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OhHello - Allison Whalen of Parentaly
25 Plays24 days ago
It's episode 95 of the OhHello pod and this founder/CEO is not only wicked smart, but
Everyone loves the “big leap” founder story.
But the truth?
The best companies aren’t built on leaps.
They’re built on small, smart, disciplined hops — over and over again.
Allison Whalen, CEO and Founder of Parentaly, joined Jeremy Bloom of OhHello to share what scaling a real company actually looks like:
- Why smart founders de-risk their bets before they jump
- How doubling her pricing (thanks to the right mentor) shifted her company’s trajectory
- The emotional pressure of building when it’s personal — and how boundaries create better leaders
- How “worst-case scenario thinking” can actually fuel, not freeze, growth
This conversation isn’t just about parental leave — it’s a blueprint for how real resilience is built.
If you’re building, investing, or mentoring the next generation of founders, this is a must-listen.
🎧 Full episode now live.
Massive thanks to Allison for keeping it honest, smart, and actionable.
#startups #founders #resilience #riskmanagement #venturecapital #ohhello
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Transcript
Intro
Introduction to Allison Whelan
00:00:05
Jeremy Bloom
Oh, hello, Allison.
00:00:08
Allison (Parentaly)
Hello, this is a first for me. And all I'm envisioning is my eight year, almost eight year old going, oh no. Seeing me attempt to dance. Also you froze a little bit. And so I was trying to use you for inspiration that I didn't see anything. So I'm just justifying my lack of dancing right now.
00:00:25
Jeremy Bloom
It wasn't a lack of dancing. It was, it's all being uploaded into the cloud in real time. So if I did freeze, then I looked like.
00:00:33
Allison (Parentaly)
Yeah, exactly.
00:00:34
Jeremy Bloom
But if I didn't freeze, then you still dance fantastically well. I guarantee it. So Alison Whelan, it is so good to see you. We've got a new budding friendship. We had a wonderful coffee meeting right before this. Why don't you tell us a little bit about yourself outside of being the founder and CEO of Parentaly. We'd love to hear and we'd love to have you share a little bit more about what you've been building and why you've been building it.
Inspiration Behind Parentaly
00:00:59
Jeremy Bloom
I'm fascinated with this company and I think it's awesome.
00:01:02
Allison (Parentaly)
Yeah, I mean, I feel like my life revolves around parental leave now and has been for the past five years. had my first child in 2017 was horrified at that experience. It was so hard to return to work for a lot of reasons, but especially from the sort of career disruption piece.
00:01:20
Allison (Parentaly)
and I looked around, there wasn't anyone who was focused on that and I thought, okay. You know, I came from a sales role where I look for problems and think, can I sell a solution? And I saw this and I thought, this is a big problem that has dollars and cents impact if We're letting people, encouraging people to take time away to expand their families.
00:01:43
Allison (Parentaly)
And if that is making them want to quit and go to another company, that is a problem. I saw a lot of ways to fix that. And so I launched it in 2019, went on to a month after I launched Parentally, I found out I was pregnant with my second child.
00:01:58
Allison (Parentaly)
So I have a whole, you know, drama in the earliest days, which I'm sure you can appreciate now that you're in early stages.
00:02:05
Jeremy Bloom
That's our second pot. When you come on again, you're going to tell us about that.
00:02:08
Allison (Parentaly)
Yeah, so I got pregnant. i COVID hit while I was five months pregnant. I got COVID while pregnant. I mean, it was just like all of the difficult
00:02:15
Jeremy Bloom
oh
00:02:17
Allison (Parentaly)
Fast forward to today, we have successfully launched and scaled the business, providing career coaching, manager training for parental leave. I now have three kids, so I'm very busy at home.
00:02:28
Allison (Parentaly)
No more parental leaves for me personally in sight. We are done.
Mentorship and Early Challenges
00:02:32
Allison (Parentaly)
And now I just get to help others instead of going through it and building at the same time.
00:02:37
Jeremy Bloom
It's amazing, amazing. Well, you're crushing it by helping others. Big thanks to our mutual friend, Jonathan Krieger, who put us in touch. Who are particular mentors that have propelled your success, that have made you the executive, the leader, the founder that you are today?
00:02:55
Allison (Parentaly)
I mean, I've had a lot of mentors over the years, but I would say one of the most interesting and maybe not intuitive folks, when I think about who has been influential most influential in this business in the earliest days where it can go forward or crash and burn, was one of my mother's best friends.
00:03:14
Jeremy Bloom
hu
00:03:17
Allison (Parentaly)
who I've known my entire life. I couldn't even tell you what she did. I mean, when you're a child, you don't know what your friend's parents do. And then when I was starting this business, I realized, oh my gosh, you know, my mom's good friend Deb, she's an executive coach and has been for decades, right?
00:03:39
Allison (Parentaly)
And the reason I bring this up is what was so interesting with her, I reached out to her, I shared her my idea, and she proactively would check up on me every few months, bring me out to lunch, ask me a bunch of questions, give me a lot of advice about what she has seen in this space.
00:03:55
Allison (Parentaly)
And I just think there's something so cool about that for like an entire generation ahead of me that she took such so much interest in what I was doing. And there was one moment, it was one of our, it was our first fortune 500 client where I said, can I send you this deck?
00:04:14
Allison (Parentaly)
You know, I just need like explicit
Risk-taking and Commitment
00:04:15
Allison (Parentaly)
feedback and told me to double the price.
00:04:16
Jeremy Bloom
Right.
00:04:19
Allison (Parentaly)
And I think back on that moment, and it sounds minor, but I was totally undervaluing my work and I didn't know it. And I don't know where you get that support other than from a mentor who has seen it, been there, done that, and is able to pay it forward, you know? And so I think back on that moment a lot.
00:04:39
Jeremy Bloom
I absolutely love that. That kind of feedback is so important for startup founders, it's important when you're early in your career, it's important at any stage, because the value that we put on our own intrinsic capabilities, and then how we can, we don't necessarily perceive our own value the same way externally that we present ourselves.
00:04:48
Allison (Parentaly)
Yeah.
00:05:03
Allison (Parentaly)
Right.
00:05:03
Jeremy Bloom
And so it could be at the time, perhaps, you come across as an extremely confident and secure person. So I just want to hat tip to you. But at the time, it could have just been because you were building and you just didn't know the right amount to charge for an amazing service to be able to be there and to help parents go and come back from parental leave.
00:05:16
Allison (Parentaly)
Right.
00:05:25
Jeremy Bloom
So kudos to Deb, that's
00:05:28
Allison (Parentaly)
She was also calling out a lot of things peeking around corners. Like you don't know these extra costs that you are going to find as you continue to grow this business. And so I just think having access to people who are both able to give advice but also understand that what you're doing is different.
Leadership and Emotional Management
00:05:46
Allison (Parentaly)
Like she wasn't telling me to do what she did, but she was able to really like support different areas in a really interesting way.
00:05:48
Jeremy Bloom
Totally.
00:05:55
Jeremy Bloom
what What was the biggest leap that you took during all of this to create your business, to be a founder, to create a platform and a service that is helping parents, that is helping businesses provide a service that when it is so essentially necessary, emotionally, mentally, physically, for individuals, for families, for teams, for businesses, when when when a parent is going to be going out on leave and teams are are going like
00:06:33
Jeremy Bloom
oh shit what do we do now
00:06:35
Allison (Parentaly)
Yeah.
00:06:35
Jeremy Bloom
Like how, help us understand just a bit more about like, what was that leap of faith? What, what, what did it take?
00:06:42
Allison (Parentaly)
I don't know that I took one leap of faith. I think I took a lot of little hops.
00:06:46
Jeremy Bloom
I like that.
00:06:47
Allison (Parentaly)
And I think that was one of the smartest things that I i have ever done is, i'm in some ways, I think I'm very risk-loving and also risk-averse, like at the exact same time.
00:06:59
Jeremy Bloom
Through bipolar.
00:07:00
Allison (Parentaly)
i'm the Yeah, I'm the type of person that's like, OK, how could this go wrong? And how do I? I don't know. I like taking risks, but I also like avoiding them. And so the leaps were very much like, I have a co-founder. She and I started working on this business back when we were working full time for our companies. And so we worked for an almost an entire year on this business off the side of our desk, taking little hops, right? and so like I think that was so smart and we invested our own money in these tests because we made a lot of money at our jobs. It was much cheaper to pay to run these tests than to quit, throw it all up in the air and and go all in on something that takes a lot of time and you need to build conviction around. And so we piloted the business while we were still working full time at our jobs.
00:07:47
Allison (Parentaly)
We even had some sales conversations before it even really existed, just to see if there was interest in buying. Because we can create the best solution in the world, but if no one will pay for it, who cares? So I guess, of course, the biggest leap of faith was when I decided to go all in. But at that stage, we had de-risked a lot about the business. So that was a big leap. And then I think like there were moments where I had to decide not to quit that almost felt like a bigger leap.
00:08:15
Allison (Parentaly)
than like the original decision. Because I think in the original stage, you're like very excited and you're very optimistic.
00:08:20
Jeremy Bloom
Absolutely.
00:08:20
Allison (Parentaly)
I think like six months in, nine months in where you always feel like you're on the verge of something big, but yeah' there's a little bit of like panic as you watch your cash in the bank personally go down.
00:08:34
Jeremy Bloom
Daily daily.
00:08:37
Allison (Parentaly)
And so in some ways, I think like the biggest leaps are just not quitting.
00:08:41
Jeremy Bloom
What about that? Don't quit. Just don't quit. I'm with you. I'm with you from having a couple different startups right now and what you just said is rings true. But this is about you. Help us understand a little bit more about just as parentally has grown just how have you adapted to your own leadership style and building teams and being a mentor both to your team internally to your clients and partners externally to your investors to
00:09:17
Jeremy Bloom
help us understand just what that is like from being previously a top enterprise sales lead to just going for it and then having to wear a bunch of multiple hats and being a mom of three kids, little kids.
00:09:30
Allison (Parentaly)
Yeah, I thought I was just a fabulous manager until I started my own business. And then I got a dose of reality around how difficult it is when it is so personal and feels like the weight is entirely on your shoulders. It introduced a level of, I don't know, reflection for me of like,
00:09:51
Allison (Parentaly)
Yeah, I'm a great manager in like a very specific environment. And I've had to learn how to be better in this different world, where it's just a totally different animal. I think one of the things that I've actually worked really hard on is almost compartmentalizing that personal and emotional side of the business. Because I think that that can, i it it sort of puts you in this position to maybe act not in the best way. like If it feels so emotional, it feels so personal, then you're not going to be the best and strongest leader make the right business decisions. um And then I would even say like that that compartmentalization
Preparing for Change and Conclusions
00:10:34
Allison (Parentaly)
and boundaries, I'm personally such a big fan of boundaries and
00:10:37
Allison (Parentaly)
I mean compartmentalizing, maybe that's the wrong word. That hasn't sometimes a negative kind connotation, but I really believe in boundaries. And so like, how do you make your time available for others?
00:10:48
Allison (Parentaly)
Like I was telling you before in our coffee chat, like I've opened up my Calendly to meet with people who want to meet with me. Well, a lot of people reach out to me because of what we do.
00:10:53
Jeremy Bloom
Totally.
00:10:57
Allison (Parentaly)
There are a lot of people who are struggling with navigating their career while pregnant. And I've struggled with like, I can't meet with everyone. And so how do I do that in a way that creates space to give to them? And then how do I write a blog post and just send that blog post out to 20 people instead of meeting with 20 people, right? And so I think like almost like trying to figure out where do I channel this emotion and passion in a way that is effective for the business and not allow it to take over everything has been really helpful.
00:11:29
Jeremy Bloom
That was insightful. Compartmentalizing is not necessarily a bad term, it's just reality, it really is.
00:11:35
Allison (Parentaly)
yeah
00:11:37
Jeremy Bloom
Understanding the the subjectivity the subjectivity that you put into your emotion when you're dealing with different business matters in real time versus saying, okay, I'm just going to put my email, my phone, my Slack away for a couple hours, either go for a run, hang out with my kids,
00:11:56
Jeremy Bloom
Go to sleep, wake up the next morning.
00:11:57
Allison (Parentaly)
Yeah.
00:11:58
Jeremy Bloom
That changes the way you think, taking a few deep breaths.
00:12:00
Allison (Parentaly)
yeah
00:12:01
Jeremy Bloom
Something that's very helpful, founder to founder, and I'm sure you know this, is also just going and standing up, changing positions, this doing the small things, you know stretching.
00:12:09
Allison (Parentaly)
Right.
00:12:13
Allison (Parentaly)
Mm hmm.
00:12:14
Jeremy Bloom
Because when you're hunched over and you're just thinking through, like we're all in our own heads. So that was super relevant.
00:12:19
Allison (Parentaly)
Mm hmm.
00:12:21
Jeremy Bloom
And when I loved how you had mentioned earlier about how you used to put yourself out there and throw out your calendly, but people take advantage of that.
00:12:28
Allison (Parentaly)
o
00:12:28
Jeremy Bloom
And that's obviously why one of the many reasons why we've created ohhello.ai is to be able to let mentors, let execs, let empathetic professionals find a platform where they can be on a platform, donate a component of their time, some of their time, some of their calendar, and then be able to help one another.
00:12:46
Allison (Parentaly)
me Right.
00:12:52
Jeremy Bloom
so How do you prepare for change? Before we close this out, like when you're when you know when you're dealing with all of these different stressors, how do you prepare for change?
00:12:56
Allison (Parentaly)
I'm a worst case scenario type of a person. Every time we have change coming up, I think what is the worst case scenario? And almost always it's not that bad.
00:13:02
Allison (Parentaly)
i'm a worst case scenariore typepe of a person
00:13:05
Allison (Parentaly)
every time we have change coming up i think what is the worst case scenario and almost always it's not that bad I get a lot of comfort from that.
00:13:12
Jeremy Bloom
I love that.
00:13:16
Jeremy Bloom
I really appreciate that. I sometimes think in a different kind of platitude. So when i when I speak with other friends and colleagues, it's really insightful.
00:13:28
Jeremy Bloom
So.
00:13:29
Allison (Parentaly)
I get very excited about change, which I think is what you're saying.
00:13:31
Jeremy Bloom
Yep.
00:13:31
Allison (Parentaly)
like You can be very ah overly optimistic.
00:13:32
Jeremy Bloom
Yep.
00:13:33
Allison (Parentaly)
And then that excitement turns into a little bit of fear. And I think it's healthy fear that's very motivating. I think oftentimes brings to light, like what are the things that you can do to avoid that worst case scenario?
00:13:47
Allison (Parentaly)
No, I've been given the advice from another founder. Your worst case scenario is never actually the worst case scenario, which that in and of itself is scary, and then he shared a very scary story with me.
00:13:57
Allison (Parentaly)
But I still think that it's actually quite motivating and helpful to think, eh, worst case, we lose out on $1,000, and who cares?
00:14:05
Jeremy Bloom
Right. Right.
00:14:06
Allison (Parentaly)
you know like Let's go for it, and let's reevaluate and move forward.
00:14:10
Jeremy Bloom
Let's move forward. Allison, this has been a fantastic conversation. I appreciate you. I appreciate the Oh, hello audience. Thank you for being a guest. Thank you, everybody.
00:14:21
Jeremy Bloom
Allison Whalen of Parentaly. Thanks, everybody. Until the next one.
00:14:24
Allison (Parentaly)
Thanks so much.
00:14:25
Jeremy Bloom
Thanks, Allison.
00:14:26
Allison (Parentaly)
Thanks.
00:14:26
Jeremy Bloom
bye
00:14:27
Allison (Parentaly)
Bye.