#217: Marketing Leadership | Why Product Marketing is the Foundation of Great Marketing Leadership with Jessica Andrews, VP of Marketing at Copper

In this episode, Matt Carnevale sits down with Jessica Andrews, VP of Marketing at Copper, a CRM built specifically for agencies, consultancies, and media companies, designed to help relationship-driven businesses find ideal clients, win new business, manage projects, and nurture customer relationships. The two discuss Jessica’s journey from Senior Product Marketing Manager to VP of Marketing, how she’s navigated imposter syndrome, and her strategies for leading a successful marketing team.

Matt and Jessica cover:

• Strategies for shifting from IC to a marketing leadership role
• Why product marketing is the foundation of great marketing
• How product marketers can position themselves for leadership

Timestamps

• (00:00) - - Introduction to Jessica
  
• (02:08) - - Transitioning from product marketing to VP of marketing
  
• (06:05) - - Dealing with imposter syndrome and learning to trust your instincts
  
• (08:48) - - The shift from execution to strategy in a leadership role
  
• (10:30) - - Why taking time to think is crucial for marketing leaders
  
• (11:53) - - The power of networking and learning from other marketing leaders
  
• (13:54) - - How talking to agencies helped shape Copper’s marketing strategy
  
• (15:13) - - Why product marketing is the foundation of great marketing
  
• (16:52) - - The importance of cross-functional alignment in marketing leadership
  
• (19:30) - - Understanding the mindset of sales teams and how to collaborate effectively
  
• (22:24) - - The challenge of getting buy-in for product marketing initiatives
  
• (27:41) - - Balancing being a strategic partner vs. an order taker
  
• (30:21) - - How to respond to last-minute requests and set expectations
  
• (32:43) - - Strategies for building strong relationships with sales and product teams
  
• (35:55) - - How to become T-shaped and prepare for marketing leadership
  
• (38:13) - - Learning demand gen and paid ads
  
• (40:23) - - Why marketing leaders need to understand revenue and business impact
  
• (42:31) - - Advice for product marketers who want to grow into leadership
  
• (43:17) - - Closing thoughts and final takeaways

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***

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Former startup CMO Dave Gerhardt and guests share their marketing knowledge to help drive revenue at your company and grow your career in marketing. The podcast mostly covers B2B SaaS, but there's something applicable for anyone working in marketing today.Dave Gerhardt [00:00:00]:

You're listening to B2B marketing with me, Dave Gerhardt.

Matt Carnevale [00:00:17]:

Cool, cool. So I'm here with Jessica Andrews. Jessica, how's it going?

Jessica Andrews [00:00:22]:

Pretty good. Thanks for having me.

Matt Carnevale [00:00:23]:

Yeah, of course. It's rare that I get to interview anyone who lives in the same city as me. Toronto, so pretty cool. I'm glad we're doing this. Don't always get to speak to my. My local marketing peep, so.

Jessica Andrews [00:00:36]:

Yeah, exactly. It's pretty rare. Whenever I come across someone who's in a kind of global leadership position in, in Toronto, it's really exciting. So this is good.

Matt Carnevale [00:00:44]:

Yeah, it's always like, oh, wow, you too. Awesome. Okay, so first thing, we'd love to get started. Why don't you just take us through your career journey?

Jessica Andrews [00:00:53]:

Yeah. So it's kind of been an interesting kind of hopping all over. So when I graduated from my master's degree in communications, I thought I was going to work in the government because most of my education experience at that point had been political science. And I learned that government is pretty boring. And I didn't really enjoy marking things all the way up the food chain and having them come back and keep repeating that process. So I ended up getting a job at a startup instead, where I was basically the only employee in Toronto with one of the co founders. I had the title of a digital account manager, but that really meant jack of all trades, basically. So was managing some customers.

Jessica Andrews [00:01:30]:

We would, I would do all the marketing, all the public relations. Basically anything that was, was needed at the time. And I got to grow with the company. So right before it ended up selling, there was, I think, 25 employees globally. And I was still kind of considered employee number one. And I felt really fortunate about kind of being part of that process. And part of being at a startup meant that you really defined what your role was. And it wasn't until I read the book Chaos Monkeys that I learned what that definition was, which was product marketing.

Jessica Andrews [00:01:58]:

And as soon as I read that part of the book that explains the product manager versus a product marketing manager, I realized, oh, that's what I want to do. That's what I'm already doing. So when the startup got sold to a larger American company, it was the perfect time for me to transition into a formal product marketing role globally to help bring the startup's functionality into the larger company and vice versa. So I did that for about a year and then kind of decided it was time to go off and go to a new company because it was time for a change. So I ended up moving over to Sigyn, which is a media monitoring and analytics company. And I stayed there for two years and learned so much about working in enterprise, which obviously I had not done before, and learned that I definitely thrive in startups and smaller environments where I can kind of sink my teeth into bigger problems. So that's when I joined Copper. So I was the solo Product Marketing manager, I think I held a senior PMM title at Copper and was working for an amazing CMO and a really small team and I was really enjoying how that all went.

Jessica Andrews [00:02:55]:

And then one day the CMO came to me and said, hey, I'm actually going to be stepping up into a further leadership role as CEO, which is rare on its own. And she asked if I wanted to move into marketing leadership. And it was a little bit of a shock to me because I'm like, but I'm only a senior pmm, how can I possibly be ready for this next step in my career? And she said, you know what, like, you just sometimes have to do it and sometimes you get pulled up to these positions and you have to take them as they come. So I did and haven't looked back since. So it's been about a year and a half that I've been in this role and really enjoying it and kind of was a really bumpy ride at the beginning. But I think I'm starting to come into my own, which is nice, Cool, awesome.

Matt Carnevale [00:03:33]:

We'll dig a lot deeper into that and what that look like. But real quick, what is Copper? What do you guys do?

Jessica Andrews [00:03:39]:

Yeah, so Copper is a CRM. We are a CRM that we've built specifically for agencies, consulting and media. So those kind of consultative businesses where relationship is really, really important. That's what we're kind of focused on. So rather than being a CRM that's focused towards salespeople or marketing, what we're trying to do is create a one stop shop for these types of companies to be able to find their ideal clients, win new business, train, bring those individuals over into projects and deliverables that they're providing to those customers and then kind of nurturing as they go. So it's kind of that end to end platform that we're trying to build out.

Matt Carnevale [00:04:12]:

Gotcha. Okay, cool. You move from a senior product marketing manager to a VP of marketing. What was the first couple of months like? I feel like a lot of people, you know, in our community talk about imposter syndrome. That's a really big topic that comes up. So I want to know from you did you feel that when you got to that marketing position? And maybe you still feel it a little bit, but did you feel in the beginning and what are some things that you've done to get around that?

Jessica Andrews [00:04:41]:

I have imposter syndrome every minute of every day. But as I'm talking to every person in my kind of position, once you get up to a certain position anyway, I feel like imposter syndrome just comes with the job and it's all about ignoring that voice and just knowing that your gut reaction is actually right most of the time. So imposter syndrome is kind of tricky because what I found in those first couple of months was that the job of VP marketing was not the job that I thought. So when I was having the initial conversation about taking on the role we the CNO CEO and I discussed that, I'm like, am I ready? Really? I don't do demand gen. I haven't really handled advertising in a long time since my first startup that I was at. Are you sure you don't want to promote X, Y, Z person instead? And she said no, like you don't quite understand what the role is yet, but you'll learn. And I have learned. So what I've learned is that you do need to be a T shaped marketer where you have to have a little bit of experience in everything.

Jessica Andrews [00:05:37]:

But what I also learned is that the VP marketing job is not a execution role. It is a completely different role. It is managing different opinions and different personalities. It is politics. So much politics. Which I now know that in product marketing we deal with the most politics out of any team. And so product marketing is almost uniquely positioned to figure that out earlier rather than some other ones that are kind of in a bubble. And we are not.

Jessica Andrews [00:06:03]:

We know how to deal with cross functional teams. So that's kind of what I learned in the first couple of months is that even if I don't know everything, that's why I have the team that I have is to be able to do the work and educate me on what we should be doing as opposed to me needing to know everything.

Matt Carnevale [00:06:18]:

Yeah, I remember a couple of months back with Exit Five, we've been wanting to run paid ads on LinkedIn forever. I mean, we have a really strong organic presence, so it only made sense for us to try out paid as well. And you know, I had dabbled a bit, but I knew that I needed to really take it serious and we needed to go hard in our paid ad strategy on LinkedIn. And for months I was kind of Just like, yeah, I'd own the bandwidth this month, but next month I will. And months went on and it never really got there. And I remember Dave, he said this thing to me and it stuck. Not in the exact words, but he pretty much said, you need to think like the GM and not the player, which is a sports reference. But, you know, you need to think like, what pieces can I move and what resources can I tap into to make this thing happen? It's not about me doing the thing.

Matt Carnevale [00:07:07]:

And it may seem pretty obvious now, looking at it, but at that time it was like, oh, like maybe we'll just work with an agency or a freelancer to do this and they'll help us. Right. So I really like how you touched on. You're not as much of a doer and more of a, you know, a piece of the puzzle mover.

Jessica Andrews [00:07:24]:

Yeah, exactly. And that was actually another thing that was very weird to me is I think month number two is suddenly my to do list is not as long, because as a product marketer, I would have five different go to market motions, and I would have 15 tasks to do a day and talk to people. And then all of a sudden that wasn't there. When we backfilled my old position, suddenly there was a new product marketer coming in and doing all that work. And my task list was open, and it's like, well, what am I supposed to be doing? And it turns out there's a lot of bigger projects and a lot of brain space that I have to, like, make to be able to do the big picture stuff that. That my role now requires.

Matt Carnevale [00:07:57]:

Yeah, that's a good point. What are some of the things that you did to figure out your to do list? Like, was it, okay, I'm just going to go through a backlog of thoughts. Was it, I'm going to go to my manager, talk to the team. Like, how did you go about tackling that?

Jessica Andrews [00:08:10]:

It was interesting. It took me a long time to kind of figure that out. I think I just needed to kind of get up to speed on what the role was. And I found longer term after I had the space, I found that kind of going and taking a break and going for a walk and listening to podcasts actually helped bring a lot of new ideas to the forefront. And so I had to be really careful at the beginning not to go to my team and say, hey, I heard about this amazing, amazing idea on Exit Five. Can you go and implement it? Because I'm not the one that's supposed to be deciding These individual tactics, it's my team. So usually I just kind of bring it up casually and be like, hey, I heard this cool idea. Like, what do you think about it? If they hated it, then they didn't have to go forward with it.

Jessica Andrews [00:08:49]:

But I think it was just getting the bigger picture stuff that unfortunately a lot of ICs don't get a lot of time to have these new bigger ideas that come up with them because they're so busy in the details that I try to be one, coming up with new ideas, but two, also trying to encourage them to have that brain space if they can.

Matt Carnevale [00:09:06]:

That's smart. Yeah, I feel like, you know, I've been on the IC side and still am. You know, sometimes you have a long to do list and your only goal is to get through your stuff and obviously you want to do it well and at high quality, but, you know, never feels right to just kind of step away and do thinking and also like to do it in a structured way. It's like, it's not just like frantically thinking in like the 10 minutes that you are sipping coffee away from your desk. It's like, like you said, like going for a walk, listening to podcasts, filling your information or filling your brain with good information and then allowing that to kind of marinate and lead to new ideas and breakthroughs. So I really like that one. I feel like for me, whenever I'm stuck or whenever I'm like I feel low on ideas or low on my thoughts, it's like, how can I go consume something of high quality that'll help stimulate everything that's in my brain.

Jessica Andrews [00:09:58]:

Yeah, I like that. I also really like talking to others kind of in my position, but in different, different companies just because the BAU or business as usual does get challenged. So what I find is that when I say, well, in our go to market strategy, we do a community post, we do a blog post, we do a LinkedIn post and sometimes we're like, why are you wasting your time with that particular strategy when you could be doing something else? I always find that some of those ideas are great.

Matt Carnevale [00:10:26]:

Cool. And how do you go about talking to others in your position?

Jessica Andrews [00:10:29]:

A lot of networking. So what's actually interesting is now that Copper, we're taking this new kind of trajectory towards kind of business and service based oriented businesses is I'm talking to a lot of people who work at agencies and are marketing consultants and that's been giving me a lot of great ideas because I'm no longer talking to technology marketers. Which of course I am one and I should be talking to more of them. And I am. But talking to agencies and people who are authentic, authentically bringing themselves in a marketing position is something that I'm trying to replicate on the tech side, which is kind of unique. So what's really interesting is getting those ideas of what individuals at agencies are doing because they are not doing the, the same kind of webinar cadence. They're not doing communities, they're not doing slack channels as much. It really depends on what they're doing.

Jessica Andrews [00:11:13]:

And so I'm taking inspiration from how they do things because it's effective and seeing how we can do it in a tech company.

Matt Carnevale [00:11:19]:

Totally. Yeah. I always love leaning on agencies for that information sharing. They're specialists in what they do for the most part. Some of them are broader, but for the most part they have a specialized area like LinkedIn ads or email or webinars, whatever it is, and they have deep expertise there and they work with like a hundred different companies in their lifetime or more on that. So they have these learnings that they can kind of like coagulate through all these experiences and have a lot of good information to share. So I think sometimes marketers hesitate to talk to them because they think like, oh, they're just going to try and sell me something or whatever it is. But they have a lot of great information.

Matt Carnevale [00:11:58]:

They're a good other side to the knowledge marketplace and marketing for sure.

Jessica Andrews [00:12:01]:

Yeah. And ironically I actually like being sold to when I'm talking to agencies just on an informational basis because I'm building a product for them to be able to do what they're doing and so to be able to see them in their element. And how do they bring up a sales conversation? What are some of the pain points that they're asking me as the, their client? So it's kind of been interesting to take the information that agencies have been doing to try and sell to me in a non confrontational way is like how can we build a product that will help them do that in a more efficient way?

Matt Carnevale [00:12:29]:

So totally.

Jessica Andrews [00:12:30]:

It's fun to have that even though sometimes I have to say no to their sales pitch. But that's okay.

Matt Carnevale [00:12:35]:

Yeah, yeah, I think it's, I think it's a good thing too. I mean like as a marketer we always need to know like what's out there and what's available too. Right. It's like you don't know what you don't know. So you know, maybe you get pitched a agency service One year, and then you're like, I don't need that. Like, stop trying to sell me stuff. But the next year you move to a new company and this thing comes in your head and you're like, oh, I know companies can help with this. Maybe that's the route to go.

Matt Carnevale [00:13:00]:

So never a bad idea to at least take the pitch and at least learn, right?

Jessica Andrews [00:13:04]:

Yep, Exactly.

Matt Carnevale [00:13:05]:

Cool. So I want to talk about obviously moving from product marketing throughout your career to a VP of marketing. I've always said that good marketing starts with good product marketing. It's the foundation of everything. If your messaging is off, if your positioning is off, if you know who your Persona is is off, if all those things are off, if you never talk to customers, it's really hard to make the other stuff good. So you obviously had that strong base moving into VP of marketing role. So first I want to know, like, did you feel like that set you up for success or did you just kind of feel like that it was reset and you didn't really feel like that experience had a huge impact?

Jessica Andrews [00:13:49]:

That is a great question, and I would say absolutely. I think that there's a lot of conversation online that I've read about whether product marketers should be the next leaders of marketing or whether there's a strategic role or something like that. And I saw this recently on LinkedIn and my immediate reaction was like, no, product marketing is the future of marketing leadership. And I feel like sometimes this new strategy title, like Chief Strategy Officer is almost because the chief marketing officer role everyone thinks is fluffier and happier and like, let's do a brand rebrand and let's do all these things, and that's not really what it is. So what I find is that product marketing is bringing marketing back to where it should be, which is that we have to know who we're selling to, what we're selling, make sure that we are saying the right things, we have the positioning locked, and that everything is kind of cohesive within the marketing structure. And I think that sometimes there's a public perception that that has been lost. So that's something that I think product marketers as leaders can correct over time. So I would say it definitely set me up.

Jessica Andrews [00:14:49]:

I think the number one thing that I already said is the politics. Some people call it politics, some people call it cross functional alignment. I love the cross functional alignment title because I think it's more positive. But I think that product marketers are exceptionally skilled in, in making their thoughts and direction known across different companies in different Departments. Sorry. So I think that when you are in another role in marketing, sometimes you can feel a little bit insulated in just marketing and you don't know what product is doing until maybe there's a launch and you have to write something about it. So that's why I think that like the future of VP marketing is probably going to be product marketing. And if you're not already there, if you're in demand gen, that's great.

Jessica Andrews [00:15:28]:

It's just how can you be more in lockstep with other departments and that could get you to the role that you want.

Matt Carnevale [00:15:33]:

Totally. Yeah. I think such a big part about leadership and what I've seen good leaders do is they're really good at getting buy in across the company. They're really good at syncing up their plans with other leaders plans. And the product marketing, you know, if done correctly, obviously is doing that all day long almost to an exhausting point. But then, you know, it translates to the ability when you're at that level to get those ideas across to multiple departments and to take your time to earn that buy in too. Right. I feel like, like so much of the time, and I've been guilty of this is marketing comes up with this plan or idea in a vacuum and then they're like, all right, we're just gonna go run and do this thing.

Matt Carnevale [00:16:15]:

But they need to spend more time talking to other departments and they don't do it or they half ass it and that's why the thing ultimately ends up flat. So I think that's such a good. If it was like one thing, one of the big things to take away from product marketing to bring into leadership, that's definitely a big one.

Jessica Andrews [00:16:31]:

Yeah. And I think that that's what makes product marketing so difficult and why it's so hard to break into that role is it's a skill that is very difficult to master and it's not something that you can take a course on. Well, you can, but there's certain characteristics of product marketers that I do feel are born and are neat that you can bring out of someone. And so that's why that role is so difficult. I also think that it's very easy to hang out with people who are like you, that think like you. So in marketing, when we have all the same metrics and we have all the same goals and we have all the same okrs, it's really easy to hang out and say, okay, designer, you're going to make something that looks really nice and paid ad specialist, you're going to try and get as many impressions and clicks as possible. And that's all nice. But when it comes to working with other departments, when you get into the product world and adoption is something, how as a marketer, can I actually go in and align my KPIs to your adoption metrics? That's really hard.

Jessica Andrews [00:17:27]:

And it gets even harder with cs. Like, what are their goals and objectives and leadership? It's all about revenue. So how can product marketing actually say, hey, revenue, how do I translate this? It's the most difficult job of all. And that's why I think that a lot of people shy away from it because they take the easy route. Not to say that they're doing something wrong. It's just innate in us to take the easiest route to success.

Matt Carnevale [00:17:51]:

Totally. No, I totally agree. It's funny. I started my career in sales. It was a brief stint. It was like less than a year. And then within the same company, I moved into marketing. But being in that department taught me so much about what it means to be in sales.

Matt Carnevale [00:18:06]:

And in marketing, we have to collaborate with sales so often, whether it's just the general marketing team, but especially the product marketing person or team. And as a marketer, you have all these ideas, all these things you want to implement, but the salesperson is just thinking, how the hell am I going to get to my target this month? Right? And when you're in the last couple weeks of the month, like, that's all that's on their brain. So it's like putting yourself in those shoes and starting to understand that is really important because otherwise it's going to be tough to get the things that you want done across because they're just not going to care. You're not going to get the buy. And if you don't understand what they care about in the psychology of what they're going through time to time.

Jessica Andrews [00:18:47]:

And what's really interesting about sales to me is that I find a lot of marketers are just like, well, how am I going to get the salesperson to say this exact line when I want them to say it? And this is not a choreographed Broadway musical where you can basically say to the actor on stage, you're going to say this at this exact time. Sales, they have a totally different skill set, which is that they listen very intently for certain keywords and they're listening to certain see what the prospect is saying, and they want to say it in the prospect's own words so that it resonates. So you kind of have to really Listen to what they're saying and potentially even take pointers from them when it comes to positioning and messaging. Because if, if your positioning and messaging in your head is amazing and the salespeople aren't saying it the same way you are, there's a reason for it. So you have to kind of go and see how are they saying these things. And maybe I need to change my perspective or just talk to them and ask them, why are you saying it this way? I'm curious. I want to learn. And you'd be surprised what you can learn from the people who are actually talking to prospects every single day.

Matt Carnevale [00:19:48]:

Yeah, totally. I feel like even I've been so guilty of, like, you give something to sales, like a new decor and you white paper, and they don't use it and you're like, sales again. They never use any of this stuff that we make for them. We're done. We're done supporting them. The next time they ask for something, I'm pushing back. But, and, and there's always some truth to that. Like there, it's a give and take on both sides.

Matt Carnevale [00:20:09]:

But you know, it's a, like you said, it's a great opportunity to be like, okay, like, maybe, maybe I didn't deliver this properly or maybe this actually is not that useful and instead I need to do it this way. So it really is a, it's an ongoing process and there's more to it than just like, I created this thing because I had an idea and gave it to them and I expected it to change how they sell and for all the numbers to go up.

Jessica Andrews [00:20:32]:

Well, it's all an experiment. Right? So if you, if you're not guilty of creating an asset and throwing it out there and seeing if it works and it just doesn't land. I mean, that's what, that's what happens. Right. It's just, that's marketing. It's all about experimentation. So if a piece of content that you were asked to create didn't land, then time to look at what you created and get some feedback and try again. And that's not to say that sales is asking for a bunch of things that they're not going to use.

Jessica Andrews [00:20:55]:

It's just obviously wasn't useful in the way that you presented it. So try again.

Matt Carnevale [00:21:00]:

Yeah, I love that. So one thing I wanted to touch upon is I feel like product marketing sometimes is a little undervalued in certain companies. I mean, it depends. You know, the founder is and the marketing leader at the time and the other people in the company and what they know of product marketing. But sometimes it's a little undervalued. What I've seen, and you can tell me if you've seen the same is like companies will hire a product marketer, they stick them in the marketing team and just expect some kind of magic out of them. But really product marketing isn't, doesn't, can't do its job if they don't have the buy in from leadership or the direct line to leadership to influence what they're doing. Right.

Matt Carnevale [00:21:40]:

For example, if you need to fix a company positioning and messaging, I mean that's something the founder and leadership team holds really near and dear to their heart. So without their buy in and then wanting to do that thing, it's going to be tough to inflict that change. So with the experience you've had, like how have you kind of made a name for product marketing in the company and how have you gotten those relationships with leaders to go and do the things you want to do?

Jessica Andrews [00:22:04]:

Yeah, that's a good question. I've had the privilege, I don't know if it's a privilege, but I've had the privilege of being both a product marketer reporting into marketing and a product marketer reporting into product. So right at the end of my time at cision is when product marketing actually got moved because the new CMO didn't have that skill set. She said I could, but I think it would be better useful use if the CPO took over product marketing because he had experience managing product marketers. And it was great because we had a very strong kinship with product because we were in their meetings, we were able to understand their pain points, we understood where they were functionally going. But then all of a sudden the isolation from the marketing department started where you're trying to, you have to give a campaign plan over to marketing and they get to decide if they agree with you or not. Whereas when you're in the marketing team, everyone in marketing is lockstep. Everybody agrees with the direction and then you bring that plan over to product and they rip it to shreds.

Jessica Andrews [00:23:00]:

Right. So you don't win in either way. I think that it's really building relationships over a long period of time and not for a particular project where you see success. So I love being in as many slack channels as possible and anytime I see a question from a salesperson or a product manager or anyone looking for advice or tips or background, I like to go in there and try to participate as much as possible. I try to have really Strong conversations with every possible team that I. That I can have. And what I've learned is that building relationships like that help you down the line when you need something from that person or when you're trying to get buy in. So me having a strong relationship with a product manager six months before we start to launch something together has been really successful for me.

Jessica Andrews [00:23:47]:

Trying to get buy in from a CS team when you have been helping them articulate a problem and solutions for their customers, it really helps to get buy in if they like you and they trust you. So I would say it's building relationships just like a salesperson would, where you know long term that you might need something out of this person and not in a negative way, but you just know that the more relationships and the stronger relationships that you have with other team members, the better off you'll be in the long term. And it's not something you can just turn on as soon as something comes up. They need to like you way in advance.

Matt Carnevale [00:24:19]:

I love that. I think that's such a great tip is getting involved in conversations that you weren't necessarily directly tagged into.

Jessica Andrews [00:24:26]:

Yeah.

Matt Carnevale [00:24:26]:

And just taking on problems that maybe you weren't asked to solve. But just being the problem solver, that's a really, really great piece of advice. And I feel like people ask me a lot of the time like those type of questions and I give answers, but that. That's really good when I have to steal that one.

Jessica Andrews [00:24:41]:

Yeah. And I mean, I have gotten in trouble for doing things. I've. I've gotten in trouble for answering questions. There was like a very directed question. I remember at Sijan where I jumped into one of the support channels and the question that was being asked by the particular customer was. Can't remember what it was at the time, but I remember it being very high level and there was a philosophical question to ask or answer first before you could go on with a recommendation. And this support person just wanted a yes, no, do this step.

Jessica Andrews [00:25:07]:

And so I got in trouble from the support organization for jumping into that conversation. But.

Matt Carnevale [00:25:12]:

Right.

Jessica Andrews [00:25:12]:

Ask for forgiveness. Right?

Matt Carnevale [00:25:15]:

Yeah, exactly. Shoot first, ask questions last. That's it. So building those relationships in the beginning, in the earlier stages of when you're building them, how do you balance being an order taker versus more of a strategic doer? Right. Because it's like you want to. You want to show people that I'm on your side. Like the things I'm working on will help you and impact you. But, you know, I found that can also turn into like, hey Matt, I need a case study about this very specific type of customer in this industry.

Matt Carnevale [00:25:46]:

Like can you get it to me in the next 48 hours because I have to pitch someone soon. Like, how do you, how do you balance those two things?

Jessica Andrews [00:25:51]:

Yeah, so usually what will happen is when I have like a very specific request. So if it is a go to market for a particular feature and they're just like, we need you to communicate this feature and we need you to do it by expert date. Or if sales is asking for, we need this case study, we need this infographic, we need this whatever one sheet. I usually go back and say, why? What prompted this show me the gong conversation where you decided that this particular piece of content needed to be created? What was the behind the scenes when product decided this feature was going to get built out? Usually for these like immediate one off questions that come up, usually I actually learn quite a bit. And so it will bring the conversation back to like, what is the problem to be solved? How can we do this in a good way? And usually that less becomes an order taker and usually that brings up other ideas. Well, what if we did a video about this? What if we put this in the help center? What if we did in app notifications for this launch? So it usually brings up a little bit more strategic. And so when you're positioning yourself as a strategic person, they won't come to you next time saying, I need you to do 1, 2, 3. They're going to come to you earlier saying, what do you think about this? Do you think that we should be doing this particular tactic? What, what else would you do? So they see you as more of an ideas person that makes them look good to their manager when they present this idea that they want to come up with.

Jessica Andrews [00:27:06]:

So it's really just like setting your route early. But don't be mean and saying, no, I'm not doing that because you didn't come to me earlier. No, it's like, oh, I love this idea. I don't have time for it right now. But what if we did this instead? Usually that is a much better conversation to have. I never say no, I just say, let's talk about it.

Matt Carnevale [00:27:22]:

Yeah, I think that's the right approach because it's so easy to get annoyed by their requests. It's the same way like, you know, we're encouraging marketers to go understand a salesperson the same way they don't necessarily understand us. Right. So it's like they'll be, they'll ask those little things and it's so easy to just be like, no, that's not a priority. Or like to ask prompting questions or probing questions in a condescending way of like, why? Why would I do that? Right now? That doesn't seem like a good fit. You know what I mean?

Jessica Andrews [00:27:49]:

Yeah. That creates a culture of negativity that is very, very difficult to go away. I mean, I've heard stories of sales and marketing teams that did not get along and it was toxic. And then the entire marketing organization just is gone because the sales team was doing well on their own without marketing's help. And there's a toxicity that they just, they have to eliminate the entire team and start again. So you don't want it to get to that point where it's suddenly marketing against sales or marketing against product because one of them is probably stronger than marketing at a given point if they're able to ask these questions. So I just try my best to reframe the entire relationship into a help me help you, if that makes sense.

Matt Carnevale [00:28:27]:

Yeah. So how do you do that? Like how do you go into a company and, or you know, you're in the company and you want to be that support arm to sales? Like, how do you start that off? Is just going to talk to people and asking them what they're working on and seeing where you can insert yourself. Like, what does that look like?

Jessica Andrews [00:28:45]:

It's really easy when you start at a brand new company because part of your onboarding is likely meeting with all the top executives and the top managers. And what I like to do is actually ask for a top seller. So beyond that, who on your team is doing really, really well that I can talk to about what their challenges are and how I can help. And so the further deeper into the team you can go, the better because the managers have a very different viewpoint on what's working for their team versus what a top seller is working for them. And I find that the top seller is the one that's the hardest to win over because if you're trying to mess with their processes, they're not going to take kindly to it. Right. So yeah, it's, it's taking a balance between what leadership wants and, and how to make the end users, the actual sellers, happy as well.

Matt Carnevale [00:29:28]:

Yeah, love that. Have you had any strategies throughout your career that you've used to like, get information out of sales? Like, you know, I've sometimes put five salespeople on a call and you have this agenda of what you want to ask them and it's It's a pretty dry conversation and it's, it's tough to pull those insights out. I know that's like part of the game, but like, yeah, do you have any, anything that you've done or used that you found has worked well for you?

Jessica Andrews [00:29:55]:

What was interesting is my last role at cision, I had a very strong relationship with an account manager and I feel like he was one of the kind of unicorns in the sales industry where he wanted to learn something from me that I had knowledge on that he wanted to learn how to sell. And so it was a product decision that I'm not sure is still there anymore where it was able to track views of PR content using kind of ad tech networks. So basically views were the same as impressions of ads, but our system could actually see how many impressions were requested on certain URLs. So super cool product and very techy, very ad tech focused. And so this particular account manager wanted to know all about it. And so I walked him through it and he was amazed and he did amazing things selling that product. This is kind of a long winded way to say that I was able to find a champion in the sales department who then started talking about, hey, Jess is going to teach you about something, pay attention because it's going to change your life. And so by having that internal best friend, almost work, husband, work wife, whatever, I actually ended up getting a lot of other sellers on board to see the product and the feature that we were launching and why it was important to us.

Matt Carnevale [00:31:01]:

Yeah, I love that. That's such a good tip. I remember at a previous company we had a pretty big sales team and you know, the marketing team was small and we, we often had things that we wanted to implement in the sales team to make them better and it was really tough to do it in mass. But what worked well was can I find the one or two sales reps who were motivated to bring this thing up to me. Can I use them as the pilot? And then can I use their success as the story to tell to everyone else? Because the second you say so and so booked five more meetings this week because they use this lead list or this email or this script, everyone's like, they, they flock, right? And they just flood that idea and they all try and do it. So I like the idea of getting that internal champion.

Jessica Andrews [00:31:47]:

I would even say it's even more successful when it's a dollar value. And so and so made X percent to quote or X dollars to quota and made X percent commission. Usually that, that is motivating. And so I like to use those metrics too.

Matt Carnevale [00:32:02]:

Yeah. And I like. You also had mentioned, like, something about who's the best seller in the team or who are some of the best sellers and working with them. I think I read this in a book somewhere and I forget which book it was. It may be a really popular one. But they suggested, like, whenever you're implementing. Whenever marketing is trying to implement a new idea into the sales team, to only work with the best sellers because their odds of success are much higher, whereas the sellers who aren't doing as well, like, they're likely to fail for many reasons beyond just your idea. So is that something that you've done as well when implementing ideas or are you just kind of whoever.

Matt Carnevale [00:32:37]:

Whoever you can get to take on your idea?

Jessica Andrews [00:32:40]:

It's a good point. I think that I like working with the people who are doing well on their own because it's one less variable to have to account for. So if someone's not doing well on the team for whatever reason, that's another variable in your exposure experiment, your test that you're trying to measure. Because we're all working off the scientific method, right?

Matt Carnevale [00:32:57]:

Yep.

Jessica Andrews [00:32:57]:

I would also say that I don't try to go after the same sellers over and over again because then they get frustrated that they're the guinea pig. There is this special type of seller who's doing well, who's making quota, who wants it all, and they may too be on a leadership trajectory. Maybe they want to be a manager, maybe they want to stand out. And so if you find somebody that's hungry like that, maybe they're trying to get to the next level and they want to experiment and show that they can work with marketing. That's usually the best types of people. So it's figuring out who on the team is motivated for similar reasons as you. That'll get you a lot better buy in than just going after the top seller who is doing well and doesn't want to be bothered.

Matt Carnevale [00:33:35]:

Got that? Smart. Smart. Okay, cool. I want to go back to in the beginning, you had talked about needing to be T shaped to step into a marketing leadership position. You know, obviously you're part of the bottom of the tee. The long part was product marketing. Right. But how did you fill up the top of the T? Like, what were some things that you did to do that?

Jessica Andrews [00:33:56]:

I think that the piece that I was missing the most is definitely the demand gen and paid ad side. And so I had run paid ads before in a previous position and I knew how to do it functionally, but I did not understand the strategy behind it at all. I just knew that I had a certain amount of money and I had to put it into Facebook ads and voila, outcome results. So what I did was I really started undertaking a lot of the free courses that are available. We use Marketo at Copper. So a lot of Marketo's certification courses and also just in my one to ones like trying to have time to ask questions to the individual contributors who are doing that day to day to ask them questions like why are you doing things a certain way? But I think that my confidence level in demand gen in particular was really where I needed to do it on my own to really understand it. And so there was a point this summer where we had lost one of our demand gen managers and we had to hire someone new and I had to manage that particular area for the summer. I kept it alive, which is good that my confidence and let go of some of the imposter syndrome.

Jessica Andrews [00:34:58]:

But when we brought on the new demand gen manager, she told me exactly what she was doing to the campaigns and why certain things weren't working out. And I'm going to change the bidding strategy, I'm going to change the lists and how they're built and how they flow into the funnel. And everything she was doing was amazing. And so I've learned so much from her as well because I actually had to get my hands on it. And so it seems like I'm a tactile learner in that kind of sense. I have to be able to do something to understand it. So I did have that opportunity this summer to have a crash course in demand gen and I'm proud of myself for not letting it that ball drop.

Matt Carnevale [00:35:31]:

Awesome. Yeah, no, that's great. Yeah. I feel like a lot of people come up to the leadership position through one of the channels, right? So it could be product marketing, demand gen content content's a big one and they get there and then it's like, okay, they still stay in their lane and they expect the people reporting up to them to be the experts in that. And it's true, like maybe they might be the experts, but they still need the leadership guidance. And if you don't understand that thing even to like a 6 or 7 out of 10 level, like it's very likely to fail. Is that something that you've seen as well?

Jessica Andrews [00:36:09]:

A little bit. What's actually interesting is I now understand product marketing a lot better now that I'm in a marketing leadership position. Because before when you're in product marketing, you, you kind of hand off some go to market strategies to other teams and you don't really get to see how that particular launch impacts different areas of the business. And I also found that as a product marketer I did not seem to care about revenue. Maybe it was just the positions I was in, I was insulated from that. But as soon as I learned about revenue it's like, okay, so my beautiful product launch, talking about all these amazing features did not result in more MQLs. What could have happened? So what I've learned is that it's not always about the product, it's about the problem before someone even realizes that there is a product that can solve that problem. And that just completely opened my eyes to how much bigger the story is and how much bigger your role is.

Jessica Andrews [00:37:08]:

So that's kind of what I've learned along the way is that product marketing isn't just the only place to go in. Demand gen isn't the only place to come in. It's. It's understanding the entire marketing cycle and how it, how all of these individual pieces fit in and, and how you have to balance everything. You can't just rely on lead generation, you can't just rely on awareness or product marketing. It has to be balanced.

Matt Carnevale [00:37:30]:

I love that. I love that. You know, a lot of people listening to this are product marketers and probably aspiring marketing leaders, whether it's VP Product Marketing or VP Marketing Director Marketing. Right. There's a lot of them that listen that are in that same boat. You know we talked about the T shape and understanding the full picture as opposed to just the product marketing side. How much of that work are you doing to become T shaped in the role of product marketing versus when you get to the leadership position? I guess it's like what came first, the chicken or the egg. But what do you feel like product marketers can do while they're product marketer to prime themselves to be there?

Jessica Andrews [00:38:08]:

Yeah, I think, I think having a lot of cross functional meetings with different marketing team members is key. So they're already doing it with the product team and CS and the everyone outside of marketing. But if you can have coffee chats with your demand gen counterparts or your content marketers or designers, anyone in marketing on a regular basis, I think that will set you up for success. Now I became more T shaped after I had this role because I did not think that I would have this role this early. So what I would say is that when you're talking to your direct manager be very clear that one day I see myself in a marketing leadership role. So just keep that in mind for me is how can I get to the next level? And usually most managers of that sort will kind of check that person off as a leadership potential. And I had done that with the cmo, and now I know it's like, oh, careful what you wish for, because she'll make it come true. But anyway, what I'm trying to say is that it's never too early to start working on that T shaped.

Jessica Andrews [00:39:04]:

It'll be. You'll feel less imposter syndrome if you get started early. But just know that you will get to that stage and your T shapedness will continue to develop. So there's only so much you can do before you're in that position.

Matt Carnevale [00:39:16]:

Yeah, yeah, yeah. I love that. Yeah, it's. It's one of those things where, you know, it's. Let's say I want to learn about how to run LinkedIn ads. I mean, I can go take all the courses in the world, but until I actually have to do it, it's. It. It sticks a lot more.

Jessica Andrews [00:39:30]:

Yeah, Exactly.

Matt Carnevale [00:39:30]:

Yeah. Cool. Jessica, this has been such a great conversation, you know, not only for anybody who wants to move from product marketing into VP marketing or who's a product marketer today, but really even anyone making any type of career jump. There's a lot of, like, fundamental principles that you've applied that have kind of helped you get there, whether it was on purpose or accidental. So this has been such a great conversation, a lot to learn here, and I appreciate you taking the time.

Jessica Andrews [00:39:56]:

Of course. Thank you so much for having me. It's been an honor to be able to talk to Exit Five in the entire community. So thank you so much.

Matt Carnevale [00:40:02]:

Love to hear it. Full circle. All right, Jessica, thanks so much.

Jessica Andrews [00:40:04]:

Thanks.

Dave Gerhardt [00:40:09]:

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