Jason went from disengaged at a big company to leading product teams at a Boston SaaS startup that grew to 1,400 employees. Through Lynne Levy's coaching, he negotiated better pay, built a LinkedIn brand, and landed three offers without referrals. He even turned down a major tech firm because the conditions weren't right.
Chapters
Jason, great to see you. I'm so excited to have this conversation.
I am too. Thanks for, uh, thanks for chatting with me.
So tell everybody, where were you before you decided to join the program?
Yeah. Uh, before I joined the program, I was working at a good company, but I was, um, extremely disengaged. I wasn't motivated. I wasn't happy in my existing role and what I was allowed to do or unable to do in my role and the resources I was being given. And I was really struggling with my purpose and not just going to work to work, but actually really thriving and growing a team within my work. And I was at the point of struggling if that was the right path for me moving forward, if product was even the right path based off the organization, organization I was in. Um, yeah, so I ran into you at, um, a local conference, fell in love with you and your personality and your approach on how you were, how you just, how you spoke about product, how you spoke about what it can be. Um, and so came to you to, uh, fix my life and fix my career problems.
Awesome. I remember that conference. It was right before the COVID lockdown.
Yes.
So tell everybody what, let's just first start with what were some of your key takeaways from the program?
Yeah, I think there was, um, my first huge takeaway was understanding your value and not being afraid to go after your value and being very ambitious with that. And that can come from a competency perspective. It can come from a leveling perspective. Um, I was underpaid, undervalued, and underleveled at my last company. And the realization and the confidence that you instill helped me have very confident conversations where before I'd be asking for a certain thing and I would be timid. And then I went into interviews and went into companies asking very confidently for these much higher roles, much higher salaries, et cetera, and having very little issue and having no pushback and realizing I just had to be confident in myself. So that's number one. And I think number 2 was about creating my own brand. And instead of— we all see LinkedIn posts where people are like, applied to hundreds of different roles, interviewed at 50, got 1 job offer, and I'm so happy. Versus taking the approach of, during a few months into your program, I interviewed or applied to 3 companies. That we had targeted. I interviewed with all 3 companies, and these are not through referrals. These are from just straight applications. Interview with all 3 companies and got offers from all 3 companies. Boom. And so like, it just so much melted away the stress and anxiety I had with my job search. Um, and made me realize there's a much more effective way to interview and apply than just kind of shooting a shotgun and seeing where everything lands.
Right. So where are you now?
Uh, so now I'm at a, um, I, I said startup because it was 200 people when I joined. We're at 1,400 now, uh, company based out of Boston, um, that is, um, It's a SaaS business. We're a historically engineering-led organization. I'm someone who's passionate about building product teams. And so when I got hired in, they gave me the flexibility and full freedom to say, we need someone whose superpower is to build people and build teams and to align people because no one here even knows what product does. And I was able to come in, I was able to create that foundation, help grow that, help grow that and foster that culture. And the team has been absolutely incredible. They've been amazing to work with, and I feel so incredibly valued, but also empowered to do what I need to do, which I was not getting before. And now I am getting in spades.
That's amazing. And tell everybody what, what job offer you just turned down. You don't need to say the name except what, what the company letter begins with.
Yeah. So, uh, big tech, and you either know them by starting with the letter G or maybe letter A as their holding company. Um, but yeah, I had, uh, the very awesome privilege of being recruited by them based off the work that Lynne helped with regards to branding yourself on LinkedIn and creating the right network, following the right communities, engaging the right way, and being a disruptor on LinkedIn, which I'm not afraid to do. I've never been afraid to do that, but I leaned into that further. But yeah, went through the entire recruiting process. They were— they actually recruited me, which has never happened before, from my LinkedIn profile, um, nothing else. Uh, went through the interview process, everything went really well, but there were a few conditions unfortunately that they actually could not meet for me. And so I had the, uh, interesting opportunity, which I never thought I'd do in my life, which was to turn it down.
Unbelievable. Amazing. You owned what you wanted. And you turned it down.
Yep.
So I get a lot of questions from people. So Lynne, group coaching, I don't know if I like group or one-on-one. What did— tell, tell everybody the impact or the value from your perspective of working collaboratively in a group from a coaching perspective.
Yeah, I think there's two big things. The first is knowing you're not alone in your pursuit where you're at with your struggles. So it's one thing for you to come in and say, yep, I've talked to so many people, I've personally been there, or other people have been there. And that's like, cool, we can all like loosely say we've heard other people there. But when I talk to other people, um, of all different ages, ethnicities, backgrounds, etc., it's a very diverse team and group, um, and you realize we are all Like everyone in product that's not super happy with their job, everyone in leadership who's not super happy, all have very similar struggles and we can share and empathize with each other. And that's just huge to not feel alone. And the second piece is we're all growing together, but at different paces and in different ways. And we can all teach each other and share our growth to inspire each other. And also maybe share what's worked and what's not. So like, I think one of the nice things is even something as simple as within the Slack community that you have is if I am going through something in a certain day, I now have literally hundreds of people that are my friends and I can lean on to say, hey, I'm going through this right now. You've already talked about this openly. Can we chat and make sure that I manage this in a healthy way? So Well, like one-on-one coaching and having that one-on-one attention might seem like, um, you're getting more attention. I think you're getting way, way, way more attention in the group setting because you're getting attention not just from Lynne Levy Levy Levy, but you're getting attention from everybody else. And we all like swarm together to help each other.
There we go. Excellent. Excellent. Excellent. So one final question. So how, at a high level, so let's zoom out at a high level, how How do you feel about your future now versus when, when you started?
When I started, I was on a speed bike, pedaling really fast and going nowhere. And now I feel like I'm on a road bike where I'm actually on the ground making fast progress. As the faster I pedal, the faster I'm making progress and I'm really in control of where I want to go. Um, so for me, I'm no longer looking at I'm too young to do something. I'm not qualified to do something. I am looking at it and having conversations around whether it is product manager, senior product manager, group director, whatever, or just founding my own company. From the conversations I've had and the work that I'm doing, none of that is out of reach anymore.
I'm so excited, Jason. You're such a rock star. Yes, yes, yes.
All right. You are too.
Thank you. I am so excited to watch your journey. I'm so excited to watch your journey. Stay in touch.
