Becoming a stepparent amid a career pivot

There are many different paths to parenthood - and regardless of how one may get there, bringing kids into our worlds is life changing in many ways.

At Parentaly, we work with employees who enter parenthood from all paths as long as they are taking parental leave - which means we don’t often have the opportunity to coach step parents.

One benefit of this podcast is that we’re able to share the profound stories of all parents, even if we’re not working with them in our coaching programs.

Jen Allen-Knuth is today’s guest, who became a step parent later in her career to four wonderful children ages 9 through 18.

Before becoming a parent, Jen spent her entire career with one company where she moved up the ranks and created new roles and opportunities for herself before eventually moving on to join a startup.

Much of her life revolved around her career, but after a lot of soul searching about what she actually wanted out of her life, she realized work was not her identity.

In this episode, we talk about how expanding her family to include her husband and children has helped give her clarity that her professional experience doesn’t dictate her self worth.

We also talk all about how this self reflection has given her the confidence to finally go out on her own - something she’s wanted to do in her career for a while.

Listen to learn more about her experience as a corporate seller, her career shift into entrepreneurship and journey into parenthood, and involvement in women in sales mentorship.

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Allison: Welcome, Jen, to the False Tradeoff podcast.

Jen: Thank you so much for having me. I'm so pumped to be here with you.

Allison: I am excited. I'm also feeling a little bit guilty that I have 30 minutes with you and I'm not even going to ask you about sales tips and tricks because I'm like, I have this amazing resource in front of me and I'm just going to throw that aside.

But what I want to talk about more is, you know, you're obviously this amazing, I heard you say you don't like to be called a sales expert, but you are. You're an amazing sales expert and you've had an incredible career. You spent, I can't even believe it, 18+ years at CEB, Gardner, Challenger, climbing the ranks, chief evangelist at Challenger. And then you threw it all up in the air.

We're gonna cover a lot of things today about parenthood and career shifts and whatnot. But I wanna start with that moment because when I was doing research on your background and your history and all of the wonderful things about you, that struck me as like, what happened? What was the inflection point after all that time that made you throw your life up in the air?

Jen: What a killer first question. So I can't say it was one thing. It was probably a combination of things, but I think the leading factor into that decision had a lot to do with my change in role from being a sales rep to the chief evangelist.

So when I became the chief evangelist, which is a role that I had created and advocated for with our CEO, it gave me an opportunity to go from a salesperson who's talking to a bunch of customers kind of in a vacuum to having this platform where I had a weekly podcast and I was writing more consistently on LinkedIn.

And I think the thing that it, two things that it did was one, it showed me that maybe I had a little bit more to offer than I initially thought. So I think I had always assumed my value or my worth was relative to the company that I was working for. So I worked for a company I was super proud of, but I think there was probably a bit of me that always thought like, well, my success is tied to that. And stepping out and getting uncomfortable helped me realize that maybe that's not the case.

And then two, I think when I started looking at how I was spending my time, I felt a pull to more of the things I was doing on the side than I was doing in my full-time job. So specifically, I was booking a lot of opportunities to speak at sales kickoffs and do things like that. And I found myself looking at my day and getting really excited about that stuff and then less excited about the things I was doing in my core job.

So, it did frankly take me a lot of time to build confidence in making the decision to leave because I was so fearful that without a brand behind me, I was just not gonna be successful. But I think those two things kept building and building and building to the point where I was like, okay, you just have to walk away because you're never gonna know.

Allison: So did you then walk away without knowing what would come next or did Lavender come to you and they convinced you to go to them?

Jen: It's so funny when you quit a job and have nothing else, it's like people start knocking on your door, which you don't think will happen. So I quit in December and then about two weeks later, I got a DM from Lavender and they had said, hey, we're looking at this role for community, would you be interested? Initially I said, I don't wanna go back to full-time work, it took me a lot to quit and make the decision to go off on my own. And it was really more about the team and the problem that they were solving that drew me to it, but there was a gap between making the decision to leave and actually that offer.

Allison: What were the other things you were considering at the time? Debating between, do I go and work for someone else? Do I work for myself in this moment? I mean, it sounded like you were gaining confidence. You had these sort of side gigs. What then were you comparing when Lavender comes and like, you must've been a huge get for them, by the way. So like, you know, it's an interesting place to be in where…I guess what I'm saying is my sense is you were drawn to this entrepreneurial, I wanna be my own boss type, run my own business. Is it that you got scared and spooked? Or is it that Lavender came in and it was like this opportunity that you just could not pass up? Or both?

Jen: I think honestly it was a little bit of both, right? So when all this happened, it was December, I was getting married that March and I had I think like 15 different sales kickoffs I was speaking at. So I'm not going to sit here and say like I was looking around being like, I've got nothing to do and well, it wasn't that. But I think there's always a little part of me that has that fear of…well, what if this is the best that happens? And when I leave, I become irrelevant. And so I'm sure that play was a part of it.

But I think it was also, if you look at the commonalities in my career, like when I worked at CEB, that was about best practice functional research, helping leaders rethink assumptions that they held around what makes them successful. Then you look at Challenger, it was a data-driven approach to figure out what makes sales professionals successful and helping people rethink that. And then you look at Lavender and it was helping people rethink their assumptions about what works in a cold email.

So there's definitely a common theme throughout all of the companies that I worked for. And I think that was a big part of the pool is…I myself had struggled a lot with cold emails when I was earlier in my career and to find something that could help. I think I'm really drawn to things like that because so many of us are looking around saying, well, someone's telling me to do this and someone's telling me to do that. Those two things are at conflict. How do I make a decision?

Allison: Yeah. So then you end up at Lavender, but you were only there for a year. So then what happened again, because then you ended up leaving Lavender after you're in and going out on your own. When you look back on that year, this is a terrible question. I was going to say, was it worth it? What did you get from that? But what happened in that year that then gave you the confidence to leave again?

Jen: It's actually a very good question because, like I said, I was a little bit worried that my success had more to do with my company than me. When I went to Lavender and I saw that I just continued to grow and get more speaking opportunities and have more opportunities where people, it felt like people really valued my perspective. I think that actually gave me more confidence because it wasn't like, okay, it was just this thing that worked at this one company you worked for forever.

And so it was around August timeframe where I just felt that pull again. And I was like, I can sit here and kick it down the line again and again. But I think making that decision to leave Challenger was so hard for me because it was the first time I had ever done it. It was really the first job I ever had. I just stayed there forever. And so having done it once, I think gave me a ton of confidence, like, you can do this again. And don't worry about what people think or if people think like you can't be cut out for a startup. That was the big kind of narrative in my head. People are gonna say, oh, she couldn't cut it. And I was like, what do I really care if people think that? People who know me know that's not the truth.

Allison: Yeah. Well, I think that's so courageous because I think most of the time when people make a pivot, they think about it forever. And like, at least in my personal situation, I was working at a startup. I was, you know, doing really well. I'd been there forever in startup years. And I started working on Parentaly. And it's funny, because when you're talking about these, doing these side gigs and gaining confidence, that was kind of my Parentaly story, which is like, I was building it on the side and it was working.

But even then I did not have the courage to quit for a variety of reasons. And luckily the company I was at was acquired by WeWork and then they blew up and we all got fired. And I don't know how long it would have taken me to get the confidence to actually quit and do this without a major push. And it sounds like in both scenarios, it wasn't that you were being pushed so much as you were going out and exploring. And then you made that decision of like, I wanna actually do this now for real.

Jen: Yeah, I think if you look at my career, so every two years across my career, I kind of made at least a little bit of a switch. So like I started off in account management and then I went to a cross-sell, up-sell motion and then I went to net new business and then I went to big game hunting and I felt like there was always this two year itch and that was the other thing. Having the opportunity to create that Chief Evangelist role was an incredible gift, right? But then after that, I was also kind of looking around and saying, well, what's my next thing? And I just didn't see it inside of the business. And it's no fault of the business. It was just more of like, if I don't see it, I have to create what I want.

Allison: So now that you are running your own business and I know you're still figuring out exactly what direction you're gonna take that in, I'm curious to hear how you will avoid that itch because when I started Parentaly, I was a one woman show and that's what I wanted. Fast forward to about actually exactly two years in and I was like, this is way too slow. I need to raise money, build a team, grow much faster. Where are you in that life cycle with this business?

Jen: I mean...so this is a really fascinating thing for me. I think when I first left, I really struggled with the notion of not having something to fix. Like I was just, I realized I was so wired to always look around and be like, that's broken, let me fix it, that's broken, let me fix it. And then you walk off and you start your own thing and there's nothing but things to fix and create, right?

And so it was like, I remember the first week I had off, you know, I was trying to create a website. I don't know anything about creating a website. I was trying to do all these things, build it. And I had someone call me that I respect and they were like, you know, what are you been doing this week? Cause I think they knew I would struggle with it. I was like, well here, I've been doing this and this and this and they were just like, why? Why don't you just take a minute, figure out what you really wanna do before you start building. And so it was a really hard switch for me. I think way harder than I anticipated to actually just slow down a bit.

But I think where I'm at in this stage of my life, I mean, you and I have spoken about this. I just got married last March, so I'm not even a year into that. It's the first time I've ever been married and my husband has four kids. And so if I reflect on my life, it was like the first 20 years of my working career, my job was everything. My job was how I assigned my self-worth. My job was how I felt about myself. If I was performing well, I would feel great about myself. If I was performing poorly, I was a mess.

And so I think at this stage in my life, one of the things that I've been trying to be really intentional about is not falling into that same trap now because I have something else that matters to me so much. So it's not to say I don't care about working. It's not to say I don't wanna set a great example for my children of working. I just don't want work to be the defining thing of how I assign myself worth.

Allison: Mm-hmm. And how did you switch over to feel that way? Was that a result of your relationship, the children, or was there something else? Like what, because to switch your identity from career to not just your career is huge.

Jen: I think it was a lot of, I mean, when you make the decision, you know this, you did it. When you make the decision to leave a job, you do so much self-reflection, so much more than I think you're capable of, than we're often capable of doing when we're really in it. And so I think one part of it was certainly recognizing this feeling like there was never going to be enough. There's never going to be enough things I could do that I felt like it was enough and that I could calm down or be good with where I was at. And so I just kept raising my own bar and it had nothing to do with the companies I work for, it had everything to do with me. So realizing that, I was like, gosh, you're just, you're always going to be chasing this feeling that you're never going to actually fulfill. That was one.

And then two is just the reality of like, you know, it's 3:30, your kids bust through the door, they want to see you, they're excited to tell you about their day. When I was not married and didn't have kids, I just didn't have that. Right? So there was nothing preventing me from not working.

And so as stupid and silly as it sounds, it's like that door kicking open was a really good alert to me. Like I've been staring at a computer screen for six hours and haven't left the house. That's why I'm very grateful for it. Because I think without it, I'm just the type of person that just gets sucked into always doing something.

Allison: Yeah. I was talking to a friend the other day about how wild it is that back when I worked at Managed by Q, pre-children, I was married, but I didn't have children. My entire identity was this company. And to the point that I would catch myself talking to my husband and I realized I'm not even listening to him. Like I'm literally just thinking about work around the clock. Every piece of my self-worth was wrapped up in that experience and that job.

And that it is so interesting to me that now I'm the face of my company, it's my company. Like everything I do is actually about this company. And if anything, now this should be my identity. I'm the face of the company. And I do not feel that way at all. I mean, obviously it's very important to me, but it doesn't feel like my identity in the way that this silly startup job did before. You know, it's almost backwards, but I think it's healthier this way.

Jen: Right. It is, but it's so much healthier. And I think sometimes, you know, obviously, I don't know the organization that you worked for or the leaders that you worked for, but sometimes, particularly in startups, I found it's like, it's almost made to be the norm. Like if you're going to work in a startup, it's got to be the grind and you've got to get like, what are we talking about? There are moments where I was like, what am I doing? I'm not curing cancer here. Like I'm helping people write emails better. Like, why am I losing sleep over this?

Allison: Right.

Jen: And so I think to some extent, the culture of the organization can drive some of that, too. And now you're setting your own culture, I'm setting my own culture. And I do think that has a huge impact on how we choose to feel about ourselves and what we value.

Allison: Yeah. And I think back to the point of this podcast, I actually think that when my identity is not wrapped up in the company, I can make better decisions. And so I actually think that the company is doing better because I'm not going to work around the clock and I'm not going to work every single weekend. And so I have to make decisions. I have to make better decisions. So, yeah, I totally resonate with what you're saying.

Let's talk about your journey into parenthood because most people become parents suddenly, right? They have a baby. So they went from not being a parent to all of a sudden being like, oh my gosh, what is this thing? Or they adopt. And so they, I mean, similar motion, right? It's like the child arrives and they didn't know the child before. You had a very gradual entry into parenthood. I'm curious if you can share more about what that was like.

Jen: Yeah, so just as context, I met my husband on an online dating service, like most of us do these days, and he had four children. So they are now, when I met them, they were five through 15. Now, obviously, it's a few years later. So the two oldest children...my husband and his first wife were divorced kind of early in their 20s. They were college sweethearts, a really amicable relationship, a really solid relationship. So we spent 50-50 with them. And then the younger two children, their mom passed away unexpectedly. And so obviously the circumstances of him dating were really, really sensitive.

And so when I met him, you know, it was an interesting situation because we had to decide like, is this something we're going to take seriously or is this something we're not, we're just going to casually date? Which is kind of weird pressure on top of already having pressure when you first meet someone. And so when he introduced the kids to me, I was very much like, this is my friend Jen. And for the first six or seven months, it was, you know, my friend Jen is coming over.

And every time I showed up, it was cupcakes and puppies and like all the good things. And so it was a very gradual introduction. But in many ways, you know, I think this is going to sound obvious, but like you don't really get a picture of what it's like to be a stepmom just by coming by and always being the one that's like bringing candy and fun stuff and doing fun things.

And so after about six or seven months, we made the decision to let the kids know and they were massively supportive. They're amazing kids. And I moved in. And that was when it was like, that's when it for me felt like a sudden transition because I went from someone who was living by themselves, downtown Chicago, like everything I did was selfish. Everything, every decision I made was for me. And then you go, you know, I moved to the suburbs of Chicago.

And all of a sudden now, it's like, there is no alone time, there is no selfish time. And I think in many ways, I struggled in the beginning a bit, because I felt this responsibility to be like, I have to be there. And I have to give everything that I have, because they don't have, you know, the younger two don't have a mom.

Allison: Yeah.

Jen: And so I think I kind of, and I talk about this with my husband a lot, like I think I kind of lost myself in the beginning because I was so focused on just being 100% there for them because that's what in my mind I perceived motherhood to be is like, it's all about your kids and not about you.

Allison: Right. Did that impact, where were you in your career journey at that point? How did that or did it not affect that sort of timeline and the career arc that we discussed before?

Jen: I think it did. I mean, I don't think at the time I realized it did, but I was doing a ton of travel at that time. I was having to leave home a lot. And normally that wouldn't have been an issue, but it just felt like I had something I was leaving that I wanted to stay with. And I think that caused me to reconsider, like, is this the right role for me and what I want out of my life?

And I think part of me struggled with it because I was like, oh, is this just like me conceding to motherhood and like motherhood takes all the things away that are important to you? And then I realized it really wasn't that it was like, this is really what I want to spend time doing. My job didn't really like…I don't want to say my job didn't allow it, but my job made it hard. And so when you feel two things pulling apart from each other, I think you naturally go where you want to spend more time.

Allison: Do you have any rules now, boundaries that you put into place? Are there certain things as it relates to parenthood that you are just like non-starters? Like you won't travel more than X or you won't be gone for more than Y days.

Jen: I would say I'm terrible with boundaries, Alison. That's a whole nother podcast. Terrible with that, but I am really mindful about when I travel, I'm trying to minimize the time away from home as much as possible. So I'll be the one that's up at three so I can get the 6am flight. And if I can do it in a day and be back, then I do it. But one of the things, and this is why I appreciate my husband so much, that's been helpful is my husband will actually encourage me.

And he'll say take the extra day, if you're going to New York and you're just gonna go to a meeting, like take an extra day and go do something that you like. And I think that's really helpful for me, because again, I tend to have this really critical point of view about myself, like, well, I should be doing this instead of that. And that's where I think the partnership has really been helpful between me and my husband to remind me of things that I probably should be telling myself to begin with.

Allison: Yeah. Tell me about what it's like to be the stepparent to teenagers. Because I do not have teenagers. I have no idea what's coming towards me, much less like, you know, you enter their life at a later stage. I can't even imagine what that is like.

Jen: Yeah. I actually think teenagers are awesome. I think there's always these horror stories and some of it I'm sure is also our children. I'm sure everybody thinks their children are the best, but our children have been through hard things. That I think shapes them in a way that I don't think I appreciated coming into it. Their perspective or their point of view around what's hard is very different because of the loss that they had.

And so in a way, I think teenagers are really cool because you start to see them showing who their future selves will be. So for example, our third oldest child, Ryan, last year was really interested in public speaking. And so she auditioned to be one of her graduation speakers and, oh, this is two years ago, I'm sorry. She auditioned to be a graduation speaker. She goes to a massive school. There were like thousands of people at graduation.

And so to see her stand up there and have this confidence and speak and speak vulnerably, I was like, this is so cool in a way that, you know, going to a band concert when someone's six, it's just like a little bit different. So that's part of it I think is super, super cool, particularly with girls.

Allison: Yeah. Let's talk about girls, women in sales. So you're on the board or you're an advisor to Women in Sales. And I know you've spoken to me about how mentorship is really important to you. What role does that play in your day to day now?

Jen: Yeah, it's one of those interesting things. I actually had a friend of mine, like I wrote a post about women in sales last year, and he was like, you know, you don't really talk about it that much. And I reflected on it. I was like, you're right, I don't really do it. I mentored a lot of women, but I wasn't really loudly talking about it on LinkedIn. And I realized I think that was a bit of a disservice because I was very fortunate to grow up in sales with really phenomenal women managers.

And I think that's very rare. And so I learned a lot of lessons. I was shaped in a way that I think made me successful regardless of whether my boss or my customer was a woman or a man, but not all women have that. And I think some women, I hate making generalized statements, but I think in general, some women really struggle to ask for help. And particularly when it comes to selling, because they already feel like people are gonna think I can't do it anyway.

And so when I met Alexine, who founded Women in Sales, what I loved about it was it wasn't this like men are the enemy and let's bond together and let's gripe about it was really truly a group of people who are like, we want to be amazing at sales and we want to lift each other up. And that was the first time I felt like I was exposed to a group where it wasn't like a, I hate to say this, but it wasn't a griping session. It was much more of a productive, like let's elevate each other. Let's help each other build the right set of skills. And that's what totally sucked me into it because I think in my opinion, that is the way that we get better and we elevate ourselves in organizations.

Allison: Yeah. What is it that draws you the most to women in sales as opposed to just like mentorship in sales? Like what is it about supporting women other than there just aren't that many women in leadership? Is that the thing or is there something else that really draws you? Like why does that give you energy?

Jen: I think because I find in the conversations, I have a lot of conversations with people that I'll reach out and be like, hey, can I pick your brain about something? And like I said, I've had a lot of people that were generous with their time, so I try to be generous with mine. And I find that women more so than men just have such a level of self-doubt when they shouldn't. And I think sometimes it's just, they need a voice of validation to say, everybody else is running their sales calls like this, or they're writing their emails like this. But to me and my gut, I feel like that's wrong and I feel like I should do this. And I'm sitting there saying, you're absolutely right. Like your gut is what makes you have a superpower in sales. But when you look around, a lot of the voices, I'm sure you see this, too, like you go on LinkedIn and tag your 10 favorite creators, and it's just a list of 10 dudes.

Allison: Right.

Jen: And so I think part of why I do it and why it's so important to me is because eventually, I'm gonna get really old and crusty and dusty, and I'm not gonna write on LinkedIn anymore, and I'm not gonna do podcasts. And I want there to be a massive line of people ready to take that over. And that's the thing I worry about is like, even with podcasting, it can be really difficult to find women that feel confident in their voice to speak up, even though they have every reason to.

Allison: Yeah, I think the confidence piece is huge. And as you were speaking, I couldn't help but think about someone who, a woman who worked for me, was an enterprise sales rep. She was interviewing and she was a great sales rep, but she didn't present as aggressive, you know, she was a little bit quieter and well-spoken and soft-spoken.

And I will never forget when she was interviewing for a huge, huge tech company, like where everyone wants to work in sales. And the hiring manager called me, and he was asking me to, and he had a generic question, oh, how was she? And I just decided, I think I must've been tired, and I just came out of the gates like, all right, I can guess what your concern is. She's very quiet. And he's like, oh, yes, I know. I just, I can't believe she's in sales. And it was like, she ended up getting the job.

Because I was like, this is your concern, I know it. She is amazing, let me tell you why, let me tell you why not being super aggressive in your face is not necessarily always the right thing when everyone out there is doing that. So I think that confidence piece, it's like, I don't know, I think a lot about the confidence, but also how you present, they're not the same thing. And I think that that's what this person was worried about is, oh, her lack of confidence. She doesn't have a lack of confidence, she's just soft spoken

Jen: And that's the thing, particularly with sales interviews, this is the thing that's always driven me mad. It's like, what do people look for? I want the person that can win over the room and I want the person that's like, you know, very confident. Well, that in many cases is exactly the opposite of what makes for a great salesperson. It's what made a great salesperson in the 1950s, but today, buyers know a lot. They don't want someone who's taking over the room and so confident. They want someone who actually will listen and pay attention and make thoughtful suggestions.

Allison: Right.

Jen: And it's just, I find that our profession is too slow to keep up with that. And I agree completely with what you said, you can have someone who wows you in an interview and then totally sucks at sales because they don't get any of those really important basics right. And so yeah, that story I feel like is a tale as old as time for women. I know, I know.

Allison: Ok, I want to end with…we've been calling this like hot takes / quick takes, but I'm going to throw out a word or a phrase and I want you to just share the first thing that comes to your mind. I did not prep you. Don't worry. And you don't have to go do with it what you want, but we've done this recently and it's worked well. Um.

Jen: Oh boy. Okay.

Allison: LinkedIn versus TikTok.

Jen: Oh, productive versus unhealthy.

Allison: Your hardest parenting decision - or a recent hard parenting decision.

Jen: Goodness, this is a hard one. Okay, I have one. Talking to your kids about feeling anxiety, them feeling anxiety is such a tricky subject because you don't wanna teach them something that maybe then they're like, okay, that's a thing, now I have it. So talking about anxiety with our youngest has been really, really challenging.

Allison: Childcare.

Jen: Childcare…expensive.

Allison: Most embarrassing sales fail.

Jen: Oh, easy. I was selling to like a Fortune 20 company, a logo anyone would know. I worked this deal for like seven months. I thought I had a deal. And I was selling to someone who I had no authority, no ability to do anything. I realized it really late and I made a cardinal sin. I went above his head, went to the president of the company and just said, Hey, I've been talking to so and so about this.

The president forwarded him the email was like, why are you talking to a vendor about this? I've been clear that we're not outsourcing this. And then the guy called my boss, told him that he should fire me and that I was a terrible person. He hangs up with him. My boss calls me and he's like get ready for a phone call. The guy calls me and just reams into me to the point where I was sobbing on the phone and he still didn't stop and then a couple months later he got fired. So I think that's probably why he was so mad. That was my worst, my worst.

Allison: Proudest career moment.

Jen: Hmm. I think it was creating the job of Chief Evangelist at Challenger. It was the first time I ever put my neck out there to say like, I believe this job should exist. It doesn't. I asked for what I wanted and I got it. And then that's not something a younger gen would have done.

Allison: Love it. I'm going to end on that high note. Last thing I'll ask is if people want to find you, work with you, what are you doing these days? What is on your menu of what you can offer for folks? Where can they find you other than on LinkedIn?

Jen: Yes. So LinkedIn and then demandjen.com with a J, not a G. Right now, it's December. We're getting into a heavy sales kickoff season. So I do a lot of kickoffs for sales teams who are saying, look, my teams are struggling with how to sell to today's buyers. So I talk about things like prospecting and selling to group consensus and competing against the status quo. So that's the big thing. But I also do virtual training workshops for sales teams as well, primarily around prospecting and writing great cold emails.

Allison: Amazing. Well, thank you so much for your time today. This was fascinating and I wish we had another hour, but I love this. Thank you so much for coming.

Jen: Me too, you're so lovely.

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