A few months ago, Daniel Klein, an elite seller who’s worked in tech for nearly 15 years, shared a personal anecdote on LinkedIn that went viral. In it, he laid out, very frankly, how he had gone from being a top-performing director of sales, to head of sales at a company that was valued at a billion dollars…to becoming an IC (individual contributor) just a few years later. He shared how his confidence took a big hit having been so successful for a decade prior, and the lessons he learned getting back on his feet.
Today, Daniel has reclaimed himself as one of the top Emerging Enterprise reps at Databricks, one of the largest and hottest companies in all of tech today.
I came across his post on my LinkedIn and knew I had to reach out — it’s rare you see true truly top-performing sellers being this open and vulnerable. In this conversation, we expand on his journey, what it felt like to go viral sharing something so personal, and the amazing lessons he took from having the courage to start over.
Before your sales leadership roles — what kind of person would you say you were, in the early part of your career?
That's a complicated question. What I really was, or what I thought I was?
I'm curious if there's any discrepancy.
There's two layers, right? I think that maybe a lot of people have this. There's one layer which was this pretty confident sales guy. I deeply believed in myself. I thought I was great at selling. I very much enjoyed what I did. I went door to door in college — I developed very, very thick skin. And I learned how to take rejection, how to overcome objections.
And then I felt like I got really lucky going to tech sales and I had a great mentor, my first two years. So it was once I figured out that I was really good at tech sales, it gave me, I think, a level of confidence I probably never experienced in my life. Some of the times where I felt the most like myself is when I was selling, like where time would just fly by. I'd be in the middle of a conversation and then an hour would be gone and it felt like five minutes. I would get into these flow states.
So that was one side, but then there was definitely this other side of me that was almost the opposite. When you're hyper competitive, you want to win all the time. But…why? What is the thing that you're trying to prove to yourself that you need to be the best at what you do all the time? And if you're not, then you think something is wrong with you. So I think that during that period of time I definitely believed in myself. But there was this underlying self doubt because if I didn't do well, that was extremely painful.
And I think that sales can really help you believe that you are the best version of yourself. When you're closing the deal, when you're getting the recognition, when you're hitting the gong, you're like, "I knew I was this thing," but really it's coming from an external source rather than yourself. So I think there were those two interesting counterbalances during that period.
You became a director of sales, then a head of sales. Managing people, leading teams — do you feel like that became your identity?
The first role, director of sales, felt extremely natural. It just felt like fun because I was just helping other people constantly. Most of my time was training my sales reps, helping them prep for calls, being on negotiation calls. And then to close a deal with one of your reps is just such a good feeling. I remember that time as feeling easy — not easy to do, but it just felt easy to wake up every day.
And there's a natural motivation that I think you get when you're helping others.
And then moving into the head of sales role, what was that like?
I think that I wanted it to be my identity. Other companies in the space had just IPO’d. And I definitely was looking at the aim of, like, "I'm gonna be this CRO at the next big IPO and make a ton of money and all this stuff." And it was massively ego-driven.
I think probably there was some fear. Because with my previous role, I didn't doubt whether I could do the job. I'd been there forever. But going to this new company, maybe there was a part of me that was trying to overcompensate for some type of fear that I might not be able to do it.
Tell us about the experience of being a head of sales.
So I got hired by the founders because they knew me from my previous company. But I had difficulty selling the product. I think that was like my biggest struggle for a long time: why am I unable to sell this thing?
Because I'd been successful selling my entire career, I couldn't quite figure out why it was happening. And I found that I actually was just blaming myself. Blaming myself for all of the problems and my confidence... all of that confidence I had built up over the years just kind of slowly slipped away.
This was also during COVID, so I'm a first time head of sales, and I'm just kind of by myself trying to figure out what to do, not being able to sell the product. So that was tough. That was a tough two years.
I’ve also done early-stage startup sales. It’s not easy!
Yeah, I felt there was a disconnect between the product's current state and how we were positioning it. And so it felt like every single conversation I was struggling to align our messaging with the product.
And candidly, I learned a lot about myself in that process too. Like, if I had been more confident in advocating for strategic changes, maybe I could have contributed to finding solutions earlier. I think building that confidence to have those crucial conversations with leadership is something I've really focused on since then.
It sounds like it was the first time you had really doubted yourself at work.
I don't know what it was about this experience that I just went deeply inward. But for the most part, yeah, my professional career was very confident and believed that I was great at what I did.
So when all of this happened, how did you process it?
Terribly. I think I blamed myself, while at the same time, I don't think I did a good job of actually figuring out what was happening and being able to have honest conversations. This is gonna sound really weird, but if you think about your company, like, it's not your family, but at the end of the day, we as humans relate with the outside world very much like how we relate with our family.
So if you look at the company as your family in this weird way…I was having difficulty being angry at them. Like, I was having difficulty with realizing that not everything might be my fault. Does that make sense?
Yeah, it does. Because in sales, you are trying to control every possible variable you can, and for the most part, that had gone very well in your career. So if you're controlling all the variables and it's not working, then of course you're going to conclude that it's you, right?
Yeah. I think in this scenario, I just was unable to come to terms with the frustration I was experiencing. And so I didn't do a good job having positive conversations with the team. And then I didn't do a good job having positive conversations with myself. I feel like I internalized a lot.
But at the end of the day, it's very possible that I might have just been looking at this and been like, "This is an impossible scenario." And I just couldn't come to grips that there was nothing that I could do.
Sometimes the circumstances just don’t work the way you want, and you just get unlucky.
Well, yeah, that's such a weird thing. I think about that a lot. Like, is it luck? If it was a different head of sales, what would have happened? Could it have been significantly different? I don't know. These are kind of weird, deeper questions.
I do think it was unlucky, but also maybe not. I think a little bit of both. But I will say that it felt like I had no choice to go with this company. Head of sales, I knew everybody already, I loved the team, everyone knew me. Super hot startup, a space that I knew, people that I knew. It felt perfect in every way.
So you posted about this experience online. What motivated you to share it?
I think when you start posting online, you just think of things that would be interesting. Like, "Would that be interesting for people to hear?" And then, "Would this benefit people?" But I think it was just one that kept coming up —"That's a story that people should hear."
And also, when you write, the process of writing is a process of figuring things out. You are unpacking, in a way, what happened. A lot of the time, it's just as much for me as it is for everybody else.
What was that like for you, sharing that personal story, going viral getting that response?
I think my fiancé wanted me to shut the f**k up about it.
Really? Ha.
Yeah, because I was just watching the likes go up and up. I was like, "This one's doing well." It crushed during the week. And I was like, "Catherine, this one's doing really well. I can't believe it." And it was kind of surreal that I had a post that was going viral.
I went to sleep with maybe like a thousand likes and then I woke up and it had popped off to like 1800 just overnight almost.
It felt good. Because also, if you put something out there like that and people are like, "Shut up, dude. You're not interesting," there's a little bit of hurt that happens. I will say, even the last few days, I've had some posts kind of flop. And that does hurt. It sucks when your posts don't get likes. I work hard on my posts!
Wow, I didn’t realize LinkedIn “influencers” cared so much about likes.
Absolutely. Any influencer says that they don't watch... (smiles). But I do think that most people do, they count their likes. They do care. I do think that the people who've been doing it for longer start to care a little less. But I'm pretty early on in the journey, so there's still this part of me that is attached to the amount of engagement that I get. But I find that the more that I do it, the less attached that I get.
What surprised you most about going through this whole experience?
That it even happened.
Good answer. What is your advice for someone who is going through a tough time in their career and is feeling a lot of self doubt?
You’ve got to keep working on yourself. Whatever that looks like for you — whether that's going to the gym, whether that's spending time with people that you care about, whether that's therapy — just keep going and working on yourself and don't give up. I am a big believer that if you work on bettering yourself in some way — when you do those types of things, you're telling yourself "Things are going to change."
You're literally telling yourself every time you pick up a book or every time you talk to a friend about it that you believe that things can change.
And I think that the more you do it, the more you say that to yourself, the more likely it'll be that when the time comes, that interview, that job, that conversation — you've told yourself enough times that you actually start to believe it. And then hopefully you're ready for that moment. So I would just say just keep working on yourself, just try to make yourself a little bit better every day.
Like in sales. You have to believe in the product you’re selling.
Well…you don't have to fully believe in yourself. Maybe you don’t yet. But if you keep trying, if you just keep going…what other choice do you have?
That’s fantastic advice. Anything else you'd want to bring up before we wrap up?
Just that I was very grateful to land at Databricks afterward and it's been a phenomenal two plus years now. Being at the right company for me, with a great product, and a great team makes a huge difference.
That’s awesome — it sounds like it was a combination of luck and hard work.
This one was not luck. I was extremely intentional about the next company that I picked. I felt like I had no choice the first time because it felt so obvious. The second time, I had a massive choice, and I'm really happy with what I chose.
Huge thanks to Daniel for sharing his story — what lessons did you take away? Comment below — and stay tuned for the reflection piece!
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