Ever wondered what it’s like to work as a Product Manager? This was an exclusive Q&A session with Alex Shih, former Twitter Product Manager, May Allen, Product Manager @ Projector and Jeremy Glassenberg, VP of Platform Product @ Pypestream. They discussed what it’s like to work in this dynamic role and what it takes to get your foot in the door. They also gave the inside scoop on the day-to-day work as a PM, the challenges of the job and personal insight from their experience at working at different companies in the valley.

1. Ask me Anything, with Product Managers from
Twitter, VMWare, and Box
/Productschool @ProductSchool /ProductmanagementSF

2. Who Are You?
-Engineer
-Design
-Business (Marketing, Sales,
Customer Success, etc.)
-Student
-Product Manager
-Aspiring Product Manager
-First time at a Product School event?
-First time hearing of Product School?
-PS student/alum?

3. May Allen
-Product Manager @ Projector
- Previously Senior PM @ VM Ware
-Former Entrepreneur & High School
Teacher
-8+ years of PM experience
-Upcoming Product School Instructor
www.productschool.co
m

4. Alex Shih
-Director of Product @ Planet
- Previously Head of Mobile Products @
Twitter
-Former Founder
-4+ years of PM experience
-Product School Instructor
www.productschool.co
m

5. Jeremy Glassenberg
-VP of Platform Product @ Pypestream
- Previously Head of Product @ Edmodo,
Box, Tradeshift, among other companies
-10+ years of PM experience
-Upcoming Product School Instructor
www.productschool.co
m

6. Talk to us about your journey into
Product Management.

7. May:
Valued creativity and independence, collaboration/teamwork, didn’t fit into marketing,
design, or eng; she started her first PM role without realizing she was technically a PM;
power user of a product when she was teaching, wore lots of hats- QA, marketing, etc. Then
was asked to be the PM.
Alex:
Also happened into the role, not an end goal, not even a goal to end up in tech. Wanted to
solve real, important problems: international development, access to info/tools to increase
productivity; started working on GoogleApps, was always interested in this product, saw a
company in India using the tools, saw the reach/power of these tools; then Twitter
International initiatives (during grad school)
Jeremy:
More “formal” route, engineering degree, got an MBA, always wanted to be in tech, don’t
need the MBA anymore, learned a lot more on the job, not as much content available, lots
of rejections to start, became obsessed with APIs/hacking away at APIs, not to get a job, but
because of passion; advice? find an area of focus, genuine enthusiasm for the product

8. Why did you decide to teach at
Product School?

9. Jeremy:
Always trained PMs: Box was scrappy in the beginning, he write code as a PM, etc, as the
team grew, he got to train up APMS, helped teammates move into the role; mentoring,
consulting; Product School? wanted to do something more formal
May:
Learned everything on the fly, would have liked some formal training early in her career;
Carlos (CEO) reached out and she was impressed with the curriculum; loves teaching and
comes from an education background
Alex:
Volunteer teaching experiences, cynical about the SV scene, wanted to contribute to the
solution, help aspiring PMs to think about solving big problems, brought in real examples of
his issues, having a conversation around his day-to-day challenges

10. What skills did you learn on the job that
would have helped you grow early in
your career?

11. May:
Negotiating with people on your team about prioritizing features; pros and cons of
choices; how to communicate with stakeholders; feature audits/data analysis
around choices; UI/UX/wireframing
Jeremy:
How to write impactful PRDs, how to write user stories, documents that resonate
with the different stakeholders
Alex:
Also PRD writing: limits PRDs to 3-5 pages, includes mock ups (Invision, Balsamiq)
writing documents that stakeholders actually read and understand

12. For Alex: What should I leave out of a PRD?
Alex:
Try not to propose a solution, don’t step on engineers’ toes, views PRD as a living
document that is a starting point, but will grow along the way; getting people
aligned in the right direction

13. Difference between startup and big
company PM roles?

14. May:
large company: many product peers, larger sets of customers/data, data analysis = key
Start up: might not have lots of data/customer; lots of customer development; Iding
needs, product market fit; communicating bad news around setbacks
Jeremy:
big: More overhead at a large company//Startup: fewer resources
Differences = structure and culture impacted by other factors besides sides
Size matters, but look at the other factors
Starting at a startup = risky; big company = credibility, good training
Alex:
Google = training machine, resources that set up new PMs for success; tools/resources
Startups: no resources/previous learnings, hard to access data (he needed to build his
own internal dashboard to find good data); not as many tools available

15. Communication challenges with devs?
Tools? Methodologies? (start up)

16. Alex:
Imposing timelines/features that didn’t align with tech stack, no visibility to roadmap, had
to work through that process
Bi-weekly sprints; Jira; Invision, Sketch, Balsamiq (tools)
May:
Her company = Heavy on engineering, light on sales; needed to build a product worth
selling; lost touch with customers/market; motivates engineering = get product out the
door that people are going to use, ship quickly, learn, fix; recognizing where those
imbalances might be; given (situation), then (solution)- smaller, more focused stories
Jeremy:
startup is going to be chaotic, you will feel the pressure! Product team should balance,
Edison strategy, bring in the right minds together to bounce the right ideas; empower
free/open communication; Agile meth - strong engineering counterpart to push to ensure
balance/Agile; Tools? GoogleDocs; Balsamiq, up to what the engineering team, Trello, Jira,
Pivotal Tracker

17. Methods in gathering user feedback?

18. May:
Feedback in the app stores; google “customer development labs” - helps to ask
questions/understand what to listen for; customer (paying for something with
value, implies PERSON) vs user
Alex:
No silver bullet to getting feedback; employ a lot of different channels, some will be
more valuable than others, but variety matters; B2B; reaches out to trusted
customers; record each testing session; come up with hypotheses is before starting
the test/analyzing the data, might be overwhelming without that frame
Jeremy:
B2B world-data is different- less data, less customers, great communication line
from sales/support, train them on asking the right question; don’t build exactly
what people ask for. Figure out the problem**

19. Advice on how to break into Product?

20. Jeremy:
Look internally first; work as closely as possible with PMs, take on some of their
work, make it clear that you are interested; find your passion and work on side
projects, volunteer, SV is built on karma, help, give, etc.
May:
Ask the PMs if you can help! Go through the bug backlog and help them figure out
how to solve a real problem; going through user feedback on the app store, make
sense of it, go above and beyond in helping out
Alex:
Regardless of role, you can practice the processes/ways of thinking that PMs user
on a day-to-day basis; learn all that you can about users

21. www.productschool.com