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HEATHER FLEMING • SENIOR DIRECTOR, PMO • GILT • @HFLEMING
JUSTIN RISERVATO • DIRECTOR, PROGRAM MGMT • GILT • @SHARKSNMERMAIDS
Beyond the Crystal Ball: The Agile PMO
Right Work, Right Time, Right People
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
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
What is Gilt?
adjective
•covered thinly with gold leaf or gold
paint
noun
•a young pig
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!
Are Traditional PMOs Set up to Fail?
•Responsibilities of Traditional PMOs
• Planning & Roadmapping
• Resource & Capacity Planning
• Implementing PM Processes & Standards
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!
You can’t predict
the future.
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
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
Remember the Triangle of Truth
QUALITY
COSTTIME
SCOPE
Remember the Cone of Uncertainty
DISCOVER DESIGN DEVELOP DEPLOY
ESTIMATEACCURACY
Don’t make promises
here!
Make them
down here!
Tell the truth!
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
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”...)
Our Fantastic
Voyage
Everybody
Loves
Roadmaps
They’re so pretty!
Project Q1 Q2 Q3 Q4
SEO V2
CMS
Email Redesign
Site Redesign
Landing Pages
WMS Upgrade
Referrals V2
How we used JIRA
ROI/Roadmap Process
Re-Prioritize!
Re-Plan!
Get Exec
Approval
3 Month
Roadmap
Who Can
Do It?
New
Project
Ideas
How Long
Will It Take?
(ROI)
CHANGE
!
CHANGE
!
Change Happens.
ROI/Roadmap Retrospective
• What works well with this model?
• What doesn’t work well?
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
Swagathon
Scientific
Wild
A$$
Guess…
-athon
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”
The Process...
Project Team
(Maybe?)
One Pager Swagathon Backlog
Product
Council
The era of false
hope.
In Discovery In Backlog In Flight Complete
Our abuse of the Fix Version
(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
We made it complicated...
Swagathon Retrospective
• What works well with this model?
• What doesn’t work well?
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...
The Social
Experiment
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!
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).
Coder
Writes feature and test
code. Create queries and
reports.
Cruise Director
Making things fun. Creating
a sense of team spirit.
Motivator
Creating a sense of urgency
while ensuring a sustainable
pace for the team.
Hooray Agile Tab!
The Social Experiment Retrospective
• What works well with this model?
• What doesn’t work well?
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
Thank you!
HEATHER FLEMING • SENIOR DIRECTOR, PMO • GILT • @HFLEMING
JUSTIN RISERVATO • DIRECTOR, PROGRAM MGMT • GILT • @SHARKSNMERMAIDS

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Beyond the Crystal Ball: The Agile PMO

  • 1. HEATHER FLEMING • SENIOR DIRECTOR, PMO • GILT • @HFLEMING JUSTIN RISERVATO • DIRECTOR, PROGRAM MGMT • GILT • @SHARKSNMERMAIDS Beyond the Crystal Ball: The Agile PMO Right Work, Right Time, Right People
  • 2. 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
  • 3. 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
  • 4. What is Gilt? adjective •covered thinly with gold leaf or gold paint noun •a young pig
  • 5. 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!
  • 6. Are Traditional PMOs Set up to Fail? •Responsibilities of Traditional PMOs • Planning & Roadmapping • Resource & Capacity Planning • Implementing PM Processes & Standards
  • 7. 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. 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
  • 10. 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.
  • 12. Remember the Triangle of Truth QUALITY COSTTIME SCOPE
  • 13. Remember the Cone of Uncertainty DISCOVER DESIGN DEVELOP DEPLOY ESTIMATEACCURACY Don’t make promises here! Make them down here!
  • 15. 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
  • 16. 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”...)
  • 19. They’re so pretty! Project Q1 Q2 Q3 Q4 SEO V2 CMS Email Redesign Site Redesign Landing Pages WMS Upgrade Referrals V2
  • 20. How we used JIRA
  • 21. ROI/Roadmap Process Re-Prioritize! Re-Plan! Get Exec Approval 3 Month Roadmap Who Can Do It? New Project Ideas How Long Will It Take? (ROI) CHANGE ! CHANGE !
  • 23. ROI/Roadmap Retrospective • What works well with this model? • What doesn’t work well?
  • 24. 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
  • 27. 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”
  • 28. The Process... Project Team (Maybe?) One Pager Swagathon Backlog Product Council
  • 29. The era of false hope.
  • 30. In Discovery In Backlog In Flight Complete Our abuse of the Fix Version
  • 31. (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 We made it complicated...
  • 32. Swagathon Retrospective • What works well with this model? • What doesn’t work well?
  • 33. 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 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!
  • 36. 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).
  • 37. Coder Writes feature and test code. Create queries and reports.
  • 38. Cruise Director Making things fun. Creating a sense of team spirit.
  • 39. Motivator Creating a sense of urgency while ensuring a sustainable pace for the team.
  • 41. The Social Experiment Retrospective • What works well with this model? • What doesn’t work well?
  • 42. 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
  • 43. Thank you! HEATHER FLEMING • SENIOR DIRECTOR, PMO • GILT • @HFLEMING JUSTIN RISERVATO • DIRECTOR, PROGRAM MGMT • GILT • @SHARKSNMERMAIDS

Editor's Notes

  1. 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.