Gilt Senior Director, Program Management Office Heather Fleming and Director of Program Management Justin Riservato discuss Agile, Gilt's PMO challenges and more in this informative presentation.

1. Today we will cover...
● Who are these people?
● Are PMOs setup to fail?
● How do we get back to Agile?
● Our Fantastic Voyage through Process Experiments
o ROIs and Roadmaps
o Swagathons
o The Social Experiment

2. Hello!
Heather Fleming, Sr. Director, PMO
● Started out in front-end development, management and design
in 1996
● PMP Certified, Myers-Briggs (MBTI®) Certified
● Heading up PMOs since 2006 XO Group 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 philosophy and never looked back!
INFJ
ESTP

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

4. What is Gilt?
• Gilt (www.gilt.com) is an e-commerce company focused on flash
sales. We provide insider access to top designers 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
● Implementing PM Processes & Standards

6. 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!

7. You can’t predict the future!

8. 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!

9. 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

11. Remember the Triangle of Truth

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

13. Tell the truth!

14. 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

15. 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”...)

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

17. Everybody
Loves
Roadmaps

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

19. ROI/Roadmap Process

20. Change Happens.

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

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

23. Swagathon

24. Scientific
Wild
A$$
Guess…-athon

25. The Spirit...

26. The Process…

27. The era of false hope.

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

29. Swagathon Retrospective
What we learned...
● We were still on the “less valued” side of the Manifesto
o ...we were following a plan instead of developing
working software
o ...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...

30. The Social Experiment

31. The Social Experiment

32. 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).

33. Coder
Write features and test code.
Create queries and reports

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

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

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

37. 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

38. Thank You!
H E AT H E R F L E M I N G • S E N I O R D I R E C T O R , P M O • G I LT • @ H F L E M I N G
J U S T I N R I S E R VAT O • D I R E C T O R , P R O G R A M M G M T • G I LT • @ S H A R K S N M E R M A I D S