From high school arts teacher to a successful career leading B2B marketing teams, Jen Spencer shares her unique journey to the top

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Episode Outline

[04:39] Jen’s background

[07:16] What is takes to be able to developed and executed inbound lead generation and content marketing strategy

[10:13] The ability to supporting a channel of referral, reseller, co-branded, and white-labeled partners

[11:18] Why great communication leads to great partnership

[12:04] Methods in developing and executing an inbound demand generation strategy, raising brand and market awareness

[14:34] Habits to be great at sales and marketing that can never go wrong

[16:35] How to embrace a more diverse set of perspectives at the decision making table

[17:04] How Jen sees the trends in the future

[19:22] Use empirical evidence to decide what, what the best option is moving forward

[23:17] How to ensure there is right technical architecture, technical infrastructure to support these efforts

[26:28] The skills to know what the buying process is on their end

Jen's inspirations:

Trish Bertuzzi

Connect with Jen



SmartBug Blog

Elias Rubel (00:31):

Super excited to welcome Jen Spencer to the show today. Jen comes from a wonderfully different background than many typical sales and marketing leaders. Having started as a, as a high school teacher and then winding her way into becoming the tremendous sales and marketing leader that she is today. Having grown many companies Jen, welcome to the show.

Jen Spencer (00:54):

Oh, thanks so much for having me. And are you telling me that most people don't start out in as, as, as high school teachers. And then I ended up in sales and marketing.

Elias Rubel (01:05):

I mean, I guess not, I think you might be the first on the show, so I I'm really fascinated and excited to hear, hear how that journey happened. Maybe let's, let's just start there. Like how, how does someone go from, from having a passion for teaching students to I'd imagine now you have a passion for for teaching companies, how to, how to grow?

Jen Spencer (01:24):

Yeah, I think, I think the common theme there is I have a passion for telling people what to do. But but no, I mean, I really, I started my career as a teacher. Interestingly not just not because I love kids, I taught high school. I loved my, I love my area of, of study. So I love English. I love writing composition. I love discourse arguments, and I like packaging things for different audiences. So I was a marketer and a salesperson. Well, before I realized I was a marketer or a salesperson, and I made my way from teaching over into this, this world by way of nonprofit professional theater, I, I took a job as like a educational liaison type of role at a nonprofit regional theater, Arizona theater company. After I had been volunteering with them for, for a little over a year.

Jen Spencer (02:30):

And from there, I, you know, after six months of being there doing education type of work and kind of aligning educational curricula to what we were producing at the theater, the marketing director at the time was like, Hey, you know, we've really been looking for someone to do PR and I think you'd be great at it. And I said, I really don't know anything about marketing. And she said, I think you do. And then, and really the rest is history because I spent eight years there. And by the time I left, I was the director of and marketing. I was responsible for all of our earned revenue versus a contributed that comes from donations and 75% of the seven and a half million dollar revenue goal that we had was on my team shoulders. And and so I just kind of got thrown in and, and, and, you know, honestly, when you are trying to position, let's say why Julius Caesar is important to a 15 year old boy, when you're trying to explain, draw those connections and align that content and align the messaging and what you want them to get out of it, to that audience.

Jen Spencer (03:35):

Hmm. You know, that sounds a lot like sales and marketing. So is actually not, not a crazy, not a crazy journey when I think about it.

Elias Rubel (03:42):

So you were just in training that whole time, right? That's right. With the hardest audience of all, which is which teenagers

Jen Spencer (03:49):

A hundred percent I did my, I did my student teaching in middle school. And that is, that is something I do not wish on anybody. I think people who teach middle school who teach like seventh and eighth graders, they are they're saints. And so I, that was, that was a, that's where I really kind of earned my stripes. I think.

Elias Rubel (04:12):

So I love this, this kind of saying that you have this all hands on deck leadership. And I remember reading that you, you know, this is super important to you. I'm curious, like, what does that actually mean to you and how have you carried that forward in all of your roles?

Jen Spencer (04:31):

It's, you know, it's, it's that I, I subscribed to this idea that, you know, we're, we're really all in this together, whatever this is, whether we're talking about business, we're talking about our personal lives. I am definitely a had that kind of tribe mentality, right. Something that really resonates with me because when I think about anything I've achieved any success, like there, it's not all on my shoulders, right? It's not all my doing. There's always been people around me that are supportive. And I've been fortunate enough to have leaders that I've worked with over the years who are truly all in all hands on deck, worked for leaders who never would ask me to do something that they wouldn't do themselves, or, you know, that, that they didn't feel was, was, you know, cause worthwhile. And I've always respected and appreciated that. And so it's something that, as a leader, I, now I try to try to do so I applaud those CEOs who will be on the frontline and, and, and be an SDR for the day, or be a customer support representative for the, for, for the day.

Jen Spencer (05:37):

I think I am not seeing enough of that. I love to see more of it because until you've actually walked in each of your team members shoes, you really don't know what their day to day is like. And if the more context you have for the world that they live in and the role that they play, the better you as a leader are going to be able to support them. And it doesn't mean you can make all their problems go away, but having that empathy I think is so critical to really leading and inspiring a team.

Elias Rubel (06:06):

Certainly that's such a great message. So I'd love to bring us onto the topic of the podcast itself best in SAS. As you know, each episode, we're trying to uncover one little nugget or a couple of nuggets from each guests career, as we try to unpackage that sprint from a million and ARR, when a company kind of has just figured out their product market fit, let's call it to that elusive first $10 million milestone. Thinking back through your career, I guess if, if you were to pick two or three highlights that we've talk about, I'd love to dig into those stories and see you know, where, where you have discovered tricks or strategies, or just these evergreen moments that you keep coming back to in everything you do now. Yeah.

Jen Spencer (07:03):

So my first, the first truly SAS company that I worked for was a company called net time solutions. And it was a small software company in Scottsdale, Arizona. And it, I had the most amazing opportunity with net time because the CEO, I was, I was an inbound marketer, a content marketer CEO said, I really want to build a direct sales channel because the company had been selling almost exclusively through channel partners, which was great. And the company, you know, he had a nice lifestyle business, but the goal was acquisition. And so he's like, listen, I got a million dollars. I want to spend it on marketing. And I want you to tell me, you know, I want you to tell me how we should do that. And that's that, that was an amazing opportunity because I was able to go in, put in the systems and processes, everything from scratch that I wanted with the security of knowing, you know, there was a successful, you know, a successful organization kind of beneath me to support me.

Jen Spencer (08:09):

So I wasn't, you know, freaked out about the idea of failure. I mean, I'm always freaked out about failure, but, but I think it, it made me feel a little bit more safe than so I could take some more risks. And what I loved also about that opportunity was I was brought in to build a marketing engine and build an inbound demand generation engine prior to building up the sales team. And even just giving me actually like just two months of runway made the world of difference to be able to go in there and kind of get everything really well set, really align our brand. The brand was a little bit all over the place. Identify the value proposition, really identify like really focusing on the messaging conduct buyer persona research. So that by the time we were bringing on salespeople, we had a pipeline of leads to be feeding them.

Jen Spencer (09:05):

And we went from feeding four sales reps with leads to, you know, to 12 and then 14 all in the matter of a year. And then we were acquired by Paychex. And that was, it was so that was so awesome and so successful. And then after, you know, seeing that through and staying on board and making sure the transition happened nicely, going over to all bound, which was a completely different type of situation where we were starting from scratch there. When I joined the team, we didn't have a product, we didn't have funding. I mean, th th we had ideas and we had some mockups and we had this, this hypothesis. And I went in there to build that market, lay that marketing foundation. And I actually was marketing by debt or bargaining by night, I'm sorry. And then selling by day and then adjusting on the fly. But again, the success came from the CEO, the cofounders, knowing that marketing was important and that it made sense to actually lay this foundation for buyer persona work, content strategy, create a demand gen pipeline before starting to just throw a bunch of sales reps in quotas, you know, into a very young organization.

Elias Rubel (10:23):

So you mentioned something there that I think is so key and frequently misunderstood, or just struggled with on both sides CEO side, founder side, and, and the operator in the marketing and sales seats about around the foundation, right. You talked about taking the time to really think through the personas and lay that groundwork. How have you been successful in setting the stage for that blank space where, you know, you're, it's not exciting for anyone else. It's not, you know, nobody's looking forward to the air quotes, downtime of persona work and messaging work because it to that to everyone else, it's like, Oh, well, we're there like leads aren't coming in yet. And this seems to be the thing that's in the way. So how have you found success in building yourself that space with the other stakeholders?

Jen Spencer (11:20):

I think especially more technical founders. They, the common theme that I hear is they think their product is amazing. They think it's the best, and they think if only people can see it, if we can just get someone to demo our software, they're going to love it. They're going to buy it. And that's such a scary message that I, that I hear from folks where I've had success is in being extremely transparent. It's, it's creating a you, you, you don't to take a year or six months to build that strategy, to do some persona research, to understand what someone's pain is and how your product or your service could potentially help solve their pain. It doesn't take that long, but you have to start with something small and then iterate on it. And so persona research messaging, it's not set it and forget the most important thing for an early SAS company is to just be comfortable with the uncomfortable and be prepared to be agile and share internally how you're shifting things.

Jen Spencer (12:33):

So if I think back to it at all, bounds, our, our CEO had, he had an idea of who he was saw that we were solving a problem for. And he had like a few different personas. One of the personas that he was convinced we were, was going to be one of our buyers. They just, they ended up not being one of our buyers. And the way that I was able to explain that was through the, the leads that we were getting. What, what, what was resonating with folks, this initial sales calls we were having, and then sharing that feedback kind of aggregated. So going back to using, using that data, sharing it with the entire organization, and then saying based off of what I'm hearing from people on these sales calls and the interactions we're having online and what kind of content people are most interested in, what are the blogs that they're reading?

Jen Spencer (13:24):

What pieces of content are they downloading? What videos are they watching based on this, my guess is we need to slightly shift this persona to this other person. And this is why. And when you lay out those data points and you have a plan, and then you say, okay, and let's test this, let's spend the next two months testing this persona and see what the, the, the effects are. It became hard to argue with, right. It was like, okay, it makes sense. It was just logical. So I think you got to strip the emotion away, especially when you're working with a founder, this is their baby. You know, some, some people like they put their entire life savings into getting this business up and running. So I think as a marketer and as a sales person, too, like, you have to understand that perspective, but also use data to be able to help tell the story and not be afraid to, to say, Hey, you know what, we got something wrong and we need to make an adjustment. I think that's, that's how I would recommend approaching that kind of a scenario.

Elias Rubel (14:26):

So I think bringing up adjustments is such a, such a great place for us to take this. So when you are looking at an experiment or a set of experiments, or even maybe something that wasn't an experiment, but you're, you're looking at the data and you have the timeline, like how long you ran this experiment, if it was one, and then you have the signal, right. The, of the experiment, how do you go about deciding when to call it? Right. Like, I know time and time again, you'll have founders or other executives push back and say, all right, enough, like this thing's been running for a week, it's performing really poorly. Let's like week, let's call it a loss and move on. But, you know, that's, it's a really subjective kind of problem space. So how in your experience have you found success, both in running successful tests and getting enough data, a substantial data that you can say to the other executives or the founders, Hey, this is, this is right. And we should either move on or double down.

Jen Spencer (15:32):

I think it's, it's really gonna depend on the level of effort and the cost associated with whatever that experiment that test is. So I would be more, you know, more willing to let experiments go a little bit longer and collect more data if it's at you know, it's, it's a lower level of effort for my team or, you know, for, for myself and which equates to kind of the, the, the ultimate cost. If I'm going to be making an investment that, you know, that takes some kind of capital, right. I I'm going to want to know, I want to have done my research, my homework to determine what do I think a smart goal for this would be. So that way it's documented, and you have that to look back at and you're able to eliminate your bias and eliminate, you know, any kind of emotion that might go into that decision.

Jen Spencer (16:26):

But you know, it, it is, it is tricky. It's there are things that we do that we kind of continue to do as, as marketers, as sales professionals that don't necessarily make sense and, you know, for just for the, for the business and it, I'm not going to lie. I mean, it can be hard. I talked to people all the time when they come to SMARTBATT and they're looking for help, and they might say, Hey, last year, our inbound marketing efforts like the customer acquisition cost for inbound efforts was a 10th or less than like what the customer acquisition costs were for outbound, but yet all of our outbound efforts are given like five X budget to inbound and that kind of stuff, just, it just blows me away because I don't, I don't understand the logic of it. And, and that's something that we kind of, we'll try to help support and say, okay, what, where would this CAC need to be in order to get you more and more additional investments so that you can, you can fund this initiative and having those honest conversations with those leaders to say, what, you know, what does success look like to you?

Jen Spencer (17:36):

I think knowing that upfront is, is, is really important before you start to even launch into any kind of an experiment.

Elias Rubel (17:45):

I think that's fantastic. So I want to put you into a scenario and kind of hear what your response would be. So let's say, you know, you jump into another startup. They've just found product market fit. Their sales team is starting to get some repeatability and you're brought in as the chief revenue officer. The board says, Hey, all right, Jen, what's your plan? Give us like your top three plays, just what you've done in the past and what you're going to bring to the table right now over the next 90 days, where do you start?

Jen Spencer (18:22):

All right. So I'm going to hold you to the fact that you said that product market fit has been established, right? So that's, so, because we have to just like, take a moment and just like, affect address that, because fortunately that does not always happen. So, you know, we, we have prospects and clients that kind of come to us and they really haven't established product market fit at all. And, and it's, that's really tough. So, but once you've established product market fit, that's beautiful because that means that you're solving a problem for somebody. And so the very first thing I want to do, if it hasn't been done already is I need to build out those buyer personas I need, and I'm not talking about, we sell to a head of HR at a software company with 3000 employees. It's not what I'm talking about.

Jen Spencer (19:13):

Right. I'm talking about understanding what their day to day is like, where they go for information, what success looks like to them, what are the things that cause them stress? What are the things that caused them joy, who are they as human beings? Because at the end of the day, you're, you're solving a problem for another human who, you know, turns off their computer, hopefully, you know, at the end of the day and has the rest of his or her life that they're, that they're living. So I want to understand those personas because the more I understand though, those people, that's the information that I would use to build out my marketing strategy and determine, okay. Are we does a like a straightforward inbound strategy makes sense as a hybrid inbound ABM strategy makes sense. And what are the types of messages and what are the verticals that I could create sub campaigns within that are going to be relevant for this audience.

Jen Spencer (20:10):

So it starts with really knowing those people that could be, and that's actually getting on the phone with them. That's actually getting on the phone, talking to those customers preferably people who have recently purchased. So they it's fresh in their mind. What, what thoughts, you know, were, were swirling around in their head when they made this decision, it is good to talk to salespeople. And it's great to talk to customer success people as well, because they're the ones who are on the front lines living with and talking with those, those buyers on a regular basis. But those people also have biases and it's important to have those direct. So that, that's the bit like the very first thing that I would do. And when you're doing those persona interviews, you've got this, this captive audience where you can, you can ask, you know, where, where did we not meet your needs?

Jen Spencer (21:01):

What was missing from the sales process as an example that would have been helpful. And that's where you might start to dig into, well, you know, we really, we struggled with getting this over the line with it insecurity. Like that's something that might come up. Oh, interesting. Tell me a little bit more about that. What is your internal process like? And from those conversations of understanding what that, what the buying process is on their end from there now, I would be able to start to kind of organize the type of content. I know I'm in need to prioritize first, because what I found is I got no shortage of ideas. It's just a matter of, what's the best idea at, you know, at the best time and what needs to, how things need to be prioritized. So once I have that information, then I can start to create an editorial calendar and make sure that that editorial calendar is in alignment with our sales goals, kind of the demand gen goals that we have for building pipeline, but also in alignment with our buyer personas, when is a busier time for them?

Jen Spencer (22:02):

When are things, when is it slower for them? You know, what, what does that kind of, how do we align the marketing process with what their buying journey is going to be, which may unfortunately be different from like the, the sales motions that are happening. So doing, doing those pieces and then producing the, those, well, actually before I even get into content, it's also then making sure there's the right technical architecture, technical infrastructure to support these efforts. So it's, I've been, I've been burned before where I think, Oh, kind of reorganizing my like lead qualified, lead qualification and set of my marketing automation and not lead scoring, but like basically qualification it, this isn't critical right now. We're getting so such few leads right now. Not, that's not a big deal. The forms, you know, thinking about progressive profiling on forms and what I might have you know, just, let's just get out there.

Jen Spencer (23:01):

Let's just start throwing things out there and seeing what sticks, unfortunately, what happens is when you're successful, that momentum just keeps building and then you don't have the luxury of looking back and making those adjustments, or the further you get the harder it's going to be to go back and make changes. So getting that foundation in a good place from a technical infrastructure perspective, with your marketing automation platform, your CMS for your website and your CRM, and making sure that things, that the data is flowing correctly, and that you've got the right foundation in place to allow you to scale. I think that's also really important before you start launching campaigns, because it's also going to give you the data points that you need to say, if the campaign was successful, which will then inform your editorial calendar and so on and so on.

Elias Rubel (23:51):

Amazing. So I'd love to shift gears now into the, as we wind this thing down, the, all of this information has been so helpful, and I'm sure some of the founders out there and other operators, whether they're in sales or marketing have learned something. I know that you sit on the board of girls in tech and so you must be a mentor and inspiration to so many women out there, but I'm curious to turn this around on you a little bit and ask, you know, who in your career have you looked up to, and, and seen as a mentor or an inspiration in your professional life?

Jen Spencer (24:29):

I owe so much to my CEO at net time solutions, Bay Han satay, who I believe is, is he still with, with paychecks, you know, who had acquired us? And the reason why is because he, he spent time with me to ensure that I had a really firm understanding of the technical architecture of our product. And he taught, he spent that time in and taught me, and the way it all started out was I was trying to just extract just information from his brain. I was trying to be a good content marketer and say, Hey, come, you know, share with me your viewpoint of the market, the time and attendance world, which I knew like a little to, nothing about, to be honest at the time. And maybe we can just schedule like 30 minutes once a week and you can download this information to me, I'll take notes and then I'll convert it into blog content.

Jen Spencer (25:24):

And that actually transformed into these hour long, weekly whiteboard sessions, where I really got to learn about the difference between the differences in API integrations. The difference in the, from a competitive perspective, the integrations we had versus integrations of our competitors, our product was a fully, fully cloud-based SAS product that whereas our competitors had on premise solutions that they had converted to, to the cloud. And there was a difference, and it was so important that I really understood the way that, that the way that the technology worked. And I appreciate that he took that time. I, and it might've been frustrating. I mean, talk with someone to be like an engineer, talking to a marketer about, about this kind of stuff without any kind of background. I mean, I, I was eager to learn, and I think, you know, that he appreciated that, but having that foundation that helped me so much moving forward, it helped me in the way that I communicated with our product team, with our sales engineers, with our sales team, with our buyer personas.

Jen Spencer (26:35):

And it's something that I've been able to take with me even today, as I'm speaking with SAS founders, I'm speaking with SAS, CRS, marketers, heads of sales. I, I have a really firm understanding of the pains that their organization is going through at the heart of their company. And, and those are the, that knowledge. I just appreciate so much. So I've just, I've really, like I said, like really appreciated him spending that time with me. It wasn't someone I, if I would have gone looking for a mentor at the time, he wouldn't have been first on my list, really. I mean, what do I have to learn from someone who was essentially like a CEO CTO? He didn't really want to be a CEO. I was a CTO who built this product, but I learned so much about marketing and sales just by spending time with him. And I, and I, and I love, I love that, that he gave me that opportunity. And so I think there are opportunities for, for folks to find those mentors within your own organization. They may just not look or sound like the kind of mentor you think you need at the time.

Elias Rubel (27:44):

Wow. Sounds, sounds like that was such a tremendous almost like a, an opportunity that you didn't necessarily know was there immediately and then presented itself and just took shape. So how wonderful that, that was there for you. And is there anyone else that you'd want to mention while we're here?

Jen Spencer (28:06):

The other, the other person that I've, you know, kind of just later, more recently in my career that I really looked up to and reached out to is Trish for choosy. So when I, when I first built it was when I joined all bound it was, it was funny, you know, I was hired to grow, to run marketing, and then like, literally like day three, the CEO said, I know we hired you for marketing, but I I'd like you to also run sales. And I had never run a sales team. I had worked very closely with the sales team at at net time. And, and I guess, I shouldn't say I never run a sales team because I did run sales at Arizona theater company, but it was more box office telemarketing. It was B to C. So I never run sales at like a B2B company let alone like a SAS company.

Jen Spencer (28:52):

And I was petrified, right. Like, Oh my gosh, how am I going to do this? But there were two books that I read to kind of help help me. One was Mark Roberto's book, the sales acceleration formula. And then when the other was Trish for twosies that sales development playbook, just to help me kind of get the right frame of mind for the hiring that I was going to be doing and building this team. And so I, I knew her then, and then it was, it was interesting. We were at an event and, and she kind of came over to me and said, Hey, like I'm a fan of yours. And I was like, what, how are you feeling? What are you crazy? And it was just one of those, this is weird, you know, meeting someone who you think is just unbelievable.

Jen Spencer (29:31):

And she even knew my name. I was just blown away. But since then, it's like, I've reached out to her to say, to ask for some like, just gut checks on things. You know, I do speaking, I am sometimes, you know, paid to go speak at events and, or deliver workshops. And the first time, you know, someone said, Hey, what's your rate? You know, what would, what would it cost for you to have you come out here and do this workshop? I had no idea what to say, you know? And, and, and Google did not, you know, it just failed me. And I said, okay, well, who can I trust? Right. And so she's been someone that I've been able to go to time and time again, just to ask a quick question, you know, we don't have any kind of regular cadence or rhythm, but I know that I, she's just a good person and I can go to her and I can ask her for advice. And I, I appreciate that so much about her.

Elias Rubel (30:22):

Wonderful. All right. Last question for you. And I have to go here because because I, I learned this about you and I was doing some some reading. I, I hear you love scotch. What's your favorite scotch and why I'm also a fellow scotch fan.

Jen Spencer (30:36):

Oh my gosh. I do, I do love scotch. I'm, I, I do like, kind of like a scotch for like the Highland areas. My favorite scotch at this point in my life is Oban 14. And I say at this point in my life, because I I'm guessing there's probably something that's way better than I just haven't had yet. I just haven't been willing to pay for it yet. But but that's one of my go tos. It's just like, it's I think it's smooth, but it's also kind of strong. I also, I love wine and I love really bold cabs. And so an Oban 14 reminds me of the scotch equivalent of like a really nice, like kind of Caymus or silver Oak cab.

Elias Rubel (31:19):

Sure. Wow. All right. Cool. Love it. Love it. Well, Jen, thank you so much for for taking the time to be on the show. I know there was a ton of a valuable insight in here for the listeners and it was a real pleasure chatting with you. Thanks.

Jen Spencer (31:33):

Great. Thank you so much for having me.

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