September 15, 2020

Is It Time to Hire Remote Engineers for My Startup?

By Wes Winham

Last week, I talked to an analyst at an investment firm who works with a ton of high-growth software companies. He told me about one company in their portfolio who was debating a big question…

Is it time to start hiring remote engineers?

They were in a mid-sized market and their entire engineering team was local, but with their growth goals they felt like they needed to expand beyond their local market to hire the engineers they needed.

With remote hires, however, comes a learning curve and some key things to consider. So I sat down with some engineers who have made this decision, and they presented me with two options:

  1. Hire More Junior/Mid-Level Engineers: Their team was pretty senior, which is great when you’re in Series A growth mode, but can be limiting when you’re looking to scale into a Series B and beyond.

    Several of our clients have seen big lifts in both production and hiring volume when they started to focus on maintaining a ratio of 1 senior to 1 mid to 1 junior.

    Not only does this widen the application pool for them (our internal data suggests that mid-level roles generate 10x the applications of senior-level roles), but it’s also a great retention tool for talented senior developers. By hiring great juniors and mids, you enable them to coach and mentor, which they like, while also taking menial tasks off of their plate.

    One of our clients partnered with us to help hire world-class junior and mid-level candidates when they were at a similar inflection point (~90 employees, $20M Series B just raised, big hiring goals, in Indianapolis, a mid-sized, midwest city) and the initiative was a huge success.

  2. Hire Remote, But Know What You’re Signing Up For: According to Woven’s CEO Wes Winham, who has run both a national and global remote team of engineers, “Remote work expands both your applicant pool and your workload.”

    One of our clients hires exclusively remote applicants, and they see about 10x the applicant volume for senior roles as clients who exclusively hire locally, even in large markets like San Francisco and Chicago.

    That said, it requires a lot of job board hacking, which our team manages for them, to generate those outsized results. It also becomes harder to accurately assess overall caliber of employee, which is why they partner with us for work simulations.

    So while it’s effective for them, for other companies it may end up being extremely cumbersome to create a DIY system for recruiting and hiring remote teams.

    If you’re looking for real-world examples of how this can be done successfully, check out Stripe, an online financial infrastructure service that has made hiring and integrating remote workers central to their business.

After going back and forth, our engineering team landed in the camp that option number two probably makes the most sense, given their growth trajectory. They’re going to need to learn how to hire remote engineers eventually anyway… so it probably makes sense to rip the band-aid off.

That said, expanding their local candidate pool with more junior and mid-level candidates could also be a great club to pull out of the bag.‍

How to know if you’re ready to hire remote engineers

My dad used to tell me “if you waited to have kids until you were ready, you’d never do it.” It sounds like the consensus is the same for remote hiring.

Remote hiring and management is really hard, even if you’ve done it successfully in a past position. If you’re debating making a remote hire, you should rip the band-aid off and do it. You’ll need to learn the skills eventually.‍

That said, invest heavily in remote engineering technical screening and communication tools to stay on the same page.

This post is part of Woven’s 100-Day Challenge, aiming to solve 100 problems related to developer hiring in 100 days. If you have a problem you want us to tackle, email Tim Hickle at

June 20, 2019