Office Hours Session Notes: Successfully Navigating Product Growing Pains

After achieving PMF, product & engineering organizations face unique scaling challenges.  Success is predicated not only on having a product that customers love and use, but on knowing and planning for the next inflection point across staffing, team-building, cross-functional interactions and changing customer expectations.

We tapped two world-class product leaders to share their advice on navigation product growing pains through the good times, and the challenging ones:

Pratima Arora: Chief Product Officer, Chainalysis and Board Member, Digital Ocean.

Pratima is responsible for the entire R&D team at blockchain data platform Chainalysis – including Engineering, Product, Design, Research, and Data Science – and has doubled the team to 200 in the last year. Previously, she was responsible for Confluence Cloud at Atlassian where she built the team and culture while growing revenue 4x in four years. Prior to Atlassian, Pratima spent nearly a decade at Salesforce, growing Sales Cloud revenue from $300M – $3B while building the product team from the ground up.

Jessica Rusin: Chief Technology Officer/Senior Advisor, Guild Education

Jessica has 20 years of technology experience and most recently was CTO at Guild Education, the high growth EdTech and upskilling startup valued at over $4B. She joined as the second employee and grew and managed the technology organization from one engineering employee to over 225 while growing revenue from <$50K to $100MM+ in ARR. Prior to joining Guild, she was the Senior Director of Engineering at MobileDay, a venture-backed startup, and has led software engineering teams at Digital River, Inc. and two large telecom companies. 

Here are a few gems they shared: 

Keep your eyes open for signals that change needs to happen: 

  • Consistent communication breakdowns
  • Inefficiency, productivity goes down
  • People feeling disconnected
  • Different customer demands

Growing means you can’t talk to everyone anymore

  • Set expectations on your team: change is the only constant. But beware, only introduce change if it’s going to make you faster
  • Have the right kind of engineering leadership – your best engineer might not be the right one to lead a team. Look ahead and see who that might be, where they are now, and how to prep them for management roles
  • Be explicit about tradeoffs when you’re prioritizing
  • Alignment reviews across the org to show what teams are working on – you used to be able to talk to everyone and that changes when you have multiple teams and larger teams

In a high-growth environment, you’re going to reinvent yourself as a leader every 6 months

  • Every time the team doubles, step back and reassess your personal leadership:  where do you have to grow, what do you have to hand off to someone else, what has outlived its relevance, what new hires do you need to make.
  • Be humble and recognize that you don’t know everything that’s happening in the org like you used to
  • Stay open to learning from the organization – what’s working, and what’s not. 
  • Listen, and ask a lot of questions. Ask people around you what the hang ups are – not just direct reports, but consider peers and skip levels to get the real picture
  • Adaptation is key
  • Trust your direct reports, rely on them. When they tell you they’re not getting enough time from you, you need to reassess what you’re doing

You’re probably holding onto something you need to give up (even…[especially] CEOs)

  • It’s a healthy realization that it’s time to grow, but it’s hard
  • Help leaders (reports, peers and your boss) who are stuck holding onto something channel their energy towards the areas where they can have the most impact
  • It’s emotional, so get to the root of it – what’s the fear around giving that thing up?  Remain curious and ask questions to help everyone realize the issue
  • Engage your peers to validate if they share your observation
  • Could be a good time to consider executive coaching – having a neutral third party can dial down the emotion 
  • If you continue to see a growth mindset in someone, it’s a signal that change will happen. If not, and the patterns are repeated and they’re not getting better – it’s a red flag. Take back control about what you’re willing to work around

Helping early adopters grow with you

  • Early customers get used to guiding where the product is heading, and it’s a great feeling that’s tough to break as you mature in your team and offerings
  • Bring them into the fold, share your roadmap and make sure you’re connecting the things they want with that roadmap
  • Be open and honest about how you’re growing as an organization and that previous methods of input need to grow
  • Make sure you understand their underlying need – they’ll often say they want a specific feature but it may or may not solve their actual problem
  • Be opportunistic about how you can continue to create special value for them, like grandfathering them into something that you charge for elsewhere
  • Customer advisory boards: Bring early adopters together as champions to create empathy – allow them to experience and recognize they’re not the only customer with needs and demands. Offer prioritization exercises where they can have a few votes, or ask them to stack rank things to help them experience the importance of tradeoffs
  • And don’t underestimate the importance of customer roles! Support, onboarding, and communication are key, and need to scale and adapt as the product architecture evolves

Roadmaps:  Prioritizing without much data or signal 

  • It can be challenging to know that what you’re working on is the right thing for long term success
  • Building product is as much science as it is art. There WILL be mistakes and you won’t always get it right. Some features early on won’t play out how you might predict 
  • Frameworks can help, but you need to start with defining business impact
  • Experiment! Find the cheapest and quickest way to test your hypotheses
  • Leverage any early adopters to help prioritize and get a feedback loop on usage and engagement
  • Consider administrative configuration a bit earlier than you think – helping something get to self-serve can save engineering time long term, but do the math (it’s always a balance as it’s not the most exciting engineering work!)

Setting – and managing – leadership expectations

  • It’s easy to assume new senior leads will come in and fix everything (afterall, that’s why you hired them!)  Sometimes they’re too eager but don’t have enough context – manage expectations all around with direct, clear communication and create space that allows them to not feel like they have to act immediately
  • Be intentional about alignment, share upfront what the best practices are when onboarding – ask new people for feedback about their experience and use it to modify practices 
  • Continue to listen more and learn more 
  • You will consistently reset with the team on best practices and how you’re all going to work – you will have to do this over and over, and over, again
  • If it’s not working – make decisions to part company early. It’s common to take too long to let someone go that isn’t working out, but they do more damage the longer they stay

 Tooling, and retooling

  • Find ways to wrap the solution or create one layer of abstraction so if you need to swap something out it doesn’t cause big problems 
  • It can be a conversation for the entire leadership to rally around 
  • Evaluate where vendor lock in doesn’t really impact the business – if it’s your bread and butter, then you need to be much more careful – if it’s part of your core business, don’t outsource too much
  • Evaluate your time spent and the criticality – see if it’s something you need to build in house. Be wary of over-engineering things up front when you may outgrow it in a few months
  • There are usually logical growth points to retool
  • Always keep in mind what will help you accelerate
  • It’s always a balance on knowing how important it is for your business – consider if something is a one way door or a two-way door where you can change the decision 

About Office Hours: This invite-only program series connects OpCo founders and CEOs with leaders in our LP community on key operating issues critical to success. These candid, interactive conversations surface best practices, how to avoid potential pitfalls, and compelling “how we did that” stories from the trenches that range from strategies to tactics. Check out past sessions like Building Your GTM Machine and Culture Scaling.