From applying online to creating a custom leadership job aligned to his goals
Manager, ConnectWise Control Sales at ConnectWise
Director of Renewals & Expansion at seoClarity
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40%
Overview
Ben had built a strong career in sales, account management and customer service at a SaaS company, leading high performing teams and consistently exceeding targets. He wasn’t trying to leave quickly—but after years of growth in the same environment, he was ready for something more intentional.
He had a clear vision for what he wanted next, but translating that into a successful job search proved harder than expected.
The Challenge
When Ben started applying, he quickly ran into a common problem—strong experience didn’t translate into traction. His resume wasn’t getting responses, even for jobs that were a clear match.
At the same time, his goals were specific. He wanted to lead a customer success function, work at a company that aligned with his values and create a lifestyle change for his family. That combination made the search feel narrow and difficult to navigate.
The Shift
Instead of continuing to apply broadly, Ben shifted to a more structured and intentional approach.
He clarified what mattered most—not just the job title, but the company, the environment and how the job would fit into his life. He rebuilt his resume and LinkedIn to better communicate his experience and strengths, making it easier for others to quickly understand his value.
He also moved beyond applications and focused on targeted outreach. Rather than waiting for opportunities, he began initiating conversations with the right people.
The Outcome
That shift led to a very different kind of opportunity.
After reaching out directly to a CEO about a customer success leadership opening, Ben entered into a series of conversations that eventually led to an onsite interview. While the original position was filled, the company created a new job for him based on his experience and the value he demonstrated.
The result was a leadership position that aligned with all of his goals—including remote work, a move for his family and the chance to play a meaningful role in a growing company.
“I was confident I could find a job but not the ideal job I had in mind. This process helped me actually get there.” — Ben B.
How This Result Was Achieved
This outcome came from moving beyond applications and building direct relationships with decision makers. By clarifying his priorities, strengthening how he communicated his experience and taking a more proactive approach, Ben created an opportunity that didn’t previously exist.
Clarify the Criteria of the
Next-Level Target
Define what a true step-change looks like—scope, role, and trajectory—not just the next logical move.
Reposition the Leadership Narrative
Translate past experience into a compelling executive story that aligns with higher-level opportunities.
Access Off-Market Opportunities
Target and create conversations with roles that aren’t visible through traditional job search channels.
Convert the
Right Opportunity
Navigate the process strategically to land a role that is not just bigger—but more aligned and energizing.
Ready for your next-level role?
You’ve already built a strong career—but if you’re aiming for a meaningful step up in scope, impact, and compensation, it requires a more strategic approach than a traditional job search. The right opportunities aren’t always visible—but with the right positioning and strategy, they’re absolutely accessible.