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

In 2022, ContactOut embarked on an ambitious journey to redefine cold outreach. Our CEO envisioned a transformation, leading to the creation of three pioneering cross-functional squads dedicated to various aspects of our product. 

Our next daunting task was to hire Product Designers. From. Scratch. (No pressure at all)

This was when I started working closely with Joseph Tan, our Head of Product Design, at ContactOut. Joseph, having been a  former VP and Design Coach at DBS Bank, was an experienced hiring manager. Together, we set out to build a lean yet robust Product Design team.

Here’s how we did it and some of our reflections along the way:

What Does “Good” Look Like?  Understanding the Hiring Manager’s Perspective 

Oftentimes, it’s the lack of alignment that sets your hiring process back. Grasping levelling concepts, for example, what separates a junior-level product designer from a mid-level one (from your hiring manager’s point of view) steers a clearer direction into what you’re looking for. Sometimes, it’s not a matter of “years of experience” but their capabilities that dictate their level. 


Here’s a sample snapshot of what our Head of Product Design had in mind for his team 🔍

How did we land our first hire? Leveraged the Hiring Manager’s first-degree connections. 

Hiring managers who have a strong pulse of what’s happening in their community are likely well-connected. That’s exactly how our first-ever Product Designer got hired in ContactOut. She was mentored by Joseph in the past and displayed enormous skill and potential. If there’s anything to be learnt from this, it’s only that the next hire may be closer than you think (i.e. their 1st-degree connection in LinkedIn). 

TIP – Identify your hiring manager’s first-degree connections by asking them to click on their top right thumbnail photo on LinkedIn > Settings And Privacy > Data Privacy > Get A Copy Of Your Data > Select Data You’re Most Interested In > Tick The “Connections” > Request Archive

Once they send you a copy of their connections, you can start sifting through the list and touching base with the talent that matches your needs. Not every hiring manager would be comfortable with this method, so ask for their consent and give them options to filter out the connections they send to you.

TIP – If the contact details aren’t available firsthand, connect with your shortlist through ContactOut. There are two ways: 

  1. Head to their LinkedIn profile and find their contact details through ContactOut’s Chrome extension

2. Find contact information in bulk – head to ContactOut’s Data Enrichment feature and click on ‘Get Work Emails’

The Recruitment Process: How do we strike a balance? 

Testing candidates’ skills accurately, efficiently, and fairly has always been tricky, not to mention tremendously labour-intensive for both sides. How exactly do you find the balance?

When we were building a Product Design team for the first time, in the context of ContactOut, we faced a lot of unknowns. Our hiring process went through tons of iterations, but the principle behind it remained the same: recruit with purpose.


Here’s what it looks like: 


Process Purpose Interviewer

Initial resume & portfolio review 

To gauge the candidate’s background for a potential interview

Having a seasoned lens conduct the initial screening increased the quality of our pipeline and saved us, and the candidates, heaps of time in the long run. 

Head of Product Design

Conversation with ContactOut

Understanding the candidate’s motivations.

Having been vetted by the hiring manager meant I could spend more time on “soft selling” and giving candidates more clarity into the next stages. This portion usually lasts anywhere from 15-30 minutes.

Talent Acquisition 

First interview 

This consists of a more interactive approach: case-study presentation, getting a sense of where they are in their career and where they want to go.  Head of Product Design

Values questionnaire 

We share a sample response coming from our Head of Product too. 

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

Take home 

Challenge Design 

The design challenge was done at the candidate’s pace. 

Evaluating technical and functional problem-solving skills. 

Head of Product Design 



Final presentation

It’s all about levelling the playing field. The candidate can present their work and ask questions in real-time – simulating a an actual working dynamic CEO 

Head of Product Design 


Despite its length, our process was efficient, focusing on highly suitable candidates. The diverse touchpoints provided candidates with a comprehensive understanding of our approach and its benefits. We faced some dropouts, but the trade-offs were worth the tailored team we built.


TIP – Integrate a give-and-take element in your recruitment process. 


In our case, to ensure that candidates still walked away with reflections and learnings, our Head of Product Design offered two 15-minute touchpoints in between the take-home challenge (optional). We also have examples of what a “good” challenge submission looks like. 


Towards the end of the process, he also offered 1:1 coaching sessions with unsuccessful candidates so they could improve their job searches, resumes and portfolios alongside a copy of his own portfolio to support them further.

The end result? Three product squads, each with their dedicated Product Designers, 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?

  • A clear vision is crucial for aligning teams with the right talent.
  • Sometimes, you don’t have to look far away to find the right talent. Your organization’s own people know people. 
  • The “Mentoring Approach” by our Head of Product created a great candidate experience by injecting a learning element.


If you enjoyed this article, then 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 Management Team