Interview Qs

Question 1

Why do you want to change from PM to AI Enablement Director?

Answer 1

Passionate about AI
Well-positioned to add value - important to me
Career growth, salary, equity/ownership - I haven’t seen the opportunity I expected on the product team
I love this company and don’t want to have to start looking at external opportunities

Question 2

How would you develop and execute an AI adoption strategy at Pax8?

Answer 2

Start with business objectives - efficiency, growth, innovation
Identify key areas where AI could provide immediate value - automation, enhanced decision-making
Engage cross-functional teams to understand challenges and opportunities
Establish communities of practice to support AI literacy
Create an “AI Advocate” program to evangelize the correct use of AI solutions across the org
Define and track key success metrics to measure ROI

Question 3

Can you share an example of a time when you led an initiative that resulted in measurable impact?

Answer 3

Via Varejo - founded a digital innovation lab to launch new fintech products to the Brazilian market
Created the integradora - central platform for online sellers to manage sales cycle
Design and launched in 8 months, and within 6 months of launch we were already at $15M ARR
Strategic - sales data from sellers on other platforms

Question 4

How do you ensure that AI initiatives comply with data privacy and security regulations?

Answer 4

Data privacy and security are non-negotiable
Engage security, compliance, and legal teams early and keep them involved as the projects progress
Create cross-functional working group to develop internal policies about responsible use of AI and communicate them across the org
Make sure that the AI solutions we use and build align with established frameworks, e.g. GDPR, CCPA, HIPAA
Use techniques like pre-mortems and risk mitigation plans for high-risk project

Question 5

How would you encourage AI literacy and adoption across non-technical teams at Pax8?

Answer 5

Starts with getting them interested - people are more likely to learn about new technologies that are actually relevant to their day-to-day, so I would do everything I can to make AI tools accessible and relatable
Collaborate with Academy and LAT TF to create engaging content that demystify AI concepts
Publicize achievements from AI-related projects in public forums like Slack channels and All Hands meetings
Establish an “AI Advocate” program that brings together people across different departments to find out what people are interested in and what questions and concerns they have related to AI

Question 6

How do you measure the success of AI initiatives within a business?

Answer 6

Start with high-level business objectives
For each project, define success metrics using the SMART framework (specific, measurable, achievable, relevant, and time-bound) that relate to our business objectives
Gathering qualitative feedback is also critical to understand friction points and drive adoption

Question 7

How would you manage AI-related risks and ensure ethical use of AI at Pax8?

Answer 7

Participate in cross-functional working groups and promote conversations around ethics and bias
Ensure that we have clear frameworks and policies for monitoring AI outcomes
Work with Legal and Compliance to develop a risk assessment process, especially in areas with sensitive data or important implications in product functionality
Establish regular audits of our AI tools, projects, and processes

Question 8

What would be your approach to staying current on AI trends and technologies?

Answer 8

Genuinely interested - in my own time, listen to podcasts, watch videos on YT, and read industry publications
Hands-on experience using and building AI tools
At work, actively participate in AI review group and learning a lot from conversations with DS and AI teams
Foster learning and teaching environment by collaborating with Academy and LAT TF

Question 9

Give me an example of a new technology that caused major issues for customers.

Answer 9

Microsoft NCE rollout
Theoretically to make subscriptions more flexible for end customers and simplify administration for MSPs
Actually caused a massive disruption for partners and actually made the things they were trying to improve worse
Tesla FSD

Question 10

Tell me about three advantages that our organization’s competitors have.

Answer 10

Focus more on customer feedback than competition, but still important to stay up-to-date on the industry
Ingram Micro, TD Synnex, and Arrow Electronics
scale: both breadth of offerings (including hardware) and global reach (regional supply chains and marketing channels)
Deep pockets, able to invest more in R&D
Arrow - Partner-facing AI assistant
Some of these can also be seen as advantages for Pax8 - cloud native and smaller scale makes us more focused and nimble, lower risk with AI implementations

Question 11

How do you prioritize tasks in a fast-paced environment?

Answer 11

Modified RICE framework to estimate ROI: Value, Cost, Confidence, and Urgency
Prioritize blockers so that my teammates or colleagues from other teams can be productive
I take lots of notes, document any follow-up tasks in Asana, and regularly reprioritize them
If some unforeseen challenge comes up, it gets added to the list like anything else - I’m pretty adaptable so I try to keep an objective mindset when prioritizing new tasks

Question 12

Give an example of how you have handled a major change in the workplace.

Answer 12

Airfox acquisition by Via Varejo
Came during pandemic and transition to work from home
Lots of preparation to ensure we maintained the innovative culture
Worked closely with VV leadership to get benefits of corporate ownership
Went as well as can be expected, but corporate culture eventually won out
Even then, had to stay positive for my team

Question 13

How do you ensure effective communication with your team and with stakeholders?

Answer 13

Team culture: Create an environment where people feel safe to engage, encourage open and honest but respectful feedback
Meet people where they are - leverage tools like Slack and Teams for quick async messages, Outlook and Confluence for project updates, and recurring meetings for ongoing projects
It’s important to understand stakeholder concerns and address their questions upfront, so I like to schedule kickoff meetings for new projects and make sure I have clear documentation that they can refer back to
Understand that everyone’s human and assume they have the best intentions

Question 14

What improvements would you suggest for our current operations at Pax8?

Answer 14

Focus
Data accessibility
Deeper QA automation
More support for cross-functional collaboration

Question 15

What’s your organizational system? How do you keep yourself and others organized?

Answer 15

Notes in Google Doc, tasks in Asana, project management in Jira, documentation in Confluence, communication in Slack, reminders in Google Calendar

Question 16

Describe a time when you implemented a process improvement. What was the outcome?

Answer 16

Downside of Kanban is that it’s difficult to set and track short-term goals
Set weekly goals at the beginning of R&R and moved replenishment to the front to reflect these goals
Biggest downside was lack of time for refinement, so we split out standup and now have time for everything

Question 17

How would you handle a sudden increase in workload?

Answer 17

Triage tasks - impact/urgency
Collaborate with stakeholders to gather information, understand priorities, and adjust timelines if necessary
Ask for help

Question 18

Tell me about a time when you had to learn something new very quickly.

Answer 18

Data PM at HubSpot
No formal PM, data infra, or coding experience
Business was pretty straightforward and I had experience managing projects, but I had to learn a ton about the data infrastructure, data transformation, ELT, and managing stakeholders
Struggled with SQL, but took some free courses on Codecademy and now I can write queries with my eyes closed
Spent a long time with data analysts and engineers, but amazing culture of support

Question 19

(father) Tell me about a time when you stumbled because you didn’t anticipate a roadblock or obstacle.

Answer 19

Father passed away unexpectedly in 2013 when I was working at an EdTech company in Miami
Huge impact on my work and life
Ended up getting laid off and moving back in with my mom
Gave me a new perspective on life and importance of family

Question 20

Describe a time when you had to make a decision without all the information you wanted or needed.

Answer 20

Dropped out of HBS to work at startup
Unclear what impact would be, but it was more aligned with my goals

Question 21

Tell me about a successful experience you’ve had implementing something across organizational boundaries.

Answer 21

Pilot programs for Matchmaker and ProdReco
Worked with Sales, Sales Enablement, and Tools & Tech
Took a lot of coordination and results weren’t always what we wanted to see, but learned a lot in both experiments that helped drive better decisions

Question 22

Is there anything else you want us to know or share about yourself?

Answer 22

Passionate about AI
Unique experience in AI development and strategy
Deep understanding of Pax8 objectives
Strong relationships with people across the org

Question 23

Weird fact

Answer 23

I’ve been doing periodic 2-3 day fasts every few months for the past 15y

Question 24

What questions do you have for us?

Answer 24

Why do you think the AI Enablement Director role is important?
What are some areas related to AI that you think need some kind of working group, task force, or community of practice?
Who are the most important stakeholders that the AI Enablement Director will need to work with?
How do you see this role evolving over the next few years?
What’s the biggest challenge or opportunity that we’re currently facing with AI adoption?

Question 25

Tell me about a time when you had to act on something important before you had time to come up with a clear answer or solution.

Answer 25

HubSpot Looker report cleanup during CMS migration
Manager wanted me to review >2k reports to determine which ones needed to be kept
Hard deadline, not enough time
Flagged most recently used, sent out comms to stakeholders that the rest would be deprecated (but archived)
Only got 2 or 3 complaints, ended up building better solutions for them

Question 26

Describe a time when you taught someone else a new technology.

Answer 26

Mom - Computers, remote control
Ester - ChatGPT

Question 27

Tell me about a time you had to solve a problem twice, when the first solution wasn’t right.

Answer 27

Microneedle retraction mechanism - foam vs. elastic membrane
Foam - got in the way of the microfluidic channel, impacted the blood sample, took up too much space, reduce vacuum capacity

Question 28

Describe a time you were faced with a complex problem and had to get to the essence in a short time period.

Answer 28

Open English - Sales team capacity planning
Calculated staffing requirements by hour based on incoming call volume and avg call duration, optimizing for minimum time on hold and minimum cost
Had to redo all calculations based on shift schedules and Brazilian workforce regulations
Iterative

Question 29

Tell me about a time when your chosen solution didn’t work, and you had to rethink the problem from scratch?

Answer 29

Housing model - scraping data with Zillow API

Question 30

Give me an example of how you gained others’ confidence when you worked with them for the first time.

Answer 30

Airfox - got down in the weeds with PMs, coached them on agile practices, mentored them in areas like defining problems, prioritizing requirements, and managing stakeholders
Still good friends and actively communicate with some of them

Question 31

Describe a project/assignment where the outcome or process was unclear.

Answer 31

Starting ACEA - nothing was clear, had to take each challenge as they came
Started with a simple prototype
Needed user feedback so created a user council to prioritize new features and test prototypes
Needed revenue so started reaching out to CME providers and associations
Needed more staff so we recruited unpaid interns from local universities
Needed funding to accelearate growth so created a deck and started pitching to angels
Needed hiring process so researched best practices and developed it from scratch

Question 32

Tell me about a time when you had to communicate something important to someone who did not understand your industry or function’s language very well.

Answer 32

HubSpot - educating Sales Enablement on product development process

Question 33

Tell me about a time when you started a community of practice.

Answer 33

Data Insights Affinity Group meetings
Started as 1:1 with tech mgr, slowly added other people
Evolved into P&E mgr meeting for entire affinity group + PSA
Discussed and revised purpose multiple times, current incarnation is focused on future initiatives and opps for collaboration
JIRA TF

Question 34

Tell me about a time when others were missing the key points in a discussion and you helped get things back on track

Answer 34

Recently discovered that defining problems is one of my strengths
A lot of people dive into solutionizing before understanding the problem
E.g. Managing the API team - billing automation vendor was asking a lot of questions about the usage summary endpoints
The team spent a long time tracking down the answers and writing feature enhancement tickets based on the endpoint limitations
I started digging into why the usage summary data was so important, and it turns out they needed it for invoicing
We actually have more reliable and granular data from the invoice endpoints

Question 35

Tell me about a time when you had to communicate the same information to different audiences and had to vary your style for each.

Answer 35

Matchmaker ML model - business and technical stakeholders
Business - high-level description of how the model identifies the best matches, how location was one of the key factors, only shared relatable metrics like accuracy, false positives, and false negatives
Technical - described the different types of ML model algorithms we considered, why we chose to go with a neural network, technical performance metrics, and some ways we could improve performance in the future like a 2-tower model infrastructure
Tailored the type of information and level of detail based on what was most important for each audience

Question 36

Describe a time you worked with multiple groups or people who had different interests.

Answer 36

Insource ML models from 3rd-party vendor to estimate partner potential segment
P&E - models were part of an important workflow and 3rd party ownership was a potential risk, opportunity to decrease the cost of our contract
3rd-party vendor - acted like they wanted to support the project, but did everything they could to hide the information that we needed to rebuild the models
Pax8 contact who owned the relationship with the vendor - didn’t want to lose control over the contract, so he worked with them to keep me out of the contract renewal discussions
I tried to escalate the issue and set up a meeting with P&E leadership, but by that time the contract had already been signed and there was nothing I could do
I assume that everyone has the best intentions, but there were a lot of red flags throughout the project, so if I were in a similar situation in the future, I would ask my manager for help to escalate the issue a lot sooner

Question 37

Tell me about a time you did not gather enough input from all the stakeholders during a project. What happened and how did you resolve it?

Answer 37

Matchmaker
Planned to launch as standalone product, but ended up getting incorporated into Buy Now customer marketplace platform
Blindsided by a bunch of requirements from Buy Now stakeholders that exploded the scope of the Matchmaker MVP
They had good intentions, but didn’t understand the level of effort that the extra requirements would take and how it would impact the delivery schedule
I had a lot of trouble managing conversations in a group, so I set up 1:1s to explain the situation and get soft buy-in before introducing a compromise to the group
We were able to complete the MVP without holding up the launch of the Buy Now marketplace

Question 38

Tell me about the most difficult stakeholder you have had to manage

Answer 38

Sales Ops stakeholder for quota and attainment system
Toxic team culture, very demanding, unwilling to compromise
Scheduled 1:1s, started making more of an effort to get to know her, and even shadowed her for a day to understand why she was under so much stress
Once the relationship improved, I was able to explain the challenges of what she was asking for and we ended up finding a better approach by buying a 3rd party quota and attainment solution and customizing it to our use case

Question 39

Describe a time when you used your network to exchange ideas, resources and know-hows

Answer 39

I have another group of friends from HubSpot where I used to work that have been releasing gen AI products to their customers for over a year, and asked them a bunch of questions about the challenges they had and best practices for setting up a RAG infrastructure, so they’ve given me a lot of insights that I’m actively employing in our latest project.

Question 40

What are three trends in your current industry

Answer 40

MSP:
Cybersecurity
AI
Consolidation
AI:
Using RAG to search internal knowledge bases
Automating complex workflows using agents with different capabilities and integrations into different systems
Research into more efficient LLMs, both to reduce costs and to use for applications that require lower latency or compute like edge-device inference

Question 41

Tell me about a time your knowledge of marketplace trends influenced a decision you made.

Answer 41

I tend to rely more on user feedback and behavioral data to drive my decisions, but I can tell you a time that someone else’s knowledge of industry trends changed my opinion
Initially, more excited about sales & marketing applications
Realized that the support assistant was a much better place to start for 2 reasons:
Interest rates were high and we weren’t able to get a new round of investment with decent terms, so cutting costs was a critical objective
More reliable data for support than S&M because of our ticketing system and technical documentation from our vendors, whereas we don’t always know why partners or end customer choose to buy certain products over others
Companies are starting to realize just how important and valuable their proprietary data is to the success of AI initiatives and long-term viability of the business, so it’s critical to understand our most valuable data to prioritize our initiatives

Question 42

Tell me about a time when you planned and organized a complex task or project from start to finish.

Answer 42

Via Varejo - founded a digital innovation lab to launch new fintech products to the Brazilian market
Integradora - central platform for online sellers to manage sales cycle
Design and launched in 8 months, and within 6 months of launch we were already at $15M ARR
Strategic - sales data from sellers on other platforms

Question 43

Tell me about a time when you divided a plan into phases and detailed tasks to organize and accomplish the objective.

Answer 43

ProdReco - ML model to identify growth opps within a partner’s existing userbase
Initial discovery - talk to users and stakeholders, understand the problems to solve, define requirements
Technical discovery - brainstorm potential solutions, compare different approaches, start to design the necessary architecture
Prioritize requirements - So many opportunities, need to limit scope of MVP based on value and level of effort
Broke down phases by opportunity type, so decided to focus on upsell because it had the highest immediate value for the least effort
Future phases: other opp types (cross-sell, add-on, upgrade, and net new), continuous learning mechanism, usage-based products, incorporating
Prototype & experiment - set up pilot test with a group of reps
Worked with OX to have everything validated and ready for beta launch
Lots of incremental improvements and bug fixes after launch
Currently working on validating a couple new opp types and plan to start building the continuous learning mechanism shortly

Question 44

Tell me about a time you had to change plans during a project or task to prioritize something unexpected

Answer 44

Matchmaker
Planned to launch as standalone product, but ended up getting incorporated into Buy Now customer marketplace platform
Blindsided by a bunch of requirements from Buy Now stakeholders that exploded the scope of the Matchmaker MVP
They all had good intentions, but didn’t understand the level of effort that the requirements would take and how it would impact the delivery schedule
I had a lot of trouble managing conversations in a group, so I set up 1:1s to explain the situation and get soft buy-in before introducing a compromise to the group
We were able to complete the MVP without holding up the launch of the Buy Now marketplace

Question 45

(Enlyft) Tell me about a time when you stumbled because you didn’t anticipate a roadblock/obstacle. How did you pivot? What would you have done differently?

Answer 45

I worked on a project last year to try to insource some ML models that a 3rd-party vendor created for us to estimate the segment that a partner might get to in the future
On one side, P&E was interested in this because the models were part of an important workflow and having them owned by a 3rd party was a potential risk, and there was also an opportunity to decrease the cost of our contract
On the other side, the 3rd-party vendor seemed like they wanted to support the project, but did everything they could to hide the information that we needed to rebuild the models
There was also the person at Pax8 who owned the relationship with the vendor didn’t want to lose control over the contract, so he worked with them to keep me out of the contract renewal discussions and negotiate a new contract that basically took away any of the value that my project would provide
I tried to escalate the issue and was able to set up a meeting between P&E leadership and the person who owned the vendor relationship, but by that time the contract had already been signed and there was nothing I could do
I tend to have a lot of trust and assume that everyone is trying to do what’s best for the business, but there were a lot of red flags throughout the discussions, so if I were in a similar situation in the future, I would try to work with my manager and escalate the issue in time to resolve it