⚠️ Your "Urgent" Request Isn't a Fire, It's Just Poorly Planned

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Featured Job Listings

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

• Role: Head of Operations

• Company: Gumloop

• Location: Remote – USA | Leadership

• Why it's great: Gumloop is a Y Combinator-backed no-code platform for automating workflows with AI, founded in 2023 by Rahul Behal and Max Brodeur-Urbas with 7 employees based in San Francisco. The platform enables users to build and host AI-powered business automations using drag-and-drop modules, with customers reporting 65% more meetings YoY and 207% more revenue. They're building the infrastructure many of the world's largest companies use to automate work with scaling operations.

• Apply here: Head of Ops 

• Role: Chief Operating Officer/Integrator

• Company: ONE2ONE Inc.

• Location: Remote – USA | Leadership

• Why it's great: ONE2ONE is a Managed Service Provider (MSP) in the IT/technology space, helping businesses manage their IT infrastructure and systems remotely. MSPs are critical partners for companies looking to scale their technology operations without building internal IT teams. This COO/Integrator role offers the opportunity to lead operational excellence in a growing technology services company.

• Apply here: COO/Integrator 

• Recruiter Contact: Kseniia Rukas

• Role: Chief of Staff

• Company: Vellum

• Location: Remote – USA | Leadership

• Why it's great: Vellum is a Y Combinator W23 company that raised $20M Series A, backed by top investors like Rebel Fund, Eastlink Capital, and co-founders of Dropbox and HubSpot. They're the AI Product Development Platform that enables companies to build reliable AI solutions through test-driven development, helping reduce what once took dozens of engineers 8 months down to 24 hours for a single engineer. Growing at 15% month-over-month, they're building the primary platform companies use to bring AI into production.

• Apply here: Chief of Staff 

• Recruiter Contact: Colman McCormack

• Role: Director, Business Systems

• Company: Boulevard

• Location: Remote – USA | Leadership

• Why it's great: Boulevard provides the first and only client experience platform for appointment-based, self-care businesses, empowering salons, spas, barbershops, and medspas to give clients magical moments that matter most. Founded by entrepreneurs who spent months interviewing salon managers and working behind front desks to understand pain points, they've built a modern, user-friendly platform that helps businesses not just survive but thrive. This Director role reports to the CTO.

• Apply here: Director, Business Systems 

• Recruiter Contact: Jamie Moore Tietjan

• Role: Programs Lead – Strategic Operations, Federal Programs and Special Projects

• Company: Hadrian

• Location: Remote – USA | Leadership

• Why it's great: Hadrian is building autonomous factories that help aerospace and defense companies manufacture rockets, satellites, jets, and ships up to 10x faster and up to 2x cheaper by combining advanced software, robotics, and full-stack manufacturing. They recently raised $260 million Series C and are launching a new 270,000 square foot factory in Mesa, Arizona, creating 350 new jobs immediately. Backed by top-tier investors including Lux Capital, A16Z, Founders Fund, and Construct Capital, they're reinventing how America produces its most critical parts.

• Apply here: Programs Lead 

• Recruiter Contact: Osei Gyamfi

Bots Take the Wheel

🤖 Request Triage Automation

The Problem: Every request feels urgent, creating constant context switching and reactive planning.

The Solution: Automated request scoring and routing based on predefined criteria.

Use Case 1: Slack Request Bot with Priority Scoring

Goal: Route and prioritize Slack requests without manual triage.

Steps:

1. Create a Slack Workflow using Workflow Builder or Zapier.

2. Add a Form Trigger with fields like:

   • Request type (bug, feature, question)

   • Business impact (low, medium, high)

   • Estimated effort (hours/days)

3. Add Scoring Logic:

   • Use a tool like Zapier or Make to score requests using the Impact vs. Effort matrix.

   • For example: High Impact + Low Effort = Priority A.

4. Route Requests Automatically:

   • Priority A → Sent to a #priority-intake channel.

   • Others → Sent to a backlog channel or tagged in Notion/Airtable for planning review.

5. Notify Requestor with a message about expected review timing (set the tone and manage expectations).

Use Case 2: Jira Auto-Prioritization

Goal: Automate ticket triage based on type and business logic.

Steps:

1. Define Rules for Priority Scoring:

   • Ex: Bugs affecting production = P1; Feature requests from Sales = P3.

2. Use Jira Automation Rules:

   • When a new issue is created:

     • Check "Component" or "Label" for system affected.

     • Check "Issue Type" and "Reporter’s department".

   • Then:

     • Set Priority field accordingly.

     • Assign SLA based on urgency.

     • Tag the relevant team lead or owner.

3. Send Auto-Notifications:

   • Alert stakeholders with expected timelines based on priority.

   • Use templates to clarify what “P3” or “P1” actually means.

Use Case 3: ServiceNow Escalation Logic

Goal: Filter true emergencies from nice-to-haves.

Steps:

1. Define Escalation Criteria:

   • System outage = Critical

   • Security breach = Urgent

   • New feature = Routine

2. Use ServiceNow Workflows:

   • Intake forms flag severity level automatically.

   • If “Critical”, auto-assign to Incident Response team.

   • If “Routine”, route to Product Ops or Delivery for intake review.

3. Auto-Educate Stakeholders:

   • Use automated email or Slack replies to explain:

     • “Your request is logged as a feature. Here’s when we review and how you’ll be updated.”

4. Track SLA Compliance:

   • Set automated reminders if a request exceeds SLA window.

   • Escalate to manager only when warranted.

Visionary Voices 

📝 Julie Zhuo — Co‑founder of Sundial, Former VP of Product Design at Meta

Why she matters:
Julie Zhuo isn’t just another high‑profile designer; she’s a systems thinker who scaled culture and operations at Meta while surviving the chaos most can’t even name. Now she’s co‑building Sundial, an AI‑first decision engine aimed at the heart of corporate paralysis: soaking in data and spitting out clarity. It’s not analytics for analytics’ sake—it’s opinionated intelligence that guides fast, right decisions, and it matters because teams everywhere are constipated with dashboards and alerts—she’s giving us tools to unplug the fog.

What she brings:
She’s the real deal: a human-centric leader who also architects scalable systems. Julie helps you spot and correct delivery anti‑patterns, think, no handoffs, frantic reprioritization, foggy roadmaps - with clear frameworks and structured interventions. Her voice balances process discipline with humanity. The result? Less chaos, more impact-driven execution.

Her insight:

That quote lands like a gut punch because it’s so true and so hard. It’s the heart of her message and her delivery playbook.

Her world in words & code:

• Her will‑read management primer, The Making of a Manager, gives leaders practical tools to build trust, clarity, and autonomy.

• Her newsletter, The Looking Glass, unpacks frameworks and reflection prompts that make thoughtful execution a daily habit.

• And at Sundial, she’s enforcing those lessons with code—transforming how teams structure and act on decisions.

Call to action:
If your teams are stuck in task triage or drowning in data, start with The Making of a Manager—then give The Looking Glass a subscription. To see where she’s heading next, dig into Sundial’s model for decision‑centric analytics. It’s where her theory meets real‑world scaling.

✨ Weekly Recommendations

Practice high-stakes negotiations before the real thing with this AI prompt.

Learn how to write messages that actually connect using the "One Extra Line" rule.

A simple under-desk sling that keeps your feet comfy during marathon Zoom calls

Chronicle makes presentations for free.

HubSpot's AI delegation toolkit to save 10+ hours per week.

Reinforcement learning workshop.

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Professional Development

📚 Why Delivery Breaks: Six Predictable Patterns (and How to Actually Fix Them)

After reviewing hundreds of failed initiatives—and studies like the Standish Group’s CHAOS report, which found 71% of IT projects overran budgets or timelines (averaging 43% cost increases), and global data showing strategy implementation failure rates between 70–90% —a few predictable breakdowns emerge. These aren’t flukes. They’re systemic—and fixable.

1. Treating Symptoms Instead of Systems

Adding more meetings won’t fix unclear decision making. Identify and formalize who decides what when. Improve the system, don’t just plaster it.

2. Mistaking Busyness for Progress

Checking off tasks doesn’t mean you’re moving the needle. Stop counting hours and story points. Start tracking customer impact, time to value, and business outcomes.

3. Building Hero-Dependent Workflows

If your project fails when you’re gone, it’s not a workflow—it’s a single point of failure. Document, automate routine steps, and delegate decisions so things keep moving when you’re offline.

4. Optimizing for the Wrong Metrics

Velocity and story points don’t matter if you’re building the wrong thing. Track metrics that reflect value delivered—customer satisfaction, conversion rates, revenue impact.

5. Skirting around ‘Definition of Done’

Ad hoc planning—“we’ll figure it out as we go”—is a fast track to scope creep and burnout. Define success up front: what "done" looks like, and how you'll measure it.

6. Rewarding Bad Planning with Burnout

If pulling late nights is how projects finish, you’re reinforcing poor planning. Set guardrails—plans, priorities, limits—and stick to them.

The Fix Framework

• Pause & Diagnose: What’s the real problem?

• Map the System: Where’s the breakdown?

• Fix the Root: Change the system, not just the people

• Measure What Matters: Track outcomes, not output

• Build to Outlast You: Create workflows that don’t fold without you

TL;DR: Delivery failures aren’t mysterious. They follow predictable patterns. The solution isn’t more heroics—it’s smarter systems. Remove single points of failure, focus on value, and build workflows that endure.

How I can Help

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

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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.