The document outlines a comprehensive program management playbook for startups, emphasizing the importance of establishing a Program Management Office (PMO) to facilitate strategic planning and execution. It details the roles and responsibilities of the PMO at various company growth stages, while providing a standardized approach to product development and resource management. Key processes include aligning teams, managing portfolios effectively, and utilizing tools for successful project execution.

1. @BeckyFlintSF
Startup Program Management Playbook
The Why, What, How of Program Management
This is was originally my interview presentation deck

2. @BeckyFlintSF
About Me
STARTUPS
NEED Program
Management
TO SCALE
my blog
Established, scaled, and optimized program
management office for startups and growth
companies.

3. @BeckyFlintSF
Here is a
view of your
roadmaps

4. @BeckyFlintSF
Here is a view
of another
portfolio
roadmaps

5. @BeckyFlintSF
Quote from Bigcommerce Co-founder Eddie Machaalani
There are a lot of startups who are in need of good processes.
The trick is most won’t know they need PMO because they won’t
identify the pain point as being a problem that's solvable. I
personally had no idea that we needed PMO until we hired Becky.
PMO = Program Management Office

6. @BeckyFlintSF
What Does Program
Management Do?

7. @BeckyFlintSF
Context Strategic Planning and Execution Process of a Healthy Company
Strategy
KPI
Portfolio
Roadmap
Portfolio
Progress
internal/
external inputs
Strategic Planning &
Execution

8. @BeckyFlintSF
Context Strategic Planning and Execution Process of a Healthy Company
Strategy
KPI
Portfolio
Roadmap
Portfolio
Progress
internal/
external inputs
Issue mgmt &
communication
Roadmap
Delivery
Evaluate &
Prioritize Projects
Define objectives &
key metrics (OKR)
PMO establishes &
leads the process
PMO establishes &
facilitates the process

9. @BeckyFlintSF
What Does PMO Do?
A Full Service PMO Leads The Strategic Planning & Delivery of The Portfolio
A suite of programs aimed to maximize
enterprise value
A structured grouping of related projects
and other business activities aimed to
achieve defined business value
A temporary endeavor undertaken to create a
unique product, service or result.

10. @BeckyFlintSF
Roles Evolve as Company Grows
From Generalists wear many small hats to Specialists wear single larger hat
Founder or
VPE
VPE VP Product VPE + PGM/PPM + VP Product
Founding Stage
(<50)
Initial Product Mkt Fit
(50-150)
Growth + New Product
(150-500)
Multiple Product Lines
(500+ employees)
PPM as Portfolio Program Manager oversee multiple product lines (in a portfolio)
PGM as Program Manager

11. @BeckyFlintSF
Lead Roles in Product Engineering Org by Company Stage*
Key Area Founding Stage
(<50)
Initial Product Mkt Fit
(50-150)
Growth + New Product
(150-500)
Multiple Product Lines
(500+ employees)
Product
strategy 1
Founder Founder + Head of Product Head of Product Head of product line
+ Head of Product
Portfolio
Roadmap 2
Founder +
engineering
Head of Product Head of Product + PGM Head of Prod Line + PGM/ PPM
Portfolio
Delivery
engineering VPE or VP Product PGM + PM + EM PGM + PM + EM
* The size by stage varies.. Especially as companies hire more ondemand teams..
PGM as Program Manager, PM as Product Manager, and EM as Engineering Manager
1.
Strategy is the outcome of collaboration between Product and leaders of various business functions and key clients/ partners
2.
Partnership between 2 functions link to strategy and execution, respectively.

12. @BeckyFlintSF
Why Do Companies Need Program Management?
At Portfolio, Program and Project level, PGM enables:
Communicates goals, plan,
resourcing, progress,
issues and resolutions to
the relevant audiences.
Align product features,
people/teams, and cross
functional activities to goals
and strategies.
PjM - deliver projects on
time on budget.
PgM - achieve program
goals within constraints
PPM - portfolio allocation
achieve intended business
outcome,
Visibility Alignment Outcome

13. @BeckyFlintSF
How Do We Do It?

14. @BeckyFlintSF
How Do We Do It? 1 / 5
Standardize A Complete* Product Development Life Cycle (PDLC)
Foundation for Cross-functional Virtual Teams Working Within An Agile Environment
Evaluate / prioritize
opportunities/ customer
problems within roadmap/
portfolio
Define/ Prioritize feature
set
Actual work by
cross-functional teams,
both engineering and
other teams, e.g.
marketing
Go to market activities from
1st customers to all intended
customers
(blogs, training, sales
enablement,throttle, etc.)
Problem
Discovery
Design
Build &
Release
Go to Market
* Reminder: Launching product takes more than engineering efforts...

15. @BeckyFlintSF
How Do We Do It? 2 / 5
Roles and Responsibility is Critical to Team Success
Collaborate with Stakeholders to
● Define Functional Roles, Responsibilities and interaction models
○ Company or org-wide
○ Program wide
● Define RSI for projects, programs and tasks
R: Responsible Person
S: Support
I: Informed

16. @BeckyFlintSF
How Do We Do It? 3 / 5
Cadences: Right level, Right People, Right Frequency
Project Level Cadence
(Project team members)
Program Level Cadence
(functional leads)
Portfolio Level Cadence
(executive team)
Meetings ● Project kickoff: Goals and RSI
definition
● Daily standups
● Bi-weekly sprint review + demo
● Later phase of PDLC: Weekly
Launch Readiness meeting
● End of Project retro
● Program kickoff and
blueprints: goals, RSI,
understand constraints and
resources
● Bi-weekly program steering
meeting
● Strategic steering (budgeting) -
annual/ semi-annual
● Portfolio alignment - quarterly
● Portfolio Success tracking -
monthly/ bi-weekly
Artifacts Weekly status update (email)
Issue Log (Jira)
Launch dashboard
Program Dashboard
Resource Map reports
Issue and Action Item log
Portfolio Roadmap Updates
Functional dashboards
Metrics dashboards

17. @BeckyFlintSF
Strategic Plan
(semi-annual or qtrly)
Exec Goals + Key Initiatives
Financial Plan
(semi-annual)
P&L @ Corp level & by Team
Roadmap Alignment
Key initiative breakdown
by Qtr
Rolling(see
appendix)
OPEXplan
How Do We Do It? 4 /5
Start with Portfolio Planning Set Strategic Foundation of All Other Activities
Monthly Success
Tracking

18. @BeckyFlintSF
How Do We Do It? 5a / 5
Configure Tool/s For Project/Task, Program, and Portfolio Management &
Enable virtual and cross-functional team collaboration:
● One source of truth on goals, projects, progresses, and references
● Effective roll up and drill down of information
● Data analysis/ reports by project, featureset, team, product strategy, use case, etc.

19. @BeckyFlintSF
How Do We Do It? 5b / 5
Build A Lightweight Tool and Process for Resource Planning and Management
❖ Context switching => 30% or more lost productivity
❖ Mis-aligned resources => 20-80% of lost productivity due to waiting/ blocked
Resource Map Enables:
● Overall view of project assignments to teams/ key technical expertise/ areas
● Reduced context switch by integrating feature work and tech debt/ bugzar duty
● Visibility to anticipate skillset needs and timing for hiring/ training
● Insight on whether we are executing towards our strategy (by assigning resources accordingly)

20. @BeckyFlintSF
Appendix
Resourcing - Critical Element
of Roadmapping

21. @BeckyFlintSF
Roadmap Scenarios:
Manage Supply and Demand - Different dimensions
Team A
Team B
Retention
+30%
Conversion
+20%
Acquisition
+20%
Strategic
investment
Demand by sources Demand by goals

22. @BeckyFlintSF
Portfolio Allocation (spreadsheet)

23. @BeckyFlintSF
Portfolio Planning and Allocation

24. @BeckyFlintSF
Confirmed
Projects
Experiments
Confirmed
Projects
validated
Experiment(s)
Q1 Q2 Q3 Time
Experiment(s)
Confirmed
Projects
Each period (quarter) we divide up resources between confirmed projects and experiments, (i.e.
hypothesis on opportunities, e.g. freemium, or vertical)
Those proven to be good opportunities will become part of roadmap (business or R&D projects)
Benefits of confirmed projects will be incorporated into next period of financial plan
Resource
Resourcing Model for Rolling Roadmap Planning (Duo Track Agile)