Sourcing Success as a PM with Sandboxx Chief Product Officer

Last week, Product School hosted Craig Zingerline, a Chief Product Officer at Sandboxx, for an exclusive #AskMeAnything session. Craig discussed the road to product leadership from diverse professional backgrounds. He also discussed key metrics as a foundation for product roadmaps and how to source success.

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Meet Craig Zingerline

Craig is an Entrepreneur, Chief Product Officer who has advised and consulted for dozens of companies around Product Strategy and Growth. Currently, he is the CPO at Sandboxx and prior to this, he held a position as a Head of Growth at Upside Business Travel, Head of Product & Growth at Red Tricycle, and the CEO of Votion. Shortly after graduation, Craig started off his career as a Lead Application Developer and he began attaining various positions, such as a Software Engineer at eBay, Web Development Instructor, Application Architect, and Lead Developer.

These roles helped him develop a deep background in technology, Product Management, and B2B/B2C marketing & Growth. Moreover, during his extensive professional work, Craig founded and co-founded 6 startups while excelling at building and leading teams and navigating the step-functions needed to get from zero to scale. He is a truly inspirational speaker who believes that every company has growth potential to unlock and that the Product Managers hold the keys to unlock that growth.

How do I get into Product Management without prior experience if I have a background in Software Engineering?

Being a software engineer can be a natural starting point to move into product down the line. It’s actually how I got my start. I joke that I was a “bad” engineer, but I studied and learned how products were built. Using that, I moved into more and more product-focused engagements.

If you want to dive right in, this community is a great place to start. But you can also start to volunteer time at your current org and act as a “junior” or “associate” PM part-time while you kick the tires and move up the learning curve!

When you’re bringing on a PM who isn’t an Engineer by training, how do you assess their technical know-how? What questions would you ask? What are you looking for specifically?

For me, this is less about the PM being technical themselves – but they at least have to know how to speak the language and communicate very well with technical folks. In terms of assessment, I’d move more into general questions about assessing how they think about how to build a product from scratch, what resources are needed, and that type of thing.

For more technical PM roles, I’d have them actually model out a prototype architecture and do a code review where they walk me through the moving pieces of what they coded. And also get other engineers into the conversations to do a deeper dive on the tech stack.

What advice would you give a CEO looking to be a Product Leader?

I think the best way to be a Product Leader is to get experience building products from scratch. If you are a nonproduct-centric CEO, which is becoming rarer, sit in on the backlog and planning meetings with the team. Have a voice and a POV but don’t be the decision-maker – let the PM do that for now. Eventually learn how to handle the day to day if that’s the direction you’d like to move in.

What are the main qualities a Product Manager should have?

  1. Communication has to be GREAT
  2. Great written skills
  3. Empathy
  4. Attention to detail
  5. The ability to make tradeoffs to ship and fail fast (counterpoint to being obsessed with #4)

You may also be interested in: 5 Qualities of a Great Product Manager

How much of a hindrance to a potential PM career is a lack of “technical” knowledge?

I personally think everyone can eventually learn the hard skills needed to be a PM, but the soft skills HAVE to be in place to succeed. If you are technical you’ll likely have more opportunities come to you faster though.

In your experience, what has been the most efficient way to discuss the use cases with the dev/analytics teams? How have you seen it make sense to address the “what’s inside for me” for these teams?

There’s something brewing at a higher level if you’re getting this type of push back at the PM level. If the team is in a “me” mindset – that’s a red flag. Figure out what is important for the team in terms of their personal, professional, and team-based goals and start there. In terms of tactics, I generally focus on growth-related metrics to share weekly – name people involved in the effort – it’s likely everyone that had a hand in moving metrics forward.

Share wins early and often. Celebrate losses. Be transparent.

What would be the main difference in the roles of a PM at a startup and at an established organization? How do you handle both situations?

At a big org, you’re going to have a playbook that you can follow. You’ll have a process that’s defined for you. You’ll have teammates to learn from. At a startup, it’s likely you are a solo PM and doing a bit of everything. It’s very different based on company and team size, number of products, and even the stage of the company revenue-wise.

How detailed and long or short and simple do you normally keep PRDs mindful the real world will fall somewhere between waterfall and agile environment?

Short and simple roll-up information – i.e. user story and maybe a chart that can be shared across the org. For more complex items, a full PRD needs to be as detailed as you need it – at scale when building iterations of features it may include things like control vs variant experiments, data analyst recommendations and thoughts, obviously UX and design considerations.

What are some insights about how to handle product strategy in a software company with multiple products? 

I tend to base this off of team size and velocity rather than the number of products since one product can be super complex and 10 small products might be very simple. Based on that, either team working the backlog horizontally by feature or function, or by vertical based on product is how I’d approach starting this.

How do I build incredible skills and a profile which complements my consulting and data science experience and makes me a good fit for a PM role as well?

I think showing that you’ve built something and haven’t just focused on the data side may go a long way – it could be a personal project or a consulting or gig you’ve done to help in a product capacity, but I’d get some experience under your belt on that side of things. 

Once someone has a few years of PM experience under his/her belt, what additional skills/experience do you think is needed to progress into a Senior PM role? And likewise from Senior PM to Director? 

It’s likely you may need a stage change – meaning – move from bigger to smaller or smaller to bigger company and with that, a new opportunity will arise. If you’re at a growing company, it’s likely this will happen naturally as your team and product grows.

Can you share how you run your regular scrum meetings with your dev team?

  • Daily 10 min standup in the AM
  • Weekly or bi-weekly backlog grooming session
  • Weekly or bi-weekly sprint planning
  • One or two-week sprints
  • We handle the round-robin in real-time, but for the sprint planning meetings come prepared with notes/PRDs, stories, customer research, data, etc.

What is your favorite approach to product metrics for your product teams? Thinking along the lines of OKRs, KPIs, etc. What are your thoughts in terms of periodicity?

It’s absolutely critical that your org is aligned on OKRs and that the OKRs are driving the main product roadmap.

  • Weekly rollup metrics for growth & product, things like visitors, conversion rates, funnel metrics, revenue Monday through Sunday (reporting and meeting on Monday)
  • Strong focus on OKRs – quarterly goals, but a bi-weekly review of OKRs as a team
  • Weekly breakout groups as needed to focus on OKRs

You may also be interested in: OKRs vs KPIs: The Difference

You mentioned to be a good PM it is important to learn how to build a product from scratch, does that mean you need to code yourself or just understand how is it built?

Ideally, go through the process of building a product – even if it’s using a product like Webflow – build something that solves a real problem and put it in front of real users. To me, that’s the best way to both be humbled (mostly by failing!) and to get enough attention to the process locked down that you understand all of the moving pieces. But no, you don’t have to code it yourself!

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How do we set the success metrics and what are the most used successful metrics? What is the best method to ensure the quality of a product and how to minimize risk?

This is highly product and vertical-specific, but some things to consider that are probably universal:

  • Customer input and ratings (maybe NPS as a leader here)
  • Something in the conversion funnel – i.e. % of visits to signup, % of signup to trial
  • Retention, retention, retention – if your products are not sticky then you are going to have a hard time scaling any business
  • Quick feedback loops from customers
  • Quick iterations of product and feature builds
  • Build smaller measurable features instead of large and unproven features

How should a person coming from a Test Lead Profiles be able to switch to PM Profiles? What kind of expertise and skill sets would it require?

I think starting with something you are passionate about and running a real product build from concept through launch is the best way to learn – doing this as a personal/pet project and/or side hustle is 100% ok – just get started.

Has being in Product Management helped you in finding 6 startups or vice versa?

Both. My career path went like this:

  1. College
  2. 1st tiny company doing website dev
  3. Bigger company doing website dev
  4. Software eng. at growth startup
  5. My own micro agency
  6. Larger agency (grew to over 100 people)
  7. Failed startup with this agency
  8. Startups for the past 8 years

What’s your favorite strategy for breaking down a large initiative from a roadmap standpoint? Do you focus on low-hanging fruit or jump into solving problems based on revenue opportunity? Or is there a good mix of approach that has worked for you?

I love this question – and it’s complex. I think you have to actually do both things at once here. It’s critical that you find the high value add items and bake those into the core roadmap, but too much effort there is probably at the expense of getting the low hanging fruit, more tactical stuff done. But if you focus too much on what’s right in front of you, it’s likely you are sacrificing the longer term.

It’s a blend. I’d use a 50% / 50% rule to start – if you have the ability to spend 50% of the resources and time on each that may be an ideal place to start. Often the highest impact wins come quick – and it gets harder as you go, so that ratio will change to where the longer term you’re working harder to barely move the needle.

Should a PM initiate more promotional tools or focus more on product adaptations?

It depends on the stage of the company, but at we are doing both. We need new customers coming in the door so we need to help expand the marketing funnel and build the things that help smooth the on-boarding experience. But we also need folks to stick around, so the product adaptation part of the roadmap is extensive around retention focused and referral focused features.

Did you miss this event? Check out our events page to sign up for the next #AskMeAnything session!

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