1.
Andrew Hsu || 2019-02-10
USING PRODUCT MANAGEMENT
TO GET A PRODUCT MANAGEMENT GIG

2.
ABOUT ME
Past
﹢ Electrical engineer
﹢ 7+ years of product management
Launched Android and iOS apps, coordinated a design refresh
of Google sign-in, grew a start-up to value homes using machine
learning, and consulted to raise company motivation and performance
Present
﹢ Oscar Health

3.
ABOUT ME
Unfortunately, and fortunately, I have experience
over these past 7+ years...
﹢ 6 companies
﹢ 2 “from scratch” job searches
﹢ 3 different cities

4.
TODAY
﹢ Product management
Processes and frameworks
﹢ Stories
Inspiration and customization ideas
﹢ Lessons
Favorite lessons learned
﹢ Ask
Take the first step

5.
PRODUCT MANAGEMENT
Processes and frameworks

6.
PRODUCT MANAGEMENT
1. Problem Solving
A process to problem solve and keep moving
2. Roadmap
A framework to articulate your goals
3. Adjust
A framework to refine your goals and process along the way

7.
PM PROBLEM SOLVING
﹢ Start
﹢ Retro
﹢ Adjust
﹢ Share

8.
PM ROADMAP
Where we’d like to go and how we’re going to get there
﹢ Vision
﹢ Mission
﹢ Monthly roadmap
• Goals
• Accomplishments

9.
PM ADJUST
What’s changed, what we’ve learned, and new goals
﹢ Retro
﹢ Accomplishments
﹢ New goals

10.
“That’s cute…”

11.
STORIES
Inspiration and customization ideas

12.
Laid off and job searching...

13.
MONTH 1
Transition and try to relax

14.
REALITY NOT RELAXING
﹢ 6 trips to T-mobile
﹢ 2 extra weeks of work
﹢ Starting to organize the entire home
﹢ Unsolicited introductory emails
﹢ Meetings

15.
REALITY INTRODUCTIONS AND MEETINGS
Unsolicited introductory emails
﹢ Forced to write a mission
Meetings
﹢ Forced to prepare

16.
﹢ Deep research on person’s background
• LinkedIn - (connections, stability)
• Greenhouse (culture)
• CrunchBase (rounds of funding)
• Blog (recent focus)
• Publications (marketing focus)
﹢ What they’re working on
﹢ Hypothesize on their problems
MEETING PREP

17.
﹢ I tell my story
﹢ They tell their story
﹢ Offer each other topical help
﹢ Talk generally about positions at their company and about what’s interesting
﹢ Drink a lotttt of coffee
﹢ Ask for help and introductions
﹢ Offer help
﹢ Never explicitly asked for a job
MEETING

18.
﹢ I'm very caffeinated
⤑ Drink tea
﹢ Past stories not specific enough
⤑ Review resume, practice my story telling
﹢ Unclear mission
⤑ Unsure what to do about it
MEETING RETRO

19.
Monthly Roadmap
AUG - Relax
PM ROADMAP
Vision
Mission

20.
PM MISSION
Here’s a quick run down on what I’m looking for:
1. A team that recognizes the world is always changing and constantly seeks to learn and improve how
it operates and how to make a better product
2. A company that is dedicated to the product they’re building
3. Products which give time back to people or create social good: Education
4. A senior product manager or director of product role
5. A medium sized company (50 to 2,000)

21.
PM ADJUST
2.1 Retro
﹢ I'm very caffeinated; Drink tea
﹢ Past stories not specific enough; Practice talking about my past accomplishments
﹢ Unclear mission; Keep searching and practicing
2.2 Accomplishments
﹢ Met many interesting people and landed an interview
2.3 Goals
﹢ Apply in earnest and interview
﹢ Get more comfortable with my story

22.
PM ROADMAP
Monthly Roadmap
AUG - Relax
﹢ Goal: Enjoy
﹢ Accomplishments: 1 interview
SEPT - Applying and interviewing
﹢ Goal: Get 3 interviews
Vision
...
Mission
*New*

23.
Month 2
Applying and interviewing

24.
﹢ Turned on LinkedIn
﹢ Email: Friends asking for job leads
﹢ In person: Mention I lost my job and explain what I’m looking for
﹢ Take every meeting: friends, recruiters, and interviews
JUST START...

25.
Public company, 20 years, 2,000 people
﹢ 2 general managers in NY (business context, key problems - situational asks)
﹢ Project manager (how we’d work together)
﹢ New manager and head of business in Seattle (company structure and new responsibilities)
﹢ Co-founder (what he’s looking for)
﹢ 5 leaders across 3 offices
JOB 1

26.
👻

27.
﹢ …..…...
﹢ No one owes you anything
﹢ Volatility is a constant
﹢ “At least half the time, when a company rejects you, it’s not you. Budgets change, needs change, the
company could be re-organizing, or it could even be shutting down.”
Adjustment:
﹢ Get used to no feedback
﹢ Evaluate company stability
JOB 1 RETRO

28.
100 person start up, Series B
﹢ COO - Get to know each other (casual)
﹢ CTO & Managing director (role of product management, different conceptual question)
﹢ CEO - Problem solving approach (business, culture shifts, problem solving)
﹢ Managing director again (role shifts, problems)
﹢ COO - Consulting problem (How many ways can you organize these paintings?)
JOB 2

29.
👻 👻

30.
Work through my feelings
﹢ What kind of BS is this
﹢ “5 rounds of interviews and then a question completely unrelated to my job”
﹢ Not even a word
JOB 2 RETRO

31.
2 weeks pass…

32.
Discussed interview in depth with multiple people, realized:
﹢ False expectations - “I should solve problems here like I solve them in the real world”
﹢ Not solving the real question being asked - Question being asked AND...
• Culture fit, expansive thinking, creativity, ability to dig, focus on customer, etc…
﹢ Not managing time - Compressed time frame, person is often late
﹢ Not being positive - Time and time again, If I’m negative or incredulous, I perform worse
JOB 2 RETRO

33.
Adjustment: Practicing against my failings
﹢ Ask friends who interview at their companies to ask me conceptual questions
﹢ Answer them in 30 minutes
﹢ Practice positivity, time management, solving different types of problems - creativity, etc.
Adjustment: Found new mental models
﹢ Anytime stuck, work backwards
﹢ After answering a conceptual question, think 3D to expand your ideation
JOB 2 RETRO

34.
PM ADJUST
Retros
﹢ Don’t expect feedback
﹢ Lose my expectations, be positive, manage time, “answer the true questions”
Accomplishments
﹢ 2 “last round” interviews
﹢ Talking about my past accomplishments more effectively
Goals
﹢ "This is an opportunity to make a world class network"
﹢ Meet more people
﹢ Get to know the NY scene
﹢ Find communities I want to be a part of long term

35.
PM ROADMAP
Vision
Still unknown, many quizzes taken
Mission
Company with more than 100 people, in
healthcare, emergency services, or energy.
AUG - Tie up loose ends; 1 interview
SEPT - Applying and interviewing
﹢ Goal: Get 3 interviews
﹢ Accomplishments: 2 interviews
OCT - Invest in networks
﹢ Goal: Expand top of funnel
﹢ Accomplishments:
NOV
DEC

36.
Month 3
Invest in networks

37.
﹢ University alumni groups
﹢ Ex-company groups
﹢ Meet-up groups
NETWORKING SET UP

38.
NETWORKING
﹢ Attended 4 events
﹢ Found two amazing companies
﹢ Met many inspiring people
﹢ Many introductions
﹢ No interviews

39.
﹢ Go with someone positive
﹢ Choose long term communities (Lessened mental angst about “networking”)
﹢ Be consistent to the events
﹢ My mission is landing better
﹢ Continue even after getting a job
NETWORKING RETRO

40.
200 people, Series D
﹢ Call - 1 recruiter interview (company background)
﹢ Call - GM (product role)
﹢ In person - General manager and Head of operations (situational)
﹢ All day (case interview + presentation)
• Group - Head of operations (defining the problem)
• Group - CTO and 2 engineers (engineering research)
• Lunch - 4 people
• 2 hours - Build presentation
• Present to 8 people - 3 month road map
JOB 3

41.
Reasons I failed and mitigation strategies
﹢ Don’t actively manage time
⤑ Maintain a sense of urgency, know I’m fighting the clock
﹢ Not positive
⤑ Regardless of what happens, stay positive and calm
﹢ Get off topic, don’t actually answer the question they need
⤑ Notice when the conversation is not flowing
⤑ “Re-base” - pull up and ask if the solution is going in the direction they need
⤑ Ask exactly what they’re looking for and expecting
JOB 3 PRE-MORTEM

42.
﹢ Group - Head of operations (defining the problem)
﹢ Group - CTO and 2 engineers (engineering research)
• Re-based with CTO: “What do you think I should focus on?”
• Answer: “Just the problem, not the customer or tech stack”
﹢ Lunch - 4 people
﹢ Problem solve
﹢ 2 hours - Build presentation
﹢ Present to 8 people - 3 month road map
JOB 3 INTERVIEW

43.
﹢ Group - Head of operations (defining the problem)
﹢ Group - CTO and 2 engineers (engineering research)
• Re-based with CTO: “What do you think I should focus on?”
• Answer: “Just the problem, not the customer or tech stack”
﹢ Lunch - 4 people
﹢ Problem solve
• Re-based with GM: “Here’s the problem I see and my solution. Does this feel right? What’s the
ideal presentation format?”
• Answer: “30, 60, 90 day plan”
﹢ 2 hours - Build presentation (30 min. build, 30 min. of feedback)
﹢ Present to 8 people - 3 month road map
JOB 3 INTERVIEW

44.
﹢ Presented a 30, 60, 90 day plan to 8 people
﹢ Conducted immediate presentation retro
﹢ Very positive feedback
﹢ Had an hour more to ask questions
JOB 3 RESULT

45.
Hired someone more experienced

46.
﹢ Past retro 100% helped
﹢ Reinforced: My performance is at most half of the equation in interviews
Adjustment:
﹢ Try to get to solution even faster and add more perspectives to it
﹢ Practice presenting design solutions
﹢ Practice presenting technical solutions
JOB 3 RETRO

47.
PM ADJUST
Retros
﹢ Practice presenting design solutions
﹢ Practice presenting technical solutions
Accomplishments
﹢ 3 interviews
﹢ I’ve made a lot of progress in getting comfortable with interviews
Goals
﹢ Meet even more people and keep expanding top of funnel
﹢ Understand how VC’s evaluate markets and choose investments
﹢ Practice getting to design and technical solutions quickly

48.
PM ROADMAP
F2.1 Vision
...
F2.2 Mission (more conviction)
I'm looking for a company that's 100 people plus, working in medical, wellness, emergency response, or
energy. I’d like to close a job by next April.

49.
PM ROADMAP
AUG - Relax
SEPT - Applying and interviewing
﹢ Goal: Get 3 interviews
﹢ Accomplishments: 2 interviews
OCT - Invest in networks
﹢ Goal: Expand top of funnel
﹢ Accomplishments: 3 interviews, strong presentation, more comfort, new friends and connections
NOV - Study the NY market
﹢ Goal: Learn how VC’s evaluate industries, find more industries I’m interested in
﹢ Accomplishments:
DEC - Pause

50.
Month 4
Study the NY market

51.
1,200 people, Series D
﹢ Call - Recruiter call
﹢ Call - Recruiter
﹢ Call - Product (situational)
﹢ On site
• 4 product managers (6 case studies, culture, role fit, interests)
• 2 engineers (problem they were working on)
JOB 4

52.
🙌

53.
﹢ I did not know all roles open
⤑ Next time: study all open roles at a company
﹢ I could have reached out earlier to people to learn about Oscar
⤑ Next time: reach out earlier
JOB 4: OSCAR RETRO

54.
REcap

55.
PM PROBLEM SOLVING
﹢ Start
﹢ Retro
﹢ Adjust
﹢ Share

56.
PM ROADMAP
Where we’d like to go and how we’re going to get there
﹢ Vision
﹢ Mission
﹢ Monthly roadmap
• Goals
• Accomplishments

57.
PM ADJUST
What’s changed, what we’ve learned, and new goals
﹢ Retro
﹢ Accomplishments
﹢ New goals

58.
LESSONS
Bonus lessons

59.
LESSONS INDUSTRY MAPS

60.
LESSONS IT’S ALL ABOUT THE PEOPLE
﹢ Don't stare at the computer screen, it's not going to give you feedback and it rarely gets you
interviews.
﹢ Keep a steady stream of conversations, meetings and interviews going.
﹢ There are a lot of what if’s when you interview, here’s how I reduce churn:
• Go long term - Any company / person I might want to have a "long term relationship" with is an
easy yes
• Follow the energy - Keep exploring people and companies that energize you

61.
ASK
Take the first step

62.
ASK
Write an email, call a friend, walk over to your roommate
Hello ____<friend>_____,
Long time. <pleasantries>
In my past, <what did you own, what did you do, what did you accomplish>
I'm interested in finding a product management job in <industry, role, topics>
Do you have time to grab a coffee or talk next week?

63.
THANKS!
﹢ ahsu@hioscar.com