From Entertainment to Executive Coaching: How Real-World Experience Shaped a Career Transition Expert

An exclusive interview with Rosalinde Rosado, Founder of URLaunchPad, by Roy Perlson, founder of Jobago.ai digital outplacement, on Rosalinde's journey from Fortune 500 professional to executive and career coach specializing in transformative career transitions. 

Rosalinde Rosado, Founder of URLaunchPad.

The Genesis of a Coaching Practice 

Roy Perlson: Rosalinde, can you tell us what led you to become an executive coach specializing in career transitions? 

Rosalinde Rosado: Honestly, I wish I had somebody like me when I was transitioning way back when. They say you might move seven times or more in your life, and I think the same is true for career transitions. Transitions are difficult to manage because it's not just about career; it's deeply personal. You need more support than just yourself. 

I worked with a great career counselor during my first transition, but at a certain point, we stopped. I felt there was more I could have done, but I didn't have the direct guidance. I thought, "This isn't the way to go." So, little by little, I started gathering information, learning from other people's stories, and collecting the best practices I could to create a roadmap for others. 

The Power of Diverse Experience 

Roy Perlson: You've worked in retail and wholesale. How do those experiences inform your coaching today? 

Rosalinde Rosado: Absolutely. I was a professional temp, which gave me vast experience in big Fortune 500 companies, smaller companies, startups, and mid-sized companies in New York and Los Angeles. In each place, you encounter people who are different, not just in personality, but in cultures and languages. It helped me to become adaptable and malleable in communicating with people, not from my language or culture. 

Those were the best experiences I've ever had because there were things you won't learn in a classroom. It was real-life, hands-on experience. Whether in wholesale, where you're building relationships at a higher B2B level, or retail, where you're building relationships on the ground level, those people follow you because they trust you. They know, like, and trust you. 

Finding Clients and Building Trust 

Roy Perlson: How do clients find you, and do you work with individuals or groups? 

Rosalinde Rosado: I work with both. Individuals find me through LinkedIn, my website, or referrals. A lot of the time, I get referrals from past clients; these are their colleagues who are ready to go because they already have a leg up on how I work. That's always the highest compliment when you get a referral. I also work with groups. I just finished a six-month program with Blue Star Families, a nonprofit that helps military spouses transition into meaningful careers. These spouses can move around with their active military partners, and especially now that everything is online, they can work remotely. We prepare them by guiding them through the entire transition period, and by adding the marketing piece, resume development, LinkedIn optimization, and interview preparation, so they're fully equipped to take on whatever they want to do. 

The Heart of Career Transition: Self-Reflection 

Roy Perlson: When working with clients, what's more needed: self-exploration and introspection, or the technical elements like polishing resumes and interview prep? 

Rosalinde Rosado: It's really about self-reflection. This is very reflective work. When we transition, we can't expect it to happen overnight. The technical aspect cannot take place first, it's like doing something backwards. You can't steer a rudderless ship. You have to have direction first. 

If you don't have that clarity, you're going to keep spinning your wheels. We need to be clear in our minds and in our hearts about what we're going to do. Because we can think of something, but if you don't feel it somatically, that it's going to be the right thing, then it's not the right thing. 

Roy Perlson: What do you say to someone who says, "This sounds inspirational, but I have a mortgage to pay"? 

Rosalinde Rosado: There's no shame in having a role to pay your bills. I don't know anyone who doesn't have to pay for something in their lives. That's what I call the "bridge role", the role that's going to get you to the other side. As you're doing this, the bridge role pays the bills while your desired career path rises, and eventually the bridge role diminishes. 

It's a slower process. Some people don't have that patience and get frustrated. However, if you really want to do this and you have to pay your bills, it's okay to have a bridge role. Just remember you're doing something over here that's going to eventually get you to the other side of that bridge. 

The Client Journey: Lost Jobs and Breaking Points 

Roy Perlson: Do most of your clients have a job but want to change, or have they lost their job? 

Rosalinde Rosado: It's a combination. Many have lost their jobs or are on the verge of losing them. But I also have people who are employed and just cannot fathom doing one more day of their job. They've reached that breaking point of "I cannot do this anymore." 

I always say it's great to explore when you have a job because you're not as stressed emotionally. Your bills are still being paid. You still have a routine and structure. But you're doing something else that's more of a discovery piece, and you can take your time with it. That's why this is reflective work; it takes time. 

The Intersection of Coaching and Therapy 

Roy Perlson: It sounds almost like working with a therapist. 

Rosalinde Rosado: Correct. When I have clients who might need more support than a coach, I'll ask, "What do you think about having a bit more support in this process?" And I'll continue down that road because certain issues might get in the way of getting to where you need to be. 

I've had people do therapy and coaching together, which I think is a great combination when you need a little more emotional support. For example, someone loses their job, and it's like PTSD because maybe way back when, they lost their job, but they also lost their house. The anxiety starts to creep in, and they can't manage those emotions. They might need a little more support, not forever, just in that period of time to get through to the next step. 

That takes courage. It's a sign of a vulnerable leader, not a weakness. 

Embracing AI in the Job Search 

Roy Perlson: To what extent do you see people using AI tools like ChatGPT for job search and resume work? 

Rosalinde Rosado: I love technology if it's helpful, and it has been extremely helpful when you don't have a lot of time. But you should always double-check your references and where you're getting information. 

I think it's a wonderful tool. People should embrace it and learn how to use it because it's here to stay. It's not going anywhere; it's only going to increase. If you're not embracing it at this point, you will be left behind. 

However, people don't understand that they've been using AI already, to get around with maps, voice chats on their phone. Everything you've been using! When people say, "Oh, I don't want to use AI," well, you've been using it without realizing it. 

Just remember: if you put garbage in, you get garbage out. If you put in rich content, you might get something rich back. It's about the prompts; what kind of prompts are you putting in? You're not getting enough or the right context if you're not putting in the right prompts. 

And here's the critical thing: AI doesn't really know you yet. It doesn't know your stories. You're the only person who knows the stories. If you don't put that information in, it's going to give you somebody else's information. 

The Hidden Job Market: Networking 

Roy Perlson: What about networking, especially for mid-career professionals? 

Rosalinde Rosado: Networking is going to be critical. They used to call it the hidden job market, and the hidden job market is the people you know. That really is it. 

The networking piece should happen well before you need your network. It's imperative that you build that network before it's needed and that you nurture the network. Because if you build it and just leave it alone, what do you think is going to happen? No one's going to be reaching out when you reach out. 

What can we do to nurture relationships? Do check-ins on some of the things you've been doing every quarter. Look at your roadmap. You might want to change a few things every three or four months. The same thing with nurturing relationships. 

Look at who you haven't reached out to. We get very busy and don't even notice that maybe six, eight, nine, or twelve months have passed by, and you haven't spoken to this person. When people cross my mind, I send out a little note just checking in. 

I had a client in tech in California, I hadn't spoken to in months. He crossed my mind, so I sent a text and called him. He sent me a text afterwards saying, "I really appreciate you reaching out and just connecting because it can be very lonely when you're working and just in your groove." 

Roy Perlson: But many people only reach out when they've lost their job, and then it's too late. 

Rosalinde Rosado: Exactly. Think of a target with circles within circles. There's the middle circle: people you constantly speak with. Then people you sometimes speak with. Then people you speak with once in a while speak with. At least every twelve months for that outer circle; Happy New Year, happy birthday. That doesn't take much. Just acknowledge them. 

When crickets happen, and you just go four years without contact, and now you want something? That doesn't work. 

The Power of Conversation 

Roy Perlson: Beyond conversations, do you provide frameworks or tools for clients to act upon? 

Rosalinde Rosado: I have tools I work with; however, the work is really through the conversations and the questions. If you're not asking the right questions, their mindset can't change. They can't become clear if the questioning isn't powerful enough. 

Most of the time, I'm on Zoom, where you can see nuances in behavior, little changes in faces. You can do the same thing on the phone because when you tune out visually, all of a sudden, you hear better. You hear the intonation in voices. You can tell when something was uncomfortable and ask, "What just came up for you?" 

I remember one client who was laid off; mid-career professional, family, kids, very nervous about the next step. I'm available to my clients as much as I am because sometimes you don't know when that moment arises. I was on break in Europe when I got a text. I could tell this person really needed to speak with me. I got back to the hotel and called. 

He said, "Oh my god, I'm so sorry. I forgot you were on break." I said no, no, and we ironed some things out. He said to me, "I spoke to my therapist three times this week. I spoke to you for fifteen minutes, and it was the best conversation I had all week." 

Sometimes, through a conversation, you can shift immediately. When people ask, "What do you say? What do I say?" I don't know until the moment is upon us. When you get on a session, you really don't know where you're going. You can't plan things out so much because they may change by the minute. You learn from the client which direction you might need to go into. 

Pathways to Becoming a Career Coach 

Roy Perlson: For someone aspiring to be a career coach, what certifications and organizations would you recommend? 

Rosalinde Rosado: All certifications are good for social proof. Anyone can put up a shingle and say, "Now I'm a coach." Some people who were in C-suite positions become coaches; people are going to them because of that, not because they're coaches, which is more like consulting. 

Coaching is more about support. Certifications help you learn to coach rather than consult, though there will be times when you take the coaching hat off and put the consulting hat on. 

The gold standard is the ICF (International Coaching Federation) with its ACC, PCC, and other levels, though it's not specific to careers. For career coaching specifically, there's the National Resume Writers Association with coaches and Career Thought Leaders; they have many certifications. There's also NCDA (National Career Development Association), which is very solid. 

Experience really helps in this area, not just coaching certifications. It makes the client feel much more comfortable knowing you've been where they've been. 

I always like to stay abreast of what's going on, so I attend webinars and at least one or two conferences a year. I'm always attracted to sessions on AI because I want to know the best way to use technology. If you know how to do that, you're going to be a much better coach to help your clients and help them learn how to use it while saving their time. 

Interview Preparation: The Human Touch 

Roy Perlson: Can you share an example of how human coaching makes a difference in interview prep? 

Rosalinde Rosado: I had a highly intelligent tech client in California. We were doing interview prep, and as I asked him a question and listened, I said, "Time out. Here's what I'm hearing." He looked at the camera and said, "Oh, this is why I'm not getting the second interview." 

Now, you're not going to get that from AI immediately. AI is going to let you go through the process, then do the assessment at the end. That shift doesn't happen immediately. I was able to make that shift for him right then and there. We had to redo the story he was saying. I asked him a few more questions, and we reorganized the story. His session was successful as he eventually landed a position not too long after. 

He did not notice he was doing the same thing over and over. People say, "Send me the questions." Well, that's not going to help you if the story doesn't fit the question. And if you think your story fits the question, but it's not answering those hidden things the question is looking for, then it's probably not the answer they were looking for. 

The Marathon of Modern Job Searches 

Roy Perlson: How has the job search timeline changed? 

Rosalinde Rosado: It used to take four or five months to find a job. Not anymore. My clients are going through eight and nine gates; gatekeepers, taking longer or not hearing back at all. If they haven't figured it out in four gates or interviews, it's not that you don't know how to interview. There could be several reasons. One issue might be that no one wants to take accountability for picking the wrong person.  

It's so expensive; a quarter of a million dollars or more to train somebody at that level if they leave. So, no one wants to have that responsibility on their hands if it doesn't work out. I understand that. However, my clients get flown to headquarters because they're so prepared. But once you get to that point, it's not about whether you're skilled enough. This is about personality and chemistry. Am I going to flow with this person? A lot of times, they're panel interviews, five people. It might seem more like an inquisition. 

I had a C-suite client who got flown into corporate headquarters. He had all his homework done, and I stress homework because if you're not doing what you're supposed to be doing, you'll never get to that point. I called him on a Saturday and said, "You really need to be able to answer this question and this question." He said, "Oh, I didn't even think about that." Guess what? It came up in the interview. 

He called me at the airport, having a beer at 1:30 in the afternoon; he deserved it. He said, "Ros, the questions were like softballs." He had the lawyer, the person who would be over him, the person he was replacing, HR, and a plant manager. Everybody looked around, saying, "That was a great answer" to a lot of their questions. 

He didn't get the job because he didn't have a certain clearance, a technicality. However, months later, he calls about another opportunity. He didn't even need me at this point because he was so well prepared for any interview, which is why I like to prepare people for any interview; however, they're going to need me again for contract negotiations. 

Mastering Salary Negotiations 

Roy Perlson: You do contract negotiations as well? 

Rosalinde Rosado: Yes. This same client was offered to move to another state and didn't really want to sell his house. I did some calculations, tax structures, because taxes are higher in the other place. I said, "You're basically going to be moving for about X more. Is this going to be worth it to you? Here's the other thing: if that contract doesn't come in at Y, you have no conversation. Because it won't be worth it." 

He texted me and said he almost smiled when the email came in. The contract came in at exactly Y, and we structured it to just under 7-figures. 

What I'm saying is, it’s all great, but it’s also why you need a human. AI is great for everyone, especially for people who don't have a lot of time and need to keep themselves going, to get through the noise. I can help in cutting the personal, the ATS, and the gatekeeper noise to help prepare you well so that you're unstoppable on the other end. 

Key Takeaways 

The Foundation of Career Transition: Career transitions are deeply personal journeys requiring self-reflection before technical preparation. You cannot steer a rudderless ship; clarity of direction must come before resume polishing and interview tactics. 

The Bridge Role Strategy: There's no shame in taking a "bridge role" to pay bills while building toward your ideal career. Transition is a gradual process where the bridge role sustains you while your desired path rises, and eventually the bridge role diminishes. 

Proactive Networking is Non-Negotiable: Build and nurture your network well before you need it. Think in circles; inner circle contacts you engage constantly, middle circle periodically, outer circle at least annually. When "crickets happen" for years, don't expect responses when you suddenly need something. 

AI as Tool, Not Replacement: Embrace AI for efficiency in resume tailoring, cover letter generation, and job searching, but remember AI doesn't know your unique stories. Quality inputs yield quality outputs, master effective prompting, and always verify information. However, human coaching remains essential for nuanced interview preparation, emotional support, and high-stakes negotiations. 

The Real Interview Challenge: Modern job searches involve eight to nine gatekeepers, not because candidates lack skills, but because no one wants accountability for a bad hire. Success at the final stages depends more on personality fit and thorough preparation than technical qualifications alone. 

Coaching Requires Asking the Right Questions: Powerful questioning creates immediate mindset shifts that frameworks and tools cannot achieve alone. The best coaching moments happen when you can identify what's not working in real-time and redirect on the spot. 

Professional Development Never Stops: Whether you're a coach or job seeker, continuous learning through conferences, webinars, and embracing new technologies like AI ensures you stay relevant and effective in an evolving landscape. 

Rosalinde Rosado is the Founder of URLaunchPad, a coaching practice specializing in executive and career transition coaching. With extensive experience across Fortune 500 companies, startups, and diverse industries, including retail, wholesale, banking, finance, hospitality, and entertainment, Rosalinde brings real-world insights to her coaching practice.

She holds multiple certifications, including Certified Master Coach, a future PCC certification from the International Coaching Federation (ICF), Certified Comp and Negotiation Coach, and Certified Career Transition Coach from Career Thought Leaders, Nationally Certified Career Strategy Coach, and Nationally Certified Profile Online Expert certifications from the National Resume Writers Association, where she also serves as Director for Member Support. Rosalinde's coaching philosophy centers on the transformative power of self-reflection, the importance of building authentic professional relationships, and strategic preparation that turns career challenges into opportunities for growth. 

Connect with Rosalinde:  

Website: https://www.urlaunchpad.com/ 

LinkedIn: https://www.linkedin.com/in/rosalinderosado/