The document discusses the challenges and evolution of the Project Management Office (PMO) within Gilt, an e-commerce company, emphasizing the shift towards agile methodologies. It highlights the need for PMOs to adapt to changing expectations and the importance of collaboration and responsiveness to change. The piece outlines various strategies, including the use of roadmaps, retrospectives, and team dynamics, to improve efficiency and alignment with company goals.

1. Beyond the Crystal Ball:
The Agile PMO
Right Work, Right Time, Right People

2. Tonight we will cover...
● Who are these people?
● PMO Challenges
● Getting back to Agile
● Our Fantastic Voyage through Process Experiments
○ ROIs and Roadmaps
○ Swagathons
○ The Social Experiment
● Q&A

3. Hello!
Heather Fleming, Sr. Director, PMO
● Started out in front-end development, management and design in 1996
● Was PMP Certified, is Myers-Briggs (MBTI®) Certified
● Heading up PMOs since 2006 for The Knot and Gilt
Justin Riservato, Director, Program Mgmt
● Started out in Customer Service and Product Marketing, realized that the
best part of every job was the Project Management
● Fell in love with Gilt’s PMO’s philosophy and never looked back!

4. What is Gilt?
Gilt (www.gilt.com) is an e-commerce company focused on
flash sales. We provide insider access to top designers at
up to 60% off, in sales typically lasting 72 hours.
We’re also one of the top tech companies in NYC!
Check out tech.gilt.com to learn more about us!

5. Are Traditional PMOs Set up to Fail?
Responsibilities of Traditional PMOs
● Planning & Roadmapping
● Resource & Capacity Planning
● PM Processes & Standards
In a recent survey by EDI International titled “The State of the Project Management Office: On the
Road to the Next Generation”, more than half of the respondents report that the value of their PMO is
being questioned by key stakeholders.

6. What’s the problem?
The company is expecting you to predict the future...
Months (sometimes years) out...
In software engineering...
Given a short (one sentence) description of the work...
And you will be held accountable for your predictions!

7. So what do most people do?
● They believe “going Agile” is a silver bullet.
● People use the word “Agile” in many ways.
● They implement Scrum

8. And then what happens?
● The company still wants you to predict the future.
● The engineers are rebelling against the Scrum process.
● The PMO is called into question anyway
Oh noes!

9. Remember the Triangle of Truth

10. Remember the Cone of Uncertainty
Image from agilenutshell.com

11. And Remember the Manifesto!
Individuals and interactions over processes and tools
Working software over comprehensive documentation
Customer collaboration over contract negotiation
Responding to change over following a plan

12. The PMO @ Gilt
We get things done.
We tackle a lot of the operational function of running
Gilt Tech.
We help Gilt Tech explore and experiment with efficient
processes to select and execute strategic projects.
(Notice we didn’t say “standardize”...)

13. Our Fantastic Voyage
● ROI, Roadmaps and RFW Process
● One Pagers and Swagathon
● The Social Experiment

14. Everybody Loves Roadmaps
Project Q1 Q2 Q3 Q4
SEO v2
CMS
Email Redesign
Site Redesign
Landing Pages
WMS Upgrade
Referral Program

15. ROI/Roadmap Process
3 Month
Roadmap
New Project
Ideas
How long will it
take? (ROI)
Who can do it?
Re-prioritize!
Re-plan!
Get Exec
Approval
CHANGE

16. ROI/Roadmaps Retrospective
What works well with this model?
What doesn’t work well?

17. ROI/Roadmaps Retrospective
What we learned...
● We were on the “less valued” side of the Manifesto
○ We were spending more time planning than doing
○ ...and more time on documentation
○ ...and more time on processes and tools
● We change a lot!
● We want transparency and a say in the order of work

18. The Spirit...

19. Swagathon
One Pager
Project
Team
(maybe?)
Backlog
Product
Council
Swagathon

20. Process States

21. Swagathon Retrospective
What works well with this model?
What doesn’t work well?

22. Swagathon Retrospective
What we learned...
● We were still on the “less valued” side of the Manifesto
○ ...we were following a plan instead of developing working software
○ ...we spent too much time on processes and tools
● Creating “on the fly” teams was challenging
● We were giving people false hope with our backlog
● We could respond to change easier, but
we were still missing a bigger story...

23. The Social Experiment
Strategy
Initiatives
KPIs
Teams
Ingredients
Execution

24. The Social Experiment
Strategy: Big Areas of Focus
Initiatives: What are we doing / not doing?
KPIs: Answering WHY
Teams: Who do we need?
Ingredients: Qualities, Not Titles
Execution: Get Working!

25. Product Visionary
Driving product vision and strategic innovation. Strong point of view.
PR and Relationship Manager
Managing the external view of the team. Communicates well both verbally
and via email. Knows how to deliver an excellent presentation.
Product Ideator
Thinking creatively and driving tactical innovation. Being the voice of the
customer.
Visual Designer
Creates on-brand visual designs.
UX
Build wireframes, runs usability tests, designs user interactions.
Coder
Writes feature and test code. Create queries and reports.
Product Marketer
Analyzes the market and competitive landscape, determines
product/feature positioning so the customer clearly understands the benefit,
figures out ways to drive traffic to the product or feature.
Business thinker
Driving KPI thinking. Understanding business mechanics. Sizing
opportunities.
Organizer
Driving planning of work, running productive meetings, keeping the team
focused on execution.
Engineering Architect
High level system design. Managing technical debt. Building for the right
amount of performance and scale. Providing technical leadership and
mentorship.
Quality Manager
Ensuring the quality of releases. Making sure that the right amount of
automation is built (unit tests).
Motivator
Creating a sense of urgency while ensuring a sustainable pace for the
team.
Cruise Director
Making things fun. Creating a sense of team spirit.
Analyst
Drives product instrumentation. Proposes tests (e.g. a/b tests). Analyzes
data. Creates and tests hypotheses and uses these to influence product
direction. Can clearly communicate what data means.
Technical Operator
Drives product instrumentation. Pays attention to production operational
parameters (alerts, tuning, etc).

26. The Social Experiment Retrospective
What works well with this model?
What doesn’t work well?

27. The Social Experiment Retrospective
What we learned...
● We know how our work ties into a bigger story
● We know we are working on the things that matter the most
● We want to continue to get better at Collaboration
● Valuing Individuals and Interactions is key
● Responding to Change will always be challenging

28. Q&A
Thank you!