Senior Principal TPM & Ex-Atlassian

Dylan
Toohey.

Senior Principal TPM & Ex-Atlassian | Service Enablement | Strategy, Scale and Customer Feedback in Cloud SaaS | Engineering Quality & Company Level OKRs

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Driving
Cloud
Outcomes
Globally

Professional Summary

Partnering with Engineering, Product and Design Heads to run programs aimed at reducing COGS, drive adoption, and unlock revenue in Atlassian Cloud Suite. Most recently led a $10M+ OKR to improve gross margin across Jira Cloud.

monitoring

Technical & Strategic Mastery

Created Atlassian's core health metric for enterprise cloud migrations, combining deep data skills (SQL, Databricks) with strong stakeholder and program management. Experienced in translating complex technical concepts into business value.

SQL / Databricks Program Management Change Management

insights

"Translating complex technical concepts into measurable business value."

Outcome Driven

Global Footprint

Atlassian

9+ Years Leadership

APAC, US, EMEA

Cross-Regional Operations

Customer Engagement

Hands-on engagement through TEAM Barcelona and Rovo AI labs, scaling enablement programs across time zones. Brings a blend of SQL/Databricks analytics, direct customer engagement, and strong stakeholder management across Product, Engineering, Design and Support.

Professional Experience

Atlassian Tenure: 2016 — Present

Senior Principal TPM

Oct 2024 – Present

location_on Sydney, Australia

Enterprise Impact & Quality Guardrails

Directly accountable for a $10M+ portfolio of customer-friction reduction initiatives focused on improving product side overheads. Improving Jira's UX, stability, and in-product content for enterprise customers, aimed at avoiding COGs and improving Gross Margin in Cloud.

check_circle Implemented scalable quality, cost transparency and budgetary guardrail processes across an 800+ engineer organisation, including automated SLOs tied to customer impact.
check_circle Achieved a 50% reduction in publicly reported bugs, saving an estimated $150K/month in customer overhead.
check_circle Produced monthly and quarterly reporting for cost actuals vs targets/forecasts, leading exec reporting cadences across 63 different engineering teams.

Principal Enablement Engineer

May 2020 – Oct 2024

Cloud Migration Health & Governance

Created and owned Atlassian's primary enterprise cloud migration health metric, used as a key indicator for the company's #1 priority in enterprise cloud migrations.

check_circle Led weekly, monthly, and quarterly executive health cadences to highlight "stuck" customers, driving coordinated action across Product, Engineering, Design and Support to unblock revenue.
check_circle Built and maintained SQL/Databricks dashboards to monitor migration adoption, risk, and progress, providing Customer Success, Product, and leadership with real-time visibility.
check_circle Translated complex technical issues into customer-friendly explanations and success plans, helping enterprise stakeholders understand tradeoffs and timelines.

Senior Service Engineer

Sep 2016 – May 2020

Scaling Support Ecosystems

Focused on reducing contact rates across Technical and Billing Support teams by identifying high friction, high cost areas and partnering with Eng & Product to roadmap and implement fixes.

check_circle Developed enablement and readiness programs that prepared support teams and customers for product changes.
check_circle Created repeatable processes for training, documentation, and communications that scaled globally and reduced confusion, misconfigurations, and support ticket volume.
check_circle Partnered with support and product teams to ensure customer feedback shaped both enablement content and future product changes, by implementing and designing feedback capture systems.

Team ScalingProcess CreationDocumentationContact Reduction

Customer-Facing Leadership

October 2025

TEAM Barcelona

Ran the Customer Feedback Booth, the most visited site at the conference; engaged 300+ customers to gather structured feedback that directly informed product and success priorities.

February 2026 (Selected Speaker)

ANZ EngFest

Spoke about how to identify, collect, and interpret customer feedback in complex scenarios, reinforcing customer-centric decision-making across engineering teams.

March 2026

Team on Tour Sydney

Facilitated the Rovo Hands-on AI Lab, helping customers set up, configure, and adopt Atlassian's newest AI offering in person.

Academic Foundation

Dual degrees providing a unique intersection of technical infrastructure and business accountability.

Bachelor of Information Technology

QUT | Brisbane, AU | 2012

ACC

Bachelor of Accountancy

QUT | Brisbane, AU | 2012

Competencies

Skills &
Expertise.

A specialised skill set focused on bridging technical complexity with operational excellence and strategic growth.

leaderboard

Strategic Leadership

Executive Stakeholder Management

OKRs, QBRs & Success Planning to align organisational vision with execution.

Voice of Customer (VoC) Programs

Strategic feedback capture, process optimisation, and roadmap prioritisation.

Enterprise Adoption & Expansion

Driving growth through consumption-based and seat-based business models.

settings_suggest

Operational Excellence

Efficiency & Scale

COGs reductions, Gross Margin improvement, Budget guardrails, and Support team scaling.

Enablement

Change Management, Organisational Enablement (Train-the-Trainer), and Centre of Excellence (CoE) creation.

Global Delivery

Orchestrating operations across APAC, US, and EMEA time zones.

Public Speaking Facilitation Influencing

analytics

Technical & Analytics

Data Intelligence

SQL & Databricks; Advanced Dashboarding, ROI analysis, Impact Quantification, and LLM theming.

Ecosystem Mastery

Jira & Confluence administration, Bitbucket, Rovo/RovoDev, and AI-assisted quality tooling.

Cross-Functional Synthesis

Deep collaboration with Product, Engineering, Design, and Support to bridge execution gaps.

Toolchain

query_stats Databricks

view_kanban Jira Admin

psychology AI Tooling

hub Confluence

database SQL

account_tree Bitbucket

Velocity of Adaptation

The modern enterprise landscape shifts weekly. My primary skill isn't just the tools listed here, but the ability to influence without authority and facilitate cross-functional alignment at speed.

Practices: Health Scoring · SLO Design · OKRs

Recommendations

What Leaders
Say.

"Engineering teams viewed him as a true enabler rather than a gatekeeper, which built strong cross-functional trust."

I've had the pleasure of partnering closely with Dylan Toohey on Product Experience and Quality programs at Atlassian. Dylan consistently drove KRs that spanned the entire Jira organisation and influenced adjacent products in meaningful ways. One standout area was his leadership in initiatives to reduce support costs and ship less bugs. He not only championed these efforts but enabled teams to execute them effectively at scale. His stakeholder management stood out: engineering teams viewed him as a true enabler rather than a gatekeeper, which built strong cross-functional trust. Dylan also excelled at interpreting customer insights, which directly informed re-prioritisation decisions in certain areas and led to improved gating processes based on real user feedback. His work strengthened quality and customer focus across multiple areas. Beyond his results, Dylan brings his genuine and professional self, collaboration, and a positive energy to everything he does. It's been a genuine pleasure working with him, and I miss having him as a partner. I recommend Dylan wholeheartedly for any role where high-impact quality leadership, tech knowledge, stakeholder alignment, and customer-driven decision-making are valued.

Ira Kudriashova

Head of Engineering @ Jira Enterprise

Worked with Dylan on different teams

"Dylan thrives in absolute ambiguity... he's adaptable and can drive an impact wherever he is. Hire this man!"

Dylan reported to me for the better part of a decade, and it was truly an honour to be able to work alongside him for all that time. Dylan thrives in absolute ambiguity, I was able to give him broad direction and Dylan would partner with R&D and figure out the best way to get it done. Most recently, Dylan drove cost avoidance with Jira R&D for the past two years and was able to have hundreds of bugs and feature requests shipped in that time, as well as quality initiatives and usability improvements. Dylan would be an asset as a TPM or any other role he puts his mind to, he's adaptable and can drive an impact wherever he is. Hire this man!

Matthew Hunter

Head of TPM & Customer Insights | Ex-Atlassian

Managed Dylan directly

"Dylan consistently served as the conduit between customer pain and product strategy."

I had the pleasure of working with Dylan for a little over four years during my time at Atlassian and was his manager for about ten months. Dylan brings a great mix of technical depth, leadership, and strategic thinking that makes him a strong fit for product management, technical program management, or leadership roles. At Atlassian, Dylan consistently served as the conduit between customer pain and product strategy, using his technical skills to develop SQL queries and data visualisations from support data. He then used these insights to influence product strategy and roadmaps through clear, compelling storytelling. Dylan was critical in driving product improvements across some of Atlassian's biggest bets, including Server to Cloud migrations and Jira. He achieved this by building strong relationships with senior stakeholders and becoming a trusted thought partner, always seeking ways to connect product strategy to better customer outcomes, which ultimately resulted in several strategic OKRs. Finally, Dylan was an all-around incredible teammate and demonstrated strong leadership skills by mentoring junior team members through onboarding and coaching them to success. Any team will be incredibly lucky to have Dylan.

Sarah Williams

Founder, Williams Coaching | Former Senior Manager @ Atlassian