Filling in leadership roles with industry Goliaths will take more than just a slingshot. Here’s how founders fresh to the battlefield can win seasoned veterans over to their side.

How Davids hire Goliaths

Filling in leadership roles with industry Goliaths will take more than just a slingshot. Here’s how founders fresh to the battlefield can win seasoned veterans over to their side.

For technology companies in Southeast Asia, true growth is all about digitally transforming entire industries and capturing several markets in the region. This means having a top-notch executive team who can follow through on company vision and strategy with on-the-ground experience. To form these A-teams, founders need to be able to source candidates and find the ones with the right fit for the company’s needs.

Filling in these leadership roles with top-notch talent often means approaching giants in the industry, long-time executives and veterans who have seen the playbook, waged their fair share of battles, and established a name and career for themselves. As a David on the field, relatively inexperienced and much less established, founders need to take a different course from the usual hiring approach when winning over these Goliaths to their side.

Battle-readiness goes both ways

It all starts with embracing a mindset shift from “Please come work for me” to “I believe we are the best fit for each other.” Once these senior candidates apply you can expect them to be battle-ready for the role they will play in the company, so the company needs to be at least as ready as they are.

This means clarity. Value exchange and culture alignment, while applicable regardless of experience or position, is more pronounced when dealing with senior candidates, who already know what they want in their career and what they can bring to the table. Given your growth trajectory and company culture, it should also be clear who exactly you are looking to bring into the company.

Interviewing industry Goliaths

From our experience linking our portfolio companies with seasoned candidates to key executive roles, here are the things to take note of when interviewing senior people: 

1. Have a compelling origin story. 

Keep it short, but set the tone of your conversation with some good old inspiration. Give them the most aspirational statement on why you are running the company. For example, “I was doing XX, but saw the problem YY. I decided to spend the rest of my career doing this.”

2. Put your best foot forward, only. 

It’s an interview, not an intervention or reflection period. There’s no point in volunteering or addressing any company issues or problems.  

3. Show clarity in explaining the role. 

Level with them on why you’re having the conversation. Tell them you already know how to do X. Now you’re looking for the person who bring X to scale, and you personally wanted to interview him/her because you want the best fit.

4. Listen to their origin story. 

Figure out if you’re on the same page in terms of #1. Get them to talk about their experiences, and also what their aspirations are — this is a huge clue to winning them over! 

5. Speak in their “language”. 

Professional language is a safer option unless getting more colloquial (eg Singlish) builds rapport. This is one unique case where it is neither easier said nor done. Instead, it’s best to listen. 

6. Frame metrics positively, if needed. 

Senior candidates have seen the playbook and worked with big companies and numbers. Don’t volunteer your company’s numbers; and if asked, try to couch it in a good light, eg “Revenue grew XX% M/M.”

On the shoulders of giants

As much as you would want to find the best fit through the hiring process, the true test will come when the company is on the shoulders of these giants and they are brought to the front lines of growth. The company should be an environment where they can fully embrace their responsibilities, take point on the teams they are in charge of, and be trusted to call their own shots. Here it comes down to company culture — a great company nurtures great talent as much as it attracts them.

+ posts

Paulo Joquiño is a writer and content producer for tech companies, and co-author of the book Navigating ASEANnovation. He is currently Editor of Insignia Business Review, the official publication of Insignia Ventures Partners, and senior content strategist for the venture capital firm, where he started right after graduation. As a university student, he took up multiple work opportunities in content and marketing for startups in Asia. These included interning as an associate at G3 Partners, a Seoul-based marketing agency for tech startups, running tech community engagements at coworking space and business community, ASPACE Philippines, and interning at workspace marketplace FlySpaces. He graduated with a BS Management Engineering at Ateneo de Manila University in 2019.