Episode 47: Why being rejected was the best thing that happened to my career

Getting rejected from roles is the worst. My imposter syndrome kicks into overdrive every time it happens. You do the research, reach out on LinkedIn, you kill the interview, but you get rejected, and without any other feedback, you assume it’s you.

It’s not you.

The hiring process is flawed in terms of scalable feedback, but that’s an episode for another day.

Instead, today I’ll cover some learnings from the rejections - learnings I may not have gotten without those rejections as counterintuitive as that may seem.

Sales —> Success

I was passed over for Sr. Sales Development Rep. Our target was 20 sales accepted opportunities, and I had 19 on the last day of the month. At the last minute, a prospect rescheduled a meeting and even though it still happened/was a viable opportunity, it didn’t count toward my promotion.

The two people I started with on my team were promoted, and I felt left behind. I started comparing my skills and background to them. I started actively rooting for my success over theirs. It was zero-sum mindset for me.

Shortly after, I realized that quota-carrying roles were not the right fit for me. What I thought was “my competitive side” was a side of me that I didn’t recognize nor did I want it to be a side of me that existed at all.

After some exploration, I decided on customer success as the next step in my journey. There was an open role internally on our customer success team who worked with our largest customers, helping them get more out of our product.

The team lead was a good friend and we spent hours preparing for the interview. I had my manager and my SVP of Sales all reach out to their counterparts to put in a good word.

I got rejected. They promoted someone from the support team for the role.

It was a hard truth to sit with. I knew I still needed to show up to work and do my job (well) to be considered for anything else in the future, but it was really hard.

For the next two months I focused on getting the promotion to Senior. I asked for feedback from my manager, skip-level manager and cross-functional teams. I improved my knowledge of the product, competitive alternatives, and our target customer.

I did get promoted to Senior. I also found that the topics I was researching were way more interesting than my current role. Even better — I found there was a job that just did those things all day: product marketing.

PMM —> Competitive Enablement

Years later, I found a company that turned audio and video into text. They were hiring for the founding product marketer. I reached out to the hiring manager on LinkedIn and got myself part of the interview process.

The final round interview conflicted with a wedding in Cancun, Mexico. I left in the middle of the ceremony to go back to my room and take the interview. I crushed the interview - no doubt in my mind.

24 hours later the VP calls me and says “I have good news and bad news”

• Bad news: I wasn’t getting the role - someone else had already gotten an offer and they accepted.

• Good news: There was another role - not yet posted - that the VP thought I would be a better fit for.

I ended up joining in this new role 2 months later. The person who was hired over me became my manager and I discovered a niche area of marketing - developer tools.

Marketing to developers had its own set of rules — facts about the product without any fluff. The documentation was the website and you were judged by the quality/ease of getting started. Pricing needed be fluid and scale with growth. You were speaking to a user who was often also the buyer.

I found what I wanted to do and the types of products I wanted to do it for. It was the first day of me developing my speciality

Competitive Enablement —> Pricing

1.5 years into the role, I was thinking about how my role would evolve. One area I spent some time on but lacked confidence was in pricing.

I talked to the folks on the team and asked them where they needed some help. They mentioned it would be helpful to have someone go deeper on how we differentiate from the competition and how we can revamp our pricing.

I wrote a doc talking through how the roles and responsibilities on the team would evolve and what additional impact we would have on the business if I changed my focus to competitive and pricing.

Everyone on the team agreed and I presented it to my manager. My manager’s response: “I wish you told me earlier”

Turns out my manager also saw the gaps and potential impact we could have if we had more focus on competitive and pricing. It was the exact thing my manager said to our VP to get an additional headcount. Someone had just accepted the offer and was starting soon.

It took me some weeks to get my head around it, but accepting I didn’t get the role was huge for my career. I did everything I could to be an asset to the new pricing person. He needed someone to help him get up to speed about the market and product. I offered to help on his projects and he walked me through his pricing methodology in return.

It was the opposite of what I wanted to do some days. One side of my brain said be grumpy, quit, spend your time doing something else. The other side said this is an opportunity to learn from someone who has expertise in something I know very little about. This will set me up to get this role in the future.

If you got passed over for a promotion or didn’t get the job you wanted, here’s what I want you to do:

1. Vent: Take the time and be pissed. be sad. Eat your feelings. Go to the gym. Whatever you gotta do, do as long as you sit with those feelings. The only way past them is through them.

2. Flip the script: There is always a positive angle to the problem. Something good you can take away. Force yourself to focus on the good.

3. Trust your struggle: You wouldn’t be where you are today without going through what you have so far. Trust that you’re better off.

As always, feedback is a gift and I welcome any/all feedback on this episode. See ya in 2025 👋 !

PS: It took me 3 hours to write, edit, and design this newsletter. If you liked today’s post, you can help me grow by forwarding it to one person with a quick “You’ll love this newsletter. Totally worth signing up.” They can subscribe below 👇️

✅ Find all resources here.

📆 Looking to connect? Find me on LinkedIn or grab some time on my cal here.

✨ Special thank you to Gigi Marquez who suggested I start this newsletter 🙏