How ContactOut Built 3 Pioneer Squads in One Year ft. Our Product Management Team

If you’ve been following this 3-part series, you would know that in 2022, ContactOut was in a hiring surge. Our CEO had a vision which directly translated to hiring goals. 

The challenge? Create three pioneer cross-functional squads to build and maintain different parts of the product. 

Identified core needs. What does “good” look like?

What was the business problem we were trying to solve? 

We’ve got a promising product, but the UI/UX wasn’t great. We wanted to build more intuitive features in different parts of the platform to add value to our users and attract new customers. 

How they’ll make an impact: 

  • Build mechanisms that attract large, relevant audiences for our data intelligence products
  • Design and run experiments to optimize the user experience for our 40k DAU, which requires the least amount of engineering effort
  • Come up with new tasks and manage backlogs for the team based on priority

Educational background:

  • Formal education in a related field (Engineering or Computer Science) 

👉 Our CEO wanted our PMs to understand the intricacies of building a product through an engineer’s point-of-view, while also understanding the big picture and relaying these to different stakeholders. 

Qualifications, both technical and functional

  • 0–3+ years experience working for or had a previous internship in a startup, scale-up, or lean operating organization; ideally working cross-functionally with product, marketing, design, and engineering teams
  • Ability to see the big picture and align activities to the highest priority business outcomes
  • Ability to align with stakeholders, projects, and team according to first principles; to take and give constructive feedback and create value

Sourcing – where and how do we find these talents?

Our sourcing efforts focused on LinkedIn since there’s a multitude of talent out there; we just needed to catch their attention and stand out of their inbox. 

I learned this short-form messaging from our CEO. It contains enough information to capture attention and pique curiosity without the information overload. 


TIP – If they don’t respond, that’s when you start building those touchpoints and feeding them more information as you go. Blend the exciting parts with factual ones. This way, it doesn’t feel too pushy or sales-y and increases the chances of engagement. 


While we went all out on sourcing, we also tapped remote tech job boards to build our talent pipeline at $0 cost and that’s how we hired two of our Product Managers. 


TIP – Experiment on different job boards till you find the most effective channels that yield a quality pool of candidates. If it works, then you’ll know which platforms to invest in. 

The Recruitment Process: How do we strike a balance? 


Process Purpose Interviewer

Conversation with ContactOut

Engaging candidates to understand their motivation, resolve concerns, set expectations and get their excitement levels up.  Talent Acquisition 

Values questionnaire 

Understand the potential synergy between candidates <> ContactOut CEO (async)

Hiring Managers


Take home PM challenge 

The PM challenge was an important piece of the puzzle.

There was a coaching element involved from our Hiring Managers so candidates could focus on areas that matter. 


Hiring Managers


Final Interview & challenge presentation

This consists of a more interactive approach: 

Challenge presentation 

Live Q&A


Hiring Managers


Much like the rest of our teams, hiring PMs was a relatively new experience for us, so it meant having plenty of iterations to the process. The game-changer for us was the “coaching piece” in STEP 3. This approach helped keep candidates engaged; it presented a learning element since they got 15-minute 1:1s with leaders to capture unique perspectives and helped candidates create more meaningful outcomes. 

What’s the secret to making candidates sticky? Always. Be. Closing.


The answer is quite simple: meaningful conversations.  Be ready to talk vision. In our initial conversations with candidates, we’re transparent about our pain points. What are those problems that need solving? Where do they come in? We also show them an actual example of what the squad formation would look like so they, too, can envision themselves in the team. 

TIP – If you come across top talent keen on understanding the culture, team, and/or roadmap better, arrange a 15-to 30-minute chat with one of your hiring managers. Accessibility to leaders builds rapport early on and helps the candidate understand the type of environment your startup has. 


Find out what matters to your candidates early on. Understand what they want to know prior to your conversation. It creates a tailored approach that helps you understand what levers to pull. You don’t have to repeat the same spiel like a broken record. 


TIP – Create a custom calendar invitation template to gather the information you need before the call. 


Leverage your hiring manager’s feedback for that personalized approach. Be transparent with what’s going on so they know that this is meant to be a collaborative journey. This also helps level the playing field for candidates. You’ll see how they adapt to information in real-time. In a startup, we all know how critical that is.  

The end result: Three product squads, each with a dedicated group of Product Managers, built in a year.

Each cross-functional team, with its unique skill sets and qualities, contributed significantly to our product development and organizational growth.

What did we learn along the way?

  • Short-form messaging works. Your goal should be to get your candidate interested enough to get them on an initial call. Be ready to send them more information if they ask for it. 
  • Involve your leaders in the process – they’re the biggest reflection of your culture and can help keep your candidates sticky, especially when there are multiple steps to your hiring. 
  • A long hiring process has its trade-offs – the least we can do is make it worth your hiring managers’ and candidates’ time. 


Want to find out how we hired the rest of our team? I’ve got some great news! This is a three-part series.

Check out Scaling our Engineering Team: How ContactOut Built 3 Pioneer Squads in One Year and How ContactOut Built 3 Pioneer Squads in One Year ft. Our Product Design Team