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Issue #31 | 12/31/2025
From the Editor
Hey fam!
The wonderful thing about community and family coming together IRL is that you might get roasted put in the hot seat. So much love was sent to me last month along with a ton of honest feedback about this here newsletter. Truth be told, I already felt it in my spirit.
This newsletter was way too long.
News flash! I’m not a designer and it shows 🤣. Those job tables rendered so ugly on mobile.
Gmail cuts off every issue so that unless you open it on the web, you can’t even see the whole thing.
I’m pretty sure no one even makes it far enough to give me feedback.
Enter experiment 1 of many for 2026. While I’ve been held hostage during winter break with the Golden Boys #toddlerfun, I’ve had a few 15 minute windows to play with some ideas and this issue will be the beginning of a new direction for the Business of Delivery.
Enjoy today’s issue!
Sincerely,
Phedra Arthur Iruke
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Job Board
🦸 Hero Role of the Week
No more ugly tables.
415+ jobs pulled. One caught my eye.
Every week I scan the board for the role I'd actually apply to. This week's pick? Let's just say it involves a company you've definitely heard of, a level most PMs dream about, and flexibility that's increasingly rare.
Squarespace is hiring a Chief of Staff and this role is a strategic goldmine for delivery professionals looking to break into true business partnership. You're not managing timelines, you're shaping the business narrative as the analytical backbone reporting directly to the VP of Product. You'll own the performance story that drives executive decisions across a $100M+ SaaS business (Acuity Scheduling). You're building the metrics frameworks, designing the dashboards, and delivering the insights that determine where Squarespace invests millions. You'll get exposure to pricing strategy, market analysis, forecasting, and cross-functional influence that puts you in rooms where business strategy gets made, not just executed. Plus, the comp range ($126K-$203K) and the title signal that this organization actually values strategic thinking, making it the perfect launchpad from tactical PM work into the strategic leadership tier where you're finally seen as essential, not replaceable.
No spoilers. Go find it. Filter on jobs posted in the last 7 days and hit Apply Now.
👉 Browse this week's top roles 👇
New roles added daily.
Professional Development
💡 Micro-Tip of the Week
The 'one-pager' that actually gets read.
Problem (2 sentences).
Recommendation (1 sentence).
Why now (1 sentence).
What I need from you (bullet list).
Industry News
A few things from Big Tech & business leaders that you can steal in 10 minutes
Touch grass often
Project Vend: Building an AI-Powered Vending Machine Source: Anthropic Research
Anthropic's experiment building an AI vending machine - lessons on AI agent development, real-world deployment challenges, and what happens when theory meets practice....
Read more → Here
10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)
Source: Lenny's Newsletter
Rippling's CPO on why you should deliberately understaff projects, how to recognize true product-market fit, why VCs want you to keep failing, and the frameworks that built a $16B company...
Read more → Here
VCs predict enterprises will spend more on AI in 2026 — through fewer vendors
Source: TechCrunch Startups
Enterprises have been experimenting with AI tools for a few years. Investors predict they will start to pick winners in 2026....
Read more → Here
In case you missed it
Community Pulse
This week in PM land, the community is fired up about Process & Productivity, AI & Automation, Leadership Challenges.
Hot discussion: What an unprocessed photo looks like (Hacker News) sparked 399 comments.
Other trending conversations:
Scrum.org Blog] [Using APOM (Agile Product Operating Model) to Fix Microsoft’s Copilot Adoption Problem
What's on YOUR mind this week? Hit reply and tell me.
Energy
🎤 Phedra's Take
This week's theme: Process & Productivity
Here's my take: Stop confusing motion with progress. Most "productivity" advice is just procrastination with better branding.
What I've learned: Kill three low-impact meetings this week and instead spend an hour modeling what happens to revenue if engineering ships two weeks late, or automating repetitive tasks, or building a relationship with a stakeholder that can influence a recompete or proposal outcome.
Your move this week: Audit your calendar. Find one recurring meeting where you're a spectator, not a contributor. Decline it. Use that hour to build something that matters.
That’s it for this week.
Keep showing up, keep cheering each other on.
How I can help?
The Delivery Career Decoder is the first comprehensive career transformation system designed specifically for delivery professionals, program managers, and technical operations experts who are ready to break through the "execution ceiling" and step into strategic leadership roles. This is a proven methodology that leverages your unique strengths as a delivery professional while systematically building the strategic positioning, executive presence, and communication skills that open doors to VP, Director, and C-suite opportunities.
The Business of Delivery Team
P.S.
You got this!