Up, Out, Across, and Down: How Director+ Software Leaders Operate Strategically
Allison Pollard
Strategic Advisor, ex-Technical Director
Paul Tevis
Executive Coach to Technology Leaders
Get your biggest engineering ideas heard, backed, and built
As a Director+ leader in software or IT, you’re expected to guide your technology organization to meet the evolving needs of your business. But at your level, even “low-effort” improvements are hard to execute because they touch everything: Product, Finance, Operations, and more. You have to align with people who have their own priorities—and no particular reason to make yours easier.
And if you can’t, you risk getting sidelined in your company.
In this fast-paced course, we’ll share practical ways to:
Get your boss to lean in when you share your ideas, instead of changing the topic two minutes in
Navigate org capacity and priority conflicts alongside your Product counterpart rather than engaging in an endless tug-of-war
Turn conversations with your managers into commitment–where they understand it, voice reservations, and own it publicly and privately
Keep executives close enough that when something unexpected threatens the work, they stick with it
This is more than influencing. It’s also key moves to create action after your boss says, “Make it happen.”
Beyond the group calls, you’ll get 3 hours of 1:1 coaching to help you actually make these moves in your org—and make your ideas real.
Learn directly from Allison & Paul
Allison Pollard
Former Technical Director | Stategic Advisor
Paul Tevis
Executive Coach to Technical Leaders
Who this course is for
Directors who are tired of surprises & firefighting
You want to focus more on strategy over day-to-day execution.
Leaders who've gotten early wins & have a bigger vision
You want to build future org capabilities beyond what today's performance delivers.
Technologists who struggle to get buy-in for their vision
You want key people to see the strategy clearly enough that execution follows.
Prerequisites
Currently Managing Managers
This course is intended for Director+ leaders. It assumes you have at least two direct reports who are themselves managers.
Managing in Software or IT
The class is engineering-centric, and the examples are all drawn from software contexts.
Ready to Do New Things
You'll experiment between sessions and apply learnings with your direct reports, your peers and stakeholders, and your boss.
What's included
Live sessions
Learn directly from Allison Pollard & Paul Tevis in a real-time, interactive format.
In-class exercises / hands-on practice in every session
You'll learn through real-life examples, Q&A, hands-on exercises, and tactics you can apply immediately. Practice frameworks during each session, not just in the job.
3 private coaching sessions ($1500 value)
Three dedicated one-on-one sessions to work through your specific leadership challenges with direct guidance from Paul.
Scripts, templates, worksheets, and checklists
Walk away with practical tools to use before a high-stakes conversation or information-gathering meeting.
Your personal leadership plan
You'll build a concrete plan tailored to your specific context, challenges, and goals during the course itself, ready to use on Monday.
Like-minded peers
Learn alongside fellow engineering leaders who are navigating similar challenges. See how others approach problems and communicate. Learn from the feedback they receive, not just the feedback you get.
Bonus content
Takeaway book recommendations, a step-by-step guide to running a book club that moves your managers from reading about leadership to practicing it, and more.
Lifetime access
Go back to course content and recordings whenever you need to.
Maven Guarantee
Your purchase is backed by the Maven Guarantee.
Course syllabus
Week 1
Sep
22
Module 1
Tue 9/224:00 PM—5:30 PM (UTC)Sep
22
Optional: Module 1 Q&A
Tue 9/225:30 PM—6:00 PM (UTC)OptionalSep
24
Module 2
Thu 9/244:00 PM—5:30 PM (UTC)Sep
24
Optional: Module 2 Q&A
Thu 9/245:30 PM—6:00 PM (UTC)Optional
Module 1: Finding the Path
Module 2: Expanding the Scope & Scale
Week 2
Sep
29
Module 3
Tue 9/294:00 PM—5:30 PM (UTC)Sep
29
Optional: Module 3 Q&A
Tue 9/295:30 PM—6:00 PM (UTC)OptionalOct
1
Module 4
Thu 10/14:00 PM—5:30 PM (UTC)Oct
1
Optional: Module 4 Q&A
Thu 10/15:30 PM—6:00 PM (UTC)Optional
Module 3: The Path is Made by Walking
Module 4: Handling Human Error Codes
Free resources
Schedule
Live sessions
6-8 hrs
Each day, we'll have 90 minutes together as a group for live exercises, plus 30 minutes of optional Q&A.
Tue, Sep 22
4:00 PM—5:30 PM (UTC)
Tue, Sep 22
5:30 PM—6:00 PM (UTC)
Thu, Sep 24
4:00 PM—5:30 PM (UTC)
Private 1:1 Coaching (BONUS!)
3 hrs
For this upcoming cohort, you'll receive three hours of private 1:1 coaching. You can schedule these sessions anytime up to six weeks after the cohort ends.
Testimonials
I'm so glad to see Paul and Allison rolling out leadership coaching for software leaders. I've known both for almost a decade. They're the real deal.
Ron Lichty
Consulting VP of Engineering | Advisor | Co-Author: Managing the UnmanageableI'm excited Allison and Paul are making this happen. They both have such a wealth of knowledge and experience.
John Cutler
Head of Product @ Dotwork | Author: The Beautiful MessI worked with Paul when I had just become a manager. He was instrumental in my growth during that time, and his partnership was a big positive influence on who I am today. I still find myself using much of the advice and wisdom he gave me. ⭐️⭐️⭐️⭐️⭐️, highly recommend working with Paul.
John Yoder
CTO & Co-Founder @ Constructable (YC Summer 23)
Frequently asked questions
Maven for Teams
Reimbursement
Get your company to pay
Everything L&D needs: email template, receipts, and certificate of completion.
Get reimbursedTeam discount
Learn with your teammates
Save 20%+ when 2 or more teammates enroll in the same cohort.
Save 20%+ with a teamPrivate cohort
Run a cohort for your org
A dedicated cohort with a custom schedule and curriculum, tailored to your team.
Book a private cohort$800
USD