Run A Job Search Like an IT Enterprise Rollout

A Case Study: How One IT Leader Landed a Role in 78 Days by Treating Their Job Search Like a Strategic IT Deployment

In the previous Spotlight, we discussed Mastering the Job Search Cycle, A Smarter Strategy for Tech Leaders! – Apr #25.  If you missed that one you can read it here. This month we look into a recent client success.

Client Snapshot

• Title: Director of IT

• Background: Former IT leader at a mid-sized SaaS firm

• Expertise: Cloud infrastructure, cybersecurity, enterprise systems, digital transformation

• Goal: Land a senior IT leadership role at a growth-stage company

• Challenge: First proactive job search in over a decade—previous roles came through internal promotion or inbound interest

The Strategy: Run the Job Search Like an Enterprise Rollout

Approaching his job search with the same discipline and structure he applied to major IT initiatives, we mapped out a plan with measurable milestones and iterative improvement cycles.

• Target Timeline: 120 days

• Key Milestone: Secure and accept a role aligned with his leadership and technical strengths

• Execution Framework: High-volume outbound outreach, warm introductions through networking, and continuous messaging optimization

Strategic Prospecting

We identified ~170 target companies using filters such as funding status, growth potential, and alignment with cloud or security initiatives.

•  From that list, we conducted direct outreach to 85 companies with high potential fit.

High-Cadence Outreach + Purposeful Networking

• Sent ~20 personalized cold messages per day (~100 per week) via LinkedIn and email

• Applied to 2–5 highly relevant roles per day on LinkedIn

• Scheduled 84 networking meetings, with ~20% from new connections, to build referrals and gather inside knowledge

• Optimized his LinkedIn profile to attract inbound leads

Personal Branding Foundation: Résumé + LinkedIn Messaging

Before launching the outreach strategy, we built a strong personal brand foundation that clearly communicated his value proposition to the job market.

• Resume and LinkedIn profile were reframed around measurable outcomes, not job duties or general responsibilities.

• We crafted a condensed value proposition that communicated how the client drives impact through cloud transformation, cybersecurity leadership, and scalable enterprise systems.

• The messaging was tailored to highlight key metrics, wins, and results—from cost savings and risk reduction to improved uptime and scalability.

This clarity helped with credibility while increasing response rates, improved recruiter interests, and create consistency across touch points.

Posting Articles to Drive Engagement

To further increase visibility and establish himself as a thought leader, we strategized to and posted relevant articles and insights related to his expertise in cloud infrastructure, cybersecurity, and digital transformation.

• These posts drove increased engagement from recruiters and decision-makers in the client’s industry, boosting credibility and visibility.

Resume & Career Summary Optimization

We created a one-page career summary for networking conversations and a customized resume that emphasized outcomes and achievements from their most recent role. This flexible format allowed for easy adaptation across multiple leadership-level job opportunities.

Warm Network Engagement

We designed a targeted strategy to activate their warm network—including alumni connections, professional associations, LinkedIn groups, past employees the client had hired, former managers and even a few neighbors.

• Using creative and impactful messaging, we reached out in ways that felt authentic and thoughtful, rather than transactional.
• These warm touches created awareness about their job search, led to introductions, and generated meaningful leads.

Question-Based Interview Prep

Once interview opportunities began to come in, we focused heavily on strategic interview preparation.  This was an ongoing process though-out or time working together.
Rather than simply practicing answers, we developed a library of smart, diagnostic questions that steered conversations toward pain points that the client was uniquely qualified to solve.

• This transformed interviews into problem-solving discussions—not just evaluations.
•  It significantly increased conversion rate from first-round interviews to final stages, ultimately leading to multiple offers.

The Insider Connection: Leveraging Influence with a “Third-Party Close”

As interview processes advanced, we introduced a tactic often overlooked: influencing behind the scenes.
We proactively identified contacts within target companies—former colleagues, second-degree connections, or shared alumni—who could credibly speak on their behalf or help validate candidacy internally.

• These “third-party closes” weren’t used in every scenario, but when applicable, they provided an edge by reinforcing credibility with hiring managers and executive stakeholders.
• Sometimes, a quick Slack or internal message from a known quantity made the difference between being shortlisted and being selected.

This tactic underscored a powerful truth: decisions are rarely made in a vacuum, and the right internal ally can shift perception and momentum.  Hence, people hire “people!” not resumes and applications.

Results: Funnel Metrics That Drove Success