Startup Interview Tips

Talent is everything. Demand for skilled talent is fiercer than ever, with the gap in supply widening. At Wahl and Case we sit in-between the most innovative, disruptive technology companies as our clients on one side, and an exceptional network of talent on the other. Each day we try to solve a key problem for our customers: how to acquire and retain the best talent, to grow their business. In the world of startups – be it mobile, analytics, ed technology, gaming, apps, monetization, advertising technology, e-commerce, enterprise, shared economy, or financial technology — we’re playing witness to the technological and digital revolution. As such, we gain valuable insights as to why companies are successful or failing. It’s one of the (many) perks to our job. We intend to pioneer a series of articles, many based on presentations and interviews with thought leaders in our primary markets in Tokyo and San Francisco, to share the insights we get to see in our world of talent acquisition in the tech startup space. Our goal? To share valuable information that is typically locked inside just a few peoples’ heads. Hopefully, the nuggets of wisdom we share can support a better decision for a critical career move, or even help newly founded startups make their way through the precipitous cliffs of growing a business.


his is a special edition of our blog featuring one of our close client partners. He kindly shared his wealth of knowledge with me on the topic of hiring for startups in Japan.



Matthew Skyrm

is currently the COO of

Gengo, Inc

. Prior to Gengo, Matthew Skyrm spent 16 years building Internet businesses in Silicon Valley and Japan. He was co-founder and CEO of Inc., held senior product management positions at Yahoo! (messenger) and Sony Corporation (PlayMemories). 



is a web-based human translation platform headquartered in Tokyo. It draws from a network of more than 17,000 pre-tested translators working across 37 languages and 64 language pairs. Translations can be ordered via direct order or API integrations.


for Startups

Matthew Skyrm has hired many different types of people at Gengo, Inc., a Tokyo based startup that provides people-powered translation, and he offered two main approaches to hiring that are summarized below. All include some combination of cash and stock options:

The (recommended) consultative approach

  • Figure out what is important to both sides as you mediate between the client and the candidate. Do they want cash or equity?

  • Ask clients for the number of shares outstanding, strike price, current valuation.

  • Find out user and / or revenue growth

  • Future funding plans – is the client going to get a new round of funding soon? It may affect the valuation and the strike price

  • Investor / management intentions / expectations (i.e. the exit strategy, is it an IPO or an acquisition?)

The hard sell approach

  • Pre-IPO or to be acquired soon? Get in now while you have the chance!

  • Are they going to get a new round of funds? Get the current low strike price by moving fast!

  • Trust us, you don’t want more salary – you want more options!

  • The last person we placed at XYZ Co. just bought a new house from the IPO windfall!

  • The CEO has done 7 startups and they all made it to the IPO stage. He’s an outstanding serial entrepreneu You should grab on to his coattails!

*Culture Point: what is more important cash or equity? Culturally most Japanese candidates will say cash. In some rare cases, candidates ask for more equity and less cash in Japan, but in Silicon Valley the reverse is more common, particularly for senior positions.Japan is UniqueThe number of VC funds is smaller in Japan than the U.S. The likelihood for a “hot” IPO is higher in the U.S. The barriers to IPO are lower in Japan, but tech IPO’s often have very low valuations by U.S. standards. In Japan companies tend not to give stock options nor do employees expect them (or even understand the concept). Employment contracts tend to be very important to Japanese candidates because job security is heavily protected by labor laws, and because of tradition. Gradually this will change and it’s up to us (recruiters and startups alike) to educate companies and individuals, encouraging them to take more risks.Often times, a candidate accustomed to Japanese companies will have certain perceptions regarding Permannt Employment Status vs. Contract Employment Status. It is critical to be aware of these perceptions.Perception of Permanent Employment Status:

  • more respected in the company

  • have title in company hierarchy

  • strong career plan

  • have the “douki” network (staff who joined company in the same year)

  • make less money, slow pay increases

  • expect lifetime employment

  • regular performance reviews

Perception of Contract Employment Status:

  • less respect within company

  • lack of a proper title

  • no career plan

  • no “douki” network

  • make more money (maybe?)

  • expect to leave after a few years

  • no performance reviews

*These points are not applicable to every company.Key Screening Questions for Candidate who are considering startups

  • Do you like to “build” something from scratch?

  • Are you proud of the things you have built in the past?

  • Do you mind doing scary amounts of decision making with minimal information?

  • Do you want stability or challenges (challenges which can be very draining emotionally)?

  • Do you like to have a “system” that you are trained in? Or do you want to make a “system” and train others?

  • How do you end the following sentence: “I’ve never done that before…..”?

  • Are you an independent thinker? Do you mind not fitting in (societal/familial pressures)?

  • Do you really understand the risks?

  • Have you considered what life would be like if the startup failed or exited?

Finally, we would like to wish all the best to Gengo and their staff. They have been able to find talent with a strong desire to win against all odds (with a little bit of Wahl and Case help) – a mentality that the nation needs even more of. Gengo have certainly helped to educate a lot of people in Japan’s still immature startup eco-system. We hope they continue their growth globally.