I'm the interim Chief Product and Technology Officer for Resort Pass. Resort Pass is about 60 people. We just raised our series B but we're still sort of operating like a series A company with a lot of growing up to do.

The reason we need to hire for this role is we have currently one Senior PM, 20+ engineers and two or three business units. And this one PM has been running everything.

To move us again beyond this series A stage, I'm building product teams to match our two business lines: a marketplace for consumers and suite of products for hotels to manage amenities for overnight guests. I want to split the teams and focus the roadmaps, and in order to do that, we have to have a second PM to work on this hotels products.

We're growing at 100%+. We need a second PM to give us longevity and depth of understanding in each of our products.

In my mind, a senior PM is very execution focused. Somebody else sets the strategy and the roadmap and then that person goes and delivers on that. Hiring a Senior PM here was going to do us a disservice because it puts all the onus on the leader (me) to set the roadmap, creation, and strategy. But I can't do that and also have dozens of customer conversations and be in the weeds with hotels.

I wanted somebody who's more of an independent thinker and really could take my ideas and evolve them because I don't pretend for a second that I have all the right ideas. So that's why I pushed it up to lead.

Then the question is why not hire a Group Product Manager or a Director. I was worried that it would attract the wrong kind of person, that it would attract a person who is too much of a thinker and not enough of a doer.

At the stage we're at, we have to straddle that line really well. My hope is that I can hire somebody who is actually slightly overqualified and wants to lead even more over time and can push up into that direction as we build more of the team going forward.

I think this model is a great way of evaluating product managers, it's a great way of evaluating internally how people are performing and it lays a really clear expectation of what you have to be really good at in order to do the job well.

The drawback is, as the person hiring for the position, you have to be really clear about where you want people to spike in this model. You're not going to find an 11/10 in all of these characteristics. So you have to be clear when you are evaluating people's interview feedback on the candidate. Where you're willing to say - you know what, that's okay because I think we can train this person, or I wouldn't expect them to have mastered this thing, but I want to know where they index across all of these things.

I think there's definitely debate around who should interview for some of these characteristics. In an ideal world, we have more PMs who can participate in the interview process. We don't have that now. So our one designer is interviewing on the customer insight competency. Our existing PM is interviewing on the execution.

I'm doing two competencies: strategy and influence, So a big challenge is me fitting an evaluation of these competencies into the allotted time.

The reason why I'm okay with a shorter interview for is because it's actually a bit more of a technical role. There's a lot of deep third party integration. There is conversation with hotels and things like that, but we have a ton of boots on the ground stakeholders that are providing well-structured feedback on hotel needs. So I'm a little less concerned about the need to be an amazing person at deeply understanding customer problems.

I'm a little more willing to accept that we can train somebody up on this. I'm unwilling to sacrifice on execution, which is super important, and the ability to think through strategy and to influence. In this case means challenging some of our internal partners on what is a priority and what isn't.

Also, I feel like if you are really great at execution and strategy/influence, you've probably got customer insight decently well.

The other challenge, and this is always a challenge, is the balance working with recruiters. Our recruiters are incentivized to get somebody in, get them interviewed, have an amazing candidate experience, etc. My incentive is to set the bar as high as humanly possible and be as thorough as possible. And so there is negotiation around, how much time should people spend in different phases? When should we ask them to do take home examples?

One of the first tips that I have for interviewers is that you don't settle for the first answer that somebody gives you. So I think one of the interesting things, especially for PM interviews, is continuing to push and probe deeper.

If you're asking them to walk through a scenario or think through a live case, continuing to add constraints and change the game on them gets people to think more in the moment and teaches you a little bit about - are there frameworks that they're providing here? What are they falling back on when the information changes?

So I always coach people to always have question one and follow up A, B, and C depending on how they answer that to make sure you're not getting surface-level answers.

The other thing I always rely on is "tell me about the work that you did." I want to hear specifically about the situations, the specifics, the challenges and how you overcame those. I very rarely ask people to give me the hypothetical/ situational interview questions because they teach that you can read 10 blogs and then tell me the "right" thing. I like to ask about your specific experience so I can uncover how involved you were, whether you understood all the nuance to the challenge that you worked on. When they talk about their own experience, you can see somebody's level of enthusiasm. When they talk about something they're super proud of, you can see the energy in them, and I care a lot about that. I want to know that people are fired up to work through the hard things.

One of the things which bought me some time on this role, and gives me the space to hire the absolute best person, is that I actually brought somebody in part-time who I have worked with in the past to do this role in the interim.

It frees me up to be really, really deep and diligent on the interview process. I don't feel pressured to get someone in the door or cut any corners because I have a product lead who just wants contract work and is very talented and can insert almost like a mercenary into these different situations.

That has given me some runway to be really diligent on finding this person. That's not going to come across in this kickoff form, but it's maybe one of the first times that I've done this. I haven't hired a lot of contract product folks but I think in this world, we've got a lot of stuff that she can sift through and get moving very quickly.

And then the person I hire can slot into a system that's already ideally humming along and none of the sort of annoying blocking and tackling has to get done.

Strategy and prioritization are a really important part of the job description. We have 1,000+hotels on the platform. Hotels are very fragmented and differentiated. It's a tough form of B2B SaaS because you get every piece of feedback under the sun about the very specific situation that that hotel finds themself in. And you have to be able to size whether you're building something that's a special for this hotel, which is a big no-no, and whether something is actually worth doing.

I push a lot on that in the interview process.

The reason I put the notes in bold here is as the recruiter was helping me do some sourcing, she wanted to know -- are all of these 110% requirements? Where would you flex on? So I was trying to provide some clarity for her on this.

I think one of the harder things to come by is experience with different facets of product work because I think people can get very pigeonholed into doing one type of thing, building feature after feature after feature. And this role, at this stage of our company requires somebody that has more of an entrepreneurial mindset and has done a few different things.

It is very likely that after you build some features, one of the next things that you will need to do is drive the adoption of those features. So having some growth experience could be beneficial. Or thinking what could this business unit look like three to five years down the road? What are some net new things that we might need to pursue, new revenue models, etc. And that's where innovation work comes in.

You don't have to have done all of these things, but I want to know that people are not a one-trick pony. It's hard to look at somebody's background on paper and know this. This is one part of the interview where I have to push and ask for information and examples so that they demonstrate some breadth of their skills and abilities.

Will this person eventually manage folks? Possibly, if they're the right person. It's also something that can be taught and trained. I want someone who is more of a doer, who understands that the role is not to hire a bunch of team members and get out of their way. The role is to do the work. So if you have managed people before and you're willing to come back to an IC world, awesome. Because I know if we're ready for this to split into multiple functions, you could be the person to manage folks. You could have the potential to be director of this area, but it's not a requirement.

This is a fairly technical role, so that's why it's important that you know how to do that work, more of a must have. I want to see -- and it doesn't have to be hotel software -- that you've connected disparate systems and you know how that works and how to work with engineers on building that."

My tips for making an offer to someone are first, make the strongest offer that you can. I think a lot of people make an offer and then they kinda brace themselves for the response. And I think people can smell fear. So don't do that. Present with confidence. You're putting your best foot forward and getting the candidate. The offer presentation is a big part of the sell, right?

Second, be armed with information and be able to answer the top questions that people will have, like value of equity, growth path, leveling, trajectory of the company, etc. Candidates may use this time to ask you questions that they were hesitant to ask during the interview process but this is the time for them to do some reverse interviewing.

I would say I've already made a couple of mistakes interviewing for this role, just to be perfectly honest. I do a really short phone screen designed to make sure that the person's not a jerk and to get a couple of basic questions answered.

I love to ask them the story of their career because I want to know if people can crisply tell me their story -- and I say, I want to hear the story of your career and why you made the decisions that you made in three minutes or less. And if they can't, I know this person can't communicate in the way that I would need them to.

Another mistake I've made is not trusting my instincts on someone's attitude and pushing them through to the next round. This means I just wasted a bunch of my team members' time that I shouldn't have wasted because my instincts were right here, even in a 15 minute conversation.

Other mistakes I've made in the past include hiring somebody who seemed really impressive and senior, but wasn't really prepared for the work at hand. I would probably sacrifice a little bit more on the strategy side for the ability to execute. But I know that personally I am wowed by people who are really great strategic thinkers. So I have to check myself against that, which is why I have other people testing for it as well.

The assessment is going through some iteration. The first one that I made was centered around ResortPass, but I got pushback from our recruiting team that I think was valid. There's different points of view on whether you should have somebody basically do free work for your company, or come up with something hypothetical that that tests their thinking in other ways.

I've reached out to my network to get some feedback on it. But I do think it's very important to do a take home assessment for a couple of reasons. One, every other question that you ask somebody is testing things that they've done in the past, and you don't necessarily know with 100% certainty how much of it was them vs. the environment they were in vs. something else. Second, I really want to understand people's communication ability and their ability to synthesize and present information in written form. Third, I use the assessment as a filter to the next round so we don't waste team time. If you can't deliver what looks on paper to be a really good assessment, then I'm not having you come back in for round two.

I always use take home assessments. I use them for analytics candidate. I've used them extensively for PM candidates. I've used them for growth. I like to know how you do when you're faced with the problem that you'll be dealing with on the job.

If somebody won't do it, that maybe says something about how many opportunities they have. Cool. But I also think it says a little bit about their ego and their willingness to do hard work.

And if you're amazing, this shouldn't be that hard.

There's a couple of engineers who are great at interviewing, but they happen to be some of our most valuable engineers. And so I have to balance how much of their time I'm using in interviews versus actually building some of the stuff that we need.

Adam Fishman

I created this process when hiring for ResortPass's second Product Manager role. It covers screening, interviews and final presentations. 

Link to job description: Job Description - Lead Product Manager, Hotels

For structuring Product Manager interviews I like to follow the 

https://www.ravi-mehta.com/product-manager-skills/

interviewers

length of interview

working with recruiters

Interviewers will come up with their own questions

Growth. We are expanding the product team so that we can drive more specialized focus on the different aspects of our product. We will have two dedicated teams: Consumer and Hotels.

Describe the most important areas of the role and what this person will be focusing on.

This person will be responsible for the Hotel experience, this includes: Hotel App, Partner Portal, Internal Tooling, Integrations, Microsites

Their primary stakeholders are the Sales and Account Management team and they will share direct accountability in the growth of the number of hotels on our platform and their satisfaction.

 for our hotel software product that powers amenity bookings for day use and overnight stays on both desktop and mobile

Working with our engineering, design and data functions own and be accountable for prioritization and execution of that hotel software roadmap

Partner with our sales and account management teams to grow the adoption and engagement of our hotel product–streamline the onboarding process, integrate with established industry partners, and help hotels maximize revenue opportunities

Identify opportunities to improve yield management between customers of our two product lines

Engage in regular customer conversations with hotel partners and become an expert on hotel technology

Can you describe which skills/past experiences are nice to have vs. must have?

7+ years of Product Management experience, with some of those in a product-led SaaS business 

Experience with different facets of product work such as innovation, growth, feature development and infrastructure

Experience mentoring and/or managing other product managers

A demonstrated track record of using qualitative and quantitative measures to prioritize a product roadmap that drives measurable business outcomes (

must; I want to know that they’ve moved metrics)

A deep understanding of leveraging APIs to integrate 3rd party software systems

must - I’d like to see that they’ve done this before or integrated 3rd party systems in some way)

Self-awareness with an openness to giving and receiving quality feedback 

Excellent written and verbal communicator; you have the ability to tell a story combining data with qualitative insights, and you understand how to tailor your communication to any audience 

Other skills / background I’m looking for:

B2B SaaS experience, specifically one with lots of disparate customers

Hotel experience would be A+ but unlikely given the general stodgy-ness of the industry

How many years of experience are you looking for?

6-7+ and no flexibility on this. You can’t be a lead PM without deep experience in the discipline.

 If so, do they need previous management experience?

No, but it has the potential to be. People who have been a Group Product Manager and are interested in leaning into the IC aspects of the role could be a good fit for this.

What other members of the team will work mostly closely with this person?

Experience managing complex systems with lots of moving parts; especially internal tooling and B2B software

Exceptional stakeholder management - knows how to prioritize really effectively

Strategic ability - can see how the Hotel side interfaces well with the consumer side in our marketplace (for example)

Leads with the outcome and impact they’ve achieved; specific on metrics

What does growth look like for this hire?

Lead PM -> Group Product Manager -> Director of Product (for the right person)

Eventually we’ll build out a broader Hotel team with multiple product teams. This person could grow into that leadership role if they demonstrate strong ability and aptitude to manage.

Are you open to fully remote for this role?

 If so, are you open to other time zones in the US?

What does the first 30/60/90 days look like for this person?

Onboard into the role, learn the stakeholders and systems, get started immediately on in-flight product work

Maybe visit properties with an AM to see how hotels use the software

Why is this an exciting opportunity for someone/how can we sell them on the first call?

ResortPass has really incredible product/market fit. Hotels love us because we’re bringing a modern user experience to an otherwise stodgy industry AND generating a ton of incremental revenue for them. This is only the 2nd PM hire in a fast-growing company and there is no ceiling for the right person.

We have very great unit economics and are hiring when other companies are laying off; we have a favorable and reasonable valuation for current hires having only recently raised our Series B

Get to work on mobile apps and desktop software - the diversity of work means it’s never boring.

What are some companies that you would want us to recruit from?

When would you like this person to start?

Have you ever delivered an offer to a candidate?

 (We can discuss what is most comfortable for you, and how I can best support you during the offer delivery stage)

The hiring process should be thoughtful, efficient, and strategic. Please keep in mind the following questions when thinking through who will be involved/what will be discussed:

Is this process efficient? Are there interviewers involved that don’t need to be? (For example: 2 people from the same team probably don’t need to be involved unless they will be working with this candidate in very specific capacities)

Is this a well rounded interview? Each person involved should have a specific focus so that the team is covering all areas. We do not want to duplicate questions/areas of focus. (For example: one interviewer focuses on culture add/team alignment, another interviewer focuses on skill fit, another interviewer focuses on ambiguity/proactivity)

Lead Product Manager Interview Process at ResortPass

Lead Product Manager Interview Process

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