Case Study: How I Worked with “Jacky” to Land His Ideal Next Job in 10 weeks.

Coaching in Action: How Jacky Reignited His Career Momentum

(Name changed for confidentiality reasons)

Jacky had been a high achiever at a fast-growing tech startup for over five years. Despite the ups and downs of the tech world, his career had been on a steady rise, joining as a junior-level individual contributor and working his way up to leading a team. He had been promoted multiple times and was doing well on paper.

But something felt off.

Jacky began to sense it was time for a change. Yes, a salary bump would be nice — but more importantly, he was unsure about the company’s direction and whether his work was helping him move closer to his long-term dream: becoming an entrepreneur. 

Around this time, he was approached by a larger company for a similar role. The catch? It was an individual contributor position — no team to lead, and a culture he wasn’t sure about, as he heard mixed reviews about the company.

Jacky’s mind was full of questions:

• Should I even consider this opportunity?

• What would my career trajectory look like if I took it?

• What compensation should I ask for in the offer?

• How does this align with my goal of becoming an entrepreneur?

  
  

Unlike many professionals who feel lost about where to begin, Jacky already had a good sense of his direction. He still likes what he is doing. But he also knew he didn’t want to navigate these decisions alone. He decided to work with me as his Career Coach to support him in this journey.

🔍 Finding Clarity

Our first focus was to help Jacky reconnect with his values, priorities, and both his short- and long-term goals — then translate these into practical job requirements. While Jacky hasn’t lost sight of his dream of becoming an entrepreneur, he’s decided to nurture it as a side pursuit for now, given his current life priorities. He has also decided that a change is what he needs. 

Together, we built a personal “job description” — his own checklist to evaluate opportunities and companies as they surfaced in his search. 

When we assessed the company that had approached him, Jacky realized it met most of his criteria despite some concerns. That gave him the clarity to explore the role further — from a position of intention, not confusion.

He also mapped out a list of targeted companies, ranked by alignment with his personal and professional goals, and his current network that he could reach out to.

📝 Strengthening His Marketing Materials

Jacky’s CV was solid but overly descriptive and brief — it read more like a job description than a story of achievement. We restructured it to highlight quantifiable results and leadership impact, turning bullet points into outcomes.

The result: a CV and LinkedIn profile that clearly told the story of his growth, value, and readiness for his next step.

🤝 Networking Strategically

Networking wasn’t new to Jacky — he was already proactive in reaching out. But we fine-tuned his approach by crafting more focused outreach messages and identifying key people who could provide genuine insight into his target companies.

I also connected him with a few professionals in my network who could share first-hand perspectives. These conversations gave him valuable clarity about company cultures and expectations beyond what recruiters would ever say.

💬 Interview Preparation

Even though Jacky wasn’t fully convinced about the new role, I encouraged him to treat every interview as a two-way exploration.

Before each interview, we reviewed likely questions, identified what the interviewers were assessing, and designed smart questions for him to ask — especially to address his “unknowns” about the role.

When Jacky was assigned a case presentation, I reviewed his slides from an interviewer’s lens. Even without technical expertise in his field, I helped him sharpen the flow, storytelling, and logic — key elements hiring panels look for.

The feedback he received after the interview was “excellent”. 

We also identified whom in the company Jacky could reach out to get more information about the role, expectations, and the culture during this process, so Jacky could assess the fit and ensure he would make the right decision if he got the offer. 

Meanwhile, Jacky is also interviewing with other companies and assessing them using his own personal “job description”.

🔄 Closing Communication Gaps

After one conversation with a senior stakeholder, Jacky felt he hadn’t performed well. We debriefed together, identified the gaps, and developed a follow-up strategy. He then sent additional materials to clarify his points and strengthen his positioning. This thoughtful communication made a strong impression on the hiring team.

💰 Offer Negotiation

When the offer arrived, we strategized on how to maximize the compensation package — breaking down the components, identifying where flexibility existed, and leveraging market benchmarks.

Jacky ultimately secured a 20% salary increase. After doing a thorough due diligence on the role and the company, he was very convinced that this would be a good opportunity for his next step.

🧭 Smooth Transition

Finally, I guided Jacky through his resignation process — helping him craft his message to his current manager with professionalism and grace. He left on good terms, maintaining strong relationships with his team and leadership.

🌈 The Results

Jacky didn’t just land a great new opportunity — he made a strategic move that aligned with his values and future goals.

He felt supported and confident throughout the process, knowing that each step — from interviews to negotiations — was handled with intention. More importantly, he regained his sense of control and clarity about where he was heading.

“I felt like I had someone who is not only my coach, but also knows how hiring decisions are made behind the scenes,” he said after landing his offer.

💭 Key Takeaways

• Coaching isn’t just for people who are lost — it’s equally valuable for high performers who want to make thoughtful, strategic moves.

• Every step in the job search counts — from clarity to communication.

• The right and personalized support can help you focus on performance, confidence, and alignment — not just the outcome.

__________________________________________________________________________________

👋 Let’s Connect if you’re navigating a career transition and want tailored support, I’d love to help. Together, we can explore your options, build your confidence, and make sure you show up with purpose in your next chapter. 

📩 Message me on LinkedIn or email me at melody@poppartners.org