🧭 Scaling Delivery @Startups (No 🚀 Launchpad Required!)

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Featured Job Listings

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

Role: Director, Project Delivery
Company: Avalere Health
Location: Remote – USA | Leadership
Why it’s great: Own delivery operations at a health analytics firm—align stakeholders and influence outcomes at scale.
Apply here: Job Link
Recruiter Contact: Anne Reese-Ternay

Role: VP of Field Service & Implementation
Company: Daniels Health
Location: Remote – USA | Leadership
Why it’s great: Oversee field service delivery in healthcare with strategic and high-impact work.
Apply here: Job Link
Recruiter Contact: Sydnee Hogan

Role: Director, Implementation
Company: Olo
Location: Remote – USA | Leadership
Why it's great: Lead complex SaaS and MarTech integrations—build change-management processes, drive implementation centers of excellence, and partner with Product and Engineering.
Apply here: Job Link
Recruiter Contact: Hannah Lawrence

Role: Chief Program Officer
Company: Climate Power
Location: Remote – USA | Leadership
Why it's great: Shape and oversee national climate-advocacy programs—strategic leadership, multi-team coordination, and high-impact execution at scale.
Apply here: Job Link

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Bots Take the Wheel

🤖 Ticket Triage Automation for Busy PMs

1. Auto-Classification (Jira → Slack)

Automatically categorize new Jira issues and route them to the appropriate queue or Slack channel.

• Trigger: Issue is created in Jira

• Conditions:

  • If the issue summary contains keywords such as "error", "bug", or "crash" → classify as Bug

  • Else → classify as Feature Request

• Actions:

  • If Bug →

    • Add label: Bug

    • Move to: Bug Triage queue (custom Jira board or swimlane)

    • Send summary + link to Slack channel #triage-bugs

  • If Feature Request →

    • Add label: Feature Request

    • Send summary + link to Slack channel #product-ops

• Tools: Jira Automation → Slack Webhook integration

2. SLA Escalation Workflow (ServiceNow or Asana → Slack + Email)

Ensure no ticket remains unassigned beyond SLA timeframes.

• Trigger: Ticket remains unassigned for more than 12 hours

• Conditions:

  • Ticket Status = Open

  • Assignee = null or unassigned

• Actions:

  • Add label/tag: Escalation

  • Send message to Slack channel #ops-leads with ticket link and escalation context

  • Email the relevant manager or team lead with ticket details

• Tools:

  • ServiceNow: Flow Designer + Slack integration

  • Asana: Rule-based automations + Zapier or Make + Gmail/Outlook integration

3. Blocked Ticket Alert (Trello → Slack + Confluence)

Track and notify stakeholders when work is blocked.

• Trigger: Trello card is moved to the “Blocked” column

• Conditions: N/A

• Actions:

  • Post to Slack channel #triage-notify with:

    • Card title

    • Link to card

    • Reason for block (pulled from custom field or comment)

  • Automatically create a Confluence stub page using the Trello card name as the page title. Include:

    • Card details

    • Block reason

    • Stakeholder fields (optional)

• Tools:

  • Trello: Butler Automation

  • Slack: Incoming Webhook

  • Confluence: REST API via Zapier or custom script

🔄 Optional Enhancements:

• Add sentiment analysis to classify tickets with emotional language (e.g. “frustrated” → escalate to CX lead).

• Use OpenAI or Claude API to summarize lengthy tickets or Slack threads before posting to triage channels.

• Create a weekly report summarizing:

  • Number of escalations

  • Average time to assignment

  • Most common block reasons

Visionary Voices 

📝 Melanie Perkins, CEO of Canva

When we talk about scaling delivery, few leaders walk the walk like Melanie Perkins. As co-founder and CEO of Canva, she’s helped guide the company from a scrappy startup into a global design powerhouse—with thousands of employees, international reach, and a pace that rivals Big Tech.

Why she matters:

Perkins didn’t just scale teams—she scaled trust. While some organizations bog down in process, Canva has emphasized people-first systems and transparent operations. Teams are empowered with high autonomy and clear ownership of outcomes, fostering a delivery culture built on accountability and speed.

What she brings:

• Distributed Delivery Teams: While Canva doesn’t publicly refer to "pods," their product and engineering teams operate in a distributed, cross-functional model with a strong emphasis on team autonomy and impact.

• Transparent Capacity Practices: Canva shares engineering practices that prioritize visibility—such as open retros, clear velocity tracking, and organization-wide collaboration tools.

• Wellbeing as a Delivery Enabler: From recharge days to flexible work hours, Canva makes mental health a priority, reinforcing that sustainable delivery starts with healthy, trusted teams.

Start here:
🎧 Listen: How I Built This – Melanie’s episode or The Secret Power of Onboarding.
📘 Read: Her take on scaling with global alignment in Fast Company

Your action:
This week, audit your visibility. What does your team see about delivery pace, blockers, and wins? Set up a simple dashboard—burn-down charts, workload distribution, capacity tags—and share it with the full team. More visibility = more ownership.

✨ Weekly Recommendations

@thejessicablack on Tiktok – “Strategic Project Management Career Advice” – crisp career growth tips for PMs through bite-size videos

Portable whiteboard – plan sprints from kitchen tables 📌

Don’t be a bottleneck.

A real story and tactics from a PM family applying delivery frameworks to parenting.

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Professional Development

📚 Scaling Delivery in Start‑Ups

Scaling delivery isn’t wishful thinking. it’s disciplined engineering. The 2024 Atlassian State of DevOps report shows that startups growing from 10 to 50 engineers experience ~25% slower cycle times due to communication overhead. Here's how to scale smarter:

1. Visualize Flow:
   Use Kanban boards + WIP limits—see bottlenecks as they appear.

2. Standardize Handoffs:
   Implement templates for triage & review; reduce context-switching by 15%.

3. Data-Led Velocity:
   Monitor cycle time and velocity together; hire when velocity dips >20%.

4. Automate Triage:
   Save ~2 hrs/week by auto-assigning, tagging, and alerting on tickets.

5. Team Size Thresholds:
   Around 25–30 people, velocity drops—start squad splits and PM hires proactively.

6. OKR Alignment:
   Track deliverables alongside business outcomes; use dashboards for transparency.

7. Embed Empathy:
   Build systems that respect life outside work—e.g., capacity swaps, flexible standups.

TL;DR:
Apply visible process, smart transitions, data-driven decisions, targeted automations, and empathy-first leadership to scale delivery without breaking the team.

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.