Whether you are a CPO or a Group Product Manager, your first 180 days in a product leadership role are critical to paving a successful path for your team. Knowing where and how to spend your energy is key, and having a clear plan for that is the best way to ensure that you’ll be effective. Doing that is not easy: you need to understand and adapt the product strategy, ask the right questions, build relationships, learn about tools and processes, overcome challenges, and understand the company’s and team’s context and goals. Fleetio’s VP of Product, Esteban Contreras, shares his take - based on his experience at companies like Fleetio, Sprinklr and Hootsuite on how to focus your first 180 days in a new product leadership role. Watch this presentation here: https://www.linkedin.com/events/masterclass-scalingproduct-thef7107733007066705920/comments/

1. SCALING PRODUCT
ESTEBAN CONTRERAS
VP OF PRODUCT, FLEETIO
OCT
2023
THE FIRST 180 DAYS AS
A PRODUCT LEADER

2. Hi, I’m Esteban
Fleetio’s VP of Product
www.fleetio.com/careers
Psst… We’re hiring!
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
2
Esteban Contreras::

3. Hi, I’m Esteban
Fleetio’s VP of Product
3
(dot) com
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::

4. 4
Product Leader Aspiring PL Looking for a PL Working with a PL
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::

5. 5
Product People are:
a/ Curious
b/ Fact-finders
c/ Problem-solvers
d/ All of the above
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::

6. 6
Our agenda for today:
● On leading with context
● On joining the team
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::

7. 1/ To lead others with confidence,
you need to lead with context
7
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::

8. The World Out There
The Product The Team
The Company
Who You Are
8
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::

9. Who You Are
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Customer-centric & outcome-driven
○ Customer success – How they win
○ Business success – How we win
People-first
○ One team: Let’s go far, Let’s go together
○ Uplevel: Challenge + support
Evidence-based, data-informed, with a point of view
○ Listen, discover & understand…
○ And then, Speak, act & lead
* This is a sample list only.
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::

10. The Company
10
>> Competitive Position
>> Stage, Size, Funding
>> Customer Segments
>> Acquisition & Retention
>> Vision & Mission
>> Company Strategy
>> Business Model
>> Opportunities & Threats
* This is a sample list only.
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
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11. The Product
11
>> Value Prop
>> Problems it solves
>> Differentiators
>> User Feedback
>> Flaws, Gaps & Risks
>> Activation, Adoption
>> Engagement
>> Tech Debt, UX Debt
* This is a sample list only.
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::

12. The Team
12
Think Big, Start Small,
Move Fast
Differentiate,
Innovate
Drive Business
Outcomes
Solve
Customer
Problems
* This is a sample list only.
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::

13. The World Out There
13
* This is a sample list only.
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
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14. DAY 1
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SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::

15. GUIDE SHIP EMPOWER DRIVE
Product Vision,
Strategy & Direction
Continuous Execution:
Discovery & Delivery
Autonomy &
Accountability
Results: Customer &
Business Success
15
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::

16. NEWS
FLASH
16
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
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17. NEWS
FLASH
17
SPEED
MATTERS.
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
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18. NEWS
FLASH
18
THE
STAKES
ARE HIGH.
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A PRODUCT LEADER
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19. 19
Product,
Design
& Eng
Customer
Success
& Support
People,
G&A
Bus Ops
& Program
Sales
& Marketing
Product
Leader
* This is a sample list only.
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
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20. 20
* This is a sample list only.
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A PRODUCT LEADER
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21. 21
“Can you build this
shiny moonshot?”
“Can you mentor
the Engineers?”
“Can you chase
this rabbit hole?”
“Can you hire this
person’s nephew?”
“Can you make
this other team
move faster?”
saying the quiet
parts out loud.”
“You should just
tell us
what to do.”
“You should focus
on the optics.”
“You should build
a personal brand.”
“You should tell
them what they
want to hear.”
“You should not
hire people better
than you.”
“You should just
do it yourself.”
* This is a sample list only.
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::

22. Current State
● Team
● Culture
● Mission
● Goals
● Strategy
● Alignment
● Operations
● Investment Mix
● Systems
● Programs
● Processes
● Tools
● Communications
● Collaboration
● Inputs
● Discovery
● Execution
● Outputs
● Outcomes
● Metrics
● Traction
● UX
● Tech
● Innovation
● Readiness
● ICP
● Messaging
● GTM
Future State
?
22
* This is a sample list only.
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::

23. Current State
● Team
● Culture
● Mission
● Goals
● Strategy
● Alignment
● Operations
● Investment Mix
● Systems
● Programs
● Processes
● Tools
● Communications
● Collaboration
● Inputs
● Discovery
● Execution
● Outputs
● Outcomes
● Metrics
● Traction
● UX
● Tech
● Innovation
● Readiness
● ICP
● Messaging
● GTM
Future State
?
23
* This is a sample list only.
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::

24. Current State Future State
?
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* This is a sample list only.
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::
● Team
● Culture
● Mission
● Goals
● Strategy
● Alignment
● Operations
● Investment Mix
● Systems
● Programs
● Processes
● Tools
● Communications
● Collaboration
● Inputs
● Discovery
● Execution
● Outputs
● Outcomes
● Metrics
● Traction
● UX
● Tech
● Innovation
● Readiness
● ICP
● Messaging
● GTM

25. The BIG question
25
SCALING PRODUCT
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A PRODUCT LEADER
Esteban Contreras::

26. What does the company need MOST from you right now?
26
SCALING PRODUCT
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27. What the team knows + What they don’t know
What customers say + what they don’t say
What users do + what they don’t do
What prospects look for + what buyers pay for
What competitors do + what they say they do
What the product promises + what the product delivers
27
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SCALING PRODUCT
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29. ● Understand VOC
● Prioritize ARR Growth
● Align org
● Differentiate core product
● Hire key leaders ● Foster collaboration
● Increase NRR
● Optimize pricing
● Define big bets
● Drive expansion
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● Edit the team
● Celebrate quick wins
● Set expectations
● Define operating principles
● Formalize roadmap
● Refine OKRs
● Define leveling
● Empower experiments
● Launch new solution
● Understand VOP
● Improve T:P
Example
* This is a sample list only.
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
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30. What we will do. And what we will not.
30
SCALING PRODUCT
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31. For example…
31
SCALING PRODUCT
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A PRODUCT LEADER
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32. ● Refine OKRs
● Prioritize ARR Growth
● Set expectations
● Hire key leaders
● Define big bets
● Edit the team
● Celebrate quick wins
● Unlock Expansion
● Differentiate core product
● Optimize pricing
● Launch new solution
● Improve GTM
● Increase NRR
● Empower experiments
32
● Improve T:P
● Track VOC + VOP insights
● Build product dashboard
● Foster collaboration
● Communicate roadmap
● Define leveling
● Refine operating principles
Horizon 1 Horizon 3
Horizon 2
* This is a sample list only.
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::

33. ● Drive traction
● Ensure P/M Fit
● Coach first PMs
● Clarify culture
● Optimize experimentation
● Figure out collaboration
● Land funding
● Drive expansion & leadership
● Ensure predictability
● Empower VPs & ICs
● Facilitate partnerships
● Mitigate risk
● Button up compliance
● Assess M&A, B/B/P
33
● Drive ARR Growth
● Ensure retention
● Hire ‘A’ Players
● Clarify ICP & messaging
● Solidify operational excellence
● Optimize pricing
● Facilitate discovery
Early Stage Startup Mature Enterprise
Growth Stage
* This is a sample list only.
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THE FIRST 180 DAYS AS
A PRODUCT LEADER
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34. Clarity of Focus
34
SCALING PRODUCT
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35. TL;DR
● Do all the things
● Listen carefully
○ Ask questions
○ Gain context about the company
○ Gain clarity about what the org needs from you
● Discern what is most needed
○ Look for evidence
○ Assess and strategize
● Lead towards impact — with context, clarity and focus
35
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::

36. 2/ To lead a team, you first
need to join the team
36
SCALING PRODUCT
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A PRODUCT LEADER
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37. SCALING PRODUCT
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SCALING PRODUCT
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SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
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43. SCALING PRODUCT
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SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::

44. TL;DR
● Tell everyone what to do
● Get to know the humans behind the product
○ Build relationships with exec team, your org, and leaders across company
○ Establish culture of open communication, transparency, and integrity
● Earn your place, and set the pace
○ Lead by example, and be accountable
● Scale a team you need (and want) to scale
○ Assess; challenge and support them
○ Invest in talent, skills and attitude
○ Consider the shape, ratios, and complementary roles
44
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::

45. Thank you for your time.
Any questions?
/in/juanestebancontreras/
@socialnerdia
www.productstate.com
45
Esteban Contreras
VP of Product
Fleetio
www.fleetio.com/careers
SCALING PRODUCT
THE FIRST 180 DAYS AS
A PRODUCT LEADER
Esteban Contreras::

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48. SCALING PRODUCT
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A PRODUCT LEADER
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Templates:
POV
Teams and Mission
PQR Agenda
Key Considerations
Big Bets
Org Chart
Quarterly Focus Areas
OKR Tracking
User Behaviors
Signals & Feedback
Strategic Cadence
Decision Tradeoffs
PIP
Working with Me
Leader Onboarding Checklist
Headcount Plan
Software Needs Plan

49. Purpose
● Align on objectives
● Align on problems to solve
● Align on big bets
● Align on expectations
● Align on the future state
People
● Assess the team
● Define the org structure
● Hire missing players
● Edit the team
● Empower the team
Culture & Process
● What and how we do when no
one’s watching
● Principles
● Communicating clearly
● Fix what’s not working well
● Scale what’s working well
Purpose
● We started to become very data-informed. Evidence for every decision,
and also an expectation that we value developing an informed POV.
● And we started to share insights. We’re doing PQRs where we look back
and we look ahead, we share about what’s worked and what hasn’t.
● Internal Roadmap and Customer Roadmap
● Meeting with stakeholders – customers, partners, prospects, board
members, investors, etc.
● Provided guidance on big bets to grow ARR and ensure retention
● We stopped doing low value things simply because they were planned for
a long time ago or because someone asked for it or because the team
was comfortable with it.
● We started to prioritize big bets – key table stakes, important
differentiators, strategic partnerships, experimentation, and hard initiatives
that will take some time
● Making high impact decisions
People
● Took leadership over the PM, PD and PMM teams – and facilitating
collaboration across these team and with Engineering
● we moved the QA team under Engineering
● Hired a GM and 3 Directors – so far we have an acceptance rate of 4 out
of 4 leaders, and
● I empowered them to do capabilities assessment, levelling, hiring, firing,
etc.
● 1:1s with everyone in the org
● We gave the team access to training programs, and tools
● Hiring plan for the next year
● We’re going to hire roles we’ve never hired before.
● We empowered the team to make strategic decisions
● We’re resizing squads and clarifying their missions
Process
● Shared what we were going to do in the Product org, and then did that
● High bar for quality
● Prioritized continuous Discovery
● We’re sharing VOC and VOP
● We’re gathering competitive intel
● We need differentiated, sticky, margin-enhancing solutions
● We’re getting the right tools in place
● Product Exec Dashboard on Metabase
● Optimize small things that need to be optimal
● We did our first hackathon
● Decision trees
● We’re defining what activation looks like for us
● We’re refining and scaling processes.
● Getting better at experimentation and iteration
● We’re prioritizng Impact over activity
● We’re figuring out our product operating system
● We’re building a multi-horizon product strategy
● Think in multiple horizons
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