Communicate Customer Needs with Square Senior PM

This week, Product School hosted Reuben George, Senior Product Manager at Square, for a special #AskMeAnything session. Reuben touches on the importance of understanding customer needs and how to effectively communicate with your engineers by explaining the why behind product decisions.

Meet Reuben

Reuben George, Senior Product Manager at Square

Reuben is a globally experienced, customer-obsessed Senior Product Manager with a background in software and hardware products. He is currently working at Square, building business tools so more users can start, run, and grow their businesses. Prior to this, Reuben was a Product Manager at Intuit working with QuickBooks. He developed mobile applications, payroll for mid-sized companies. He also developed an infrastructure strategy to manage web assets, reduce friction and speeding web content creation, define a product bundling strategy, and create product specs by working with PMs across Intuit.

How do you approach developing Product Strategy?

Great question. Let me first share mistakes I’ve made in the past (and still do). The wrong approach I feel is to blindly align with the senior leadership, and build around their learnings. Often times leadership has gaps in their awareness of customer needs or the strategy may not apply 100% to your product. So I feel it’s very important but often overlooked, to actually understand what customers want first. Then you can layer in the strategic direction the company wants to take, and build your product strategy.

What tactics do you use when working with engineers? Does it change based on their seniority?

Something that has worked for me with engineers of all levels, but especially more junior engineers, is sharing the customer pain points. Oftentimes, engineers are focused on the technical details (especially the less senior ones), and as a PM it’s always good to share the customer pain points so that you can explore together.

Something that I feel is not helpful and is a sign of a bad PM, is when a PM gives directives on how it should be done. The engineers know much better about the “how”, and the PM can add most value by explaining the “why.”

two people sitting in front of a laptop in an office space. one is pointing towards the screen as if explaining something to the other

How do you switch to fintech without any prior experience?

It depends on the role to be honest. Some roles are very industry-specific, like Product Managers who work on risk management for fintech companies. But there are many roles that apply across companies, like project management or marketing or engineering.

Read next: Unpacking Fintech: Impactful Product Management

What are your thoughts about Product Marketing and Product Management? For one just venturing into the space which do you advise one should go for first?

I have worked in both capacities in a previous company. I started off in product marketing and then moved to Product Management. This is just my personal experience, so take it with a grain of salt. There is a lot of overlap between the roles, depending on the company culture. In general product marketing (PMM) is more focused on the strategy at a more aggregated level. PMMs are thinking about pricing, marketing channels, user segmentation, and hitting revenue goals. Product Managers (PMs) are more focused on a specific product/feature and making it the best it can be. PMs are focused on the user experience, the roadmap, understanding specific user needs, and then executing. PMs are also measured by success goals, but they may not directly be $$$.

Right up your alley: The Differences: Product Manager vs Product Marketing Manager

What are the three things a PM should do to succeed while making a switch from one company to another?

In my view these are the three things I’d do when I switch to a new company or team.

  1. Understand the current product. I’d buy or try to use it myself. Many companies let you buy their products for free or highly discounted prices.
  2. Understand the customer needs. If this is a consumer product with hundreds of millions of users (e.g. at Facebook) I’d look through usage data. If any less than that I’d definitely suggest talking directly to your customers, reading reviews, etc.
  3. Talk to my team and leadership. I’d set up 1:1s with each engineer, designer, marketer, content creator, etc. to understand what the team is going through, what are the challenges they face, what their morale is, etc.
person serving customer and smiling behind laptop with Square company logo on it

What techniques do you use to align difficult stakeholders?

I assume you mean stakeholders external to the core team (i.e. not your own engineers). It always helps to cast a vision in the form of customer needs, and to bring data to back that. This shifts the narrative from “here’s why I think this is important” to “here’s why we all should make our customers’ lives better”. Not many people push back against that.

For a deeper dive: Product Management Skills: Stakeholder Management

For a newbie looking to pivot from Finance to Product Management  what are the other “must have” certifications to acquire for someone without experience at all?


I honestly couldn’t name a single certification that would get you a Product Manager role. Your best bet to make the switch is to first ask yourself “why do I want to be a Product Manager?“. If your reason is to build products that customers want, then I’d say the best way to do that is through hands-on experience trying to build something. Try to build something simple, even something like a blog, and you’ll learn what your customers want, how to prioritize, and many other skills that a PM needs.

Have you made a switch from from individual contributor to people manager roles? Any tips on how to communicate externally you’re ready for that responsibility?

I have made that switch recently. My tip would be to not do that externally, but rather do it internally by growing into that within your team. This builds a lot more credibility, you don’t have to learn the team’s processes and you can make an impact since you already know the product.

Are you cut out for a senior PM position? Find out in this podcast episode.

person standing by two people seated in professional environment and showing one of the seated people something on a laptop

How would you structure the product lines team (product, design, engineering) in a product with multi lines (sub product in one huge product)?

My answer would depend on a lot of variables unique to your product. But if I were to speak high level, my advice would be to create teams that include all the functional roles that work closely (i.e. Product, Design, Data, and Engineering in most companies, but it may vary for you). In other words, don’t split the engineers but keep the designers aggregated. This creates a lot of friction and it constantly pits PMs against each other to get bandwidth from a central resource. So if you have 5 PMs, then you should split the engineering and design team also 5 ways.

What would you suggest when any product feature is not gaining motion at the market?

Sorry to hear that. I’ve been there, but fortunately I was able to pivot quickly. Do you know why it’s not gaining traction? Is it because there’s no need for the product? Or because you need to build more features for it to be a viable solution (e.g. if you build a banking product that only allows inflows but not outflows)? Or is it because you priced it too high or put significant barriers to use? Or are you targeting the wrong customers? Or is it something else entirely? I think asking yourself similar questions would help you understand if the right course of action is to pivot completely or change some things about your marketing strategy or to build more features before you go to your customers.

I am trying to transition from software development to Product Management. What path and resources would you suggest for this transition?

You are in an enviable position, since you can relate with your engineers. A great way to make the transition is to do it as part of your job. Try to work more closely with your PM, to understand the customer pain points, the product strategy and the stakeholders that the PM deals with. Ask them questions about why they make the decisions they make. You’ll learn a lot doing so, and you can pair that with reading good product blogs or following high-profile PMs on Twitter, etc.

Read next: Transitioning to Product Management From ANY Background

Any final tips?

I think a piece of parting advice is to always seek to understand your customers. A great way to do it is by being a customer yourself, but it’s also important to talk to your customers on a very regular basis. As PMs, we have so many time constraints that we often forget to speak to the people who use our products.

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