🧭 Stop Playing Career Roulette: Your Leadership Track is Hiding in Plain Sight

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Featured Job Listings

🏆 Top Picks of the Week (Hand-Picked, High-Impact Roles)

🔹 Chief of Staff to the CEO

Company: EliseAI
Location: New York, NY (On-site)
Apply: Apply here

EliseAI builds conversational AI to automate leasing, customer support, and scheduling for real estate companies. As Chief of Staff, you’ll operate as a force multiplier for the CEO—streamlining internal decision-making, driving special projects, and influencing the long-term company strategy. The role sits at the intersection of AI innovation, operations, and product-led growth. EliseAI is backed by Foundation Capital and Boldstart Ventures.

Recruiter Contact: Maria Morin

🔹 Chief of Staff

Company: Profound
Location: New York, NY (Hybrid)
Apply: Apply here

Profound is a behavioral health company scaling access to measurement-based care. The Chief of Staff will work closely with the CEO to drive strategic initiatives, shape company priorities, and coordinate cross-functional execution. This is a critical role in a mission-driven company focused on improving mental health care outcomes through evidence-based interventions. Profound is backed by First Round Capital and is rapidly scaling across the U.S.

Hiring Manager Contact: James Cadwallader

🔹 Director of Program Delivery

Company: Skylight
Location: Remote (U.S.-based)
Apply: Apply here

Skylight is a digital consultancy helping government agencies deliver more effective, human-centered public services. The Director of Program Delivery oversees the implementation of cross-functional initiatives that support federal clients. This leadership role is ideal for someone with strong experience in government delivery, service design, and agile product teams. Skylight is a key player in the civic tech ecosystem, partnering with agencies like HHS and VA.

Recruiter Contact: Cheyenne Meredith

🔹 Program Director

Company: Ford Motor Company
Location: Hybrid at Local Ford Location
Apply: Apply here

This leadership position sits within Ford’s global enterprise tech team. The Program Director is responsible for managing complex initiatives across engineering, systems integration, and business strategy. While located in Columbia, MD, the role aligns with Ford’s larger mobility and electrification efforts. It’s ideal for someone with a systems-thinking mindset, strong cross-functional leadership skills, and a passion for next-gen transportation innovation.

Recruiter Contact: Nicole Sookhai

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Bots Take the Wheel

🤖 Auto-Generate Team Skill Gap Analysis

The Problem: Quarterly reviews sneak up, and suddenly you're scrambling to assess your team's capabilities against strategic goals. Manual skill assessments are time-consuming and often outdated by the time you finish them.

The Solution: Automated skill gap analysis using Jira, Slack, and Google Sheets integration.

Use Case 1: Project Complexity Tracking

• Set up Jira automation to tag tickets by complexity level (1-5)

• Track which team members consistently handle high-complexity work

• Auto-generate monthly reports showing skill progression patterns

Use Case 2: Cross-Functional Collaboration Scoring

• Use Slack analytics to identify who's collaborating across teams most effectively

• Correlate with project success metrics in Jira

• Surface natural relationship builders for strategic partnership roles

Use Case 3: Strategic Initiative Readiness

• Create ServiceNow workflows that assess team readiness for strategic projects

• Auto-score based on past performance, current workload, and skill alignment

• Generate recommendations for skill development or role transitions

This automation runs weekly, updating a dashboard that shows exactly where your team stands against strategic leadership competencies—no more guessing who's ready for the next level.

Visionary Voices 

📝 Satya Nadella, CEO of Microsoft

Before becoming one of tech's most transformational CEOs, Satya Nadella spent 22 years in delivery and operations roles at Microsoft. His path from engineering manager to CEO offers a masterclass in strategic career evolution.

"The true scarce commodity is leadership without ego. I think that's what you need in technology."

Nadella's career trajectory shows how delivery professionals can leverage their operational foundation for strategic leadership. He moved from server and tools division leadership to cloud and enterprise group—always focusing on customer outcomes and business transformation rather than just technical delivery.

His approach to career development emphasizes three key principles:

• Customer obsession.

• Continuous learning.

• Empowering others to succeed.

These same principles that made him successful as a delivery leader became the foundation of his CEO philosophy.

Want to study his approach?

Read his book "Hit Refresh" for insights on transformational leadership.

✨ Weekly Recommendations

Stop applying to jobs randomly and start using a strategic system that actually gets you hired.

The fastest way to kill your credibility in any meeting is asking "what do you mean?" instead of this.

Sam Altman just made a move that could make Elon Musk's Neuralink obsolete overnight.

Most professionals are terrible at self-promotion because they're afraid of being shameless - here's why that's backwards.

The smartest people I know are willing to look stupid in public - and it's their secret weapon.

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AskALawyerOnCall.com gives you exactly that.

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Professional Development

📚 The Leadership Track Decoder Method

The Problem: "Many project managers often experience hampered occupational prospects during their career... career paths and systems within firms are often not adequately developed, resulting in fewer or no career opportunities, ultimately leading project managers to be stuck in a rut".

The issue isn't capability—it's clarity.

The Solution: Strategic career path mapping based on natural strengths and market demand.

5 Strategic Tracks for Delivery Professionals:

1. Strategy & Operations Track

• Core focus: Business strategy execution and operational excellence

• Key skills: Strategic planning, data analysis, cross-functional leadership

• Typical progression: Senior PM → Strategy Manager → Director of Strategy → VP of Operations

2. Chief of Staff Track

• Core focus: Executive partnership and organizational effectiveness

• Key skills: Executive communication, project orchestration, strategic analysis

• Typical progression: Senior PM → Program Director → Chief of Staff → COO

3. Program/Delivery Operations Track

• Core focus: Scaling delivery capabilities and operational systems

• Key skills: Process design, team development, performance optimization

• Typical progression: Senior PM → Program Manager → Director of PMO → VP of Delivery

4. Corporate Development Track

• Core focus: M&A, partnerships, and strategic growth initiatives

• Key skills: Financial analysis, deal execution, integration management

• Typical progression: Senior PM → Strategy Analyst → Corp Dev Manager → VP of Corporate Development

5. Digital Transformation Track

• Core focus: Technology-enabled business transformation

• Key skills: Change management, technology strategy, stakeholder alignment

• Typical progression: Technical PM → Transformation Manager → Director of Digital Strategy → Chief Digital Officer

How to Choose Your Track:

Step 1: Assess your natural strengths using the 80/20 rule—what 20% of your current work drives 80% of your energy and results?

Step 2: Analyze market demand in your industry and geography using LinkedIn job search data.

Step 3: Identify skill gaps and create a 90-day development plan.

Step 4: Test your hypothesis through informational interviews with people in your target track.

Step 5: Make strategic positioning changes to your resume, LinkedIn, and networking approach.

TL;DR:

Career clarity beats career chaos. Most delivery professionals are already doing strategic work—they just need to identify which strategic track aligns with their strengths and market opportunities. Use the Leadership Track Decoder Quiz to stop playing career roulette and start building toward a specific, achievable strategic leadership role.

How I can Help

Wanna chat IRL? Connect with me on LinkedIn and we can set up some time.

Stop being seen as "just a project manager" - the Delivery Career Decoder shows you how to position yourself as a strategic execution expert.

I love feedback. If you have topics you want to see? Or thoughts or ideas on how to serve the community better, please hit reply. I read all emails.

Until next time,

The Business of Delivery

Quiet moves. Bold Careers.