Beyond the Crystal Ball: The Agile PMO


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The slides from Gilt Senior Director, Program Management Office Heather Fleming and Director of Program Management Justin Riservato's Agile NYC presentation of April 14, 2014.

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Beyond the Crystal Ball: The Agile PMO

  1. 1. Beyond the Crystal Ball: The Agile PMO Right Work, Right Time, Right People
  2. 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. 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. 4. What is Gilt? Gilt ( 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 to learn more about us!
  5. 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. 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. 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. 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. 9. Remember the Triangle of Truth
  10. 10. Remember the Cone of Uncertainty Image from
  11. 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. 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. 13. Our Fantastic Voyage ● ROI, Roadmaps and RFW Process ● One Pagers and Swagathon ● The Social Experiment
  14. 14. Everybody Loves Roadmaps Project Q1 Q2 Q3 Q4 SEO v2 CMS Email Redesign Site Redesign Landing Pages WMS Upgrade Referral Program
  15. 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. 16. ROI/Roadmaps Retrospective What works well with this model? What doesn’t work well?
  17. 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. 18. The Spirit...
  19. 19. Swagathon One Pager Project Team (maybe?) Backlog Product Council Swagathon
  20. 20. Process States
  21. 21. Swagathon Retrospective What works well with this model? What doesn’t work well?
  22. 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. 23. The Social Experiment Strategy Initiatives KPIs Teams Ingredients Execution
  24. 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. 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. 26. The Social Experiment Retrospective What works well with this model? What doesn’t work well?
  27. 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. 28. Q&A Thank you!