like consulting, the management consulting style. Here's the umbrella. And let me break it down to you, one, two, three. And then let me double click into one and upclick to two and doubleclick to three. She's so structured and her thinking it's incredible.

And the second reason why I like it, it's because she gets into the details. It's not just like, here's the theory of how you can cross the chasm. She actually got into the details of what she went through from the series A to B and then B to C. And I feel like it's very practical and people can kind of reflect into their own journey and say, okay, where I'm at and how am I doing and what, compared to what she experienced, is there anything I can learn from her experience that

I can bring home. 

Christian: To the example at the conference. 

Trinity: Yeah, it's these little things, right? But these little things make the experience better and more personal. So is there anything else that stuck out to you, Christian? 

Christian: I think there was things that stuck out. I think the first part, it was just interesting that apparently the marketing skills around the family.

The mother does B2B, the daughter does B2C. I need to check out the Tik-Tok channel. 

Trinity: She's great. I did. I did check her out. Yeah, that is impressive. 

Christian: I think the other two things that I really liked was the always come back to your superpower because I think it also addresses the second, the second part that women so often, women mention, was the imposter syndrome.

I think it's a better way to dealing with it because, you know, you have your superpower. If you know, one thing where you good at, like, stay with that, to deliver the value there, but it allows you to branch out into other things and maybe you deliver, and maybe you don't, that's how you learn, but at least, you know, that you will always deliver value 

Trinity: based on this.

I mean, it's like the whole premise of Strength Finder, like the personality test to find out where you're strong, because society tends to be like, oh, you got to be good at, you got to always improve yourself, being like a well-rounded person. Right. But I think I really like a strength finders is just like, here's your super power and own that, but here are also like the areas that you need to be mindful of. But, hey, here are your super powers to always go back to it. Yeah. Yeah. I think it 

Christian: gives you the confidence. It allows you to do things. Yeah. 

Trinity: And also allows you to take more risks when you know that you have a route, so to speak, to come back, then you can try other things.

And well, if it doesn't work out too bad, but I will be okay because they have other skills. Yeah. I think 

Christian: it's important to say. The other thing I saw, I thought was interesting, was just the, actually that she actually made an argument for spray-and-pray in terms of it gives you insights into what is actually what it is that you should be focusing on.

Because so often we see the spray and pray approach as a failure of strategy. It can actually help you guide the strategy by getting the data points they didn't need in the first place. 

Trinity: I think it's, I took it more like experiment, try a lot of different areas, try with a lot of different, I guess, creatives or approaches.

And only through trying, like, trials and errors that you can find out what works for you versus I think the term spray and pray is more than like, just blanket it out to everywhere. I don't care what not. I think that the team went, to go from A to B, she said that it was mostly volume. I'm pretty sure it wasn't just like, let's just advertise the entire Facebook and see who requests them, alright. I'm sure there was already thinking in there, but just like more experimenting. Don't just stick with one and just keep experimenting. I think we discussed all of the areas. I mean we went in-depth about the BDR sitting within marketing, but I think we covered that in a number of episodes already.

Christian: Interesting. I mean, maybe it's because we do it and that's why it comes up in the conversation, but it feels like it comes up more and more in the conversation that is actually in marketing. 

Trinity: I do see that in a lot of, like, the CMO communities, this discussion of I should BDR SDR, ADR, I sit within marketing. I'm a hundred percent on the same thought, like, school of thought with Ruth – that, yeah, it helps with alignment, then sales focus only on closing these qualified leads and leave marketing to source leads, whether it's from content or like outbound from BDR. Like marketing sources, the entire pipeline sales close to the pipeline, so it makes things a lot easier whether it's 

Christian: inbound or outbound.

Trinity: Are you going through a major transition within your organization or your career? Do you have a first 100 day journey to share recently or in the past? If yes, I want to hear from you. Email me@podcastatusergems.com. And if you're looking for the ultimate revenue leader cheat sheets, sign up to receive them@usergems.com/podcast.