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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

COST TIME

SCOPE

Remember the Cone of Uncertainty

DISCOVER DESIGN DEVELOP DEPLOY

ESTI

MAT

E AC

CU

RAC

Y

Don’t make p romises 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”...)

NOTES:

• If you want to divide your talk

into chapters, use this slide for

Chapter titles

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-Priorit ize!

Re-Plan!

Get Exec

Approval

3 Month

Roadmap

Who Can

Do It?

New

Project

Ideas

How Long

Will It Take?

(ROI) 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 Wil l 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