Perhaps we've set our project management officers (PMOs) up for failure. Without knowing it, we ask them to predict the future using a one-size-fits-all approach to best practices – and that just doesn't work. There is no magic crystal ball! Learn how an agile PMO can help your organization tackle the right work, at the right time, with the right teams using JIRA.

1. #atlassian

2. Beyond the Crystal Ball: The Agile PMO
Right Work, Right Time, Right People
HEATHER FLEMING • SENIOR DIRECTOR, PMO • GILT • @HFLEMING
JUSTIN RISERVATO • DIRECTOR, PROGRAM MGMT • GILT • @SHARKSNMERMAIDS

3. Tonight we will cover...
• Who are these people anyway?
• Are PMOs set up to fail?
• How do we get back to Agile?
• Our Fantastic Voyage through Process Experiments
• ROIs and Roadmaps
• Swagathons
• The Social Experiment

4. Hello!
• Heather Fleming, Senior Director, PMO
• Started out in front-end development, management and design in 1996
• PMP Certified, Myers-Briggs (MBTI®) Certified
• Heading up PMOs since 2006 for The Knot (XO Group) and Gilt
• Justin Riservato, Director, Program Management
• 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!
INFJ
ESTP

5. What is Gilt?
adjective
• covered thinly with gold leaf or gold
paint
noun
• a young pig

6. 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!

7. Are Traditional PMOs Set up to Fail?
• Responsibilities of Traditional PMOs
• Planning & Roadmapping
• Resource & Capacity Planning
• Implementing PM Processes & Standards

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

9. You can’t predict
the future.

10. 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

11. 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

13. Remember the Triangle of Truth
SCOPE
QUALITY
TIMECOST

14. Remember the Cone of Uncertainty
DISCOVER DESIGN DEVELOP DEPLOY
ESTIMATE ACCURACY
Don’t make
promises here!
Make them
down here!

15. Tell the truth!

16. 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

17. The PMO @ Gilt: How are we different?
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”...)

18. Our Fantastic
Voyage

19. Everybody
Loves
Roadmaps

20. They’re so pretty!
Project
Q1
Q2
Q3
Q4
SEO V2
CMS
Email Redesign
Site Redesign
Landing Pages
WMS Upgrade
Referrals V2

21. How we used JIRA

22. ROI/Roadmap Process
Re-Prioritize
!
Re-Plan!
Get Exec
Approval
3 Month
Roadmap
New
Project
Ideas
Who Can
Do It?
How Long
Will It Take?
(ROI)
CHANGE!

23. Change Happens.

24. ROI/Roadmap Retrospective
• What works well with this model?
• What doesn’t work well?

25. ROI/Roadmap 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

26. Swagathon

27. Scientific
Wild
A$$
Guess…
-athon

28. The Spirit...
The Team Will Have
• 1-2 Week Sprints
• Public Commitments at Sprint Start
• Public Results at Sprint End
• What was done? What wasn’t?
• Retrospectives
The Self-Managing Team
Dedicated, Cross-Functional Team
Includes Tech, Product, and Business Roles
“The Mini-Startup”

29. The Process...
Project Team
(Maybe?)
One Pager
Swagathon
Backlog
Product
Council

30. The era of false
hope.

31. Our abuse of the Fix Version
In Discovery
In Backlog
In Flight
Complete

32. We made it complicated...
!(project in ("Customer Support", Mobile, "Taste Project Management",
"Business Development") AND status in ("In Progress") and type not in
(sub-task, Bug)) OR (project = PMO AND resolution = Unresolved AND
fixVersion in ("Active Projects") and type not in (Sub-task, Bug)) OR
(category in (Applications, Shared) AND status not in (Open, Closed) AND
fixVersion not in (Graveyard, "In Discovery", "Sprint Backlog", "Product
Backlog", "Someone Else's Problem", "PnB: Feature Backlog", "PnB: Search
Backlog", "On Deck", "PnB IE Issues", "In Backlog") and type in (Epic,
Story)) ORDER BY key ASC"

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

34. 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...

35. The Social
Experiment

36. The Social Experiment
STRATEGY
INITIATIVES
KPIs
TEAMS
INGREDIENTS
EXECUTION
Big Areas of Focus
What are we doing / not doing?
Answering WHY
Who do we need?
Qualities, Not Titles
Get Working!

37. You are more than your job title!
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).

38. Coder
Writes feature and test
code. Create queries and
reports.

39. Cruise Director
Making things fun. Creating
a sense of team spirit.

40. Motivator
Creating a sense of urgency
while ensuring a sustainable
pace for the team.

41. Hooray Agile Tab!

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

43. 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

44. Thank you!
HEATHER FLEMING • SENIOR DIRECTOR, PMO • GILT • @HFLEMING
JUSTIN RISERVATO • DIRECTOR, PROGRAM MGMT • GILT • @SHARKSNMERMAIDS