#122 What Leading Sales for 6 Months Taught Me About RevOps– Nicole Bradshaw (PandaDoc)

Janis Zech: Hello, and welcome to another episode of the RevOps Lab Podcast. Unfortunately, Philipp's out. He's never out, but he's actually taking a week off vacation, which is very well deserved, to be very honest, which means you have to, you know, spend the next thirty minutes with me and our guest, Nicole Bradshaw. Nicole, great to have you.

Nicole Bradshaw: Thanks, Janis. Good to be here.

Janis Zech: Yeah. Thanks for joining. Super excited about this episode. So before we kick off with the topic, who are you? What do you do? Tell us a bit more about your journey.

Nicole Bradshaw: Yeah. So Nicole Bradshaw, I'm out of the Nashville, Tennessee area. I started my tech career at part of marketing automation when it was a forty person startup, actually as a CSM, asked a lot of questions about how do we know if what we're doing is having an impact, which little did I know at the time is RevOps. So I ended up creating that function there. We were acquired by Salesforce, of course, spent some time there, ended up at Box, Campaign Monitor, a small CRC startup in manufacturing tech, then at Eventbrite. And currently I'm at PandaDoc leading our centralized RevOps function here. It's been really fun. I've really enjoyed solving different problems at different stages. So publicly traded, recently IPO'd, Series D, all kind of all over the board. And that's really fun to see, like, what are some of the common problems that we have to solve in RevOps and what are some nuances based on company maturity and company culture and making some adjustments there. So it's been a fun ride for sure.

Janis Zech: Yeah. I mean, I actually when we prepped for this, right, like, we thought about, hey, the topic could be how to best onboard in RevOps, and I think, you know, what you just said is so true that, like, you have the common things and then you have the company specifics and the DNA, right, and that's always a bit different, and the go-to-market motion and, you know, kind of what segments and how international you are, like, kind of the complexity scale is obviously always a bit different. But actually, that's not our topic today. We wanna talk about how sales made you a better RevOps leader, and I find that actually quite interesting. And, you know, when we double click on that, you know, like how do we navigate exec stakeholders, create alignment, and then also, you know, especially in the context of AI because I think that's something that a lot of people I talk to these days face, right, like there's a lot of expectations, but I'd say a lot of things that the board and the executive team wants — there's not one magic wish and someone has to still implement it and I think the dreams are wild these days and that often, you know, puts a lot of stress and anxiety on the RevOps teams particularly. But, yeah, I'm curious like, you know, what are some of the learnings you've had, you know, how to best align with the exec stakeholders?

Nicole Bradshaw: Yeah. I'll tell you a little bit about how I ended up thinking about that topic. I actually had my daughter when I was at Eventbrite. I came back from maternity leave and our global VP of sales and our CRO both left the business. And the executive team said, well, Nicole, you're probably the closest to understanding how that function operates. Can you be the interim leader of our global sales organization while we fill that role? And I did that for about six months. It was a pivotal time in my career. I didn't know it at the time. Of course I was like, I've been doing this for a decade. I know what I'm doing. I know I have the hard skills to execute RevOps well. I know what industry best in class looks like. I've been able to recreate it in a number of organizations. And then I led a sales team and I was like, oh, there's a lot I did not know about RevOps. And I didn't realize it until I was my own stakeholder. So there were a couple of pieces that I took with me. The first was, I prided myself on seeing around the corners and anticipating problems before they materialize. And I surfaced all those problems. And as the global sales leader, when my own team did that to me, I was like, oh no, no, no, I don't care about all of those things. I actually only care about the first two things you mentioned. Everything else — I don't have the mental capacity for it. There are so many other things in flight. There's so much else on my plate that I need my RevOps partner to actually prioritize for me and to tell me what to care about. So that was one of the biggest pieces that I learned. And then I think it kind of came out after I was back in my fully dedicated RevOps seat that I've realized my team and myself, we are here monitoring sales performance. We know what methodologies look like. We know what best in class looks like. We know what good enablement looks like, but we weren't actually applying it to our own behaviors. So if you think about RevOps again, like you can be so good at your job, but if you can't get your stakeholders to heed your recommendations, you're not going to have a business impact. And so every day we're running up against objection handling, the need to multi-thread, competing priorities, compelling events. We are just kind of trying to like power through a wall versus taking a step back and being like, if I were a seller, I know exactly how I would navigate this situation because I see the data and I know what works. And so I've really evolved my approach to stakeholder management, prioritization, even how I lead my RevOps team on, you know, there are some really important things that you've found and some really meaningful things you've found. And the reality of the situation is if you want to drive business impact, let's whittle this down. And so it's really helped me be more effective. I would say, very grateful. I learned this after my daughter was born. I've been able to drive greater impact doing less. So kind of like pick two things that make a difference versus I would be executing on like half a dozen things and just be wearing myself to the bone. To what end?

Janis Zech: I think it's funny because, so I have two kids and I felt like when I became a father, I just naturally had a little bit less time to work compared to my crazy times where I worked sometimes sixty to seventy hours a week, right, like without kids and during the weekend, you know, early startup life. And what I realized was like I have to just prioritize a lot stronger. And I'm curious what you — how you feel about that because I think obviously when you drive initiatives, not just with yourself, but like across a wider angle of people, like, prioritization is obviously crucial. So when you say, you know, kind of, like, don't share everything, be the filter — like, what are things like, you know, how do you know what the execs want? Right? Because obviously if you filter out the wrong thing, then that's not great. So like, I mean, I'm curious, like, what's your learning there?

Nicole Bradshaw: Yeah. The way that I've talked to my team about it is there's kind of two different things to consider. One is like business impact — what is the degree of business impact? And the other is time to impact. So it's all well and great if you can drive really meaningful business impact, but if it's going to take you twelve months to get there, you need to balance that with something else that's going to get you better time to impact. So we do a lot of sequencing in my work, which is: let's focus on the thing that will get us there faster. That will buy us a little bit of time. Give us a little bit of padding to work on the thing that maybe is a little more long tail, but will have the greater business impact. And so you can imagine that means kind of making sure that you're massaging the messaging. You're getting your timing right on getting the buy-in for those efforts, figuring out like what needs to be true as a prerequisite for those longer tail options. And the reality is like, before I was an interim head of sales, I would just like fight tooth and nail for the right thing, which is usually those longer term, larger impact efforts. And then I realized, no, no, no, no. Building the plane and flying it is a very real challenge for executives. And so how do I give them quick wins while behind the scenes building up to those bigger picture items or bigger ticket items? And so that's been a really helpful approach for my teams.

Janis Zech: And is there any rule of thumb, like when you go to an executive and you present your roadmap, right? Like, kind of what is the timeframe that you see typically clicks, right? Is it like three months, six months, nine months, twelve months, right? Like, how many items do you typically present, right, and how do you describe the trade-offs, and like, is it something where you come with a clear recommendation or you discuss it? And I mean, I think that depends also a bit on the role, right, like, but as a VP of RevOps that reports into the CRO and to the CFO, right, like, what would be your recommendation?

Nicole Bradshaw: Yeah, that's a great question. I think about it in two different ways. So one, I'm a very big OKR fan. I think OKRs are often blamed for poor operational execution, whereas like they are a vehicle, not the solution. And the way that I think about it is I've had great success with like three month increments. So like every quarter we're going to make meaningful progress. That doesn't mean we're not doing smaller things to get like greater time to impact in the meantime, like quick wins that I mentioned before. It just means I'm more thoughtful about what level do those plays work at. So those bigger items go to the executive team. We have this every three quarters — how are we unlocking and delivering impact? But in the meantime also, are there like director level folks or senior manager or frontline leader folks that can really help us on some of the more tactical, like buying our time, getting some results to bridge the gap in the meantime, and kind of dividing and conquering with that approach as well.

Janis Zech: Yeah, yeah. And so, Philipp and I, we like product to good by heart — I mean, the way we build Weflow, right, is like we have kind of the big vision, right? There's no like kind of clear code for go-to-market as of today and I don't mean that chat interface, but like the end-to-end workflow automation intelligence system that, you know, like frees up a lot of the people from the day-to-day doing, and meeting prep, follow-up, yada yada yada, right? Like, lots of different use cases, but obviously that's like a grander vision, right? Like, where you wanna get to and not something you do in three months or even a year. And then, you know, you have these like small things where like customers come back and say, well, wouldn't it be great, or, you know, this is missing. Right? And then there's this like, you know, very specific roadmap. And I think that's actually very similar to what you're describing here. It's like, you think about like the stories, you know, the features and the bigger picture, and it all has to come together. But at the same time, right, like, if you only talk about vision or if you'd only talk about the small stuff, that really doesn't excite any, you know, customers or executives. Right? Because it doesn't really have the meaningful impact you're looking for. Do you have, like, specific meetings or setups to ensure that, like, people actually know what you're presenting and, like, is there a specific cadence you follow for getting these kinds of buy-ins?

Nicole Bradshaw: Absolutely. So, the operating cadence is relative to the levels that we're working with. Right? We do have our like monthly business reviews and quarterly business reviews at the executive level, but more at the director level, we're meeting weekly and keeping a pulse. The idea being that there won't be any surprises by the time we meet with the executive team. We've ended up proactively tackling some of the more tactical opportunities that we've uncovered. And then we can use those MBRs and those QBRs with the executives on those bigger picture, more cross-functional initiatives, more long-tail impact that we mentioned. That's worked really well too, because I think with RevOps, there's so much you could be doing that any opportunity you have to fold it into existing cadences and existing deliverables is the approach that I want to take. Otherwise you end up — your remit just grows and grows versus, oh, this is just part of how we work day in and day out.

Janis Zech: Yeah. Yeah. Yeah. I a hundred percent agree. It's so important. We talked a lot about agency, right? Like, and like, you know, kind of, I think you said something and correct me if I'm wrong, but like sometimes you've seen RevOps not having enough agency. And obviously it depends, right? But like, what do you mean with that? And obviously showing up with agency is I think what you mean, right? So curious how you think about that because I think that's obviously super interesting.

Nicole Bradshaw: Yeah. I think if you take it back to, if you were a seller, how would you drive the deal? Your successful sellers are not letting the customers drive the conversations. They're coming with a point of view. They're willing to be wrong. They ask a lot of questions in discovery. They share their point of view. They receive feedback and adjust accordingly. That's how I want my teams and how I want myself to show up. It's based on the information I have available to me — here's the perspective I have. That whole idea of strong opinions held loosely and coming in to be that thought partner. I found that a lot of organizations are really hungry for that thought partner and have given the seat at the table to RevOps and RevOps is kind of reticent to lean in at that table. But the business is hungry for it and the business knows that we have a skill set that is complementary to what the rest of the organization has. And so if we don't speak up, that perspective is missing and the business is kind of making decisions with a blind spot and we are here to fill that blind spot. So, I think RevOps is a tricky place. Like we're kind of the hub of where all the information, processes, systems live. So we're uniquely positioned to understand how everything is interconnected. And therefore if we don't speak up, there's a pretty big gap likely to take place. So, I kind of explain it to my teams as like, if you think about a conspiracy theorist wall, we are that wall. And so if we aren't the ones showing those connections, there's gonna be a miss in the execution of what's being talked about in the room. So be bold, be willing to be wrong. But if you're doing it from a place of understanding business context, leveraging the data, sharing your expertise, and you're building that relationship in the way that a strong account executive would, you're not gonna be penalized for having that perspective.

Janis Zech: Yeah. Exactly. I think as long as you optimize for the business, right, and you come with this, like, hey, look, this is best and these are the three to five points that would really make a difference. Right? Like, every exec appreciates that. Right? Like, I mean, why wouldn't they? And then of course, right, like it doesn't mean all of those need to happen immediately and there should be kind of an alignment, but at the same time, if you don't speak up, you know, like, I think you're also not kind of keeping the place at the table, right, because that's almost like — in the good organizations we've been working with, right, like where CRO and the kind of VPs or SVPs or COOs at some point, right, like closely work together — I think that is really, like, the best ideal state. And if that state is not in place, then right, like the question is really like, what can you do to change it? And like, I think proactively suggesting change that has high business impact and like significant business impact. Right? Like if you come in and like you had like a hundred fifty million run rate and you come and you say, we can save you a hundred k here. Right? No exec is actually interested. And it's not like — it's not what they are goaled for. Right? So like understanding what are the board goals, what are the budgets, right? And then understand what are kind of the financial goals of the business and then really like thinking about like, we have a pipe gen problem here and if we don't act on this now, right? Like we need to — or like we have a conversion problem or you know, we have an expansion renewal problem, we have a churn problem, right, like really speaking in that language that they have and then tying that back and then tying initiatives to that, right, I think is just so, so, so important.

Nicole Bradshaw: Yeah. I think it's really interesting in the context of AI, right? Everyone's talking about, is AI taking our jobs? And I haven't heard a lot of people talking about the fact that being an order-taker RevOps function — forget AI — out of the box automation can take your job. Right? So having that consultative approach is going to be your differentiator as technology evolves, as you become more nuanced in both your consultative approach, but also your stakeholder management that we've been talking about. Like that's something that AI could probably get there eventually. AI can absolutely take orders and execute. So I think that's a really meaningful part of the story for the teams that I work with as well is like, do you wanna AI-proof your role? You really have to have a POV. Otherwise, you're kind of just a cog in this workflow.

Janis Zech: Yeah. A hundred percent. A hundred percent. I love that. Like, I mean, your experience, right, like, if you compare it to the sales world, like, how do you create impact? Right? Like, what are some of the key principles that you apply?

Nicole Bradshaw: Yeah. It's a good question. I think one of the things that we kind of touched on earlier is like, how do you operate at the strategic and tactical levels? And I think that's really how you have to think about driving impact is holding the organization accountable to all of those altitudes of decision making. I'll work in organizations where they're tactically executing and you're like, oh, we could really ten X this if we got really clear about our strategy here. Because now it feels like we're getting results, but they are suboptimal because we don't have a bigger picture understanding. Or vice versa. A lot of times you'll have a really clear strategy set, but then nobody to turn that into a practical application. And I think RevOps again is positioned to figure out how to thread the needle between both of those two pieces. And again, both of those parties, right? Boots on the ground and your executives — understand the pain points for both of those parties and you can bridge them effectively. That's the impact that I don't think other teams within the organization are well positioned to bridge. And so that's kind of where I think about where my teams often can drive the most impact — is there clarity we can drive from a strategy perspective, or we have clear strategy and is there clarity on like, what does that practically mean for the boots on the ground doing the work itself?

Janis Zech: Yeah. What do you find harder?

Nicole Bradshaw: Oh, I think what I find harder is when the strategy is less clearly defined. I think once you've got the strategy defined, typically there's a cascade effect and you're like, we're fully empowered. Let's just go do it. When you've got people executing and you're like, oh, we could optimize this if we just had strategic alignment here — there's a lot more nuance. It's a lot more cross-functional in nature. It's a lot more senior in level. And there's a lot more sensitivities and political dynamics at play there. So it's a lot harder I'd say from that. Because you can just run if you've got the strategy and you just have to interpret and execute.

Janis Zech: Yeah. Yeah. I mean, I think if the strategy is unclear, right? Like, because you need like the buy-in from the executives, but then especially from the middle management. Right? Like, I think the middle management is so crucial to execute. And so if they are all running into different directions, right, like, then obviously, like the people side of things in RevOps is really hard to execute, right, like the execution layer. And that is something that, you know, like as a more product-minded person, I find always so hard to do in the go-to-market org is like, well, you know, we go out and, you know, we kind of spec the tickets and then, you know, like engineers are executing them. And yes, they can be done at different quality levels. Here, often the execution has also a lot to do with kind of the human element and the quality of the humans also kind of being spread, I feel like, more widely than on the engineering orgs typically. Right? Like, where you have a few top performers and then, you know, kind of like, the distribution there is quite different in my experience and that makes the execution part sometimes really hard. But yeah, I think if you don't have a strategy or like, let's say, conflicting strategies, it's painful.

Nicole Bradshaw: Well, you can experiment with tactics, but experimenting with strategy is incredibly costly. So you can't move as quickly. It's a lot less of that two-way swinging door that tactics are.

Janis Zech: Yeah. And I mean, typically, right? Like if you're like a kind of fifty million to two billion revenue, right, like, also strategy means that those are the things where you take some bets that cost money, that cost a lot of money, right, like sixty percent of the SaaS P&L is in like go-to-market typically, right, so it costs a lot of money, and you actually don't know whether it works, and you will only find out, you know, one or two, three years later. And that's obviously, right, like — and then there's a lot of change often like in executive teams, which is also not great. I think it's actually devastating, I feel, like, you know, every eighteen months new CRO on average, right, like, it's a devastating stat for companies, how I would think of it. But maybe outside of that, like, what are other kind of sales best practices that, you know, helped you, like, create impact? I think you mentioned something like multi-threading. Like, what do you mean with that?

Nicole Bradshaw: Yeah. Multi-threading is something that's been super helpful in my career. You know, you might have a recommendation that the business isn't heeding, but there are lots of people with a vested interest in revenue performance. And so how do you bring in the right folks at different levels? We've got partners across the organization, right? My financial planning partners, my data team partners, whether it's marketing, sales, or even the post-sale side of the house. I've had product marketing be really strong advocates for some of the recommendations we're making, even folks on the product side as well. Like it kind of depends on the challenge you're facing and where the pushback is. But again, like we are uniquely positioned to have built and established all of these relationships to bring more people into our cause. Right? So when you're going into something that you're advocating for, that you think is going to be a meaningful impact on the business, you also think might be a hot button issue — seeding it ahead of time with those advocates where, you know, they have a vested interest in this success and you know that you can speak their language and get them to chime in on your behalf. It's going to be a much more compelling case to enter the room with the person who's going to push back, with a cross-functional alliance essentially, which has been great and not adversarial, right? At the end of the day, we're all trying to achieve the same thing. We just might have different interpretations of it. And so if we can bring folks along, just understanding and aligning with our interpretation, that's only good things for the business.

Janis Zech: Right. Yeah. Fully, fully agree. I mean, what about champions, right? Like if you multi-thread, like, do you have multiple champions? Do you have like a strong champion? Do you try to always have a champion in the executive team or multiple or like, yeah. How do you think about that?

Nicole Bradshaw: Yeah, absolutely. I mean, I think the ideal state would be that you've established relationships across all the functions I've mentioned, and you're very thoughtful about who is going to be the most influential on this specific topic. Let me tap that person here. Because you also don't want to tap out your champions for all the things and you want to kind of allocate those appropriately. So, for conversations around rules of engagement, usually compliance-related things, Finance will be much more of an advocate for you. For things around data integrity, obviously your data team will be an advocate for you. And so figuring out like who has a vested interest and who will also have a louder voice in the room on this topic and be very mindful about that being your champion for that specific initiative.

Janis Zech: Do you feel there's a risk that, like, this seems to be kind of manipulative or, that, you know, people — like, that it destroys trust rather than it earns it?

Nicole Bradshaw: That's a great question. I really struggled with that early in my career. I am a people pleaser by nature. And so the idea of politics just kind of feels slimy, but I think what's really helped me is I had a mentor frame it as we want what's best for the business. We all do. And if you truly think this is what's best for the business, then the goal here is not — you're not like tricking anybody. You're saying this is a perspective I have. Can I get other people to come along? Feel free to poke holes in it. But if other people start to go along and I'm like, oh no, this is definitely the best thing for the business. Okay, great. Now, in order to drive that impact, we've got to work together to get this other person on board. It's a little bit of a shift of perspective of like, if you focus on the intention rather than feeling like you're playing a game of politics — best of intentions, like you're motivated by driving that business result. And at the end of the day, if people say no, you can accept the loss, but you want to make sure you're not regretting. I think I have a lot of regrets early in my career where shoot, I couldn't get them on board. And then eighteen months later, what I predicted would happen, happened. And I never want to feel that again. And so I'm willing to make myself uncomfortable and build these bridges to avoid a failure that I see coming down the line. I think that's — it's almost like that nightmare is what motivates me to get past the discomfort.

Janis Zech: I love that. I mean, I think, you know, if you — I mean, the way you talk about taking agency, right? Like being proactive, really driving for outcome, not just having the recommendation, but actually, you know, having that perspective, having that point of view, and then also kind of, you know, fighting for the business to execute it. Right? I think that obviously — I think that's what you need to become an executive at some point. Right? Like, I think without that, like, I don't think you'll become an executive. And I think without, you know, the buy-in of the other folks, you actually don't execute well. Right? So it is a super skill that is super important. I mean, how do you handle the objections, especially from the executive team? Right? Like, what if you have this initiative, you have some good, you know, kind of folks that are supporting it but there's just like, there's just a few folks that — or like one person maybe in the executive team that just says, look, I mean — or like, do you go into the risk, right? And like, how far do you go there and like, how do you handle those objections?

Nicole Bradshaw: Yeah. Yeah, that's a great question. I think of objection handling as kind of like planting a tree. Like you want to get to know your audience and your stakeholders well enough before you have the objection so you can anticipate the objection. Right? So if I know I'm going into a conversation with a recommendation, I will immediately go into — I know this person, what do I anticipate they'll push back on and what prep work do I need to do to anticipate that? So we're talking about making changes in what's in scope for our account management team, for example. We know there are some sensitivities around a specific cohort of customers. Great. Let me run some analysis to answer questions I anticipate will be pushed back on this change we want to make. So then when the objection comes up, I'm ready. Like I have the data. I know that question's coming. If there's something that comes up that's unexpected, that's totally fine too. We go back to — I'm willing to be wrong. Let's look at the data. Let's let the data inform us. We'll come back. We'll do our diligence. And I think that really helps lend credibility because I'm not arguing for my position. I'm saying this is what we think is right. And based off of your objection, you know, I think there's an objective way for us to figure out whether or not this is a concern and we should halt, or if it's something that we can move past. So it's a very nuanced approach. But one that I think — to your point, like it's all about establishing trust and credibility and being able to react in the moment in a way that's constructive and gets us to — if all I want is what's best for the business, let's let the data help us understand what the answer is for that.

Janis Zech: Yeah. I love that. I love that. Yeah. That's really strong. I think that's really, really important and right, like the outcome might be that you change initiatives but you don't give up so easily and like you follow through. Maybe like one last question, like kind of you mentioned in our prep talk, you know, kind of partnering, partnership, right, like what do you mean with that? You know, how do you build that? What do you think builds trust right in the partnerships with the key stakeholders?

Nicole Bradshaw: Yeah. I think something that's been really key from a partnership perspective is how do we make other people's lives easier? Right? I think in RevOps, we've talked about so much of what we do is making other people's lives easier, but we do so reactively. So how do we proactively find ways to make things easier? Very simple things. Our intake process is laborious. How do I simplify that to make it easier for people to get help from us? Our sales process requires twelve clicks to update technically one thing. How do I proactively solve for that? And the more you do that — again, it's kind of like planting a tree. The more you do that, the more that partnership is just going to organically form where when I need to call in favors for advocacy or prioritization from a team that I don't manage, it's a lot easier because they're like, oh my gosh, you really helped us out on this thing. Or you proactively made my life easier in this way. Of course, I'm going to help figure out how to get some resources to support this initiative. Again, to your earlier question, I think young Nicole would have been like, feels like you're playing, you're like gaming the system, but the reality is like, we're all people and we want to help each other when we want to like drive meaningful progress. And so the best way to do that is like, how are you making decisions day to day? How do you get other people to come along with you by going along with them when appropriate?

Janis Zech: Yeah. Yeah. I love that. I mean, I think it goes a long way and people, right? Like, people feel whether you have your own agenda or you're truly helping them. Right? And if you, like, right, like, you sit down, you understand their problem, you've like, maybe you don't fix them all, but you fix some and the quick wins. Right? And they'll remember that. And I think yeah. I think that's just super, super important, this role in general. Right? Because, like, in the end it's cross-functional, you have a lot of stakeholders and, you know, thinking about also the different stakeholders, not just the executives, right, I think especially middle management, also reps, right, like, you know, it goes a long way if you help them make their life easier, if the managers feel like you help them achieve their numbers. Right? Like, you know, and so that's really how you fundamentally drive change, right, like, as a — in a company, which is essentially what, you know, everyone in this role should aim for. Right? And this is hard sometimes because the circumstances and the organization structure and the interests might not be aligned and there's complexity around those things given that you deal with different interests, also compensation, different compensation schemes and things like that.

Nicole Bradshaw: Yeah. It's actually, makes me think of — I had a coach once that introduced this whole framework for me of like these win-win scenarios, right? So you can think about this when you're talking about getting executive alignment or getting, currying that cross-functional help — is what you're really going for is a win-win scenario, right? Because at the end of the day, you don't want a lose-lose scenario, but if you're winning and the other person is losing, it only takes so long before you've lost their trust. And you're going to move into a lose-lose because neither of you is going to get what you want. Or if they're winning and you're losing, you're