👁️ Delivery Leadership in Real Life

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Featured Job Listings

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

Role: VP of Client Delivery
Company: Fueled
Location: Remote – USA | Leadership
Why it’s great: Lead a globally distributed project management team for high-profile digital work (think Google, Apple, ESPN). Own quality, profitability, and client satisfaction in a high-velocity agency environment.
Apply here: Job Link

Recruiter Contact: Heather Marshall

Role: Special Projects Lead – Office of the CEO
Company: Clover Health
Location: Remote – USA | Leadership
Why it’s great: This “CEO-mandated” role is designed for a strategic operator to translate ambiguity into structured, cross-functional execution. It’s high-visibility, high-impact work driving company-wide initiatives.
Apply here: Job Link

Recruiter Contact: Shay Jones

Role: Chief of Staff to the CEO
Company: Mercury
Location: SF, NY, Portland, or Remote (Canada/USA) | Leadership
Why it’s great: Mercury is scaling fast—200,000+ customers and counting—and this role puts you at the strategic nerve center. As Chief of Staff to the CEO, you’ll lead cross-functional efforts that drive top company priorities, making ambiguity your playground and impact your currency. Perfect for a sharp operator who thrives in high-growth environments.
Apply here: Job Link

Recruiter Contact: John Kempe

Role: Vice President & Chief of Staff
Company: Google
Location: Sunnyvale, CA | Leadership
Why it’s great: This is one of the most high-leverage roles at Google—leading strategy and operations for the company’s Core organization. You’ll drive cross-functional alignment, advise senior leadership (including acting as a proxy), and shape decisions at the highest level. With visibility across Alphabet and compensation to match, this is where operational excellence meets true executive impact.
Apply here: Job Link

Recruiter Contact: Lisa Reyes

Role: Director, Transformation
Company: Stitchfix
Location: USA | Leadership
Why it’s great: This is a front-row seat to lead transformation at one of retail’s most tech-forward brands. As Director of Transformation at Stitch Fix, you’ll shape strategy directly with C-level leaders and architect the systems and processes that fuel sustainable, profitable growth. It’s high-impact work at the intersection of fashion, data, and innovation.
Apply here: Job Link

Recruiter Contact: Haley Pike

Start learning AI in 2025

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Bots Take the Wheel

🤖 Turn Time Off Into a Non-Issue with Automation

Here's how you can automate team availability, capacity planning, & stakeholder comms around planned and unplanned absences in Atlassian (Jira + Confluence + Slack + Calendars).

We'll cover 3 use cases and structure each with the automation logic for:

1. Adjusting capacity

2. Notifying the right people

3. Minimizing project impact

🍼 Use Case 1: Parental Leave

Scenario: A team member is taking 24 weeks (a girl can dream!) of parental leave starting next month.

🔧 Automation Strategy:

🧮 Capacity Adjustments (Jira):

• Create a “Parental Leave” custom field or tag for the user.

• Use Jira Capacity Planning (Advanced Roadmaps):

  • Mark their velocity as 0 during the leave window.

  • Automatically reallocate work using “Auto-schedule” based on remaining capacity.

  • Optional: Add a placeholder assignee (e.g., “Frontend Backup”) to all future issues.

📣 Stakeholder Communication (Slack + Confluence):

• Jira Automation Rule: When the “Parental Leave” tag is added or a calendar event is created:

  • Post to Slack:

  • Auto-generate a Confluence status page: Parental Leave Plan – Sarah W. including:

    • Transition plan

    • Backups

    • Team impact analysis

    • Link to updated roadmap

😷 Use Case 2: Unplanned Day Off (e.g., Sick Day)

Scenario: A team member messages at 8:00 AM that they’re sick and out today.

🔧 Automation Strategy:

🧮 Capacity Adjustments (Jira):

• Create a "Today: Unavailable" label that can be toggled via Slack command or Jira issue.

• A Jira Automation Rule:

  • Watches for label/tag

  • Reduces daily capacity to 0 just for the day (Advanced Roadmaps)

  • Defers non-blocking issues or flags blockers

📣 Stakeholder Communication (Slack):

• Slack to Jira integration: /pto @david sick → triggers rule

• Bot posts in #project-channel:

📊 Optional:

• Create a JQL dashboard of “Tasks Impacted by Out-of-Office”

• Have Slack DM the PM daily at 9 am with an out-of-office impact.

✈️ Use Case 3: Planned 1-Week Vacation

Scenario: A designer is out for 1 week, 3 sprints from now.

🔧 Automation Strategy:

🧮 Capacity Planning (Jira Advanced Roadmaps):

• Mark availability as 0% for that sprint week (resource planner view).

• Auto-shift sprint stories based on availability drop.

• Add a "Coverage Plan" checklist to their assigned issues:

  • Backup assignee

  • Pre-vacation handoff notes

📣 Comms (Confluence + Slack):

• 2 weeks before PTO: Jira Automation sends Slack reminder:

• Confluence page auto-generated:

  • Title: Coverage Plan – Lena – July 8–12

  • Contains assigned work, backup owner(s), timeline adjustments

• PM Alert: Jira notifies assignee of any blocking dependencies

🎁 Bonus Automation Ideas

• Vacation Slack Bot: Each morning, it pings Jira for who's OOO and posts to team channels.

• Capacity vs. Demand Report: Auto-generate every Monday showing % available per team and flag risk zones.

• Work Rebalancer: A dashboard for PMs to drag and drop reassignments on-the-fly.

Visionary Voices 

📝 Voice of the Modern Work Mindset: Jessi Hempel’s Delivery Lessons

Senior Editor-at-Large, LinkedIn | Host of Hello Monday

Why she matters:
Jessi Hempel isn’t just narrating the future of work—she’s helping us feel our way through it. As host of Hello Monday, she’s interviewed Brené Brown, Priya Parker, and Malcolm Gladwell to explore what leadership, team culture, and reinvention really mean. Her lens? Sharp. Human. And wildly relevant to delivery and ops pros leading through complexity.

What she brings:
From soft skill fluency to stakeholder wisdom, Hempel’s conversations are masterclasses in managing the human side of execution. She gets that strategy is personal, and that career moves are often more emotional than rational.

Start here:
🎧 Hello Monday – Suzy Welch’s Guide to Authenticity
📚 The Family Outing (memoir with insights on reinvention)

Try this:

• Drop Hello Monday in your team Slack as a culture-builder.

• Use her listening-first style in your next stakeholder conversation.

• Bring one quote to your next retro or kickoff.

✨ Weekly Recommendations

Some visual clarity into all of these overlapping tech fields. Is it a Data Scientist or a Data Engineer?

How to Succeed and Thrive in a Career You Love.

She gives no-BS career advice from the recruiter’s side of the table so you stop guessing and start landing offers.

It’s like getting an MBA in project delivery without the tuition or the fluff.

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Professional Development

🧠 Think Like a Director: How to Win the Interview Before It Starts

What separates a standout candidate from the rest? Strategic storytelling, business fluency, and showing up with a 90-day plan. {This is a link to a template I modified to land me an interview at a well-known tech company.}

Landing a director-level interview in delivery isn’t just about reciting your résumé; it’s about showing you can lead with strategy, empathy, and influence. Drawing from the frameworks in that video and seasoned delivery pros, here are core strategies to prepare for and ace the next-level screen:

1. Master Your Leadership Stories (The STAR+Impact Approach)

Directors don’t just solve tasks, they shape teams and strategy. Pick 4–5 stories that highlight:

• Situation: The scope and pressure (e.g., a delayed major rollout)

• Task: Your leadership role (e.g., align stakeholders, restructure team)

• Action: What you did (e.g., implemented a new communication rhythm)

• Result: Outcomes in hard metrics (e.g., 30% faster delivery, $X saved)

• Impact: What did it mean for the org? Scalability, culture shift, risk mitigation.

Be precise: “We cut delivery variance by 20pp, enabling predictable planning across 5 teams.”

2. Speak Business — Not Just Projects

At the director level, they want business partners as much as delivery managers. Prepare to talk executive-level strategy:

• How did your delivery approach enable revenue growth, customer retention, or cost savings?

• Can you show how your roadmap or plan aligns with the company's OKRs or market shifts?

• Frame your actions in the language of outcomes and organizational value.

3. Showcase Systems Thinking & Framework Fluency

Use video highlights frameworks like CIRCLES and systems thinking. Adapt them for delivery:

• Use a structured problem-solving tool (like RACI or DACI) when walking through resource conflicts or cross-functional mishaps.

• In case of questions (“We’re blowing deadlines, fix it”), model your answer: assess root causes, propose a solution framework, and discuss measurement.

Even if you don’t name the framework, hiring directors appreciate structure backed with rigor.

4. Highlight Influence & Stakeholder EQ

By director time, your power is in persuasion, alignment, and conflict navigation—not just authority.

• Talk about a time you secured executive buy-in for a tough pivot.

• Or how you managed a team through change, keeping morale and output high.
  Empathy and political navigation matter. If you can show emotional intelligence and results, you’ll stand out.

5. Prepare for Behavioral & Hypothetical Scenarios

Expect a mix:

• Behavioral: “Tell me about a time you failed.”

• Hypothetical: “We’ve got 3 teams missing milestones. What’s your first 90-day plan?”
  Practice both:

• For behavioral, go deep on your lessons learned.

• For hypotheticals, outline a structured assessment, quick wins, and long-term actions.

6. Ask Strategic, Insightful Questions

Your questions signal your mindset. Good ones include:

• “What’s our biggest delivery-wide bottleneck right now?”

• “How does this role support broader product or business objectives?”

• “What’s the current delivery rhythm, and where’s the friction?”
  These show you’re already thinking about impact, alignment, and change agility.

7. Lean Into Executive Presence

Director-level interviews are performance:

• Confident posture.

• Concise answers.

• Calm pacing.

  They want someone who looks like they belong in the C-suite. Run mock interviews, get feedback on tone, and practice leading discussions.

Bonus: Come in with a 90-Day Plan (Even If They Don’t Ask)

Hiring managers love initiative. Prepare a 90–100 day outline showing how you’d diagnose delivery bottlenecks, build stakeholder trust, and spark early wins. Tailor it to the company’s context, pull from their press releases, product updates, or Glassdoor reviews.

Here’s an example of one I created to land an interview at a well-known Product company.

Structure it around:

• Phase 1 (0–30 days): Discovery & relationship building

• Phase 2 (31–60): Process evaluation & quick wins

• Phase 3 (61–90+): Strategic roadmap & org impact

It doesn’t have to be a deck; just a one-pager shows foresight and readiness to lead.

TL;DR

Prepare the mix:

1. Quantified leadership stories.

2. Business-first mindset.

3. Framework-informed case answers.

4. Emotional intelligence in action.

5. High-impact questions.

6. Polished presence.

7. Have a 90 day plan before meeting the hiring manager.

Blend outcome-driven substance with strategic communication, and you’ll walk into that director interview knowing you belong.

How I can Help

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

Free Career Guide Coming Soon!

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.